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Chemical investigation on the 80% EtOH extract of the air dried aerial parts of Hypericum sampsonii resulted in the isolation of two new polycyclic polyprenylated derivatives, hypersampines A and B (1 and 2). The structures of the new compounds were elucidated by spectroscopic data (NMR, IR, and UV) and high resolution mass analysis. The two isolated polyprenylated acylphloroglucinols were tested in vitro for cytotoxic activities against 6 pancreatic cell lines. As a result, compounds 1 and 2 possessed modest cytotoxic activities against all the tested tumor cell lines with IC50 values less than 40 μM. [ABSTRACT FROM AUTHOR]

In this study, a novel ligand, benzilmonoximethiocarbohydrazide-O-methoxybenzaldehyde (HBMToMB), was synthesized and subsequently complexed with Cu(II), Fe(II), Co(II), Ni(II), and Mn(II) ions. The metal complexes were comprehensively characterized using techniques such as NMR, IR, Mass Spectrometry, UV–Vis, elemental analysis (CHNS), and magnetic susceptibility measurements. The complexes exhibited superior antibacterial and antifungal activity compared to the free ligand. In addition, cytotoxicity was evaluated using the brine shrimp lethality bioassay, demonstrating significant activity. Computational studies, including molecular docking, DFT, and ADMET analysis, provided further insights into the compounds' binding affinities and electronic properties. These findings underscore the potential of these metal complexes as promising candidates for therapeutic applications, particularly in antimicrobial and anticancer therapies. [ABSTRACT FROM AUTHOR]

A new morphinan alkaloid (6S, 9S, 13 R, 14S)-6-O-acetyl-7,8-Didehydro-4-hydroxy-3,7-dimethoxymorphinan-6-ol (1), and a new naturally occurring cularine alkaloid (S)-2, 3, 12, 12a-tetrahydro-5, 6, 9, 10-tetramethoxy-1-methyl-1H-[1]benzoxepino[2, 3, 4-ij]isoquinoline(5), along with four known alkaloids were isolated from the roots of Stephania cepharantha. The structures of these compounds were elucidated based on spectroscopic data analyses. Cytotoxic activities of the compounds against three human cancer cell lines (A549, MCF-7 and SW480) were also evaluated. [ABSTRACT FROM AUTHOR]

The essential oil isolated by hydro-distillation from Magnolia tiepii leaves was analyzed by GC-MS and assessed for antimicrobial and anticancer activities. Thirty-three components of the essential oil were identified, and the major components were β-pinene (40.8%), β-funebrene (12.0%), and trans-meta-mentha-2,8-diene (8.1%). The oil's antimicrobial activity was assessed using IC50 values to determine its efficacy against six bacterial strains and one fungus strain. The IC50 values ranged from 2.30 mg/mL to 42 mg/mL, except for C. albicans, whose IC50 did not reach the highest concentration tested (>42 mg/mL). In addition, the anticancer activity of the M. tiepii essential oil was evaluated on KB, HepG2, MCF-7, and A549 cancer cell lines using the MTT method. These cell lines were treated with essential oil samples at concentrations ranging from 0.16 to 42 μg/mL. The M. tiepii essential oil exhibited high anticancer activity, with IC50 values ranging from 0.90 μg/mL to 2.07 ± 0.06 μg/mL across the four tested cell lines. These promising results underscore the potential of M. tiepii essential oil for cancer treatment, offering hope for future research and applications. [ABSTRACT FROM AUTHOR]

Two new furanone derivatives, byssochlanones A–B (1–2) were purified from the endophytic fungus Byssochlamys sp. isolated from the wetland plant, Phragmites australis. Their structures were elucidated on the basis of extensive spectroscopic analyses. Compounds 1–2 represented typical furanone analogues which are not common in natural products. The absolute configuration of compounds 1–2 were identified through quantum-chemical electronic circular dichroism (ECD) calculation compared with their experimental CD. In addition, compounds 1–2 were tested for their cytotoxic activities against HCT-8 and Hela cancer cell lines, and compound 2 showed moderate activity against HCT-8 cells with IC50 value of 21.3 μM. [ABSTRACT FROM AUTHOR]

N-(5-((3E,5E)-10-Acetoxy-5,7,9,11-tetramethyltrideca-3,5-dien-1-yl)-2-oxotetrahydrofuran-3-yl)acetamide (1), a new amide compound, and five known ones (2–6) were isolated from the EtOH extract of the solid culture of Fusarium sp. Their structures were determined by means of extensive 1D and 2D NMR techniques, as well as comparison with literature values. Additionally, compounds 1–6 were tested for their cytotoxic activities. The results showed that compounds 2, 3, 6 exhibited cytotoxic activities against five human cancer cell lines with IC50 values ranging from 2.088 to 26.40 μM. [ABSTRACT FROM AUTHOR]

Ten previously undescribed dammarane-type triterpenoid glycosides, cyclocarysaponins A–J (1–10), were isolated from the leaves of Cyclocarya paliurus (Batal.) Iljinskaja. The structures of these compounds were characterized through detailed spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The cytotoxic activities of all isolates were assessed against five human cancer cell lines (Bel-7402, Caski, BGC-823, A2780, and HCT-116). Of the tested compounds, compounds 1 , 7 , and 9 exhibited selective cytotoxicity against one or more human cancer cell lines. [ABSTRACT FROM AUTHOR]

Two new sesquiterpene lactones, laurenolide A (1) and laurenolide B (2), along with six known compounds, palmitic acid (3), (R,R)-hexahydrofarnesyl acetone (4), trans-phytol acetate (5), cholesterol (6), cholesteryl acetate (7), cholesteryl heptadecanoate (8) were isolated from Palisada intermedia. The chemical structures of all compounds were elucidated by 1D and 2D-NMR spectroscopy and HR-ESI-MS analysis as well as compared with data in the literature. The petroleum ether, chloroform, ethyl acetate, methanol extracts and compounds 1, 2 were tested for the inhibition of two cancer cell lines MCF-7, NCI-H460 and they showed weak or none activities. [ABSTRACT FROM AUTHOR]

