49 results on '"Chiung-Yao Huang"'
Search Results
2. Cembranolides and Related Constituents from the Soft Coral
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Chih-Hua, Chao, Yi-Ju, Chen, Chiung-Yao, Huang, Fang-Rong, Chang, Chang-Feng, Dai, and Jyh-Horng, Sheu
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Molecular Structure ,Animals ,Antineoplastic Agents ,Diterpenes ,Drug Screening Assays, Antitumor ,Anthozoa - Abstract
In an attempt to explore the bioactive metabolites of the soft coral
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- 2022
3. 5-epi-Sinuleptolide from Soft Corals of the Genus Sinularia Exerts Cytotoxic Effects on Pancreatic Cancer Cell Lines via the Inhibition of JAK2/STAT3, AKT, and ERK Activity
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Wen-Hung Wang, Wan-Chi Tsai, Bo-Cian Huang, Chiung-Yao Huang, and Jyh-Horng Sheu
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MAPK/ERK pathway ,STAT3 Transcription Factor ,MAP Kinase Signaling System ,pancreatic cancer ,Pharmaceutical Science ,Organic chemistry ,Article ,Analytical Chemistry ,STAT3 ,QD241-441 ,Pancreatic cancer ,Cell Line, Tumor ,Drug Discovery ,medicine ,Cytotoxic T cell ,Animals ,Physical and Theoretical Chemistry ,Protein kinase B ,Cell growth ,Chemistry ,Cytotoxins ,Cancer ,Janus Kinase 2 ,medicine.disease ,Anthozoa ,5-epi-sinuleptolide ,Pancreatic Neoplasms ,soft corals ,Chemistry (miscellaneous) ,Apoptosis ,Cancer cell ,Cancer research ,Molecular Medicine ,cytotoxicity ,Diterpenes ,Proto-Oncogene Proteins c-akt ,Carcinoma, Pancreatic Ductal - Abstract
Pancreatic ductal adenocarcinoma is one of the most lethal malignancies: more than half of patients are diagnosed with a metastatic disease, which is associated with a five-year survival rate of only 3%. 5-epi-Sinuleptolide, a norditerpene isolated from Sinularia sp., has been demonstrated to possess cytotoxic activity against cancer cells. However, the cytotoxicity against pancreatic cancer cells and the related mechanisms are unknown. The aim of this study was to evaluate the anti-pancreatic cancer potential of 5-epi-sinuleptolide and to elucidate the underlying mechanisms. The inhibitory effects of 5-epi-sinuleptolide treatment on the proliferation of pancreatic cancer cells were determined and the results showed that 5-epi-sinuleptolide treatment inhibited cell proliferation, induced apoptosis and G2/M cell cycle arrest, and suppressed the invasion of pancreatic cancer cells. The results of western blotting further revealed that 5-epi-sinuleptolide could inhibit JAK2/STAT3, AKT, and ERK phosphorylation, which may account for the diverse cytotoxic effects of 5-epi-sinuleptolide. Taken together, our present investigation unveils a new therapeutic and anti-metastatic potential of 5-epi-sinuleptolide for pancreatic cancer treatment.
- Published
- 2021
4. Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri
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Jyh-Horng Sheu, Tsong-Long Hwang, Chiung-Yao Huang, Tzu-Yin Huang, and Chia-Chi Peng
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Sarcophyton cherbonnieri ,Stereochemistry ,Cytochalasin B ,Neutrophils ,QH301-705.5 ,Anti-Inflammatory Agents ,Taiwan ,isosarcophine derivatives ,Pharmaceutical Science ,Phenylalanine ,tetrahydrooxepane ,Article ,chemistry.chemical_compound ,Superoxides ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Biology (General) ,Cytotoxicity ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Nuclear Magnetic Resonance, Biomolecular ,Cell Proliferation ,Pancreatic Elastase ,Superoxide ,Circular Dichroism ,Elastase ,Absolute configuration ,Anthozoa ,N-Formylmethionine Leucyl-Phenylalanine ,chemistry ,Cell culture ,cytotoxicity ,Diterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM.
- Published
- 2021
5. New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral
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Tzu-Yin, Huang, Chiung-Yao, Huang, Shu-Rong, Chen, Jing-Ru, Weng, Tzu-Hsuan, Tu, Yuan-Bin, Cheng, Shih-Hsiung, Wu, and Jyh-Horng, Sheu
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Cell Survival ,Interleukin-1beta ,Anti-Inflammatory Agents ,Antineoplastic Agents ,Article ,Structure-Activity Relationship ,LPS-stimulated J774A.1 macrophage cells ,Neoplasms ,Animals ,Humans ,PPAR-γ transcription factor ,anti-inflammatory ,Sarcophyton tenuispiculatum ,Molecular Structure ,Macrophages ,Hep G2 Cells ,Anthozoa ,Hydroquinones ,hydroquinone ,MCF-7 Cells ,Monoterpenes ,cytotoxicity ,Diterpenes ,Inflammation Mediators ,cembranoid ,HeLa Cells - Abstract
Chemical investigation of the marine soft coral Sarcophyton tenuispiculatum resulted in the isolation of a 1,4-dihydrobenzoquinone, sarcotenuhydroquinone (1), three new cembranoids, sarcotenusenes A‒C (2‒4), and ten previously reported metabolites 5–14. The chemical structures of all isolated metabolites were determined by detailed spectroscopic analyses. In biological assays, anti-inflammatory, cytotoxic, and peroxisome proliferator-activated receptor γ (PPAR-γ) transcription factor assays of all compounds were performed. None of the isolated compounds were found to exhibit activity in the PPAR-γ transcription factor assay. The anti-inflammatory assays showed that (+)-7α,8β-dihydroxydeepoxysarcophine (13) inhibited the production of IL-1β to 56 ± 1% at a concentration of 30 µM in lipopolysaccharide (LPS)-stimulated J774A.1 macrophage cells. In addition, 1 and 2 were found to exhibit cytotoxicity towards a panel of cancer cell lines.
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- 2020
6. Anti-Inflammatory Cembranoids from a Formosa Soft Coral Sarcophyton cherbonnieri
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Atallah F. Ahmed, Chiung-Yao Huang, Chia-Chi Peng, Jyh-Horng Sheu, and Tsong-Long Hwang
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Adult ,Sarcophyton cherbonnieri ,Stereochemistry ,medicine.drug_class ,Neutrophils ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Phenylalanine ,Anti-inflammatory ,Article ,Proinflammatory cytokine ,chemistry.chemical_compound ,Structure-Activity Relationship ,Young Adult ,Superoxides ,Drug Discovery ,medicine ,Animals ,Humans ,Triphenylphosphine ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Cytochalasin B ,superoxide anion generation ,lcsh:QH301-705.5 ,Molecular Structure ,Chemistry ,Superoxide ,Elastase ,elastase release ,Anthozoa ,lcsh:Biology (General) ,Diterpenes ,Leukocyte Elastase ,cembranoid ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
The present investigation on chemical constituents of the soft coral Sarcophyton cherbonnieri resulted in the isolation of seven new cembranoids, cherbonolides F&ndash, L (1&ndash, 7). The chemical structures of 1&ndash, 7 were determined by spectroscopic methods, including infrared, one- and two-dimensional (1D and 2D) NMR (COSY, HSQC, HMBC, and NOESY), MS experiments, and a chemical reduction of hydroperoxide by triphenylphosphine. The anti-inflammatory activities of 1&ndash, 7 against neutrophil proinflammatory responses were evaluated by measuring their inhibitory ability toward N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced superoxide anion generation and elastase release in primary human neutrophils. The results showed that all isolates exhibited moderate activities, while cherbonolide G (2) and cherbonolide H (3) displayed a more active effect than others on the inhibition of elastase release (48.2% ±, 6.2%) and superoxide anion generation (44.5% ±, 4.6%) at 30 µ, M, respectively.
- Published
- 2020
7. Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium
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Atallah F. Ahmed, Chuan-Hsiang Chang, Chiung-Yao Huang, Tian-Sheng Yang, Jyh-Horng Sheu, You-Cheng Lin, and Tsong-Long Hwang
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prenyleudesmane ,food.ingredient ,Stereochemistry ,Neutrophils ,Coral ,Anti-Inflammatory Agents ,Pharmaceutical Science ,01 natural sciences ,Lobophytum ,Article ,Lobophytum varium ,chemistry.chemical_compound ,food ,Biosynthesis ,Superoxides ,Drug Discovery ,Animals ,Humans ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,Pancreatic Elastase ,010405 organic chemistry ,Chemistry ,Superoxide ,Absolute configuration ,Stereoisomerism ,Carbon-13 NMR ,Anthozoa ,lobane ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,Diterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F&ndash, P (1&ndash, 11) of lobane&ndash, and prenyleudesmane&ndash, types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher&rsquo, s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.
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- 2020
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8. Bioactive new withanolides from the cultured soft coral Sinularia brassica
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Chih-Chuang Liaw, Tsong-Long Hwang, Chiung-Yao Huang, Jyh-Horng Sheu, Jui-Hsin Su, Chang-Feng Dai, Atallah F. Ahmed, Pei-Lun Chiang, and Ping-Jyun Sung
- Subjects
Models, Molecular ,Cytochalasin B ,Neutrophils ,Stereochemistry ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Ethyl acetate ,Pharmaceutical Science ,Antineoplastic Agents ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Superoxides ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,Animals ,Humans ,Cytotoxicity ,Withanolides ,Molecular Biology ,Pancreatic elastase ,Alanine ,Pancreatic Elastase ,010405 organic chemistry ,Superoxide ,Organic Chemistry ,Elastase ,Anthozoa ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Withanolide ,chemistry ,Molecular Medicine - Abstract
Continuing study of the ethyl acetate (EtOAc) extract of the cultured soft coral Sinularia brassica afforded five new withanolides, sinubrasolides H-L (1-5). The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxicities of new compounds 1-5 and a known compound sinubrasolide A (6) against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of compounds 1-6 were evaluated by measuring their ability to suppress N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils.
