Flavanones from the Twigs and Barks of Artocarpus lakoocha Having Antiplasmodial and Anti-TB Activities.

Chromatographic separation of the acetone extracts from the twigs and barks of Artocarpus lakoocha led to the isolation of the one new flavanone, lakoochanone (1), together with eleven known compounds (2-12). Lakoochanone (1) and moracin C (4) exhibited weak antiplasmodial activity against Plasmodium falciparum Dd2 with IC50 values of 36.7 and 33.9 µM, respectively. Moreover, moracin C (4) and sanggenofuran B (5) showed cytotoxic activity against A2780 cell line with the respective IC50 values of 15.0 and 57.1 µM. In addition, cyclocommunin (7) displayed strong antimycobacterial activity against Mycobacterium tuberculosis H37Ra with the minimum inhibitory concentration (MIC) value of 12.3 µM.

Antimalarial Oxoprotoberberine Alkaloids from the Leaves of Miliusa cuneata.

Five new oxoprotoberberine alkaloids, miliusacunines A-E (1-5), along with nine known compounds, 6-14, were isolated from an acetone extract of the leaves and twigs of Miliusa cuneata. Their structures were elucidated by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicities against the KB and Vero cell lines and for antimalarial activities against the Plasmodium falciparum strains TM4 and K1 (a sensitive and a multi-drug-resistant strain, respectively). Compound 1 showed in vitro antimalarial activity against the TM4 strain, with an IC50 value of 19.3 ± 3.4 µM, and compound 2 demonstrated significant activity against the K1 strain, with an IC50 value of 10.8 ± 4.1 µM. Both compounds showed no discernible cytotoxicity to the Vero cell line at the concentration levels evaluated.

The anti-leukemic activity of a luteolin-apigenin enriched fraction from an edible and ethnomedicinal plant, Elsholtzia stachyodes, is exerted through an ER stress/autophagy/cell cycle arrest/ apoptotic cell death signaling axis.

BACKGROUND: Elsholtzia is a genus in the family Lamiaceae, and some species in this genus are commonly used for food and in ethnomedicinal formulations by some ethnic groups of China and Thailand. Despite their apparent utility, few studies have been conducted to evaluate their potential as sources of medicinally active agents. PURPOSE: We aimed to investigate the cytotoxicity of ethanolic extracts from three selected edible plant species of the genus Elsholtzia and the most promising extract was further characterized for the bioactive constituents and signaling mechanisms associated with the anti-leukemic activity. MATERIALS AND METHODS: Ethanolic extracts were screened for cytotoxicity using flow cytometry. HPLC and LC-MS were used to analyze the chemical constituents of the most potent fraction from E. stachyodes. The relevant mechanism of action was assessed by western blot and multispectral imaging flow cytometry (MIFC). RESULTS: The most potent anti-leukemic activity was observed with the ethanolic extract from E. stachyodes. Luteolin and apigenin were characterized as the major constituents in the fraction from E. stachyodes. Mechanistically, the luteolin-apigenin enriched fraction (LAEF) induced the UPR, increased autophagic flux, induced cell cycle arrest and apoptotic cell death. LAEF showed significantly less cytotoxicity towards peripheral blood mononuclear cells (PBMCs) as compared to leukemia cell lines. CONCLUSION: This study is the first to report E. stachyodes as a new source of luteolin and apigenin which are capable of triggering leukemic cell death. This could lead to a novel strategy against leukemia using ethnomedicinal plant extracts as an alternative or supplemental anti-cancer agent.

Limonoids and carbazole alkaloids from the twigs of Chalcas siamensis Tanaka.

One new limonoid, named siamensinolide (1), together with two known limonoids (2 and 3) and eight carbazole alkaloids (4-11) were isolated from the twigs of Chalcas siamensis Tanaka. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopy. O-methylclausenolide (2) displayed strong cytotoxicity against A2780 cell lines with the IC50 value of 9.2 µM, while clausenolide (3) exhibited strong antibacterial activity against methicillin-resistant Staphylococcus aureus with the MIC value of 0.5 µg/mL.

Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154.

Three new sesquiterpenes, named aspergillusenes A and B and (+)-(7S)-7-O-methylsydonic acid, and two new hydrogenated xanthone derivatives, named aspergillusones A and B, were isolated from the sea fan-derived fungus Aspergillus sydowii PSU-F154 together with 10 known compounds. Their structures were identified on the basis of spectroscopic data. The isolated compounds were evaluated for their antioxidant activity.

Anthraquinone, cyclopentanone, and naphthoquinone derivatives from the sea fan-derived fungi Fusarium spp. PSU-F14 and PSU-F135.

Five new metabolites, fusaranthraquinone (1), fusarnaphthoquinones A-C (2-4), and fusarone (5), were isolated from the sea fan-derived fungi Fusarium spp. PSU-F14 and PSU-F135 along with 18 known compounds. The structures were elucidated on the basis of spectroscopic evidence. Their antibacterial, antifungal, antimycobacterial, antimalarial, and cytotoxic activities were examined.

Pyrone derivatives from the marine-derived fungus Nigrospora sp. PSU-F18.