Delphinium grandiflorum , one of the well-known Delphinium species, contains diverse bioactive diterpenoid alkaloids (DAs), which promoted a systematic phytochemical study on this plant. As a result, two new DAs, namely 16-demethyl tuguaconitine (1) and 6- O -acetyl-16-demethyldelsoline (2), together with one known analogue pseudophnine A (3) were obtained from the whole herbs of D. grandiflorum. Their structures were elucidated by use of extensive spectroscopic analysis (HR-ESIMS, IR, 1D and 2D NMR). Additionally, the inhibitory effects of these obtained individual compounds were also evaluated in vitro for lung cancer cell line (A549), liver cancer cell line (SMMC-7721), and breast cancer cell line (MCF-7). The results of cytotoxic activities showed that only compound 2 exhibit weak inhibitory effect on SMMC-7721 and MCF-7, and their IC 50 values were 37.4 and 33.1 μM, respectively. However, compound 1 and 3 had no obvious cytotoxic activities (IC 50 >80 μM). [Display omitted] • Two new diterpenoid alkaloids were obtained from the whole herbs of Delphinium grandiflorum. • The inhibitory effects of 1–3 were evaluated in vitro against A549, SMMC-7721 and MCF-7 cancer cell lines. • 2 exhibited weak inhibitory effects on SMMC-7721 and MCF-7 with IC 50 values of 37.4 and 33.1 μM, respectively. [ABSTRACT FROM AUTHOR]

Two new sesterterpenoids, atractylodes japonica terpenoid acid I (1) and atractylodes japonica terpenoid aldehyde I (2), were isolated from the rhizomes of Atractylodes japonica Koidz. ex Kitam together with ten known compounds (3–12). Their structures were elucidated on the basis of comprehensive spectroscopic analysis (1D/2D NMR, HRESIMS and IR). In addition, all of these isolated compounds were evaluated for their cytotoxic activities against human gastric cancer cell MGC-803 and human hepatocellular cancer cell HepG-2. Most of them exhibited moderate to weak inhibitory effects with IC50 values in the range of 25.15–88.85 μM except for 9–12. [ABSTRACT FROM AUTHOR]

Two new isoquinoline alkaloids, hypecocarpinine (1) and leptocaramine (2) along with five known ones including leptopidine (3), corydamine (4), protopine (5), dihydroprotopine (6) and oxohydrastinine (7), were isolated from Hypecoum leptocarpum Hook. f. et Thoms. Structures of the compounds were elucidated using spectroscopic methods, including UV, IR, HR-ESI-MS, 1 D and 2 D NMR. The cytotoxic activities of these compounds were evaluated using MTT assay. The results showed that compounds 2, 4, and 7 have moderate cytotoxicity against human lung cancer (A549) and human gastric carcinoma (MGC-803) cell lines. [ABSTRACT FROM AUTHOR]

Pyrazole compounds have garnered attention due to their potential biological and medicinal qualities. Therefore, the purpose of the research being described is to utilize 3,5‐dimethyl‐1H‐pyrazole‐1‐carbothiohydrazide (1) as a starting material in a one‐pot synthesis to create novel pyrazole derivatives with potential biological applications. When either ethanol or acetic acid was added, components 1 and 1,3‐diphenylpropane‐1,3‐dione (2) reacted to produce derivative 3. Compound 1, when combined with ethanol, chemical 2, or acetyl acetone 5 and triethylamine, yielded chemicals 4 and 6 respectively. When ingredient 1 was mixed with ethyl cyanoacetate (7), stearic acid (10), or carboxylic acids 12 a–c, 9, 11, and 13 a–c were formed as a result. The equivalent 1,3,4‐thiadiazine derivatives, 15 and 17, were produced when 1 was mixed with either 14 or 16. The developed compounds′ cytotoxic properties were evaluated against lung and liver cancer. Our research identified a number of interesting bioactive chemicals, among which chemical 17 exhibited the greatest effectiveness against lung and liver cancer as well as the highest selectivity index measurements. It indicated a strong IC50 value of 5.35 and 8.74 μM, accordingly, when compared with 3.78 and 6.39 μM for the reference medication cisplatin. Additionally, its safety for use has been confirmed. [ABSTRACT FROM AUTHOR]

Streptocarbazoles are a class of indolocarbazole (ICZ) compounds produced by Streptomyces strains that feature unique cyclic N-glycosidic linkages between the 1,3-carbon atoms of the glycosyl moiety and the two indole nitrogen atoms. Although several streptocarbazole compounds display effective cytotoxic activity, their biosynthesis remains unclear. Herein, through the inactivation of the aminotransferase gene spcI in the staurosporine biosynthetic gene cluster spc followed by heterologous expression, two new streptocarbazole derivatives (1 and 3) and three known ICZs (2, 4, and 5) were generated. Their structures were determined by a combination of spectroscopic methods, circular dichroism measurements, and single-crystal X-ray diffraction. Compounds 1–4 displayed moderate cytotoxicity against HCT-116 cell line, and compounds 3 and 4 were effective against Huh 7 cell line. Double-gene knockout experiments allowed us to propose a biosynthetic pathway for streptocarbazole productions. Furthermore, by overexpression of the involving key enzymes, the production of streptocarbazoles 1 and 3 were improved by approximately 1.5–2.5 fold. IMPORTANCE Indolocarbazoles (ICZs) are a group of antitumor agents, with several analogs used in clinical trials. Therefore, the identification of novel ICZ compounds is important for drug discovery. Streptocarbazoles harbor unique N-glycosidic linkages (N13-C1′ and N12-C3′), distinguishing them from the representative ICZ compound staurosporine; however, their biosynthesis remains unclear. In this study, two new streptocarbazoles (1 and 3) with cytotoxic activities were obtained by manipulating the staurosporine biosynthetic gene cluster spc followed by heterologous expression. The biosynthetic pathway of streptocarbazoles was proposed, and their productions were improved through the overexpression of the key enzymes involved. This study enriches the structural diversity of ICZ compounds and would facilitate the discovery of new streptocarbazoles via synthetic biological strategies. [ABSTRACT FROM AUTHOR]