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- 2017
9. Bioactive Capnosanes and Cembranes from the Soft Coral
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Wan-Ru, Tseng, Atallah F, Ahmed, Chiung-Yao, Huang, Yi-Ying, Tsai, Chi-Jen, Tai, Raha S, Orfali, Tsong-Long, Hwang, Yi-Hsuan, Wang, Chang-Feng, Dai, and Jyh-Horng, Sheu
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Magnetic Resonance Spectroscopy ,Pancreatic Elastase ,Cytochalasin B ,Neutrophils ,Anti-Inflammatory Agents ,Anthozoa ,Article ,Cell Line ,N-Formylmethionine Leucyl-Phenylalanine ,Biological Factors ,capnosane ,cembrane ,Superoxides ,Cell Line, Tumor ,soft coral ,Animals ,Humans ,Diterpenes ,Drug Screening Assays, Antitumor ,Klyxum flaccidum ,anti-inflammatory activity ,Cell Proliferation ,cytotoxic activity - Abstract
Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.
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- 2019
10. New cytotoxic and anti-inflammatory steroids from the soft coral Klyxum flaccidum
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Yi-Ying Tsai, Tsong-Long Hwang, Yun-Sheng Lin, Chiung-Yao Huang, Wan-Ru Tseng, Jyh-Horng Sheu, Jui-Hsin Su, Chang-Feng Dai, and Ping-Jyun Sung
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medicine.drug_class ,Stereochemistry ,medicine.medical_treatment ,Clinical Biochemistry ,Pharmaceutical Science ,Antineoplastic Agents ,01 natural sciences ,Biochemistry ,Anti-inflammatory ,Steroid ,Mice ,Structure-Activity Relationship ,chemistry.chemical_compound ,Superoxides ,Cell Line, Tumor ,Drug Discovery ,medicine ,Animals ,Humans ,Cytotoxic T cell ,Cytotoxicity ,Molecular Biology ,Cell Proliferation ,Dose-Response Relationship, Drug ,Molecular Structure ,Pancreatic Elastase ,010405 organic chemistry ,Chemistry ,Superoxide ,Anti-Inflammatory Agents, Non-Steroidal ,Organic Chemistry ,Elastase ,Anthozoa ,Molecular biology ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Molecular Medicine ,Steroids ,Drug Screening Assays, Antitumor ,Two-dimensional nuclear magnetic resonance spectroscopy ,K562 cells - Abstract
Four new steroids, namely klyflaccisteroids G-J (1-4) were isolated from the Formosan soft coral Klyxum flaccidum. The structures of compounds 1-4 were established by spectral data analysis (IR, MS, 1D and 2D NMR) and comparison of spectral data with those of the related known compounds. Cytotoxicity assay revealed that 4 exhibited inhibition activity against the growth of HT-29, P388 and K562 cancer cell lines, whereas 2 showed selective cytotoxicity toward P388 cells. Compound 4 was also found to display significant anti-inflammatory activity for suppressing superoxide anion generation (O2(-)) and elastase release.
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- 2016
11. New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri
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Chia-Chi Peng, Chang-Feng Dai, Tsong-Long Hwang, Atallah F. Ahmed, Chiung-Yao Huang, and Jyh-Horng Sheu
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Sarcophyton cherbonnieri ,Cytochalasin B ,Neutrophils ,Stereochemistry ,Coral ,elastase release inhibition ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Phenylalanine ,01 natural sciences ,Peroxide ,Article ,chemistry.chemical_compound ,Superoxides ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,biscembranoid peroxide ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,Molecular Structure ,Pancreatic Elastase ,010405 organic chemistry ,Superoxide ,Elastase ,Anthozoa ,Peroxides ,0104 chemical sciences ,N-Formylmethionine Leucyl-Phenylalanine ,010404 medicinal & biomolecular chemistry ,chemistry ,lcsh:Biology (General) ,Diterpenes ,cembranoid - Abstract
Six new cembranoids, cherbonolides A&minus, E (1&ndash, 5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1&ndash, 7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLF/CB)-induced human neutrophils.
- Published
- 2018
12. A Sterol from Soft Coral Induces Apoptosis and Autophagy in MCF-7 Breast Cancer Cells
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Chiung Yao Huang, Li Yuan Bai, Jing Ru Weng, Jing Lan Hu, Chang Fang Chiu, Jyh-Horng Sheu, and Chia Hsien Feng
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0301 basic medicine ,MAPK/ERK pathway ,autophagy ,PPARγ ,p38 mitogen-activated protein kinases ,Pharmaceutical Science ,Breast Neoplasms ,Article ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Cyclin D1 ,sterol ,breast cancer ,Cyclin-dependent kinase ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Phosphorylation ,Extracellular Signal-Regulated MAP Kinases ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,Cell Proliferation ,biology ,Chemistry ,Kinase ,Autophagy ,apoptosis ,Cyclin-Dependent Kinase 6 ,Anthozoa ,PPAR gamma ,Sterols ,030104 developmental biology ,MCF-7 ,lcsh:Biology (General) ,030220 oncology & carcinogenesis ,biology.protein ,Cancer research ,MCF-7 Cells ,Female ,Growth inhibition ,Reactive Oxygen Species - Abstract
The peroxisome proliferator-activated receptor &gamma, (PPAR&gamma, ) is a nuclear receptor that plays a key role in regulating cellular metabolism, and is a therapeutic target for cancer therapy. To search for potential PPAR&gamma, activators, a compound library comprising 11 marine compounds was examined. Among them, a sterol, 3&beta, 11-dihydroxy-9,11-secogorgost-5-en-9-one (compound 1), showed the highest PPAR&gamma, activity with an IC50 value of 8.3 &mu, M for inhibiting human breast adenocarcinoma cell (MCF-7) growth. Western blotting experiments showed that compound 1 induces caspase activation and PARP cleavage. In addition, compound 1 modulated the expression of various PPAR&gamma, regulated downstream biomarkers including cyclin D1, cyclin-dependent kinase (CDK)6, B-cell lymphoma 2 (Bcl-2), p38, and extracellular-signal-regulated kinase (ERK). Moreover, compound 1 increased reactive oxygen species (ROS) generation, upregulated the phosphorylation and expression of H2AX, and induced autophagy. Interestingly, pre-treatment with the autophagy inhibitor 3-methyladenine rescued cells from compound 1-induced growth inhibition, which indicates that the cytotoxic effect of compound 1 is, in part, attributable to its ability to induce autophagy. In conclusion, these findings suggest the translational potential of compound 1 in breast cancer therapy.
- Published
- 2018
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13. Cembranoid-Related Metabolites and Biological Activities from the Soft Coral
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Chia-Hua, Wu, Chih-Hua, Chao, Tzu-Zin, Huang, Chiung-Yao, Huang, Tsong-Long, Hwang, Chang-Feng, Dai, and Jyh-Horng, Sheu
- Subjects
Pancreatic Elastase ,Cytochalasin B ,Neutrophils ,Anti-Inflammatory Agents ,cembranoid-related compounds ,Antineoplastic Agents ,Anthozoa ,Article ,N-Formylmethionine Leucyl-Phenylalanine ,Superoxides ,Sinularia flexibilis ,Cell Line, Tumor ,secoflexibilisolide ,Animals ,Humans ,Diterpenes ,Drug Screening Assays, Antitumor ,flexibilisin ,flexibilisolide - Abstract
Five new cembranoid-related diterpenoids, namely, flexibilisins D and E (1 and 2), secoflexibilisolides A and B (3 and 4), and flexibilisolide H (5), along with nine known compounds (6–14), were isolated from the soft coral Sinularia flexibilis. Their structures were established by extensive spectral analysis. Compound 3 possesses an unusual skeleton that could be biogenetically derived from cembranoids. The cytotoxicity and anti-inflammatory activities of the isolates were investigated, and the results showed that dehydrosinulariolide (7) and 11-epi-sinulariolide acetate (8) exhibited cytotoxicity toward a limited panel of cancer cell lines and 14-deoxycrassin (9) displayed anti-inflammatory activity by inhibition of superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils.
- Published
- 2018
14. Isolation and Structure Elucidation of Cembranoids from a Dongsha Atoll Soft Coral Sarcophyton stellatum
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Chang-Feng Dai, Yang Chang Wu, Atallah F. Ahmed, Yen Ju Tseng, Jyh-Horng Sheu, Chiung Yao Huang, Yi Wei Chen, and Chi-Chen Lin
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Lipopolysaccharides ,Magnetic Resonance Spectroscopy ,Lipopolysaccharide ,Stereochemistry ,Coral ,Ethyl acetate ,Pharmaceutical Science ,Nitric Oxide Synthase Type II ,01 natural sciences ,Article ,Proinflammatory cytokine ,chemistry.chemical_compound ,Inhibitory Concentration 50 ,Mice ,Cell Line, Tumor ,Drug Discovery ,Cytotoxic T cell ,Animals ,Humans ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,cytotoxic activity ,Sarcophyton stellatum ,biology ,Cyclooxygenase 2 Inhibitors ,Molecular Structure ,010405 organic chemistry ,Sarcophyton ,Macrophages ,biology.organism_classification ,Anthozoa ,0104 chemical sciences ,Nitric oxide synthase ,010404 medicinal & biomolecular chemistry ,chemistry ,lcsh:Biology (General) ,Cyclooxygenase 2 ,Cancer cell ,soft coral ,biology.protein ,Diterpenes ,Drug Screening Assays, Antitumor ,cembranoid - Abstract
Six new polyoxygenated cembrane-based diterpenoids, stellatumolides A&ndash, C (1&ndash, 3), stellatumonins A and B (4 and 5), and stellatumonone (6), were isolated together with ten known related compounds (7&ndash, 16) from the ethyl acetate (EtOAc) extract of soft coral Sarcophyton stellatum. The structures of the new compounds were established by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and data comparison with related structures. Compounds 8 and 14 were isolated from a natural source for the first time. The isolated metabolites were shown to be not cytotoxic against a limited panel of cancer cells. Compound 9 showed anti-inflammatory activity by reducing the expression of proinflammatory cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) proteins in lipopolysaccharide (LPS)-stimulated mouse leukaemic monocyte macrophage (RAW 264.7) cells.
