Resorcylic Acid Lactones Produced by an Endophytic Penicillium ochrochloron Strain from Kadsura angustifolia.

Four new ß-resorcylic acid lactones, including penochrochlactone A (2: ), 4-O-desmethyl-aigialomycin B (4: ), and penochrochlactones C and D (5: and 6: ), two compounds isolated from a natural source for the first time, 5α, 6ß-acetonide-aigialomycin B (1: ) and penochrochlactone B (3: ), together with six known compounds, aigialomycin F (7: ), aigialomycins A, B, and D (8: -10: ), zeaenol (11: ), and oxozeaenol (12: ), were isolated from a mycelial solid culture of the endophytic fungus Penicillium ochrochloron SWUKD4.1850 from the medicinal plant Kadsura angustifolia by sequential purification over silica gel, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by extensive spectroscopic analysis and chemical conversions. In addition, all the new compounds were evaluated for their cytotoxic and antibacterial activities in vitro. Penochrochlactone C (5: ) displayed moderate cytotoxicity against the HeLa tumor cell line with an IC50 value of 9.70 µM. In the antibacterial assays, compounds 4:  - 6: exhibited moderate activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa with MIC values between 9.7 and 32.0 µg/mL.

Secondary metabolites of plants from the genus chloranthus: chemistry and biological activities.

Chloranthus, a genus of the family Chloranthaceae, which is mainly distributed in eastern and southern Asia, has been used in Chinese folk medicine due to its antitumor, antifungal, and anti-inflammatory activities. This review compiles the research on isolation, structure elucidation, structural diversity, and bioactivities of Chloranthus secondary metabolites reported between 2007 and 2013. The metabolites listed encompass 82 sesquiterpenoids, 50 dimeric sesquiterpenoids, 15 diterpenoids, one coumarin, and five other compounds. Among them, dimeric sesquiterpenoids, the characteristic components of plants from the genus Chloranthus, have attracted considerable attention due to their complex structures and significant biological features, e.g., antitumor, antibacterial, antifungal, anti-inflammatory, and hepatoprotective activities, and potent and selective inhibition of the delayed rectifier (IK) K(+) current and tyrosinase.

Microbiological transformation of the triterpene nigranoic acid by the freshwater fungus Dictyosporium heptasporum.

The microbiological transformation of the triterpene nigranoic acid (3,4-secocycloarta-4(28),24(Z)-diene-3,26-dioic acid) (1) to 3,4-secocycloarta-4(28),17(20),24(Z)-triene-7ß-hydroxy-16ß,26-lactone-3-oic acid (2) and 3,4-secocycloarta-4(28),17(20)(Z),24(Z)-triene-7ß-hydroxy-16ß-methoxy-3,26-dioic acid (3) by the freshwater fungus Dictyosporium heptasporum YMF1.01213 has been demonstrated. The structures of the biotransformation products were determined by spectroscopic and MS analyses. Compound 2, characterized by the presence of a formed C-16/C-26 ester bridge, provided a novel nine-membered lactone ring structural skeleton for 3,4-secocycloartane triterpenoid derivatives. In addition, Compounds 1-3 exhibited weak anti-HIV activity in vitro. Compounds 2 and 3 were reported for the first time as natural product derivatives.

Compounds from Kadsura angustifolia with anti-HIV activity.

Four new cycloartane triterpenoids, angustific acid A (1), angustific acid B (2), angustifodilactone A (3) and angustifodilactone B (4) were isolated from the branches of Kadsura angustifolia together with six known compounds, micranoic acid B (5), nigranoic acid (6), schisandrin (7), schisantherin D (8), interiotherin B (9), schisantherin B (10). Their structures were established on the basis of extensive spectroscopic data analyses and comparison with spectroscopic data reported. Compound 1, characterized by the presence of a C-16/C-17, C-20/C-21 conjugated diene and a C-1/C-7 ester bridge formed in rings A and B, provided a novel structural skeleton for 3,4-secocycloartane triterpenoid derivatives. In addition, the anti-HIV activities of these compounds were determined in infected C8166 cells, and it was found that angustific acid A (1) exhibited the most potent anti-HIV activity with an EC(50) value of 6.1 µg/mL and a therapeutic index of more than 32.8.

Two unusual naphthalene-containing compounds from a freshwater fungus YMF 1.01029.

Two novel naphthalene-containing compounds, colelomycerones A and B (1 and 2, resp.), and three known metabolites, including preussomerin D (3), (2RS,2'SR,3'E,3SR,4E,8E)-1-O-(beta-D-glucopyranosyl)-3-hydroxy-2-[(2-hydroxyoctadec-3-enoyl)amino]-9-methyloctadeca-4,8-diene (4), and 3beta-hydroxy-5alpha,8alpha-epidioxyergosta-6,22-diene (5), were isolated from the culture broth of an unidentified freshwater water fungus YMF 1.01029. This fungus was collected from a decaying branch of an unidentified tree near Lake Fuxian in Yunnan Province, China. The structures of these five compounds were determined on the basis of their spectroscopic and mass-spectrometric data. Colelomycerones A and B (1 and 2, resp.) represent unprecendented examples of naphthalene-1,2-diones with novel cyclic acetals. Compounds 1-3 showed noticeable antifungal and antibacterial activities.

Ymf 1029A-E, preussomerin analogues from the fresh-water-derived fungus YMF 1.01029.

Five new preussomerin analogues, ymf 1029A (1), B (2), C (3), D (4), and E (5), were isolated from the liquid cultures of an unidentified freshwater fungus YMF 1.01029, along with four known compounds, preussomerin C (6), preussomerin D (7), (4RS)-4,8-dihydroxy-3,4-dihydronaphthalen-1(2H)-one (8), and 4,6,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one (9). The structures of new metabolites were determined by analysis of NMR and MS data and by analogy with the data for the known bis-spirobisnaphthalene preussomerins. In vitro immersion experiments showed that these metabolites displayed weak nematicidal activity against Bursaphelenchus xylophilus, while compound 7 was the most potent. This is the first report of these compounds, which antagonize the Bursaphelenchus xylophilus nematode.

Hydroxylation of the triterpenoid nigranoic acid by the fungus Gliocladium roseum YMF1.00133.

The ability of the fungus Gliocladium roseum YMF1.00133 to transform the bioactive nigranoic acid (=(24Z)-9,19-cyclo-3,4-secolanosta-4(28),24-diene-3,26-dioic acid) was investigated. Three new products from the co-cultures of nigranoic acid and G. roseum YMF1.00133 were obtained by employing a combination of Sephadex LH-20 and silica-gel column chromatography. The major metabolite was identified as 15beta-hydroxynigranoic acid, and the minor metabolites as 6alpha,15beta-dihydroxynigranoic acid and 7beta,15beta-dihydroxynigranoic acid by mass spectrometry and NMR spectroscopy. This is the first report of the biotransformation of the A-ring-secocycloartene triterpenoid, nigranoic acid.