Search

Graphical abstract A new eudesmane lactone (1) and two new carabrane lactones (2 and 3) were isolated from the whole plant of Carpesium abrotanoides. Highlights • Three new sesquiterpene lactones were isolated from the whole plant of Carpesium abrotanoides. • Their structures were established by extensive spectroscopic methods and X-ray diffraction analyses. • Compound 2 showed cytotoxic activity against HL-60 cells. Abstract Three new sesquiterpene lactones, 5 α -hydroxy-4 α ,15-epoxy-11 α H-eudesman-12,8 β -olide (1), carabrol-4- O -palmitate (2) and carabrol-4- O -linoleate (3), along with five known ones, were isolated from the whole plant of Carpesium abrotanoides. The structures of new compounds were determined by extensive spectroscopic analysis, and compound 1 was also elucidated by X-ray single-crystal diffraction analysis. The cytotoxic activities of these new compounds against human leukemia cells HL-60 and human breast cancer cells MCF-7 were also evaluated by MTS method. [ABSTRACT FROM AUTHOR]

Two previous undescribed cyclic pentapeptide-type compounds ( 1 – 2 ), with two known ones ( 3 – 4 ), were first isolated and purified from Clerodendrum japonicum (Thunb.) Sweet. Their structures were elucidated by extensive spectroscopic data (1D and 2D NMR) analysis. The absolute configurations of the two compounds were assigned using a combination of Marfey’s method and HPLC-MS analysis. All four compounds showed weak cytotoxicity against four human cancer cells lines (T24, A549, HepG2, MGC-803), with IC 50 values ranging from 23.8 to 39.6 μM. [ABSTRACT FROM AUTHOR]

A series of planar chiral cyclopalladated ferrocene compounds were synthesized and characterized. The absolute configurations of three compounds were determined by single-crystal X-ray analysis. The binding of the compounds with Native Calf Thymus DNA (CT-DNA) was monitored using UV-visible absorption spectrophotometry, fluorescence spectroscopy and circular dichroism (CD) studies. The results indicate that these compounds can interact with DNA via intercalation mode. In addition, the HSA interactions of these compounds were investigated using UV-visible absorption spectrophotometry and fluorescence spectroscopy. The results of fluorescence spectroscopy show that the fluorescence quenching mechanism of HSA is a static process. The cytotoxic activities of the synthesized compounds and cisplatin exhibited different inhibition potencies on the viability of MCF-7, HCT-116, MDA-MB-231 and Hela cancer cell lines. Compound ( R p, S ) - 6 was 17-fold more potent than cisplatin in breast cancer cells. [ABSTRACT FROM AUTHOR]

Five novel compounds, including four neoclerodane diterpenoids, named ajugacumbins K N ( 1 – 4 ) along with a phytoecdysterone, named ajugacetalsterone E ( 5 ), were isolated from the whole herbs of Ajuga decumbens (Labiatae). Their structures were elucidated on the basis of detailed spectroscopic analysis including IR, HRESIMS, CD, 1D and 2D NMR spectroscopic experiments. Compounds 1 – 5 were evaluated for their cytotoxic activities and the effects on superoxide anion generation and elastase release in FMLP/CB-induced human neutrophils. [ABSTRACT FROM AUTHOR]

Samarones A–D ( 1 – 4 ), four new acylphloroglucinol derivatives bearing a C 17 alkyl side chain, along with five known analogues ( 5 – 9 ), were isolated from the leaves of Syzygium samarangense . Their structures were characterized on the basis of extensive spectroscopic methods including HR-ESI-MS/MS analysis. The cytotoxic activities of compounds 1 – 3 and 5 – 9 against HepG2 and MDA-MB-231 cells were also evaluated. [ABSTRACT FROM AUTHOR]

Three new dimeric kavalactones, designated as diyangonins A-C (1-3), along with two known analogs were isolated from the roots of Piper methysticum. Their structures were elucidated by means of extensive analysis of their 1D, 2D NMR, and mass spectroscopic data. All these dimers possess a skeleton featuring a cyclobutane ring connecting two kavalactone units in head-to-tail or head-to-head mode. Compounds 1-5 were evaluated for their cytotoxic activities against human tumor cell lines. [ABSTRACT FROM AUTHOR]

Four new cinnamoyl-phloroglucinols ( 1 – 4 ) were isolated from the leaves of Xanthostemon chrysanthus . Compounds 1 and 2 represent the first example of natural phloroglucinols with an oxazole unit. Their structures were elucidated on the basis of NMR spectroscopic data and single crystal X-ray diffraction. Compound 3 showed moderate cytotoxic activity against MDA-MB-231 and SGC-7901 cells with IC 50 values of 25.26 ± 0.35 μM and 31.2 ± 0.94 μM, respectively. [ABSTRACT FROM AUTHOR]

Six new cassaine diterpenoids ( 1 , 3–7 ), along with three known ones ( 2 , 8 – 9 ) were isolated from the seeds of Erythrophleum fordii . Their structures were elucidated by extensive spectroscopic methods and acid hydrolysis. Compound 2 was tested to be the most potent one and showed more sensitive activities on MCF-7 and A549 cancer cells with IC 50 values of 3.66 ± 1.20 and 2.87 ± 0.46 μM, respectively. Furthermore, compound 2 reduced the number of cell colonies significantly in a dose-dependent manner in the colony formation assay and triggered apoptosis of MCF-7 cell. [ABSTRACT FROM AUTHOR]