- Published
- 2018
15. Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae
- Author
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Chiung-Yao Huang, Wan-Ru Tseng, Chi-Jen Tai, Jyh-Horng Sheu, Atallah F. Ahmed, Pei-Lun Chiang, Tsong-Long Hwang, and Chang-Feng Dai
- Subjects
food.ingredient ,Magnetic Resonance Spectroscopy ,medicine.drug_class ,Cytochalasin B ,Neutrophils ,Ethyl acetate ,Anti-Inflammatory Agents ,Pharmaceutical Science ,01 natural sciences ,Lobophytum ,Anti-inflammatory ,Article ,chemistry.chemical_compound ,food ,Superoxides ,Cell Line, Tumor ,Drug Discovery ,medicine ,Animals ,Humans ,Cytotoxicity ,anti-inflammatory activity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Cell Proliferation ,Pancreatic Elastase ,010405 organic chemistry ,Superoxide ,Cytotoxins ,Elastase ,Anthozoa ,0104 chemical sciences ,N-Formylmethionine Leucyl-Phenylalanine ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,Biochemistry ,chemistry ,A549 Cells ,Cancer cell ,soft coral ,cytotoxicity ,Steroids ,Lobophytum michaelae - Abstract
Three new polyoxygenated steroids, michosterols A–C (1–3), and four known compounds (4–7) were isolated from the ethyl acetate (EtOAc) extract of the soft coral Lobophytum michaelae, collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds 1–3 against the proliferation of a limited panel of cancer cell lines was assayed. Compound 1 was found to display moderate cytotoxicity against adenocarcinomic human alveolar basal epithelial (A549) cancer cells. It also exhibited potent anti-inflammatory activity by suppressing superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-stimulated human neutrophils. Furthermore, 3 could effectively inhibit elastase release, as well.
- Published
- 2018
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16. Lobohedleolide suppresses hepatitis C virus replication via JNK/c-Jun-C/EBP-mediated down-regulation of cyclooxygenase-2 expression
- Author
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Chih-Ku Wei, Chiung-Yao Huang, Chun-Kuang Lin, Chih-Chuang Liaw, Jyh-Horng Sheu, Chin-Kai Tseng, and Jin-Ching Lee
- Subjects
0301 basic medicine ,MAP Kinase Kinase 4 ,Hepatitis C virus ,lcsh:Medicine ,Down-Regulation ,Drug resistance ,Hepacivirus ,medicine.disease_cause ,Virus Replication ,Antiviral Agents ,Cell Line ,03 medical and health sciences ,Bridged Bicyclo Compounds ,Downregulation and upregulation ,medicine ,Animals ,Humans ,Replicon ,lcsh:Science ,Protein kinase A ,Furans ,Transcription factor ,Multidisciplinary ,business.industry ,lcsh:R ,JNK Mitogen-Activated Protein Kinases ,medicine.disease ,Anthozoa ,Virology ,Hepatitis C ,030104 developmental biology ,Cell culture ,Cyclooxygenase 2 ,Hepatocellular carcinoma ,CCAAT-Enhancer-Binding Proteins ,lcsh:Q ,business ,Signal Transduction - Abstract
Hepatitis C virus (HCV) chronically infects 2–3% people of the global population, which leads to liver cirrhosis and hepatocellular carcinoma. Drug resistance remains a serious problem that limits the effectiveness of US Food and Drug Administration (FDA)-approved direct-acting antiviral (DAA) drugs against HCV proteins. The objective of our study was to discover new antivirals from natural products to supplement current therapeutics. We demonstrated that lobohedleolide, isolated from the Formosan soft coral Lobophytum crassum, significantly reduced HCV replication in replicon cells and JFH-1 infection system, with EC50 values of 10 ± 0.56 and 22 ± 0.75 μM, respectively, at non-toxic concentrations. We further observed that the inhibitory effect of lobohedleolide on HCV replication is due to suppression of HCV-induced cyclooxygenase-2 (COX-2) expression. Based on deletion-mutant analysis of the COX-2 promoter, we identified CCAAT/enhancer-binding protein (C/EBP) as a key transcription factor for the down-regulation of COX-2 by lobohedleolide, through which lobohedleolide decreased the phosphorylation of c-Jun NH2-terminal protein kinase and c-Jun to suppress HCV-induced C/EBP expression. The combination treatment of lobohedleolide with clinically used HCV drugs synergistically reduced HCV RNA replication, indicating that lobohedleolide exhibited a high biomedical potential to be used as a supplementary therapeutic agent to control HCV infection.
- Published
- 2018
17. New anti-inflammatory tocopherol-derived metabolites from the Taiwanese soft coral Cladiella hirsuta
- Author
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Chokkalingam Uvarani, Chang-Feng Dai, Chiung-Yao Huang, Tsong-Long Hwang, Jyh-Horng Sheu, and Bo-Wei Chen
- Subjects
food.ingredient ,Neutrophils ,medicine.drug_class ,Stereochemistry ,Coral ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Taiwan ,Tocopherols ,Pharmaceutical Science ,Biochemistry ,Anti-inflammatory ,chemistry.chemical_compound ,food ,Superoxides ,Drug Discovery ,medicine ,Animals ,Humans ,Cladiella ,Tocopherol ,Molecular Biology ,Chemistry ,Superoxide ,Organic Chemistry ,Elastase ,Anthozoa ,In vitro ,Molecular Medicine - Abstract
Two new tocopherol-derived metabolites, hirsutocospiro A (1) and hirsutocoquinone A (2), were isolated from the soft coral Cladiella hirsuta. The structures of 1 and 2 were determined by extensive spectroscopic analysis. The in vitro anti-inflammatory activity of compounds 1 and 2 was evaluated by measuring their ability in suppressing superoxide anion generation and elastase release in fMLP/CB-induced human neutrophils. Compound 1 was shown to exhibit significant anti-inflammatory activity.
- Published
- 2015
18. Bioactive Steroids with Methyl Ester Group in the Side Chain from a Reef Soft Coral Sinularia brassica Cultured in a Tank
- Author
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Chih-Chuang Liaw, Tsong-Long Hwang, Chiung-Yao Huang, Jyh-Horng Sheu, Pei-Lun Chiang, Ping-Jyun Sung, Jui-Hsin Su, and Chang-Feng Dai
- Subjects
Neutrophils ,medicine.medical_treatment ,Ethyl acetate ,Pharmaceutical Science ,soft coral ,Sinularia brassica ,steroid ,cytotoxic activity ,anti-inflammatory activity ,Phenylalanine ,Biology ,Acetates ,01 natural sciences ,Article ,Steroid ,chemistry.chemical_compound ,Superoxides ,Drug Discovery ,Side chain ,medicine ,Animals ,Humans ,Cytotoxicity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Cytochalasin B ,Xylose ,Pancreatic Elastase ,010405 organic chemistry ,Superoxide ,Elastase ,Anti-Inflammatory Agents, Non-Steroidal ,Anthozoa ,0104 chemical sciences ,N-Formylmethionine Leucyl-Phenylalanine ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,chemistry ,Biochemistry ,Steroids - Abstract
A continuing chemical investigation of the ethyl acetate (EtOAc) extract of a reef soft coral Sinularia brassica, which was cultured in a tank, afforded four new steroids with methyl ester groups, sinubrasones A–D (1–4) for the first time. In particular, 1 possesses a β-D-xylopyranose. The structures of the new compounds were elucidated on the basis of spectroscopic analyses. The cytotoxicities of compounds 1–4 against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of these new compounds 1–4 were also evaluated by measuring their ability to suppress superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils. Compounds 2 and 3 were shown to exhibit significant cytotoxicity, and compounds 3 and 4 were also found to display attracting anti-inflammatory activities.
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- 2017
19. Isoprenoids from the Soft Coral Sarcophyton glaucum
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Chih-Hua Chao, Chih-Chuang Liaw, Mei-Chin Lu, Wen Liang Li, Chiung Yao Huang, Chang-Feng Dai, Jyh-Horng Sheu, Atallah F. Ahmed, and Yang Chang Wu
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Circular dichroism ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Coral ,Pharmaceutical Science ,Antineoplastic Agents ,Biology ,01 natural sciences ,Article ,ent-sarcophyolide E ,Sarcophyton glaucum ,Cell Line, Tumor ,Drug Discovery ,Botany ,Animals ,Humans ,lobocrasol ,sarcophine ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Terpenes ,010405 organic chemistry ,Circular Dichroism ,sarcophyton glaucum ,Sarcophine ,Anthozoa ,biology.organism_classification ,Terpenoid ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Lobocrasol ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Five new isoprenoids, 3,4,8,16-tetra-epi-lobocrasol (1), 1,15β-epoxy-deoxysarcophine (2), 3,4-dihydro-4α,7β,8α-trihydroxy-Δ2-sarcophine (3), ent-sarcophyolide E (4), and 16-deacetyl- halicrasterol B (5) and ten known compounds 6‒15, were characterized from the marine soft coral Sarcophyton glaucum, collected off Taitung coastline. Their structures were defined by analyzing spectra data, especially 2D NMR and electronic circular dichroism (ECD). The structure of the known compound lobocrasol (7) was revised. Cytotoxicity potential of the isolated compounds was reported, too.