Aspidiatas C and D (1 and 2), two new spirostanol saponins, were isolated along with two known compounds, (25 R*)-spirost-5-en-3β-yl α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3), (25 R*)-spirost-5-en-3β-yl α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (4) from the whole plant of Aspidistra triradiata collected in Vietnam. The chemical structures were determined by HRESIMS, 1D- and 2D-NMR analysis, and comparison with published data. Compound 3 exhibited potent cytotoxicity against MCF7, HepG2, SK-LU-1, and HT-29 human cancer cell lines with IC50 values ranging from 0.19 to 0.65 µM. Compounds 1, 2, and 4 displayed moderate cytotoxic effects with IC50 values ranging from 12.32 to 82.27 µM. Compounds 1–4 were isolated from the genus Aspidistra for the first time. [ABSTRACT FROM AUTHOR]

A new alkaloid, demethylorychophragine A (1), together with 18 known compounds was isolated from the aerial parts of Orychophragmus violaceus. Structure of the new compound was identified by extensive spectroscopic techniques. 2 and 3 were isolated from nature for the first time. Known compounds were identified by comparison with data reported in the literature. All compounds were evaluated for anti-radiation activities against X-ray irradiation in HUVEC cell line. Results showed that 10, 12, and 15 showed excellent anti-radiation activity. All compounds were tested for cytotoxic activity against SH-SY5Y and HeLa cell lines. 16 exhibited significant cytotoxicity activity against SH-SY5Y cells, with IC50 value of 23.86 ± 0.38 µM (p = 0.045). The anti-inflammatory effects of all compounds were assessed by determining their ability to inhibit the production of NO, which was induced by stimulating the RAW264.7 murine macrophage cell line with lipopolysaccharide. 16 markedly decreased NO to a level of 27.34 ± 1.29 µM. [ABSTRACT FROM AUTHOR]

Three new dammarane-type triterpenoids, namely elliptaglin A-C (1–3) were isolated from the stem bark of Aglaia elliptica (C.DC.) Blume along with three known derivatives, namely (20S)-hydroxydammar-24-en-3-on (4), cabralealactone (5), and E-25-hydroperoxydammar-23-en-20-ol-3-one (6). Subsequently, their chemical structures were determined using HR-ESI-MS, FTIR, 1D and 2D-NMR spectroscopic analysis as well as comparison with previous studies. The cytotoxicity activities of the isolated compounds against MCF-7 breast cancer and B16-F10 melanoma cell lines were then tested using PrestoBlue reagent. The analysis results showed that elliptaglin B (2) had the strongest activity against both cell lines with IC50 values of 60.98 and 51.83 µM, respectively. [ABSTRACT FROM AUTHOR]

Three new compounds (1, 11, and 12), together with 32 known ones, were isolated from the root bark of Morus alba L. using various chromatographic methods. The structures of the undescribed compounds were elucidated based on 1D, 2D NMR, and HRESIMS dataanalysis, while the known ones were identified by comparison of their spectroscopic data with those reported in the literature. All the isolates were evaluated for their cytotoxic activities against human gastric cancer HGC27 cells by CCK-8 assay. Among them, compounds 5, 8, 10, and 30 exhibited cytotoxic activities on HGC27 cells with IC50 values of 33.76 ± 2.64 μM, 28.94 ± 0.72 μM, 6.08 ± 0.34 μM, and 10.24 ± 0.89 μM, respectively. Furthermore, compound 10 was confirmed to reduce proliferation ability, increase apoptosis rate, and inhibit cell migration pathway by annexin V/PI double staining experiment, transwell experiment, and Western blot analysis. [ABSTRACT FROM AUTHOR]

A new abietane diterpenoid, 1β, 11-epoxyabieta-12-hydroxy-8, 11, 13-triene-7-one (1), along with three known compounds (2–4), was isolated from Lycopodium complanatum. Their structures were confirmed by the analysis of 1D, 2D NMR and HRESIMS data, and comparison with previous spectral data. All compounds were tested for inhibitory activities against A549, HepG2 and MCF-7 tumor cell lines. [ABSTRACT FROM AUTHOR]

Highly nutritious traditional plants which are rich in bioactive substances are attracting increasing attention. In this study, the nutritional value, chemical composition, biological activities, and feed indices of different parts of Millettia speciosa were comprehensively evaluated. In terms of its nutritional value, this study demonstrated that the leaves, flowers and seeds of M. speciosa were rich in elements and amino acids; the biological values (BVs) of these ingredients ranged from 85% to 100%, showing the extremely high nutritional value of this plant. GC-MS analysis suggested that the main chemical components of the flower volatile oil were n-hexadecanoic acid (21.73%), tetracosane (19.96%), and pentacosane (5.86%). The antibacterial activities of the flower and seed extracts were significantly stronger than those of the leaves and branches. The leaf extract displayed the strongest antifungal activities (EC50 values: 18.28 ± 0.54 μg/mL for Pseudocryphonectria elaeocarpicola and 568.21 ± 33.60 μg/mL for Colletotrichum gloeosporioides) and were the least toxic to mouse fibroblasts (L929) (IC50 value: 0.71 ± 0.04 mg/mL), while flowers were the most toxic (IC50 value: 0.27 ± 0.03 mg/mL). In addition, the abundance of fiber, protein, mineral elements, and functional metabolite contents indicated the potential applicability of M. speciosa as an animal feed. In conclusion, as a traditional herbal plant used for medicinal and food purposes, M. speciosa shows potential for safe and multifunctional development. [ABSTRACT FROM AUTHOR]