Five new guaiane-type sesquiterpene lactones, caroguaianolide A–E ( 1 – 5 ), along with nine known sesquiterpene lactones ( 6 – 14 ) were isolated from the whole plant of Carpesium abrotanoides L. Their structures were elucidated on the basis of spectroscopic date, HRESIMS analysis, and comparison of experimental and calculated ECD data. All isolated compounds ( 1 – 14 ) were tested in vitro for their cytotoxic activities against the MDA-MB-231, HGC-27 cancer cell lines, of which compounds 1 – 3 , 6 , 7 , 11 and 12 showed significant cytotoxic activities with IC 50 values ranging from 2.67 to 12.34 μM. [ABSTRACT FROM AUTHOR]

A new furostan type steroidal saponin, kingianoside Z (1), along with four known compounds (2-5), was isolated from the ethanolic extract of Polygonatum sibiricum Delar. ex Redoute. Their structures were determined by spectroscopical method and by comparison with previously reported spectroscopic data. Compounds 3-5 showed significant cytotoxicity against HepG2 cell lines with IC50 values of 14.2, 12.1 and 8.5 μM, respectively. [ABSTRACT FROM AUTHOR]

Molybdenum(VI) complexes of different nuclearity, mononuclear, [MoO 2 (L 1 or 2 )(MeOH)]·MeOH ( 1 ·MeOH and 2 ·MeOH), [MoO 2 (L 1 or 2 )(D)] [D = pyridine, ( 1a and 2a ), 3-methylpyridine, ( 1b and 2b ) and 4-methylpyridine, ( 1c and 2c )], binuclear [{MoO 2 (L 1 or 2 )} 2 (D)] (D = 4,4′-bipyridine ( 1d , 1d′ and 2d ), and polynuclear complexes [MoO 2 (L 1 or 2 )] n ( 3 and 4 ) were synthesized by solution based reactions of enaminones ( H 2 L 1  = 3-(2-hydroxy-4-methylphenylamino)-1-phenylbut-2-en-1-one; H 2 L 2  = 3-(2-hydroxy-5-methylphenylamino)-1-phenylbut-2-en-1-one) with the dioxo bis (acetylacetonato)molybdenum(VI) complex, [MoO 2 (acac) 2 ]. Reactions of the mononuclear complexes 1 ·MeOH and 2 ·MeOH with pyridine and its derivatives resulted in corresponding mononuclear [MoO 2 (L 1 or 2 )(D)] or binuclear [{MoO 2 (L 1 or 2 )} 2 (D)] complexes. In case of [{MoO 2 (L 1 )} 2 (4,4-bpy)] two polymorphic forms are obtained ( 1d and 1d′ ). The cross-linked transformations of [MoO 2 (L 1 or 2 )(D)] complexes in solution or when exposed to vapors of N -heterocyclic bases have been explored. Crystal and molecular structures of ten complexes ( 1 ·MeOH, 2 ·MeOH, 1a – d , 1d′ , 2b – d ) were determined by the single-crystal X-ray diffraction analysis. Enaminone ligands and their molybdenum complexes were characterized by elemental and TG analysis, IR and NMR spectroscopy and screened for their in vitro cytotoxic and antibacterial activities. None of the tested compounds showed cytotoxic ability against THP-1 and HepG2 cell lines. Compounds 1 ·MeOH, 1b , 2 ·MeOH, 2a and 3 , exhibited weak antibacterial activity on Moraxella catarrhalis strain while other complexes did not show antibacterial properties towards Staphylococcus aureus , Enterococcus faecalis and Escherichia coli bacteria. [ABSTRACT FROM AUTHOR]

Nine compounds, including two new triterpenoid saponin C-20 epimers (4 and 5) and seven known ginsenosides (1-3, 6-9), have been isolated and purified from the alkaline-degradation products of ginsenoside Re. Their structures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR and HR-ESI-MS. Among them, (20S,22E)-6-O-β-D-glucopyranosyl-dammar-22(23),24-diene-3β,6α,12β-triol (4) and (20R,22E)-6-O-β-D-glucopyranosyl-dammar-22(23),24-diene-3β,6α,12β-triol (5) were identified as new triterpenoid saponins and they were assayed for cytotoxic activities against five human tumor cell lines. [ABSTRACT FROM AUTHOR]

A phytochemical investigation of Ajuga forrestii Diels led to the isolation of 14 compounds, including eight neo-clerodane diterpenes (1–8), two phytoecdysteroids (9, 11), one stigmastane sterol (10) and three iridoid glycosides (12–14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of compounds 1–14 from A. forrestii. The cytotoxic activities of the aqueous extract of A. forrestii and several compounds have been studied and the chemotaxonomic significance of isolated compounds has also been summarised. [ABSTRACT FROM AUTHOR]

A new series of Schizandrin ( 1 ) derivatives were synthesized utilizing the C-9 position of the Schizandrin core and evaluated for their cytotoxic activities against HeLa (cervical cancer), A549 (lung cancer), MCF-7 (breast cancer) and DU-145 (prostate cancer) cell lines. Among the synthesized series, 4e , 4f, 4g and 5 showed potent activities against tested cell lines. More significantly, compound 5 exhibited most potent cytotoxic activity against DU-145 with an IC 50 value of 1.38 μM which is comparable to the standard agent, doxorubicin. Further, flow cytometry analysis indicated that 5 arrested cells in G2/M phase and consequently leading to apoptosis. Molecular docking analysis showed that 5 occupied the colchicine binding pocket of tubulin. Overall, the present study demonstrates that 5 , as a mitotic-agent. [ABSTRACT FROM AUTHOR]