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- 2017
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20. Klyflaccicembranols A–I, New Cembranoids from the Soft Coral Klyxum flaccidum
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Chia-Ruei Tsai, Chiung-Yao Huang, Jyh-Horng Sheu, Atallah F. Ahmed, and Sheng-Yang Wang
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Lipopolysaccharides ,Magnetic Resonance Spectroscopy ,Stereochemistry ,soft coral ,Klyxum flaccidum ,cembranoid ,NO inhibition ,cytotoxicity ,Coral ,Pharmaceutical Science ,Biology ,Nitric Oxide ,01 natural sciences ,Article ,Nitric oxide ,chemistry.chemical_compound ,Mice ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,No production ,Cytotoxicity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,IC50 ,Biological Products ,010405 organic chemistry ,Macrophages ,Anthozoa ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Coal ,lcsh:Biology (General) ,chemistry ,A549 Cells ,Cancer cell lines ,Drug Screening Assays, Antitumor ,K562 Cells ,Two-dimensional nuclear magnetic resonance spectroscopy ,HT29 Cells - Abstract
New cembranoids klyflaccicembranols A–I (1–9), along with gibberosene D (10), have been isolated from the organic extract of a Formosan soft coral Klyxum flaccidum. Their structures were established by extensive spectroscopic analyses, including 2D NMR spectroscopy, and spectral data comparison with related structures. The cytotoxicity of the isolated metabolites, as well as their nitric oxide (NO) inhibitory activity, were evaluated and reported. Metabolites 2, 4, 6, 8 and 9 were found to exhibit variable activities against a limited panel of cancer cell lines in a range of IC50 16.5–49.4 μM. Among the tested cembranoids, compounds 4, 5, 6, and 9 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages at a dose of 50 μg/mL.
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- 2017
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21. Cytotoxic and Anti-Inflammatory Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi
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Ming-Shyan Huang, Wen Zhi-Hong, Chiung-Yao Huang, Chi-Jen Tai, Jyh-Horng Sheu, Jui-Hsin Su, and Chang-Feng Dai
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Lipopolysaccharides ,Stereochemistry ,medicine.drug_class ,Coral ,Anti-Inflammatory Agents ,Taiwan ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Antineoplastic Agents ,Biology ,Cladiella krempfi ,Article ,eunicellin-based diterpenoids ,Anti-inflammatory ,Mice ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,medicine ,Animals ,Humans ,Cytotoxic T cell ,Cytotoxicity ,Inos protein ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Inflammation ,Eunicellin ,Macrophages ,Spectrum Analysis ,Anthozoa ,cytotoxicity ,anti-inflammatory agents ,lcsh:Biology (General) ,Biochemistry ,Cyclooxygenase 2 ,Diterpenes ,Cancer cell lines - Abstract
Five new eunicellin-based diterpenoids, krempfielins E–I (1–5) and seven known compounds (6–12) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. Metabolites 5, 6, 10 and 12 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines. Furthermore, compounds 6 and 10 could potently inhibit the accumulation of the pro-inflammatory iNOS protein, and 6 and 12 could significantly reduce the expression of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.
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- 2013
22. Klyflaccisteroids K-M, bioactive steroidal derivatives from a soft coral Klyxum flaccidum
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Ping-Jyun Sung, Chiung-Yao Huang, Pei-Lun Chiang, Tsong-Long Hwang, Wan-Ru Tseng, Jyh-Horng Sheu, Yi-Ying Tsai, Jui-Hsin Su, and Chang-Feng Dai
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Stereochemistry ,Cell Survival ,Neutrophils ,Coral ,medicine.medical_treatment ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,01 natural sciences ,Biochemistry ,Steroid ,chemistry.chemical_compound ,Inhibitory Concentration 50 ,Superoxides ,Cell Line, Tumor ,Drug Discovery ,medicine ,Animals ,Humans ,Cytotoxicity ,Molecular Biology ,010405 organic chemistry ,Superoxide ,Organic Chemistry ,Elastase ,Anthozoa ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Cancer cell ,Molecular Medicine ,Steroids ,Klyxum flaccidum - Abstract
New steroids, klyflaccisteroids K-M (1-3), were isolated from a soft coral Klyxum flaccidum. Their structures were elucidated on the basis of extensive spectroscopic analysis. Klyflaccisteroid K (1) is the unique 9,11-secosteroid with a 5,8-epidioxy-9-ene functional group. Klyflaccisteroid L (2) has an unusual 11-norsteroid skeleton and is the first example of 11-oxasteroid isolated from natural sources. Cytotoxicity assay showed that 1 and 3 possessed moderate to weak cytotoxicity against these cancer cells. Compound 1 was also found to display significant anti-inflammatory activity of suppressing superoxide anion generation (O2-) and elastase release, and compound 3 was found to show notable anti-inflammatory activity toward inhibition of elasstase release, too.
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- 2016
23. Bioactive Steroids from the Formosan Soft Coral Umbellulifera petasites
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Hui-Chun Wang, Ping-Jyun Sung, Jui-Hsin Su, Chang-Feng Dai, Jessica Lee, Yen-Ju Tseng, Che-Wei Chang, Chiung-Yao Huang, Tsong-Long Hwang, and Jyh-Horng Sheu
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Petasites ,Stereochemistry ,Coral ,medicine.medical_treatment ,Oceans and Seas ,Anti-Inflammatory Agents ,Taiwan ,Pharmaceutical Science ,Antineoplastic Agents ,soft coral ,Umbellulifera petasites ,steroid ,cytotoxic activity ,anti-inflammatory activity ,01 natural sciences ,Article ,Steroid ,Nitric oxide ,chemistry.chemical_compound ,Structure-Activity Relationship ,Cell Line, Tumor ,Drug Discovery ,medicine ,Animals ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,biology ,010405 organic chemistry ,Superoxide ,Elastase ,biology.organism_classification ,Anthozoa ,0104 chemical sciences ,Umbellulifera ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,chemistry ,Biochemistry ,Steroids ,Cancer cell lines - Abstract
Three new steroids, petasitosterones A and B (1 and 2) and a spirosteroid petasitosterone C (3), along with eight known steroids (4–11), were isolated from a Formosan marine soft coral Umbellulifera petasites. The structures of these compounds were elucidated by extensive spectroscopic analysis and comparison of spectroscopic data with those reported. Compound 3 is a marine steroid with a rarely found A/B spiro[4,5]decane ring system. Compounds 1–3 and 5 displayed inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 2 and 5 exhibited significant anti-inflammatory activity to inhibit nitric oxide (NO) production. The inhibitory activities for superoxide anion generation and elastase release of compounds 1–11 were also examined to evaluate the anti-inflammatory potential, and 2–4 were shown to exhibit significant activities.
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- 2016
24. Bioactive Isoprenoid-Derived Natural Products from a Dongsha Atoll Soft Coral Sinularia erecta
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Yen-Ju Tseng, Uvarani Chokkalingam, Tsong-Long Hwang, Chang-Feng Dai, Chiung-Yao Huang, Jyh-Horng Sheu, Chi-Hsin Hsu, and Ping-Jyun Sung
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Stereochemistry ,Coral ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Atoll ,Marine Biology ,01 natural sciences ,Analytical Chemistry ,Terpene ,Sinularia erecta ,Anthozoa ,Drug Discovery ,Botany ,Animals ,Humans ,Nuclear Magnetic Resonance, Biomolecular ,Pharmacology ,geography ,Biological Products ,geography.geographical_feature_category ,biology ,Molecular Structure ,010405 organic chemistry ,Terpenes ,Macrophages ,Organic Chemistry ,biology.organism_classification ,Terpenoid ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Cyclooxygenase 2 ,Molecular Medicine ,Cancer cell lines ,Diterpenes ,Drug Screening Assays, Antitumor - Abstract
Four new isoprenoids, including two norcembranoids sinulerectols A and B (1 and 2), a cembranoid sinulerectol C (3), and a degraded cembranoid sinulerectadione (4), along with three known isoprenoids, an unnamed norcembrene (5), sinularectin (6), and ineleganolide (7), and a known nitrogen-containing compound (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (8), were isolated from an extract of the marine soft coral Sinularia erecta. The structure of sinularectin (6) was revised, too. Compounds 3, 4, and 8 exhibited inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 1, 2, and 8 displayed potent anti-inflammatory activity in fMLP/CB-stimulated human neutrophils.