The ligand N-{[(phenyl amino) thioxomethyl] hydrazino carbonyl methyl} trimethyl ammonium chloride (PTHAC) was prepared by the refluxing phenyl isothiocyanate and Girard-T (trimethyl ammonium-acethydrazide) in a molar ratio (1:1). The metal complexes derived from NiCl2.6H2O, CuCl2.2H2O and Co(CH3COO)2.6H2O were synthesized and purified. The PTHAC and its Cu(II), Co(II), and Ni(II) metal complexes(1–3) were characterized using a variety of various instrumental performances such as elemental analysis, magnetic moment, spectra (IR, UV–Vis, 1H NMR, mass) and thermal analysis (TGA and DTG).The results of element analysis, magnetic moment, spectra (IR, UV–Vis, 1H NMR, mass), and thermal (TGA and DTA) analyses provide the structures of the produced ligand and its (1–3) complexes. According to the spectroscopic results, PTHAC acts as an O, N and S tridentate donor, creating a mononuclear complex with copper(II), cobalt(II), and nickel(II) ions with an octahedral geometry. All of the atomic properties, including bond lengths, bond angles, HOMO, LUMO, dipole moments, and charges, have been determined. The cytotoxic activities of the PTHAC and the produced (1–3) complexes against breast carcinoma cells have been studied and correlated to the molecular modeling. When compared to the free ligand, CoII-L, and NiII-L, the CuII-L complex inhibits breast cancer cell growth more effectively. Furthermore, the PTHAC ligand was successfully applied for separation via flotation and spectrophotometric determination of Co(II) in several natural water, certified ore and pharmaceutical samples using oleic acid surfactant (HOL). At pH 6.5, PTHAC reacted with Co(II) to create a dark green (1:1) Co(II):PTHAC complex that was floated significantly using oleic acid (HOL) surfactant. The different experimental variable affecting the separation procedure e.g. pH, concentration of Co(II), HOL, PTHAC, temperature etc...., were investigated. Co(II) had a linear range of (0.1–7.0) mgL−1. In the aqueous and scum layers, the molar absorptivities for the coloured complex are 0.14 × 104 and 0.16 × 105Lmol−1 cm−1, respectively. The LOD was 0.04 mgL−1, which is related to Sandell sensitivity of 3.7 × 10−3 µg cm−2 with a preconcentration factor of 200 and a RSD, % (n = 5) less than 4.2%. In addition, the mechanisms involved in the process of coordination of PTHAC with Cu(II), Co(II) and Ni(II) and the mechanism involved in the process of flotation of the PTHAC-Co(II) complex using HOL surfactant were elucidated. [ABSTRACT FROM AUTHOR]

A new spirostanol steroid, aspidiata A (1), and a new spirostanol steroidal saponin, aspidiata B (2), along with three known compounds, paris saponin VII (3), daucosterol (4), and (25R)-spirostane-1β,2β,3β,4β,5β,6β-hexol (5), were isolated from whole plants of Aspidistra triradiata collected in Vietnam. Their chemical structures were established by spectroscopic analysis and comparison with previously published data. Compound 3 showed strong cytotoxicity against LU-1, Hep-G2, MCF-7, and KB human cancer cell lines with half maximal inhibitory concentration (IC50) values ranging from 0.57 to 1.23 µM. Compound 5 exhibited weak cytotoxic activity against the LU-1 cell line, with an IC50 value of 95.81 µM. [ABSTRACT FROM AUTHOR]

Phytochemical investigation the resins of Ferula sinkiangensis K.M.Shen yielded three new tetrahydrobenzofuran derivatives named as Sinkiangensis A-C (1–3). The structures of the new compounds were elucidated by analysis of their NMR, HRMS, and ECD spectra, and the absolute configurations were established through the comparison of experimental and calculated ECD spectra. Compound 3 exhibited moderate antitumor activities against AGS cancer cell with IC50 values of 15.6 µM. Moreover, assays demonstrated that compound 3 could induce AGS cancer cell apoptosis. [ABSTRACT FROM AUTHOR]

In line with the global interest and demand in finding sustainable ways to the emerging antimicrobial and cytotoxic activities, our study highlights the unique chemical composition of G. barbadense stem. Petroleum ether extracts were analyzed via headspace-gas chromatography/mass spectrometry (HS-GC/MS) revealing 48 compounds, thirteen major and accounting for 56.29% of total peak areas. By using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) identify 16 major phenolic compounds from the methanolic extract. Both petroleum ether and methanolic extracts were tested for antibacterial activity against four pathogenic bacterial strains (Escherichia coli ATCC10536, Staphylococcus aureus ATCC6538, Salmonella enterica ATCC 14028, and Pseudomonas aeruginosa ATCC 9027) by using disk diffusion method. The antifungal activity against two fungal strains (Aspergillus niger and Aspergillus fumigatus) was evaluated. The results were compared to the activity of ciprofloxacin as a stander. The in-vitro cytotoxic activity of the methanolic extract showed a potent effect against liver (HEPG2) with IC50 values (18.8±7.4 µg/mL) and moderate activity against colon (HCT116) and breast (MCF7) cancer. [ABSTRACT FROM AUTHOR]

Phytochemical investigation on whole plants of C. damayeshu led to the isolation of six tigliane diterpenoids (1 − 6), including two new compounds, 12- O -tiglylporbol-13-isobutyrate-20-tetradecanoate (1) and 12- O -(2-methyl)butyryl-4-deoxy-4 α -phorbol-13-decanoate (2). The structures of these compounds were determined by extensive spectroscopic methods including 1D, 2D NMR, HR-ESI-MS, ECD, and by comparing their NMR data with those of previously reported compounds. All isolated tiglianes (1 – 6) were evaluated for their cytotoxic activities against five human cancer cell lines (including HL-60, A-549, SMMC-7721, MDA-MB-231, and SW-480). Compounds 2 – 4 displayed cytotoxic potential with IC 50 values ranging from 1.99 to 20.57 μM. Particularly, the new tigliane 2 exhibited significant cytotoxicities against all five tested tumor cell lines, HL-60 (IC 50 3.298 ± 0.105 μM), A-549 (IC 50 2.628 ± 0.049 μM), SMMC-7721 (IC 50 2.691 ± 0.027 μM), MDA-MB-231 (IC 50 1.992 ± 0.094 μM), and SW-480 (IC 50 2.890 ± 0.053 μM), and tigliane 4 showed highly selective cytotoxicities against A-549 (IC 50 5.113 ± 0.397 μM). [Display omitted] • Two new tigliane diterpenoids, together with four known ones were isolated from Croton damayeshu. • Their structures were elucidated on the basis of spectroscopic methods. • The new tigliane 2 exhibited significant cytotoxicity with IC 50 values ranging from 1.99 to 3.30 μM. [ABSTRACT FROM AUTHOR]