Three new sesquiterpenes of canusesnol K (1), canusesnol L (2) and 12, 15-dihydroxycurcumene (3), along with five known ones (4-8), were isolated from the heartwood extract of Pterocarpus santalinus. Their structures were established by extensive analyses of 1D and 2D NMR spectroscopy, including 1H NMR, 13C NMR, HSQC, HMBC and NOESY, and HRESI-MS. The absolute configurations of the new compounds were established with Modified Mosher’s method. The cytotoxic activities of all these compounds against HepG2 (human liver cancer), MCF-7 (human breast cancer), MDA-MB-231 (human breast cancer), and Hela (human cervical carcinoma) cancer cell lines were evaluated. Compound 1 exhibited moderate cytotoxic activity toward MDA-MB-231 cell lines. [ABSTRACT FROM AUTHOR]

Six previously undescribed oleanane-type triterpenoid saponins, fortunosides A–F, together with six known ones, were isolated from the aerial parts of L ysimachia fortunei Maxim. Their structures were established by spectroscopic data analyses (1D, 2D-NMR and HRESIMS) and chemical methods. All isolated triterpenoid saponins were evaluated for their cytotoxicity against four human liver cancer cell lines (SMMC-7721, Hep3B, HuH7, and SK-Hep-1). Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC 50 values ranging from 4.76 to 15.12 μM. [ABSTRACT FROM AUTHOR]

Three new diterpenoids, spicatusenes A–C ( 1 – 3 ), and eleven known ones ( 4 – 14 ) were isolated from the aerial parts of Clerodendranthus spicatus . Their structures were identified by spectroscopic methods. The cytotoxic activities of all the compounds against human cancer cells (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) were examined and found that compounds 2 , 3 , 6 , 8 , 10 , and 13 were active against one or more cancer cell lines. Besides, the renoprotective effects of all the isolates in TGF-β1-induced rat kidney fibroblasts revealed that compounds 3 – 7 , 9 , 13 , and 14 were beneficial for renal fibrosis. Finally, a plausible biosynthetic pathway for 1 via a Hantzsch-type reaction was proposed. [ABSTRACT FROM AUTHOR]

Ten previously undescribed sesquiterpenes, carpespenes A–J (1 – 10), and eight known compounds (11 – 18), were isolated from the whole plants of Carpesium faberi. Their structures were established by extensive analysis of HRESIMS, NMR, and ECD spectra. Carpespene A (1) is eudesmanolide-type sesquiterpene lactone with an open five membered ring involving C-2 and C-3. Furthermore, compound 1 showed significant cytotoxic effects against four cancer cell lines with IC 50 values from 8.20 to 18.45 μM, compared with the positive controls cisplatin and doxorubicin. Mechanistically, compound 1 induced apoptosis in the HepG2 cells by triggering excessive ROS accumulation. The latter however induced cytoprotective autophagy, which impaired the cytotoxicity of compound 1. Simultaneous antophagy inhibition with compound 1 treatment augmented the cytotoxic effects of the latter on HepG2 cells. Our findings further establish the structural diversity and bioactivity of sesquiterpenes, and provide an experimental basis for targeting cytoprotective autophagy as a potential chemotherapeutic strategy. Carpespene A (1), is eudesmanolide-type sesquiterpene lactone with an open five membered ring involving C-2 and C-3 from Carpesium faberi. Compound 1 induced apoptosis in the HepG2 cells by triggering excessive ROS accumulation, and simultaneous antophagy inhibition with compound 1 treatment augmented the cytotoxic effects of the latter on HepG2 cells. [Display omitted] • Ten undescribed sesquiterpenes (1–10) and eight known compounds (11–18) were isolated from C. faberi. • Compound 1 is eudesmanolide-type SL with an open five membered ring involving C-2 and C-3. • Compound 1 showed significant cytotoxic effects against four cancer cell lines with IC 50 values from 8.20 to 18.45 μM. • Compound 1 induced apoptosis in the HepG2 cells by triggering excessive ROS accumulation. • The combination of compound 1 with autophagy inhibitors augmented the cytotoxic effects. [ABSTRACT FROM AUTHOR]

Thirteen previously undescribed (9 β -H)-pimarane derivatives, icacinolides A−G (1 − 7) and oliviformislactones C–H (8 − 13), together with four known analogs (14 − 17), were isolated from the leaves of Icacina oliviformis. Their structures were constructed by extensive spectroscopic analysis, 13C NMR-DP4+ analysis, ECD calculation, single-crystal X-ray diffraction, and chemical methods. These structurally diverse isolates were classified into six framework types: rearranged 3- epi -17- nor -(9 β -H)-pimarane, rearranged 17- nor -(9 β -H)-pimarane, 16- nor -(9 β -H)-pimarane, 17- nor -(9 β -H)-pimarane, 17,19-di- nor -(9 β -H)-pimarane, and (9 β -H)-pimarane. Among them, compounds 1 , 5 , and 7 were the first examples of three rearranged 3- epi -17- nor -(9 β -H)-pimaranes featuring a unique (11 S)-carboxyl-9-oxatricyclo[5.3.1.02,7]dodecane motif with contiguous stereogenic centers, whereas their C-3 epimers, compounds 2 − 4 and 6 were the second examples of four rearranged 17- nor -(9 β -H)-pimaranes. Additionally, compounds 8 and 12 / 13 represented the second examples of a 16- nor -(9 β -H)-pimarane and two 17,19-di- nor -(9 β -H)-pimaranes, respectively. In cytotoxic bioassay, compound 2 exhibited significant cytotoxic against HT-29 with IC 50 values of 7.88 μM, even stronger than 5-fluorouracil, and 15 showed broad-spectrum cytotoxic activities against HepG2, HT-29, and MIA PaCa-2 with IC 50 values of 11.62, 9.77, and 4.91 μM, respectively. Meanwhile, a preliminary structure-activity relationship suggested that 3,20-epoxy, 6,19-lactone, 2-OH, 7-OH, and 8-OH in (9 β -H)-pimarane derivatives might be active groups, whereas ring C aromatization may decrease the cytotoxic activities. Thirteen undescribed diterpenoids, including three rearranged 3- epi -17- nor -(9 β -H)-pimaranes featuring a unique (11 S)-carboxyl-9-oxatricyclo[5.3.1.02,7]dodecane motif, were isolated from the leaves of Icacina oliviformis. Some diterpenoids exhibited cytotoxic activities, even more potent than 5-fluorouracil. [Display omitted] • Thirteen undescribed (9 β -H)-pimarane derivatives were isolated. • This is the first report of rearranged 3- epi -17- nor -(9 β -H)-pimaranes. • This is the first report of the crystal structure of 16- nor -(9 β -H)-pimarane. • This is the second examples of 16- nor - and 17,19-di- nor -(9 β -H)-pimaranes. • Some diterpenoids showed anti-tumor activities, more potent than 5-fluorouracil. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of EtOAc extract from the stem bark of Berlinia confusa yielded a new and two known polysaturated monoacylglycerides characterised as 1-O-docosanoyl-sn-glyceride (3), 1-O-(13-methyltetradecanoyl)-sn-glycerol (4) and 1-O-pentadecacanoyl-sn-glycerol (5); along with the known compounds betulinic acid (1) and sitosteryl-β-d-glucoside (2). The structures of these compounds were elucidated using analytical methods, including 1D and 2D-NMR together with MS spectroscopy. The extracts and isolated compounds demonstrated concentration-dependent anthelmintic activities against Fusciola gigantica (liver flukes) and Taenia solium (tapeworm) at 10–100 mg/ml. The extracts and isolated compounds were evaluated for cytotoxicity against a small panel of three human tumour cell lines.