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- 2016
25. A new 9,11-secosterol from the soft coral Sinularia granosa
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Chang-Yih Duh, Yao-Haur Kuo, Bo‐Wei Chen, Jui-Hsin Su, Jyh-Horng Sheu, Chiung-Yao Huang, and Zhi-Hong Wen
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Magnetic Resonance Spectroscopy ,medicine.medical_treatment ,Coral ,Metabolite ,Clinical Biochemistry ,Molecular Conformation ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Antineoplastic Agents ,Apoptosis ,Biochemistry ,Steroid ,Mice ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,Botany ,medicine ,Animals ,Humans ,Secosteroids ,Cytotoxic T cell ,Sinularia ,Cytotoxicity ,Molecular Biology ,biology ,Chemistry ,Organic Chemistry ,Anthozoa ,biology.organism_classification ,Nmr data ,Nitric oxide synthase ,Cyclooxygenase 2 ,biology.protein ,Molecular Medicine ,Steroids ,Drug Screening Assays, Antitumor ,HeLa Cells - Abstract
Chemical investigations on the EtOAc-soluble fractions from the EtOH extract of Formosa soft coral afforded a new 9,11-secosteroid, 8αH-3β,11-dihydroxy-5α,6α-expoxy-24-methylene-9,11-secocholestan-9-one (1), along with one known steroid 3β,11-dihydroxy-5β,6β-expoxy-24-methylene-9,11-secocholestan-9-one (2) from Sinularia granosa. The structure of the new metabolite was elucidated on the basis of extensive spectroscopic analysis and by comparison of their NMR data with the known compounds, including 2. Both 1 and 2 were shown to significantly inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase protein, and 1 also was found to effectively reduce the level of cyclooxygenase-2 protein, in lipopolysaccharide-stimulated RAW264.7 macrophage cells at 10 μM. Furthermore, cytotoxic activity of 1 and 2 toward a limited panel of cancer cell lines was also discovered.
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- 2012
26. Bioactive cadinane-type compounds from the soft coral Sinularia scabra
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Yi Lu, Yao-Haur Kao, Zhi-Hong Wen, Jui-Hsin Su, Po-Ju Li, Chiung-Yao Huang, and Jyh-Horng Sheu
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Metabolite ,Coral ,Pharmacology toxicology ,Cell Line ,Mice ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,Botany ,Animals ,Humans ,Cytotoxicity ,Incubation ,Polycyclic Sesquiterpenes ,biology ,Cytotoxins ,Macrophages ,Organic Chemistry ,Anthozoa ,Sinularia scabra ,Nitric oxide synthase ,chemistry ,Biochemistry ,biology.protein ,Molecular Medicine ,Cancer cell lines ,Sesquiterpenes - Abstract
Two new cadinane-type sesquiterpenoids, scabralins A (1) and B (2) were obtained from the soft coral Sinularia scabra. Metabolite 1 was shown to exhibit moderate to weak cytotoxicity against MCF-7, WiDr, Daoy, and HEp 2 cancer cell lines. Also, incubation with 10 µM compound 1 significantly inhibited the accumulation of the pro-inflammatory inducible nitric oxide synthase protein in lipopolysaccharide-stimulated RAW264.7 macrophage cells.
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- 2012
27. Sarcocrassocolides M–O, Bioactive Cembranoids from the Dongsha Atoll Soft Coral Sarcophyton crassocaule
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Jui-Hsin Su, Chang-Feng Dai, Wan-Yu Lin, Chiung-Yao Huang, Yi Lu, Zhi-Hong Wen, Jyh-Horng Sheu, Yao-Haur Kuo, and Bo‐Wei Chen
- Subjects
Models, Molecular ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Coral ,Sarcophyton crassocaule ,Molecular Conformation ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Atoll ,Article ,Cell Line, Tumor ,Anthozoa ,Drug Discovery ,Animals ,Humans ,Inos protein ,Cytotoxicity ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,cytotoxic activity ,geography ,geography.geographical_feature_category ,Cyclooxygenase 2 Inhibitors ,biology ,Macrophages ,Anti-Inflammatory Agents, Non-Steroidal ,soft coral ,biology.organism_classification ,Up-Regulation ,lcsh:Biology (General) ,Diterpenes ,Drug Screening Assays, Antitumor ,Cancer cell lines - Abstract
Three new cembranoids, sarcocrassocolides M–O (1–3), have been isolated from the soft coral Sarcophyton crassocaule. The structures of the metabolites were determined by extensive spectroscopic analysis. Compounds 1–3 were shown to exhibit moderate cytotoxicity toward a limited panel of cancer cell lines and display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein.
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- 2012
28. Steroids from the Soft Coral Sinularia crassa
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Chih-Hua Chao, Kuei Ju Chou, Chi Hsin Hsu, Chiung Yao Huang, Zhi-Hong Wen, Jyh-Horng Sheu, Chang-Feng Dai, and Yang Chang Wu
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Stereochemistry ,Coral ,Anti-Inflammatory Agents ,Taiwan ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Antineoplastic Agents ,Stereoisomerism ,Biology ,Article ,o-tolylthiocarbamate ,Inhibitory Concentration 50 ,Mice ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,Animals ,Humans ,Glycosides ,anti-inflammatory activity ,Sugar ,Cytotoxicity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Cell Line, Transformed ,chemistry.chemical_classification ,Pacific Ocean ,Molecular Structure ,Macrophages ,Absolute configuration ,Glycoside ,Sinularia crassa ,Anthozoa ,Sterol ,Sterols ,crassarosterosides A–D ,crassarosterol A ,lcsh:Biology (General) ,chemistry ,Biochemistry ,Cyclooxygenase 2 ,Acid hydrolysis - Abstract
One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A–D (2–5) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher’s method. The absolute configurations for the sugar moieties of 2–5 were determined by HPLC analysis on the o-tolylthiocarbamates derived from the liberated sugar after acid hydrolysis. Compounds 2 and 4 could significantly inhibit the expression of pro-inflammatory iNOS protein at 10 µM. In contrast, 1–3 were found to stimulate the expression of COX-2 protein at this concentration. Steroids 1 and 4 also showed cytotoxicity toward the selected human liver cancer cells.
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- 2012
29. Glaucumolides A and B, Biscembranoids with New Structural Type from a Cultured Soft Coral Sarcophyton glaucum
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Jui-Hsin Su, Chang-Feng Dai, Shwu-Li Wu, Ping-Jyun Sung, Chokkalingam Uvarani, Tsong-Long Hwang, Mei-Chin Lu, Chiung-Yao Huang, and Jyh-Horng Sheu
- Subjects
Lipopolysaccharides ,Cytochalasin B ,Neutrophils ,Coral ,Anti-Inflammatory Agents ,Nitric Oxide Synthase Type II ,Antineoplastic Agents ,HL-60 Cells ,Inflammation ,Precursor T-Cell Lymphoblastic Leukemia-Lymphoma ,Article ,Lactones ,Mice ,chemistry.chemical_compound ,Leukemia, Promyelocytic, Acute ,Superoxides ,Cell Line, Tumor ,Botany ,medicine ,Animals ,Humans ,Macrophage ,Cytotoxicity ,Multidisciplinary ,biology ,Superoxide ,Macrophages ,Elastase ,Anthozoa ,Nitric oxide synthase ,Biochemistry ,chemistry ,Cyclooxygenase 2 ,biology.protein ,Diterpenes ,Drug Screening Assays, Antitumor ,medicine.symptom - Abstract
Glaucumolides A (1) and B (2), novel biscembranes composed of an unprecedented α,β-unsaturated ε-lactone, along with the known metabolites ximaolide A (3) and isosarcophytonolide D (4), were isolated from the cultured soft coral Sarcophyton glaucum. The structures of the new metabolites were determined by extensive spectroscopic analyses. Compounds 1 and 2 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines. In anti-inflammation assay, compounds 1 and 2 displayed strong inhibition of superoxide anion generation and elastase release in human neutrophils stimulated by fMLP/CB. Furthermore, both 1 and 2 were shown to significantly inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase protein and compounds 1−3 were found to effectively reduce the expression of cyclooxygenase-2 protein, in lipopolysaccharide-stimulated RAW264.7 macrophage cells.
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- 2015
30. Bioactive Cembranoids from the Soft Coral Sinularia crassa
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Kuei Ju Chou, Chang-Feng Dai, Chih-Hua Chao, Yang Chang Wu, Jyh-Horng Sheu, Chiung Yao Huang, Zhi-Hong Wen, and Chi Hsin Hsu
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,Coral ,Anti-Inflammatory Agents ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Biology ,Article ,Human liver cancer ,Sinularia crassa ,Cell Line, Tumor ,Drug Discovery ,crassarines A–H ,Animals ,Humans ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,anti-inflammatory ,Cyclooxygenase 2 Inhibitors ,Cytotoxins ,Absolute configuration ,Anthozoa ,lcsh:Biology (General) ,crassarines A-H ,Diterpenes - Abstract
Eight new cembranoids, crassarines A–H (1–8) were isolated from the Formosan soft coral Sinularia crassa. Compounds 1–3 represent the rare cembranoids with a 1,12-oxa-bridged tetrahydrofuran ring, while 4 and 5 are the firstly discovered 1,11-oxa-bridged tetrahydropyranocembranoids. The absolute configuration of 6 was determined using the Mosher’s method. Compounds 6 and 8 were found to significantly inhibit the expression of both pro-inflammatory iNOS and COX-2 proteins at 10 µM, respectively, while compounds 4–8 were found to be non-cytotoxic toward the selected human liver cancer cells.
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- 2011
31. Nardosinane-Type Sesquiterpenoids from the Formosan Soft Coral Paralemnalia thyrsoides
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Jui-Hsin Su, Zhi-Hong Wen, Chi-Hsin Hsu, Chang-Feng Dai, Bo‐Wei Chen, Ping-Jyun Sung, Chiung-Yao Huang, and Jyh-Horng Sheu
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Magnetic Resonance Spectroscopy ,Stereochemistry ,Coral ,Paralemnalia thyrsoides ,Pharmaceutical Science ,soft coral ,nardosinane ,neuroprotective activity ,Biology ,Article ,Mice ,Cell Line, Tumor ,Anthozoa ,Drug Discovery ,Animals ,Humans ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Absolute configuration ,biology.organism_classification ,Neuroprotective Agents ,lcsh:Biology (General) ,Sesquiterpenes - Abstract
Five new nardosinane-type sesquiterpenoids, paralemnolins Q–U (1–5), along with three known compounds (6–8), were isolated from the Formosan soft coral Paralemnalia thyrsoides. The structures of new metabolites were elucidated on the basis of extensive spectroscopic methods, and the absolute configuration of 1 was determined by the application of Mosher’s method on 1. Among these metabolites, 1 and 3 are rarely found nardosinane-type sesquiterpenoids, possessing novel polycyclic structures. Compounds 1, 3, 6 and 7 were found to possess neuroprotective activity.