Two new tigliane- and daphnane-type diterpenoids, given the trivial names daphnegens A–B (1–2) were isolated from the buds of Daphne genkwa. Their structures were assigned on the basis of extensive spectroscopic. The absolute configurations of both compounds were determined by comparison of their calculated and experimental CD curves. In addition, compounds 1–2 were tested for their cytotoxic activities against MCF-7 and HepG-2 human cancer cell lines, and compound 2 showed remarkable cytotoxic activity against HepG-2 cell line with the IC50 value of 11.5 μM. [ABSTRACT FROM AUTHOR]

One monoterpene indole alkaloid, atheruramine (1) bearing an ether bridge linking, one hydrobenzoin derivative, tricalydioloside (2) and two ursane-type triterpenes, atherurosides (A and B) (3 and 4) were isolated from the leaves of Tricalysia atherura, together with eight known compounds. The structures of these new compounds were elucidated on the basis of the results of spectroscopic analysis, and the relative configurations of compounds 1–3 were established by NOE difference. Four of the metabolites were screened in vitro against both chloroquine (CQ)-sensitive (3D7) and -resistant (Dd2) strains of Plasmodium falciparum; they were found to exhibit moderate activity against chloroquine-resistant (Dd2) (IC50 64.99–92.29 μg/mL). Meanwhile, crude extract possesses high antiplasmodial activity against both 3D7 and Dd2 strains of P. falciparum (IC50 4.39–7.54 μg/mL) and high selectivity indices values (SI > 10) and was found to be safe. [ABSTRACT FROM AUTHOR]

Cutaneous melanoma is one of the most aggressive human cancers and is the deadliest form of skin cancer, essentially due to metastases. Novel therapies are always required, since cutaneous melanoma develop resistance to oncogenic pathway inhibition treatment. The Imiqualine family is composed of heterocycles diversely substituted around imidazo[1,2-a]quinoxaline, imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline scaffolds, which display interesting activities on a panel of cancer cell lines, especially melanoma cell lines. We have designed and prepared novel compounds based on the [1,2,4]triazolo[4,3-a]quinoxaline scaffold through a common synthetic route, using 1-chloro-2-hydrazinoquinoxaline and an appropriate aldehyde. Cyclization is ensured by an oxidation-reduction mechanism using chloranil. The substituents on positions 1 and 8 were chosen based on previous structure–activity relationship (SAR) studies conducted within our heterocyclic Imiqualine family. Physicochemical parameters of all compounds have also been predicted. A375 melanoma cell line viability has been evaluated for 16 compounds. Among them, three novel [1,2,4]triazolo[4,3-a]quinoxalines display cytotoxic activities. Compounds 16a and 16b demonstrate relative activities in the micromolar range (respectively, 3158 nM and 3527 nM). Compound 17a shows the best EC50 of the novel series (365 nM), even if EAPB02303 remains the lead of the entire Imiqualine family (3 nM). [ABSTRACT FROM AUTHOR]

From the roots of Euphorbia fischeriana Steud., a new ent-rosane diterpenoid, ebracteolatas D (1), were isolated together with five known ones (2–6). Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. Compound 1 exhibited moderate cytotoxic effects against A549, with IC50 values of 22.03 ± 0.39 μM, respectively. Compound 4 showed antiproliferative activities against HCT-116, A549, and HepG-2 cells with IC50 values of 33.18 ± 0.47 μM, 2.81 ± 0.65 μM, and 27.24 ± 0.41 μM. Moreover, preliminary biological tests showed that compound 1 promoted the apoptosis of the A549 cell line. [ABSTRACT FROM AUTHOR]

Chemical examination of the rice solid fermented cultures of the fungus Penicillium pinophilum J70 isolated from the fresh leaves of Hypericum japonicum Thumb led to the isolation of one new polyketide, namely penioctadecatrienoic A (1), together with two known compounds (2 and 3). The structure of the new metabolite 1 was resolved on the basis of extensive spectroscopic analysis (NMR and HRESIMS data), in association with the modified Mosher's method for the absolute configurational assignment. All isolated metabolites were evaluated for their cytotoxic activity against ECA-109, the anti-inflammatory activity against NO production in lipopolysaccharides (LPS) stimulated RAW264.7 cells, and the antibacterial activity on Staphylococcus aureus ATCC 29213. As a result, compounds 1-3 showed moderately anti-inflammatory effects with the inhibitory rates ranging from 44.5% to 60.7% at the concentration of 20 μM. In addition, compound 1 exhibited weakly antibacterial effect with an MIC value of 32 µg/mL. [ABSTRACT FROM AUTHOR]