Objective: To prepare different polarities leave crude extracts of Juniperus excels (J. excels) and to determine their phytochemical screening, antioxidant, antimicrobial and cytotoxic activities. Methods: The phytochemical screening of different crude extracts was determined by well-established methods. The antioxidant activity was determined by free radical scavenging (2,2-diphenyl-1-picrylhydrazyl, DPPH) method. The antimicrobial activity was evaluated by agar disc diffusion method and cytotoxic activity was determined through brine shrimp lethality assay. Results: The phytochemical tests showed that alkaloids, flavonoids, saponins, steroide, triterpenoids and tannins are present in all leave crude extracts except chloroform crude extract do not contain tannins. The antioxidant results of crude extracts were found to be in the order of hydro alcoholic > chloroform> ethyl acetate >hexane. All leave crude extracts showed moderate antibacterial against gram positive and gram negative food borne pathogen bacteria. The cytotoxicity results revealed that hexane and chloroform extracts have killed all the shrimp larvae at the concentration of 500 μg/mL. Conclusion: More in-vivo and in-vitro studies along with detailed phytochemical investigations are needed in order to potentially use this plant in the prevention and therapies of some oxidative damage related diseases.

Objective: To isolate and characterize the cytotoxic compounds from Diospyros quercina (Baill.) G.E. Schatz & Lowry (Ebenaceae). Methods: An ethno-botanical survey was conducted in the south of Madagascar from July to August 2010. Bio-guided fractionation assay was carried out on the root bark of Diospyros quercina, using cytotoxicity bioassay on murine P388 leukemia cell lines as model. The structures of the cytotoxic compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Results: Biological experiments resulted in the isolation of three bioactive pure compounds (named TR-21, TR-22, and TR-23) which exhibited very good in vitro cytotoxic activities with the IC50 values of (0.0175±0.0060) μg/mL, (0.089±0.005) μg/mL and (1.027±0.070) μg/mL respectively. Thus, they support the claims of traditional healers and suggest the possible correlation between the chemical composition of this plant and its wide use in Malagasy folk medicine to treat cancer. Conclusions: The ability of isolated compounds in this study to inhibit cell growth may represent a rational explanation for the use of Diospyros quercina root bark in treating cancer by Malagasy traditional healers. Further studies are, therefore, necessary to evaluate the in vivo anti-neoplastic activity of these cytotoxic compounds as effective anticancer drugs.

Five new anthraquinone derivatives, auxarthrols D−H (1−5), along with two known analogues (6−7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis of NMR, HRESIMS, and circular dichroism (CD) spectroscopic techniques. Among them, compound 4 represents the second isolated anthraquinone derivative with a chlorine atom, which, with compound 6, are the first reported anthraquinone derivatives with anticoagulant activity. Compounds 1 and 3 showed cytotoxic activities with IC50 values from 4.5 μM to 22.9 μM, while compounds 1, 3−4, and 6−7 showed promising antibacterial activities with MIC values from 12.5 μM to 200 μM. In addition, compound 7 was discovered to display potential antitubercular activity for the first time.

Natural daphnane diterpenoids, mainly distributed in plants of the Thymelaeaceae and Euphorbiaceae families, usually include a 5/7/6-tricyclic ring system with poly-hydroxyl groups located at C-3, C-4, C-5, C-9, C-13, C-14, or C-20, while some special types have a characteristic orthoester motif triaxially connectedat C-9, C-13, and C-14. The daphnane-type diterpenoids can be classified into five types: 6-epoxy daphnane diterpenoids, resiniferonoids, genkwanines, 1-alkyldaphnanes and rediocides, based on the oxygen-containing functions at rings B and C, as well as the substitution pattern of ring A. Up to now, nearly 200 daphnane-type diterpenoids have been isolated and elucidated from the Thymelaeaceae and Euphorbiaceae families. In-vitro and in-vivo experiments of these compounds have shown that they possess a wide range of biological activities, including anti-HIV, anti-cancer, anti-leukemic, neurotrophic, pesticidal and cytotoxic effects. A comprehensive account of the structural diversity is given in this review, along with the cytotoxic activities of daphnane-type diterpenoids, up to April 2019.