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- 2011
32. Anti-inflammatory Cembranoids from the Soft Corals Sinularia querciformis and Sinularia granosa
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Chiung-Yao Huang, Yao-Haur Kuo, Yi Lu, Jyh-Horng Sheu, Yu-Fang Lin, Zhi-Hong Wen, Michael Y. Chiang, and Jui-Hsin Su
- Subjects
Lipopolysaccharides ,Stereochemistry ,Taiwan ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Biology ,Pharmacognosy ,Analytical Chemistry ,Mice ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Moiety ,Sinularia ,Pharmacology ,chemistry.chemical_classification ,Cyclooxygenase 2 Inhibitors ,Molecular Structure ,Macrophages ,Anti-Inflammatory Agents, Non-Steroidal ,Organic Chemistry ,Absolute configuration ,Tetrahydropyran ,Anthozoa ,biology.organism_classification ,Terpenoid ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Diterpenes ,Drug Screening Assays, Antitumor ,Diterpene ,Lactone - Abstract
Four new cembranoids, querciformolides A-D (1-4), along with two known cembranoids, 7 and 8, have been isolated from the soft coral Sinularia querciformis. Furthermore, chemical investigation of Sinularia granosa has afforded three new cembranoids, querciformolide B (2) and granosolides A (5) and B (6). The structures of the new metabolites were elucidated on the basis of extensive spectroscopic methods, and that of 2 was further confirmed by X-ray diffraction analysis. The absolute configurations of 1 and 2 were determined by a modified Mosher's method. Among these metabolites, 2-6 are rarely found cembranoids possessing a tetrahydrofuran moiety with a 4,7-ether linkage; in addition, 1 is the first epsilon-lactone cembrane found that possesses a tetrahydropyran moiety with a 4,8-ether linkage. None of these compounds were found to be cytotoxic toward a limited panel of cancer cell lines. However, compounds 3, 7, and 8 significantly inhibited the accumulation of the pro-inflammatory iNOS and COX-2 proteins in LPS-stimulated RAW264.7 macrophage cells.
- Published
- 2008
33. Anti-Inflammatory Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium
- Author
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Atallah F. Ahmed, Wan-Ting Teng, Chiung-Yao Huang, Jyh-Horng Sheu, Tsong-Long Hwang, and Chang-Feng Dai
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prenyleudesmane ,food.ingredient ,Cytochalasin B ,Neutrophils ,medicine.drug_class ,Stereochemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,01 natural sciences ,Lobophytum ,Article ,Anti-inflammatory ,Lobophytum varium ,chemistry.chemical_compound ,food ,Superoxides ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,medicine ,Animals ,Humans ,anti-inflammatory activity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,IC50 ,soft coral ,lobane ,Pancreatic Elastase ,010405 organic chemistry ,Superoxide ,Elastase ,Absolute configuration ,Anthozoa ,Terpenoid ,0104 chemical sciences ,N-Formylmethionine Leucyl-Phenylalanine ,010404 medicinal & biomolecular chemistry ,lcsh:Biology (General) ,chemistry ,Biochemistry ,Diterpenes - Abstract
New lobane-based diterpenoids lobovarols A–D (1–4) and a prenyleudesmane-type diterpenoid lobovarol E (5) along with seven known related diterpenoids (6–12) were isolated from the ethyl acetate extract of a Taiwanese soft coral Lobophytum varium. Their structures were identified on the basis of multiple spectroscopic analyses and spectral comparison. The absolute configuration at C-16 of the known compound 11 is reported herein for the first time. The anti-inflammatory activities of compounds 1–12 were assessed by measuring their inhibitory effect on N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils. Metabolites 2, 5, and 11 were found to show moderate inhibitory activity on the generation of superoxide anion, while compounds 5, 8, 11, and 12 could effectively suppress elastase release in fMLP/CB-stimulated human neutrophil cells at 10 μM. All of the isolated diterpenoids did not exhibit cytotoxic activity (IC50 > 50 μM) towards a limited panel of cancer cell lines.
- Published
- 2017
34. Eunicellin-Based Diterpenoids, Hirsutalins N–R, from the Formosan Soft Coral Cladiella hirsuta
- Author
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Chang-Feng Dai, Chiung-Yao Huang, Jyh-Horng Sheu, Bo-Wei Chen, Tsong-Long Hwang, and Tzu-Zin Huang
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Models, Molecular ,food.ingredient ,Stereochemistry ,Coral ,Molecular Conformation ,Taiwan ,Pharmaceutical Science ,Antineoplastic Agents ,Article ,chemistry.chemical_compound ,food ,Anthozoa ,Cell Line, Tumor ,Drug Discovery ,Cladiella ,Animals ,Humans ,anti-inflammatory activity ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Eunicellin ,biology ,Superoxide ,Elastase ,Anti-Inflammatory Agents, Non-Steroidal ,biology.organism_classification ,In vitro ,lcsh:Biology (General) ,chemistry ,Neutrophil Infiltration ,Cladiella hirsuta ,soft coral ,eunicellins: cytotoxic activity ,Cancer cell lines ,Diterpenes - Abstract
New eunicellin-type hirsutalins N–R (1–5), along with two known eunicellins, (6 and 7) were isolated from the soft coral Cladiella hirsuta. The structures of the metabolites were determined by extensive spectroscopic analysis. Cytotoxic activity of compounds 1–7 against the proliferation of a limited panel of cancer cell lines was measured. The in vitro anti-inflammatory activity of compounds 1–7 was evaluated by measuring their ability in suppressing superoxide anion generation and elastase release in fMLP/CB-induced human neutrophils.
- Published
- 2014
- Full Text
- View/download PDF
35. Bioactive Cembranoids, Sarcocrassocolides P–R, from the Dongsha Atoll Soft Coral Sarcophyton crassocaule
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Chiung-Yao Huang, Ping-Jyun Sung, Jyh-Horng Sheu, Wan-Yu Lin, Zhi-Hong Wen, Bo-Wei Chen, Jui-Hsin Su, and Chang-Feng Dai
- Subjects
Lipopolysaccharides ,Lipopolysaccharide ,Stereochemistry ,Coral ,Sarcophyton crassocaule ,Anti-Inflammatory Agents ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,Atoll ,Antineoplastic Agents ,Article ,Cell Line ,Mice ,chemistry.chemical_compound ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,Animals ,Humans ,Macrophage ,Cytotoxicity ,anti-inflammatory activity ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,cytotoxic activity ,geography ,geography.geographical_feature_category ,biology ,Macrophages ,Anthozoa ,soft coral ,In vitro ,Nitric oxide synthase ,chemistry ,Biochemistry ,lcsh:Biology (General) ,Cyclooxygenase 2 ,Cell culture ,biology.protein ,Diterpenes - Abstract
New cembranoids, sarcocrassocolides P–R (1–3) and four known compounds (4–7) were isolated from the soft coral Sarcophyton crassocaule. The structures of the metabolites were determined by extensive spectroscopic analysis. Compounds 3–5 and 7 were shown to exhibit cytotoxicity toward a limited panel of cancer cell lines and all compounds 1–7 displayed potent in vitro anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells by inhibiting the expression of inducible nitric oxide synthase (iNOS) protein. Compound 7 also showed significant activity in reducing the accumulation of cyclooxygenase-2 (COX-2) protein in the same macrophage cells.
- Published
- 2014
- Full Text
- View/download PDF
36. Withanolide-based steroids from the cultured soft coral Sinularia brassica
- Author
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Chih-Chuang Liaw, Ping-Jyun Sung, Bo-Wei Chen, Jui-Hsin Su, Chang-Feng Dai, Michael Y. Chiang, Pei-Chin Chen, Chiung-Yao Huang, and Jyh-Horng Sheu
- Subjects
Stereochemistry ,Coral ,Molecular Conformation ,Pharmaceutical Science ,Antineoplastic Agents ,Crystallography, X-Ray ,Molecular conformation ,Analytical Chemistry ,chemistry.chemical_compound ,Anthozoa ,Drug Discovery ,Botany ,Animals ,Humans ,Nuclear Magnetic Resonance, Biomolecular ,Withanolides ,Pharmacology ,biology ,Sinularia brassica ,Molecular Structure ,Leukemia P388 ,Organic Chemistry ,Absolute configuration ,biology.organism_classification ,Complementary and alternative medicine ,Withanolide ,chemistry ,Molecular Medicine ,P388 leukemia ,Cancer cell lines ,Drug Screening Assays, Antitumor ,K562 Cells ,HT29 Cells - Abstract
Seven novel withanolides, sinubrasolides A-G (1-7), have been isolated from the cultured soft coral Sinularia brassica. The structures of the new metabolites were determined by extensive spectroscopic analyses, and the absolute configuration of 1 was established by X-ray crystallographic analysis. The cytotoxicities of compounds 1-7 against a limited panel of cancer cell lines also were determined.