Pyrones, named nigrosporapyrones A-D (1-4), and five known compounds were isolated from the marine-derived fungus Nigrospora PSU-F18. Their structures were elucidated on the basis of spectroscopic evidence. The antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.

Lactone derivatives from the marine-derived fungus Penicillium sp. PSU-F44.

Two new fungal metabolites, penicipyrone (1), and penicilactone (2), were isolated from the marine-derived fungus Penicillium sp. PSU-F44 along with three known macrolides, (+)-brefeldin A (3), (+)-brefeldin C (4), and 7-oxobrefeldin A (5). Their antimicrobial activities against methicillin-resistant Staphylococcus aureus SK1 and Microsporum gypseum SH-MU-4 were examined.

Epoxydons and a pyrone from the marine-derived fungus Nigrospora sp. PSU-F5.

Nigrospoxydons A-C (1- 3) and nigrosporapyrone (4), four new metabolites, were isolated from the marine-derived fungus Nigrospora sp. PSU-F5 together with nine known compounds. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopic techniques. The antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.

A new benzoquinone derivative from the leaves of Garcinia parvifolia.

Parvifoliquinone (1) was isolated from the leaves of Garcinia parvifolia together with six known compounds: parvifoliols B (2), C (3), E (4), garcidepsidone B (5), nigrolineaisoflavone A (6), and mangostinone (7). The structures were elucidated by spectral analyses. Their antibacterial activity against methicillin-resistant Staphylococcus aureus was evaluated.

Naphthoquinones from the leaves of Rhinacanthus nasutus having acetylcholinesterase inhibitory and cytotoxic activities.

Four new naphthoquinones (1-4), named rhinacanthins S (1), T (2), U (3) and V (4), together with 13 known naphthoquinones were isolated from the leaf extract of Rhinacanthus nasutus. The structures of isolated compounds were elucidated by spectroscopic methods, especially 1D and 2D NMR spectroscopy and mass spectrometry. Rhinacanthin S (1) exhibited acetylcholinesterase inhibition activity with a % inhibition value of 48.04±3.25. The known rhinacanthin A (5) showed cytotoxicity against a MCF-7 cell line with an IC50 value of 8.79µM, while rhinacanthin N (15) was active against the NCI-H187 cell line with an IC50=2.24µM and Vero cells (IC50=3.00µM).

Cytotoxic and Antimalarial Alkaloids from the Twigs of Dasymaschalon obtusipetalum.

One new p-quinonoid aporphine alkaloid, obtusipetadione (1), and eleven known compounds (2-12) were isolated from the acetone extract of the twigs of Dasymaschalon obtusipetalum. Their structures were elucidated by spectroscopic methods. The cytotoxic and antimalarial activities of the isolated compounds were evaluated. Compound 1 showed significant in vitro antiplasmodial activity against the P. falciparum strains TM4 and K1 (multidrug resistant strain) with IC50 values of 2.46 ± 0.12 and 1.38 ± 0.99 µg/mL, respectively with no cytotoxicity. Compound 9 had more modest antiplasmodial activity, but significant cytotoxicity.

Antibacterial tetraoxygenated xanthones from the immature fruits of Garcinia cowa.

A phytochemical investigation of the acetone extract from the immature fruits of Garcinia cowa led to the isolation of two novel tetraoxygenated xanthones, garcicowanones A (1) and B (2), together with eight known tetraoxygeanted xanthones. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their antibacterial activity against Bacillus cereus TISTR 688, Bacillus subtilis TISTR 008, Micrococcus luteus TISTR 884, Staphylococcus aureus TISTR 1466, Escherichia coli TISTR 780, Pseudomonas aeruginosa TISTR 781, Salmonella typhimurium TISTR 292 and Staphylococcus epidermidis ATCC 12228. α-Mangostin showed potent activity (MIC 0.25-1 µg/mL) against three Gram-positive strains and garcicowanone A and ß-mangostin exhibited strong antibacterial activity against B. cereus with the same MIC values of 0.25 µg/mL.

Benzophenone and xanthone derivatives from the inflorescences of Garcinia cowa.

The purification of the acetone extract from the inflorescences of Garcinia cowa led to the isolation of a new benzophenone derivative, cowanone (1), together with seven known xanthones, α-mangostin (2), ß-mangostin (3), cowanin (4), fuscaxanthone A (5), 9-hydroxycalabaxanthone (6), garcinianone A (7) and cowanol (8). The structures of the isolated compounds were elucidated by analysis of their spectroscopic data including 1D and 2D NMR data. All isolated compounds were evaluated for their antibacterial activities against Staphylococcus aureus (SA) and methicillin-resistant S. aureus (MRSA).

Modiolide and pyrone derivatives from the sea fan-derived fungus Curvularia sp. PSU-F22.

Investigation of secondary metabolites from the sea fan-derived fungus Curvularia sp. PSU-F22 resulted in isolation of three new metabolites, curvulapyrone (1), curvulalide (2) and curvulalic acid (3) together with six known compounds, modiolides A (4) and B (5), pyrenolide A (6), stagonolide E (7), mycoepoxydiene (8), and deacetylmycoepoxydiene (9). Their antimicrobial activity against Staphylococcus aureus ATCC 25923, methicillin-resistant S. aureus and Microsporum gypseum SH-MU-4 were examined.