Seven resorcylic acid lactones (RALs) including five new analog rhinoclactones, A–E (1, 2, 4–6), were isolated from an endophytic fungus Rhinocladiella similis in the plant Agriophyllum squarrosum collected from the Tengger Desert of the Ningxia Province, China. The structures of these new compounds were determined by HR-ESI-MS (High Resolution Electrospray Ionization Mass Spectrometry), NMR data, modified Mosher’s method, and X-ray diffraction experiments. All compounds isolated from this fungus possessed the 16-OMe/14-OH, not the common 16-OH/14-OH or 16-OH/14-OMe groups on the aromatic ring, which are rarely found in nature. Compound 7 displayed cytotoxic activities against HCT116 and HeLa cancer cell lines. The possible biosynthesis of 1–7 is suggested, and the potential ecological roles of these fungal secondary metabolites is discussed.

Physalis angulata L. is a medicinal plant of the Solanaceae family, which is used to produce a variety of steroids. The present study reports on the cytotoxic withanolides of this plant. The species of Physalis angulata L. was identified by DNA barcoding techniques. Two new withanolides (1–2), together with six known analogues (3–8), were isolated from the whole plant of Physalis angulata L. The structures of these new compounds were determined on the basis of extensive spectroscopic data analyses and electronic circular dichroism (ECD) calculations. The withanolides exhibited strong cytotoxic activities against A549, Hela and p388 cell lines. Furthermore, compounds 1 and 2 induced typical apoptotic cell death in A549 cell line according to the evaluation of the apoptosis-inducing activity by flow cytometric analysis.

The chemical investigation of whole plants Piper terminaliflorum Tseng led to the isolation of one new furofuran lignan, 7-methoxyasarinin (1), along with three known amide alkaloids (2–4) as N-3,5-dimethoxy-4-hydroxycinnamoylpyrrole (2), dihydropipercide (3) and 1-[(2E,4E,9E)-10-(3,4-Methylenedioxyphenyl)-2,4,9-undecatrienoyl]pyrrolidine (4). Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS, and by comparison with the literature. Compounds (2–4) were isolated from Piper terminaliflorum Tseng for the first time. All isolated compounds (1–4) were evaluated for their cytotoxic activities against five human cancer cell lines (including A-549, SMMC-7721, HL-60, MCF-7 and SW-480). [ABSTRACT FROM AUTHOR]

Sesterterpene, erectusolide A ( 1 ), six phenolic alkenes, erectuseneols A−F ( 2 – 7 ) and nine known compounds, luffalactone ( 8 ), luffariolide E ( 9 ), (6 E )- and (6 Z )-neomanoalide 24,25-diacetates ( 10 and 11 ), 6,6-dimethylundecane-2,5,10-trione ( 12 ), threo - and erythro -cavernosines ( 13 and 14 ), (4 E ,6 E )-dehydromanoalide ( 15 ), echinoclerodane A ( 16 ), were isolated from the marine sponge Hyrtios erectus . Compound 13 was isolated for the first time from a natural source. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The phenolic alkenes 3 and 7 , the sesterterpenes 8 – 11 and 15 , and compounds 12 – 14 were evaluated for cytotoxic activities against six cancer cell lines, MOLT-3, HepG2, HeLa, HuCCA-1, A549, and MDA-MB-231. [ABSTRACT FROM AUTHOR]

Five new sulfur-containing compounds, with a new geometry ( cis ) of the propenyl moiety, and five known compounds were isolated from the roots of Ferula latisecta . The structures of these compounds, were elucidated on the basis of spectroscopic data including 1D and 2D NMR experiments and HRMS. All of the isolated compounds were tested against A2780, A549, HeLa, and HCT116 human cancer cell lines and some of them showed moderate cytotoxic activities. [ABSTRACT FROM AUTHOR]

Five previously undescribed monoterpenoid indole alkaloids, mappianines A−E, along with twelve known analogues, were isolated from the stems of Mappianthus iodoides Hand.-Mazz. Their structures and absolute configurations were determined by spectroscopic analysis, single-crystal X-ray diffraction, and ECD calculations. The plausible biogenetic pathway of mappianine A was proposed. All the isolated compounds were evaluated for their cytotoxic effects on MGC-803, Bel-7404, A549, NCI-H460, and HepG2 cancer cell lines. Mappianine B, tetrahydroalstonine, β -carbolin-1-one, and 1,2,3,4-tetrahydronorharman-1-one displayed moderate cytotoxicity against all cell lines tested, with IC 50 values ranging from 5.19 to 42.86 μ M. [ABSTRACT FROM AUTHOR]

Bioassay-guided fractionation of an ethanol extract of the pericarps of Garcinia mangostana led to the isolation of two new prenylated xanthones, named 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)-8-(3-hydroxy-3-methylbutyl)-xanthone (1) and 1,3,8-trihydroxy-2-(3-methyl-2-butenyl)-4-(3-hydroxy-3-methylbutanoyl)-xanthone (2), together with the five known compounds garcinones C (3) and D (4), gartanin (5), xanthone I (6), and γ-mangostin (7). Their structures were elucidated primarily based on MS and NMR data. Compounds 1–7 showed significant cytotoxic activities against various human cancer cell lines.