- Published
- 2013
37. Eunicellin-based diterpenoids from the Formosan soft coral Klyxum molle with inhibitory activity on superoxide generation and elastase release by neutrophils
- Author
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Chiung-Yao Huang, Chang-Feng Dai, Ming-Chang Lin, Jyh-Horng Sheu, Tsong-Long Hwang, and Bo-Wei Chen
- Subjects
Stereochemistry ,Cytochalasin B ,Neutrophils ,Metabolite ,Taiwan ,Pharmaceutical Science ,Phenylalanine ,Ether ,Antineoplastic Agents ,Analytical Chemistry ,chemistry.chemical_compound ,Superoxides ,Drug Discovery ,Animals ,Humans ,Cytotoxicity ,Nuclear Magnetic Resonance, Biomolecular ,Pharmacology ,Molecular Structure ,Pancreatic Elastase ,Superoxide ,Organic Chemistry ,Elastase ,Anthozoa ,N-Formylmethionine Leucyl-Phenylalanine ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Diterpenes ,Drug Screening Assays, Antitumor ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Eleven new eunicellin-based diterpenoids possessing a cladiellane skeleton with a C-2, C-9 ether bridge, klymollins I-S (1-11), have been isolated from the EtOAc extract of the soft coral Klyxum molle from Taiwan waters. The structures of compounds 1-11 were elucidated by extensive spectroscopic analysis, including 2D NMR spectroscopy (COSY, HSQC, HMBC, and NOESY). Compound 5 exhibited cytotoxicity toward several cancer cell lines. Compound 5 is the first eunicellin-based metabolite bearing a phenyl group and displays significant inhibition of both superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils.
- Published
- 2013
38. A Soft Coral Natural Product, 11-Episinulariolide Acetate, Inhibits Gene Expression of Cyclooxygenase-2 and Interleukin-8 through Attenuation of Calcium Signaling
- Author
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Siou Jin Chiu, Che Mai Chang, Yao Ting Tsai, Eric Terry Wang, Jaw Yan Wang, Wei Chiao Chang, Chiung Yao Huang, Jyh-Horng Sheu, Wen Li Hsu, and Ming-Feng Hou
- Subjects
Pharmaceutical Science ,Biology ,Article ,marine compound ,Cell Line ,Analytical Chemistry ,lcsh:QD241-441 ,lcsh:Organic chemistry ,Drug Discovery ,Gene expression ,EGF ,COX-2 ,IL-8 ,calcium ,Animals ,Humans ,Calcium Signaling ,Epidermal growth factor receptor ,Interleukin 8 ,Physical and Theoretical Chemistry ,Transcription factor ,Biological Products ,Cyclooxygenase 2 Inhibitors ,Dose-Response Relationship, Drug ,Epidermal Growth Factor ,NFATC Transcription Factors ,Interleukin-8 ,Organic Chemistry ,NF-kappa B ,Interleukin ,Anthozoa ,Molecular biology ,Gene Expression Regulation ,Epidermoid carcinoma ,Cyclooxygenase 2 ,Chemistry (miscellaneous) ,Cancer cell ,biology.protein ,Molecular Medicine ,Cyclooxygenase ,Diterpenes ,Signal Transduction - Abstract
Epidermal growth factor receptor (EGFR) is overexpressed in many types of cancer cells. EGFR-mediated signaling involves inflammatory gene expression including cyclooxygenase (COX)-2 and interleukin (IL)-8, and is associated with cancer pathogenesis. In a search of phytochemicals with anti-inflammatory activity, the COX-2 and IL-8 inhibitory activities of some marine compounds were examined. After screening these compounds 11-episinulariolide acetate (1) from soft coral exhibited the most potent activity. Reverse-transcription PCR; western blotting; ELISA and luciferase assays were used to test the effect of compound 1 on EGF-stimulated expressions of COX-2 and IL-8 in A431 human epidermoid carcinoma cells. After exposure to 10 μM of compound 1, expression levels of COX-2 and IL-8 were reduced. In addition; intracellular Ca2+ increase and Ca2+-dependent transcription factor activation were blocked by compound 1. Thus, compound 1 can potentially serve as a lead compound for targeting Ca2+ signaling-dependent inflammatory diseases.
- Published
- 2013
- Full Text
- View/download PDF
39. 5-Episinuleptolide Decreases the Expression of the Extracellular Matrix in Early Biofilm Formation of Multi-Drug Resistant Acinetobacter baumannii
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Po-Liang Lu, Chiung-Yao Huang, Jyh-Horng Sheu, Lin Lin, Min-Yu Chan, Wei-Chun Hung, Yin-Shiou Lin, and Sung-Pin Tseng
- Subjects
Acinetobacter baumannii ,0301 basic medicine ,beta-Glucans ,030106 microbiology ,Pharmaceutical Science ,multi-drug resistant A. baumannii ,Levofloxacin ,Article ,biofilm ,Microbiology ,Extracellular matrix ,03 medical and health sciences ,Drug Resistance, Multiple, Bacterial ,Drug Discovery ,Gene expression ,medicine ,Animals ,Humans ,lcsh:QH301-705.5 ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Biological Products ,Cross Infection ,biology ,5-Episinuleptolide ,Biofilm ,Drug Synergism ,biochemical phenomena, metabolism, and nutrition ,5-episinuleptolide ,Anthozoa ,biology.organism_classification ,medicine.disease ,Anti-Bacterial Agents ,Extracellular Matrix ,lcsh:Biology (General) ,Genes, Bacterial ,Biofilms ,Bacteremia ,Microscopy, Electron, Scanning ,Equipment Contamination ,Diterpenes ,Bacteria ,Acinetobacter Infections ,medicine.drug - Abstract
Nosocomial infections and increasing multi-drug resistance caused by Acinetobacter baumannii have been recognized as emerging problems worldwide. Moreover, A. baumannii is able to colonize various abiotic materials and medical devices, making it difficult to eradicate and leading to ventilator-associated pneumonia, and bacteremia. Development of novel molecules that inhibit bacterial biofilm formation may be an alternative prophylactic option for the treatment of biofilm-associated A. baumannii infections. Marine environments, which are unlike their terrestrial counterparts, harbor an abundant biodiversity of marine organisms that produce novel bioactive natural products with pharmaceutical potential. In this study, we identified 5-episinuleptolide, which was isolated from Sinularia leptoclados, as an inhibitor of biofilm formation in ATCC 19606 and three multi-drug resistant A. baumannii strains. In addition, the anti-biofilm activities of 5-episinuleptolide were observed for Gram-negative bacteria but not for Gram-positive bacteria, indicating that the inhibition mechanism of 5-episinuleptolide is effective against only Gram-negative bacteria. The mechanism of biofilm inhibition was demonstrated to correlate to decreased gene expression from the pgaABCD locus, which encodes the extracellular polysaccharide poly-β-(1,6)-N-acetylglucosamine (PNAG). Scanning electron microscopy (SEM) indicated that extracellular matrix of the biofilm was dramatically decreased by treatment with 5-episinuleptolide. Our study showed potentially synergistic activity of combination therapy with 5-episinuleptolide and levofloxacin against biofilm formation and biofilm cells. These data indicate that inhibition of biofilm formation via 5-episinuleptolide may represent another prophylactic option for solving the persistent problem of biofilm-associated A. baumannii infections.
- Published
- 2016
40. Isobicyclogermacrene-type Sesquiterpenoids from the Soft Coral Sinularia lochmodes
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Yun-Sheng Lin, Jui-Hsin Su, Ching-Li Lo, Chiung-Yao Huang, and Jyh-Horng Sheu
- Subjects
Pharmacology ,biology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Sinularia lochmodes ,Coral ,Plant Science ,General Medicine ,biology.organism_classification ,01 natural sciences ,Nmr data ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Anthozoa ,Drug Discovery - Abstract
A new isobicyclogermacrene-type sesquiterpenoid, lochmolin H (1), along with one known sesquiterpenoid 2, were isolated from the soft coral Sinularia lochmodes. The structure and relative configuration of the new compound was assigned by a combination of one- and two-dimensional NMR spectroscopic analysis and comparison of the NMR data with those of known analogues.
- Published
- 2016
41. Lochmolins A-G, new sesquiterpenoids from the soft coral Sinularia lochmodes
- Author
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Hui-Li Lin, Yen-Ju Tseng, Kuo-Ping Shen, Chiung-Yao Huang, Chang-Feng Dai, and Jyh-Horng Sheu
- Subjects
Sinularia lochmodes ,Magnetic Resonance Spectroscopy ,biology ,Cyclooxygenase 2 Inhibitors ,soft coral ,sesquiterpenes ,aromadendrane ,germacrane ,Chemistry ,Coral ,Pharmaceutical Science ,biology.organism_classification ,Anthozoa ,Article ,Cell Line ,Biochemistry ,Drug Discovery ,Botany ,Animals ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) - Abstract
Seven new sesquiterpenoids, lochmolins A–G (1–7), were isolated from a Taiwanese soft coral Sinularia lochmodes. The structures of these metabolites were elucidated by extensive spectroscopic study. Compounds 1–4 were found to inhibit the accumulation of the LPS-induced pro-inflammatory COX-2 protein in RAW264.7 macrophage cells.
- Published
- 2012
42. Simplexins P-S, eunicellin-based diterpenes from the soft coral Klyxum simplex
- Author
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Shwu-Li Wu, Jui-Hsin Su, Chih-Chung Liaw, Ping-Jyun Sung, Chiung-Yao Huang, Chi-Jen Tai, and Jyh-Horng Sheu
- Subjects
Magnetic Resonance Spectroscopy ,Klyxum simplex ,Stereochemistry ,soft coral ,eunicellin-based diterpenes ,cytotoxicity ,Coral ,Pharmaceutical Science ,Biology ,Article ,Terpene ,Cell Line, Tumor ,Drug Discovery ,Botany ,Animals ,Humans ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,Eunicellin ,Terpenes ,Nuclear magnetic resonance spectroscopy ,Anthozoa ,Cancer cell lines ,Diterpenes ,K562 Cells ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Four new eunicellin-based diterpenes, simplexins P–S (1–4), and the known compound simplexin A (5), have been isolated from the soft coral Klyxum simplex. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis, particularly 1D and 2D NMR experiments. Compounds 1 and 3–5 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines, 3 being the most cytotoxic.