The goal of the current study was to synthesize zinc oxide nanoparticles (ZnO-NPs) using ZnCl2.2H2O salt precursor and an aqueous extract of Nephrolepis exaltata (N. exaltata), which act as a capping and reducing agent. N. exaltata plant extract-mediated ZnO-NPs were further characterized by various techniques, such as X-ray diffraction (XRD), scanning electron microscopy (SEM), Fourier transforms infrared spectroscopy (FT-IR), UV-visible (UV-Vis), and energy-dispersive X-ray (EDX) analysis. The nanoscale crystalline phase of ZnO-NPs was analyzed by the XRD patterns. The FT-IR analysis revealed different functional groups of biomolecules involved in the reduction and stabilization of the ZnO-NPs. The light absorption and optical properties of ZnO-NPs were examined by UV-Vis spectroscopy at a wavelength of 380 nm. The spherical shape morphology of ZnO-NPs with mean particle size ranges between 60 and 80 nm was confirmed by SEM images. While the EDX analysis was used to identify the elemental composition of ZnO-NPs. Furthermore, the synthesized ZnO-NPs demonstrate potential antiplatelet activity by inhibiting the platelet aggregation induced by platelet activation factor (PAF) and arachidonic acid (AA). The results showed that synthesized ZnO-NPs were more effective in inhibiting platelet aggregation induced by AA with IC50 (56% and 10 μg/mL) and PAF (63% and 10 μg/mL), respectively. However, the biocompatibility of ZnO-NPs was assessed in human lung cancer cell line (A549) under in vitro conditions. The cytotoxicity of synthesized nanoparticles revealed that cell viability decreased and the IC50 was found to be 46.7% at a concentration of 75 μg/mL. The present work concluded the green synthesis of ZnO-NPs that was achieved by N. exaltata plant extract and showed good antiplatelet and cytotoxic activity, which demonstrates the lack of harmful effects making them more effective for use in pharmaceutical and medical fields to treat thrombotic disorders. [ABSTRACT FROM AUTHOR]

The secondary metabolites of clerodane diterpenoids have been found in several plant species from various families and in other organisms. In this review, we included articles on clerodanes and neo-clerodanes with cytotoxic or anti-inflammatory activity from 2015 to February 2023. A search was conducted in the following databases: PubMed, Google Scholar and Science Direct, using the keywords clerodanes or neo-clerodanes with cytotoxicity or anti-inflammatory activity. In this work, we present studies on these diterpenes with anti-inflammatory effects from 18 species belonging to 7 families and those with cytotoxic activity from 25 species belonging to 9 families. These plants are mostly from the Lamiaceae, Salicaceae, Menispermaceae and Euphorbiaceae families. In summary, clerodane diterpenes have activity against different cell cancer lines. Specific antiproliferative mechanisms related to the wide range of clerodanes known today have been described, since many of these compounds have been identified, some of which we barely know their properties. It is very possible that there are even more compounds than those described today, in such a way that makes it an open field to discover. Furthermore, some diterpenes presented in this review have already-known therapeutic targets, and therefore, their potential adverse effects can be predicted in some way. [ABSTRACT FROM AUTHOR]

Three new sesquiterpenes, colletotrins A−C (1 − 3), were obtained from the liquid culture of endophytic fungus Colletotrichum iris strain S11 The endophytic fungus was isolated from the stem of Euphorbia lathylris collected from Xishuangbanna, Yunnan Province of China. Their structures were elucidated by spectroscopic analysis, including extensive 1D NMR, 2D NMR and HRESIMS techniques. All the sesquiterpenes were tested for their cytotoxicities against five human cancer cell lines. However, no significant activities were detected at concentrations up to 40 μ M. [Display omitted] • Three new sesquiterpenes were isolated from Colletotrichum iris. • Their structures were were elucidated by spectroscopic analysis. • Compounds 1 – 3 were evaluated for their cytotoxicities. [ABSTRACT FROM AUTHOR]

Dalbergia melanoxylon Guill. & Perr (Fabaceae) is widely utilized in the traditional medicine of East Africa, showing effects against a variety of ailments including microbial infections. Phytochemical investigation of the root bark led to the isolation of six previously undescribed prenylated isoflavanones together with eight known secondary metabolites comprising isoflavanoids, neoflavones and an alkyl hydroxylcinnamate. Structures were elucidated based on HR-ESI-MS, 1- and 2-D NMR and ECD spectra. The crude extract and the isolated compounds of D. melanoxylon were tested for their antibacterial, antifungal, anthelmintic and cytotoxic properties, applying established model organisms non-pathogenic to humans. The crude extract exhibited significant antibacterial activity against Gram-positive Bacillus subtilis (97% inhibition at 50 μg/mL) and antifungal activity against the phytopathogens Phytophthora infestans, Botrytis cinerea and Septoria tritici (96, 89 and 73% at 125 μg/mL, respectively). Among the pure compounds tested, kenusanone H and (3R)-tomentosanol B exhibited, in a panel of partially human pathogenic bacteria and fungi, promising antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and Mycobacterium showing MIC values between 0.8 and 6.2 μg/mL. The observed biological effects support the traditional use of D. melanoxylon and warrant detailed investigations of its prenylated isoflavanones as antibacterial lead compounds. [ABSTRACT FROM AUTHOR]

Beauvercin H (1), a new cyclic hexadepsipeptide, and two known ones (2 and 3) were isolated from the EtOH extract of the solid culture of Fusarium sp. Their structures were elucidated by spectroscopic analysis, including extensive 1D and 2D NMR techniques, as well as comparison with literature values. Additionally, compounds 1–3 were tested for their cytotoxic activities. The results showed that all isolated compounds exhibited cytotoxic activities against five human cancer cell lines with IC50 values ranging from 1.379 to 13.12 μM. [ABSTRACT FROM AUTHOR]

A new kavalactone dimer, named kavalactone B (1), and three known compounds, 11-methoxy-5,6-dihydroyangonin (2), methysticin (3), dihydromethysticin (4), were isolated from the leaves of Piper methysticum (kava). Their structures were determined by spectroscopic methods, mainly 1D, 2D NMR, and mass spectrometric data. Primary bioassays showed that compound 2 had very strong cytotoxicity against A549 and NCI-H460 cells with IC50 values of 10.6 and 10.7 μg/mL, respectively, whereas compounds 1, 3, and 4 had very weak cytotoxicity against A549 and NCI-H460 cells. [ABSTRACT FROM AUTHOR]