The study evaluated the antitumor activity of tylopilan, aβ- (1→3) (1→6) linked glucan isolated from fruiting bodies of Tylopilus felleus (Bull.: Fr.) P. Karst. (Boletaceae), and Propionibacterium acnes (P.a.) preparation. The antitumor effect of tylopilan and P.a. used alone or in combination was studied in NMRI mice inoculated i.p. with 106 180-TG Crocker tumor cells. All experiments were based on a pretreatment with tylopilan and/or P.a. 5 days and/or 2 h before tumor cell inoculation. Mean survival time (MST) of tumor - bearing mice was significantly prolonged in comparison to control mice by a single injection of tylopilan (25 µg/mouse or 50 µg/mouse) or P.a. (1 mg/mouse). MST was 23.6; 22.8 days in the tylopilan injected mice and 17.5 in the control animals. Tylopilan injected in conjunction with P.a. prolonged signifi-cantly MST in comparison to control mice as well as to tylopilan alone treated mice. We have found that P.a. which stimulate immune response enhanced significantly antitumor activity of tylopilan. The cytotoxicity of tylopilan at concentrations of 300, 150, 75 and 37.5 µg/ml towards 180-TG Crocker cells in vitro studies was evaluated. All examined tylopilan concentrations showed cytotoxic activity.

The reaction of 2-acetyl- and 2-benzoyl-1,4-naphthoquinone with (Z)-methyl 3-(hydroxymethyl)aminocrotonate proceeds through a formal [3+3] process to yield the corresponding 1,2-dihydrobenzisoquinolinequinones in 63% and 72% yield, respectively. The reactions of 2-acyl-1,4-naphthoquinone with enaminones, derived from diverse L- and D-amino acid methyl esters, produced the corresponding naphthoquinone amino acids conjugates bonded through a vinyl spacer in the yields range 40-71%. The presence of not-separable isomers of the naphthoquinone amino acids conjugates in the ¹H- and 13C-NMR spectra is explained by the existence of conformational isomers generated by hindered rotation of the substituent bonded to the quinone double bond. These new naphthoquinone amino acids conjugates were screened in vitro on normal and cancer cell lines and showed moderate cytotoxic activities. [ABSTRACT FROM AUTHOR]

Two new citrinin derivatives, pencitrin ( 1 ) and pencitrinol ( 2 ), and a known compound citrinin ( 3 ), together with its two known dimers, penicitrinone A ( 4 ), penicitrinone E ( 5 ), were isolated from an endophytic fungus P. citrinum 46 derived from Salicornia herbacea Torr. by adding CuCl 2 into fermentation medium. The structures of these compounds were elucidated by detailed spectroscopic analysis, and the absolute configurations of 1 , 4 , and 5 were determined by comparison of quantum chemical time-dependent density functional theory (TDDFT) calculated and electronic circular dichroism (ECD) spectra. Compound 1 exhibited potent cytotoxic activities towards A549 human lung cancer cells and HepG2 human liver cancer cells with IC 50 values of 23.73 ± 3.61 and 35.73 ± 2.15 μM, respectively, whereas compound 5 showed moderate cytotoxic activities towards A549 and HepG2 cancer cells with IC 50 values of 40.47 ± 4.52 and 53.57 ± 3.24 μM, respectively. The results from the current research highlighted the effectiveness and usefulness of the pipeline to discover novel bioactive fungal secondary metabolites by modification of the culture media. [ABSTRACT FROM AUTHOR]

Seven new furostanol saponins have been isolated from the rhizomes of Smilax davidiana . Their structures were established by 2D NMR spectroscopic techniques ( 1 H, 1 H-COSY, NOESY, HSQC and HMBC), mass spectrometry and comparison with the literature. The isolated compounds were subjected to evaluate anti-inflammatory and cytotoxic activities in vitro. Compounds 3 , 5 and 7 were found to have modest anti-inflammatory effects through suppression of IL-1β production and promote the expression of IL-10 in LPS-stimulated RAW 264.7 cells. Davidianoside F ( 6 ) showed activity against MCF-7 and HELA cell lines at the concentration of 10.2 µM and 4.3 µM, respectively. [ABSTRACT FROM AUTHOR]

Three new kavalactone dimers, designated as yangonindimers A-C (1–3), along with one known analogue were isolated from the roots of Piper methysticum. Their structures were elucidated via extensive analysis of their 1D, 2D NMR and mass spectroscopic data. All these dimers possess a skeleton featuring a cyclobutane ring connecting two kavalactone units. Compounds 1–4 were evaluated for their cytotoxic activities against human tumour cell lines NCI-H46, SW480 and HepG2, but none showed significant activity. [ABSTRACT FROM AUTHOR]