- Published
- 2012
43. Klymollins A-H, bioactive eunicellin-based diterpenoids from the formosan soft coral Klyxum molle
- Author
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Yang Chang Wu, Jui-Hsin Su, Chang-Feng Dai, Bo Wei Chen, Jyh-Horng Sheu, Chiung Yao Huang, Fang Jung Hsu, and Zhi-Hong Wen
- Subjects
Pharmacology ,Eunicellin ,Lipopolysaccharides ,Cyclooxygenase 2 Inhibitors ,Molecular Structure ,Stereochemistry ,Coral ,Macrophages ,Organic Chemistry ,Anti-Inflammatory Agents, Non-Steroidal ,Absolute configuration ,Pharmaceutical Science ,Nitric Oxide Synthase Type II ,Biology ,Anthozoa ,Analytical Chemistry ,Mice ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine ,Bioassay ,Animals ,Diterpenes ,Inos protein - Abstract
Eight new eunicellin-based diterpenoids, klymollins A–H (1–8), were isolated during the chemical investigation of the soft coral Klyxum molle from Taiwan waters. Their structures were elucidated by extensive spectroscopic analysis. The absolute configuration of 4 was determined by Mosher’s method. Bioassays of the new metabolites showed that compounds 3–8 displayed significant in vitro anti-inflammatory activity by inhibiting the expression of the iNOS protein, and compounds 3, 4, and 6–8 also could effectively reduce the accumulation of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.
- Published
- 2011
44. Crassocolides N-P, three cembranoids from the Formosan soft coral Sarcophyton crassocaule
- Author
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Chi-Hsin Hsu, Jyh-Horng Sheu, Ho-Cheng Huang, Jui-Hsin Su, Yao-Haur Kuo, Chiung-Yao Huang, and Guey-Horng Wang
- Subjects
Magnetic Resonance Spectroscopy ,Molecular Structure ,Stereochemistry ,Chemistry ,Cell Survival ,Coral ,Organic Chemistry ,Clinical Biochemistry ,Taiwan ,Pharmaceutical Science ,Antineoplastic Agents ,Anthozoa ,Biochemistry ,Inhibitory Concentration 50 ,Drug Discovery ,Sarcophyton crassocaule ,Molecular Medicine ,Animals ,Humans ,Cancer cell lines ,Diterpenes ,Molecular Biology ,HeLa Cells - Abstract
Three new cembranoids crassocolides N–P (1–3), was isolated from the organic extract of a Formosan soft coral Sarcophyton crassocaule. These structures were elucidated on the basis of spectroscopic analyses and by comparison with those previously reported in literature. The cytotoxicity of these compounds toward various cancer cell lines has also been determined.
- Published
- 2011
45. Sesquiterpenoids from the Formosan soft coral Lemnalia flava
- Author
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Yi Lu, Ping-Jyun Sung, Jui-Hsin Su, Chiung-Yao Huang, Jyh-Horng Sheu, Wen-Yu Hung, Yao-Haur Kuo, and Michael Y. Chiang
- Subjects
Magnetic Resonance Spectroscopy ,Chemistry ,Coral ,Absolute configuration ,Molecular Conformation ,General Chemistry ,General Medicine ,Anthozoa ,Cell Line, Tumor ,Drug Discovery ,Botany ,Animals ,Humans ,Drug Screening Assays, Antitumor ,Sesquiterpenes - Abstract
Four new nardosinane-type sesquiterpenoids, flavalins E—H (1—4) and two new nornardosinane-type norsesquiterpenoids, flavalins I (5) and J (6), along with five known compounds (7—11) have been isolated from a Formosan soft coral Lemnalia flava. The structures of these compounds were elucidated on the basis of their spectroscopic data. Moreover, the absolute configuration of 10 was further determined by Mosher's method.
- Published
- 2011
46. Klysimplexins I-T, eunicellin-based diterpenoids from the cultured soft coral Klyxum simplex
- Author
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Wei Hsien Wang, Chiung Yao Huang, Bo Wei Chen, Chung Wei Tsai, Yang Chang Wu, Jyh-Horng Sheu, Jui-Hsin Su, Ping-Jyun Sung, Chih-Hua Chao, and Zhi-Hong Wen
- Subjects
Eunicellin ,Models, Molecular ,Chemistry ,Stereochemistry ,Coral ,Macrophages ,Organic Chemistry ,Nitric Oxide Synthase Type II ,Anthozoa ,Biochemistry ,In vitro ,Cell Line ,Mice ,Cyclooxygenase 2 ,Animals ,Physical and Theoretical Chemistry ,Cancer cell lines ,Diterpenes ,Inos protein ,Cytotoxicity ,Two-dimensional nuclear magnetic resonance spectroscopy ,Klyxum simplex - Abstract
New eunicellin-base diterpenoids, klysimplexins I–T (1–12), were isolated from a cultured soft coral Klyxum simplex. Their structures were elucidated by spectroscopic methods, particularly in 1D and 2D NMR experiments. The absolute stereochemistry of 4 was determined by Mosher's method. Compounds 9 and 12 have been shown to exhibit cytotoxicity toward a limited panel of cancer cell lines. Compounds 2–6, 10 and 11 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein. Compounds 10 and 11 also could effectively reduce the level of COX-2 protein.
- Published
- 2010
47. Hirsutalins A-H, eunicellin-based diterpenoids from the soft coral Cladiella hirsuta
- Author
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Bo Wei Chen, Chih-Hua Chao, Zhi-Hong Wen, Yang Chang Wu, Jui-Hsin Su, Chang-Feng Dai, Chiung Yao Huang, Jyh-Horng Sheu, Shu Ming Chang, and Chi Hsin Hsu
- Subjects
Lipopolysaccharides ,food.ingredient ,Stereochemistry ,Pharmaceutical Science ,Nitric Oxide Synthase Type II ,Antineoplastic Agents ,Biology ,Pharmacognosy ,Analytical Chemistry ,chemistry.chemical_compound ,Mice ,food ,Drug Discovery ,Cladiella ,Animals ,Humans ,Cytotoxicity ,Nuclear Magnetic Resonance, Biomolecular ,Pharmacology ,Cyclooxygenase 2 Inhibitors ,Molecular Structure ,Macrophages ,Organic Chemistry ,Anti-Inflammatory Agents, Non-Steroidal ,Absolute configuration ,Biological activity ,Anthozoa ,Terpenoid ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Diterpene ,Diterpenes ,Drug Screening Assays, Antitumor ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Eight new eunicellin-base diterpenoids, hirsutalins A-H (1-8), were isolated from the soft coral Cladiella hirsuta. Their structures were elucidated by spectroscopic methods, particularly in 1D and 2D NMR experiments. The absolute configuration of 1 was determined by Mosher's method. Compounds 1, 5, and 6 have been shown to exhibit cytotoxicity toward several cancer cell lines. Compounds 2-4 and 8 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein, with compound 2 also effectively reducing the level of COX-2 protein.
- Published
- 2010
48. Cembranoids from the soft corals Sinularia granosa and Sinularia querciformis
- Author
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Jui‐Hsin Su, Yi Lu, Yung-Chun Liu, Zhi-Hong Wen, Chiung-Yao Huang, Jyh-Horng Sheu, Chi-Hsin Hsu, and Yao-Haur Kuo
- Subjects
Lipopolysaccharides ,biology ,Molecular Structure ,Chemistry ,Stereochemistry ,Cell Survival ,Macrophages ,Anti-Inflammatory Agents ,General Chemistry ,General Medicine ,biology.organism_classification ,Anthozoa ,Cell Line ,Cyclooxygenase 2 ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Sinularia querciformis ,Sinularia ,Diterpenes ,Nitric Oxide Synthase - Abstract
Two new cembranoids, namely granosolides C (1) and D (2), along with one known cembranoid 4, were isolated from the soft coral Sinularia granosa. Chemical investigation of Sinularia querciformis also afforded one new cembranoid, querciformolide E (3), along with four known cembranoids 4—7. The structures of these compounds were elucidated on the basis of their spectroscopic data. Both 4 and 5 were shown to significantly inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase protein in lipopolysaccharide-stimulated RAW264.7 macrophage cells.
- Published
- 2010
49. Hirsutosterols A–G, polyoxygenated steroids from a Formosan soft coral Cladiella hirsuta
- Author
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Yang Chang Wu, Shu Ming Chang, Jui‐Hsin Su, Chiung Yao Huang, Jyh-Horng Sheu, Zhi-Hong Wen, and Bo‐Wei Chen
- Subjects
Models, Molecular ,food.ingredient ,Molecular Structure ,Cell Survival ,Chemistry ,Stereochemistry ,Coral ,Organic Chemistry ,Anthozoa ,Hydroxylation ,Biochemistry ,Oxygen ,Mice ,Structure-Activity Relationship ,food ,Isomerism ,Cell Line, Tumor ,Animals ,Humans ,Cladiella ,Steroids ,Physical and Theoretical Chemistry ,Cancer cell lines ,Cytotoxicity ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Seven new polyoxygenated steroids, hirsutosterols A-G (1-7), were isolated from the Formosan soft coral Cladiella hirsuta. Their structures were elucidated by spectroscopic methods, particularly in 1D and 2D NMR experiments. The absolute configurations of 1 and 5 were determined by Mosher's method. Sterols 4-6 possess hydroxy groups at C-9 and C-11 and might be oxidatively cleaved to the corresponding 9,11-secosterols. Hirsutosterol A (1) was found to exhibit a stronger cytotoxicity against a limited panel of cancer cell lines.
- Published
- 2011
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