Two new furanoeremophilane sesquiterpenoids, namely, 6,9-dioxo-1α,4α-dihydroxy-furanoeremophilane (1) and 4α,5α-epoxy-6,9-dioxo-1α-hydroxyl-furanoeremophilane (2), and 10 known compounds were isolated from the whole plant of Chloranthus multistachys, and compound 3 was converted to derivative 3a. Their structures were determined based on extensive spectroscopic analysis. All compounds were evaluated by using five cancer cell lines: PC3, LNcap, A549, K562, and HEL. The derivative 3a exhibited excellent cytotoxic activities, with the IC50 against HEL cells being the lowest at 1.322 ± 0.08 μM, which was comparable to that of the positive control (doxorubicin). Mechanism studies showed that the anticancer activity of 3a may be associated with cell cycle regulation. [ABSTRACT FROM AUTHOR]

• Fourteen compounds were identified from Penicillium sp. DWS853. • The structures were deduced by spectroscopic and quantum chemical methods. • Questin showed cytotoxicity against HCT116 and inhibited its migration/invasion. • The potential target of questin was implied to be DNA topoisomerase II. A total of fourteen compounds, including two previously undescribed depside derivatives penicidepsides A (1) and B (2), three phenyl ether derivatives (3 – 5), three benzophenone derivatives (6 – 8), four anthraquinone derivatives (9 – 12), one flavonoid derivative (13), and one bisnaphthalene derivative (14), were isolated from the solid-state fermentation medium of fungus Penicillium sp. DWS853. The structures of these compounds were determined through comprehensive analysis of UV, HRESIMS, and 1D/2D NMR spectroscopic data, along with quantum-chemical calculations. In vitro bioactivity assays showed that questin (9) exhibits cytotoxicity against human colorectal cancer HCT116 cell line, and can induce apoptosis and inhibit its migration/invasion in a dose-depended manner. The potential target of the active compound was implied to be DNA topoisomerase II, using similarity ensemble search, molecular docking, and quantum chemical calculations. [ABSTRACT FROM AUTHOR]

• Two new ursane-type triterpenoids (1 – 2), were isolated from the syzygium handelii. • Compounds 1 – 3 possess a caffeoyl group at C-27, which is rare for triterpenoids in natural products. • New compounds (1 and 2) showed weak cytotoxicity against HepG2 cells with IC 50 of 81.3 and 72.1 μM, respectively. Two new ursane-type triterpenoids with a rare caffeoyl group at C-27, 3 β -acetoxy-27- trans -caffeoyloxyurs-12-en-28-oic acid-methyl ester (1) and 3 β -acetoxy-27- cis -caffeoyloxyurs-12-en-28-oic acid-methyl ester (2), together with three known triterpenoids (3 – 5), were isolated from the leaves and twigs of Syzygium handelii. Their structures were elucidated by detailed NMR, MS spectroscopic data interpretation, calculated NMR, and DP4+ methods. Anti-microbial and cytotoxic activities of new compounds were evaluated. Compounds 1 and 2 showed weak cytotoxicity against HepG2 cells with IC 50 value of 81.3 and 72.1 μM, respectively. The optimal molecule docking results showed that compounds 1 and 2 could bind stably to COX-2 protein. [ABSTRACT FROM AUTHOR]

Sinningia bullata is a tuberous member of the flowering plant family Gesneriaceae. Prior to this work, the antibacterial, antioxidant, and cytotoxic properties of S. bullata were undetermined. Here, we prepared different extracts from the leaf, stem, and tuber of S. bullata and investigated their pharmacological activities. The leaf extract of S. bullata, obtained by 100% acetone (Sb-L-A), had the highest total flavonoid content, antioxidation capacity, and cytotoxic and antibacterial activities. Sb-L-A displayed a broad range of antibacterial activities against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The inhibition zones of Sb-L-A ranged from 8 to 30 mm and were in the following order: S. aureus > E. coli > P. aeruginosa. Incubation of B16F10 melanoma cells with Sb-L-A at a concentration of 80 μg/mL caused deaths at the rate of 96%, reduced migration by 100%, suppressed proliferation and colony formation by 99%, and induced apoptosis, which was observed in 96% of the B16F10 cells. In addition, the cytotoxic activities of Sb-L-A were synergistically enhanced when coacting with the antitumor drug epothilone B. Sb-L-A was also used to determine the cytotoxic effects against 4T1 mammary carcinoma cells. Sb-L-A of 60 μg/mL boosted the distribution of the G2 phase from 1.4% to 24.4% in the B16F10 cells. Accordingly, Sb-L-A might suppress melanoma cell proliferation by inducing G2 cell-cycle arrest. The most abundant compounds in Sb-L-A were identified using gas chromatography–mass spectrometry. The top two contents in this extract were adlupulone and villosin. Overall, the collective data in this study may indicate the pharmacological potentials of Sb-L-A for possible medical applications. [ABSTRACT FROM AUTHOR]

As a part of our ongoing studies on cytotoxic triterpenoids from the genus Bupleurum , a 70 % ethanol extract of Bupleurum scorzonerifolium Willd. was systematically separated by silica gel column chromatography, HP-20 macroporous resin column chromatography, ODS column chromatography and HPLC, 15 triterpenoids were obtained, of which two were new compounds. Their structures were elucidated by 1D and 2D NMR, HR-ESI-MS, and other spectroscopic methods. Additionally, these compounds were evaluated for their cytotoxic activities against four selected cancer cell lines using the MTT assay. Some of the isolated compounds exhibited appreciable cytotoxic activities against these four human cancer cell lines. [Display omitted] • 15 triterpenoids saponins were isolated from the roots of Bupleurum scorzonerifolium Willd. (Apiaceae). • Two new compounds were elucidated by spectroscopic methods. • The cytotoxicity of all isolates were assessed against four cancer cell lines via the MTT assay. • Five saponins (1, 6, 8, 11 and 12) exhibited significant cytotoxicity. [ABSTRACT FROM AUTHOR]