Cyclometalating iridium(III) complexes with formula, [Ir(cpy) 2 (biim)Cl] 1 , [Ir(cpy) 2 (bpy)Cl] 2 and [Ir(cpy) 2 (dppe)Cl] 3 (where, cpy = 9-(pyridine-2-yl)-9 H -carbazole, biim = biimidazole, bpy = 2,2′-bipyridine, dppe = 1,2-bis(diphenylphosphino)ethane) were synthesized and characterized by elemental analysis, 1 H, 13 C NMR, and ESI-Mass spectral studies. The complex 1 – 3 show their emissions in green emitting region (λ PL , max = 536–580 nm), and the emission maxima can be tuned by changing the ancillary ligand. The phosphorescent line shape indicates that the emissions originate predominantly from 3 MLCT states with little admixture of ligand-based 3 (π-π ∗ ) excited states. These complexes exhibited biexponential phosphorescence decays with relatively short lifetimes of 0.40–12.35 µs in solution state at room temperature and the relaxation dynamics of 1 – 3 are O 2 dependent. The electrochemical and thermal properties were systematically evaluated. Binding of these complexes ( 1 – 3 ) with calf thymus DNA was investigated by UV–Vis, fluorescence, circular dichroic spectroscopy, viscosity measurements and computer aided molecular docking studies. The binding constant of complexes ( 1 – 3 ) with ct-DNA obtained by UV–Vis absorption studies were 2.28 × 10 4 , 1.98 × 10 4 and 2.98 × 10 4 M −1 , respectively. The result indicated that the complexes ( 1 – 3 ) were able to bind to DNA with different binding affinity in the order: 3 > 1 > 2 . Complexes ( 1 – 3 ) also exhibit a good binding propensity to bovine serum albumin (BSA). Gel electrophoresis assay demonstrated that complexes ( 1 – 3 ) cannot promote the cleavage ability of the pBR322 plasmid DNA or plasmid pBluescript II KS + DNA or pUC19 DNA in the presence of the reducing agent 3-mercaptopropionic acid. The cytotoxicity studies of complexes 1 – 3 were tested in vitro on in human cervical cancer cell line (HeLa) and they found to be active. We propose that the phosphorescent iridium(III) complexes ( 1 – 3 ) are possible candidates for the green phosphors in organic light emitting diodes (OLEDs) applications as well as better anticancer agents. [ABSTRACT FROM AUTHOR]

A series of benzo[ b]furans was synthesized with modification at the 5-position of the benzene ring by introducing different aryl acetylenyl and acrylic acid moiety as combretastatin A-4 analogues. The compounds were evaluated by MTT assay for cytotoxic effects against lung cancer (A549), liver cancer (BEL-7404), colon cancer (SW620), and cervical cancer (HeLa) cell lines and the compounds were more sensitive to A549 and Hela cell lines. One compound exhibited the highest inhibition against A549 and Hela cells (IC = 0.18 and 0.14 μM) and very close to that of CA-4 (IC = 0.16 and 0.12 μM). This compound elicited cell-cycle arrest in the G/M phase and significantly induced apoptosis in HeLa cells. Molecular docking studies indicated that it displayed hydrogen-bonding interactions with the amino acid residues Gln-11 and Tyr-224 would be a potential tululin inhibitor. Graphical abstract: [ABSTRACT FROM AUTHOR]

Five new α-pyrones namely nocapyrones O-S (2–6) and nocapyrone F (1) were isolated from a deep-sea sediment strainNocardiopsissp. YIM M13066. Their structures were elucidated by their NMR spectroscopic data, HR-ESI-MS and crystal X-ray diffraction. Their cytotoxic activities against H1299, HeLa, HL7702, MCF-7, PC3 and U251 cell lines were evaluated. [ABSTRACT FROM PUBLISHER]

We investigated the cytotoxic effects of the newly synthesized cyclotriphosphazene derivatives on A2780 (ovarian), PC-3 and LNCaP (prostate) cancer cell lines. 4′-hydroxy-substituted-chalcone compounds(2–8)were reacted with diphenyl-cyclotriphosphazene(DPP)in the presence of acetone/K2CO3in order to obtain novel cyclotriphosphazene compounds(DPP 2–8). The structures ofDPP 2–8were characterized by MALDI-TOF mass spectrometry, FT-IR, elemental analysis,1H,13C-APT, and31P NMR measurements. The thermal properties of all phosphazene compounds have been studied after synthesis and characterization procedure. The cytotoxic effects ofDPP 2–8were examined primarily by applying the MTT method based on the measurement of mitochondrial activity. In this regard, several phosphazene compounds have shown high chemotherapeutic effect at low dose (p< 0.05). When the cytotoxic effects ofDPP 2–8at doses of 1, 5, 25, 50 and 100 µM on A2780 cells were examined, it was observed thatDPP-3, DPP-4, DPP-5andDPP-7were more effective than other derivatives suggested by their high Log IC50values (p< 0.05). The compoundsDPP 2–8possess cytotoxic activity against PC-3 and LNCaP cells (especially compoundsDPP-4andDPP-5,p< 0.05). [ABSTRACT FROM AUTHOR]

Twenty-six novel isosteviol derivatives coupled with two types of nitric oxide ( NO) donors (furoxans and NONOates) were synthesized and screened for cytotoxic activities against four human cancer cell lines with sunitinib as the positive control. The results showed that seven furoxan-based derivatives ( 8a, 8b, 8c, 8d, 8e, 9e, and 9f) exhibited desirable cytotoxic activities, while NONOate-based derivatives displayed poor potency because of unstability. Compared with sunitinib, compounds 8a and 8e were more active on all tested cell lines, especially in HCT116 ( 8a, IC50 = 0.48 ± 0.02 μ m; 8e, IC50 = 0.94 ± 0.01 μ m); compounds 8b and 8d were more potent on HCT116 ( IC50 = 3.39 ± 0.06 and 3.29 ± 0.03 μ m), HepG2 ( IC50 = 1.05 ± 0.03 and 5.37 ± 0.08 μ m), and SW620 ( IC50 = 1.33 ± 0.02 and 4.11 ± 0.05 μ m) cell lines, and 8c exhibited higher activities on HepG2 cells with an IC50 = 4.76 ± 0.14 μ m. NO-releasing experiment of compounds 8a- e, 17a, 18a, 19a, and 21a reminded us that NO-releasing amount of this series of isosteviol derivatives positively correlates with their cytotoxic activities. [ABSTRACT FROM AUTHOR]

Inspired by the significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP, 1 ), we synthesized and characterized a series of novel 5α,8α-epidioxyandrost-3β-ol-17-( O -phenylacetamide)oxime derivatives ( 9a – o ). The anti-proliferative activity of the synthesized compounds against human hepatocellular carcinoma cells (HepG2, Sk-Hep1) and human breast cancer cells (MCF-7, MDA-MB231) were investigated. Compounds 9d , 9f , 9h , 9j and 9m displayed good anti-proliferative activity (most IC 50 < 20 μM) in vitro . Furthermore, fluorescence imaging showed that the designed coumarin- 9d conjugate ( 12 ) localized mainly in mitochondria, leading to enhanced anticancer activities over the parent structure. [ABSTRACT FROM AUTHOR]

Three new benzolactones (1–3), together with four known ones (4–7), were isolated from the whole herb ofLavandula angustifolia. Their structures were established on the basis of detailed spectroscopic analysis (1D- and 2D-NMR, HRESIMS, UV, and IR) and comparison with data reported in the literature. New compounds were evaluated for their anti-tobacco mosaic virus (TMV) activities and cytotoxic activities. The results revealed that compounds1–3showed obvious anti-TMV activities with inhibition rates of 26.9, 30.2, and 28.4%, which were at the same grade as positive control. Compounds1–3also showed weak inhibitory activities against some tested human tumor cell lines with IC50values in the range of 32.1–7.6 μM. [ABSTRACT FROM PUBLISHER]

By inspiration of significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP), a series of novel steroidal 5α,8α-endoperoxide derivatives 5a – d and 14a – f were designed, synthesized, and biologically evaluated for their in vitro anti-proliferative inhibitory and cytotoxic activity. The results revealed that most of these compounds showed moderate-to-excellent anti-proliferative effects against the tested cancer cell lines ( i.e. HepG2, SK-Hep1, MDA-MB-231 and MCF-7). Among them, compound 5b and 14d exhibited preferable inhibitory activities (IC 50 of 5b and 14d are 8.07 and 9.50 μM against HepG2, respectively). The structure-activity relationships indicated that incorporation the peroxidic bridge to the steroid scaffolds at C-5 and C-8 positions together with the aliphatic side-chain at the C-17 position would provide synergistic effect for the bioactivity. [ABSTRACT FROM AUTHOR]

The bioassay-guided fractionation of the n-hexane extract of Citrus reticulata Blanco (Rutaceae) stem bark yielded scoparone (1), xanthyletin (2), lupeol (3), β-amyrin (4), stigmasterol (5), β-sitosterol (6) and palmitic acid. The structures of these compounds were determined by comprehensive spectroscopic analyses, i.e., 1D and 2D NMR and EI-MS, and by comparison with the reported data. Extracts, fractions and isolated compounds 1-6 were assessed for cytotoxicity by the 3-(4,5-dimethylthiazol-2-yl)-2,5-dphenyltetrazolium bromide (MTT) assay against three human cancer cell lines, i.e., human lung adenocarcinoma cell line A549, human breast adenocarcinoma cell line MCF7 and human Caucasian prostate adenocarcinoma cell line PC3. Significant activity of the n-hexane and the dichloromethane extracts was observed against the breast cancer cell line MCF7 with IC50 s of 45.6 and 54.7 μg/mL, respectively. Moreover, the 70% ethyl acetate in n-hexane chromatographic fraction showed significant activity displaying IC50 values of 53.0, 52.4 and 49.1 μg/mL against the cancer cell lines A549, MCF7 and PC3, respectively. Encouragingly, an IC50 of 510.0 μg/mL against the human normal prostate cell line PNT2 indicated very low toxicity and hence favourable selectivity indices for the 70% ethyl acetate in n-hexane fraction in the range of 9.6-10.4 towards cell lines A549, MCF7 and PC3. Because compounds isolated from the above fraction only delivered IC50 values in the range of 18.2-96.3, 9.2-34.1 and 7.5-97.2 μg/mL against A549, MCF7 and PC3 cell lines, respectively, synergistic action between compounds is suggested. Bioassay results valorize the anticancer effectivity of the stem bark of this plant in Cameroonian pharmacopoeia. Copyright © 2017 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

One new norsesquiterpene polyalone A (1), and one new natural product 9-keto-cyclocolorenone (2), along with three known analogues (3–5) were isolated from the roots of Polyalthia laui. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their cytotoxic activities and antibacterial activities. [ABSTRACT FROM AUTHOR]

Seven new cucurbitane triterpenoids, Pengxianencins A–G ( 1 – 7 ) including one alkaloid, were isolated from the ethanol extract of the tubers of Hemsleya penxianensis . Their structures were elucidated on the basis of extensive spectroscopic data, including 1D and 2D NMR spectra as well as HR-ESI-MS. The evaluation of inhibition activity against human Hela, MCF-7, and A-549 cell lines showed that compounds 1 , 4 , 6 , 7 have different levels of cytotoxic activities, with IC 50 values ranging from 1.67 to 45.28 μM. [ABSTRACT FROM AUTHOR]

Three new bisditerpenoid alkaloids, navicularines A–C ( 1 – 3 ), and three known ones ( 4 – 6 ), were isolated from the ground parts of Aconitum naviculare . Their structures were elucidated by spectroscopic methods. All the new compounds were tested against five cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480). It was found that navicularine B exhibited certain cytotoxic activities in vitro, with IC 50 values of 13.50, 18.52, 17.22, 11.18, and 16.36 μM, respectively. [ABSTRACT FROM AUTHOR]

Tow new arylalkenyl α,β-unsaturated δ-lactones named cryptoconcatones K (1) and L (2) were obtained from the leaves and twigs of Cryptocarya concinna. Their structures were established on the basis of spectroscopic data (MS, 1D and 2D NMR). Compounds 1 and 2 showed cytotoxic activities with IC50 values of 4.5 and 3.9 μM against Huh7 cancer cell line, respectively. [ABSTRACT FROM AUTHOR]