In this study, effective and environmentally friendly methods were used to achieve the synthesis of silver nanoparticles (Ag NPs) by an aqueous plant extract. The Ag NPs were synthesized via Zingiber officinale plant extract that acted as a reducing and stabilizing agent. Various techniques, including UV-Visible spectroscopy (UV-Vis), X-ray diffraction pattern (XRD), Fourier transform infrared spectroscopy (FT-IR), and scanning electron microscopy (SEM) were used. The plant extract treated with silver nitrate solution at room temperature (27 ± 20) resulted in the successful synthesis of the Ag NPs, that were confirmed by UV-Vis spectroscopy. The crystalline morphology and size of the nanoparticles were calculated using Scherrer equation, that specify a face-centered cubic (fcc) crystalline structure with size ranges as 16 nm. The spherical geometry of Ag NPs was confirmed from scanning electron microscopy. FT-IR study validates the existence of several functional groups of active biomolecules such as -OH, C-O, C=C, C-O-C, and N-H that act as a reducing and capping agent for the synthesis of Ag NPs and were found in the extract. The synthesized Ag NPs were used to evaluated antimicrobial activity against different bacterial and fungal strains. The Zingiber officinale-Ag NPs exhibited maximum zone of inhibition against Staphylococcus aureus bacterial strain which were 17.8 ± 0.03 mm, and Fusarium graminium fungal strain showed 11.0 ± 0.01 mm at 80 µg/mL concentrations, respectively. Furthermore, the Ag NPs were considered to be a significant anti-asthma agent that decreased the white blood cells (WBC), eosinophils (EOS) in blood level, and wet/dry (W/D) weight proportion of the lung at 24 µg/g/day. The cytotoxicity of synthesized nanoparticles shows that the concentration under 90 µg/mL were biologically compatible. [ABSTRACT FROM AUTHOR]

A new triterpenoid saponin, 3-O-β-D-allopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl (1→4)-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl ester (IV), together with six known ones Hederacholichiside F (I), Tanguticoside B (II), Tauroside St-H1 (III), Hederoside H1 (V), Kalopanaxsaponin G (VI), Hederasaponin B (VII) were separated from Clematis tangutica (Maxim.) Korsh. Their cytotoxic activities were evaluated. Saponins IV (new compound) and I showed selective inhibitory activities against HGC-27 with IC50 values of 20.17 and 66.18 μM. Saponin VII exhibited extensive inhibitory action against HGC-27, Hela and SK-OV-3 with IC50 values of 16.47-71.36 μM. Saponin III showed selective inhibitory activity against SK-OV-3 with the IC50 value of 48.70 μM. All isolated saponins were inactive (IC50 >150 μM) to GES-1. [ABSTRACT FROM AUTHOR]

The chemical constituents of the methanolic extract of Emex spinosa shoots were primarily characterized by gas-chromatography-mass spectrometry analysis (GC-MS), forty components were identified. The major components were ethyl 2-hydroxycyclohexane-1-carboxylate (10.11%), 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (38.09%), 2-propyltetrahydro-2H-pyran-3-ol (5.75%), oleic acid (8.02%), and methyl (E)-octadec-16-enoate (5.91%). The results of antioxidant activity of leaves extract presented the most potent activity (IC50 = 29.92 mg mL-1), followed by stem extract (IC50 = 41.17 mg mL-1), and root extract (IC50 = 50.14 mg mL-1), comparable to that of the standard ascorbic acid (IC50 = 13.3 mg mL-1). The antibacterial results revealed that leaves extract is the most potent (22.0 mm) antibacterial agent against the variety of the tested species. Stem and leaves extracts are more potent (20 and 20 mm, respectively) than azithromycin (13.0 mm) against Pseudomonas aeruginosa species, while root and leaves extracts displayed potent antibacterial activities than tetracycline (10 mm). The most potent activity was recorded for leaves extract against Bacillus cereus species (22.0 mm) higher than the standard antibiotics (5.0-20.0 mm). The cytotoxic activity of E. spinosa MeOH extract specified the EC50 value at 2.68 µg mL-1 attended by a cytotoxic effect on HepG2 cell lines with the effective dose of the plant extract at a higher concentration. [ABSTRACT FROM AUTHOR]

Bioassay-guided fractionation of dichloromethane extract from Athenaea velutina leaves led to the isolation of three withanolides, all being reported for the first time in this species. They were identified as withacnistin (1), withacnistin acetate (2) and a new withanolide, designated as withalutin (3). The structures were established by spectral data analysis, including MS, 1D and 2D NMR. In addition, in silico ADMET studies were employed to understand the pharmacokinetic properties of these withanolides. The withanolides isolated from A. velutina reduced cancer cell viability with IC50 values ranging from 1.52 to 5.39 µM. In silico prediction revealed that withanolides have good gastrointestinal absorption or oral bioavailability properties; and are not likely to be mutagenic or hepatotoxic. These findings revealed that A. velutina is an important source of cytotoxic withanolides. [ABSTRACT FROM AUTHOR]

Fourteen phenolic derivatives including two new compounds (1, 2), one new natural product (10) and eleven known ones (3 - 9 and 11–14) were obtained from the roots of Fallopia multiflora var. ciliinervis. The structures were determined using IR, MS, 1D and 2D NMR spectroscopy and the absolute configuration of the new structure (2) was deduced by ECD experiments. All of the isolated compounds were assayed for their cytotoxic activities against three tumor cell lines (A549, HCT116 and SW620) and the results showed that compounds 12－14 showed cytotoxicities against A549 cells while compounds 10 and 11 showed cytotoxicities against SW620 cells. [Display omitted] • Two new compounds (1−2) and one new natural product (3) were isolated from the roots of Fallopia multiflora var. ciliinervis. • The absolute configuration of the compound 2 was elucidated by ECD experiments. • Compound 11 showed moderate activities against SW620 cells. [ABSTRACT FROM AUTHOR]