| The chemical constituents and their bioactivities of four endophytic fungi isolated from Melia azedarach, two actinomycetes of animal origin and one higher fungus were studied. 121 compounds were obtained from the cultures of the microbial materials. Among them, the structures of 97 products were established on the basis of extensive spectroscopic analyses including 1D- and 2D NMR (1H-1H COSY, TOCSY, HSQC, HMBC, and NOESY) experiments, as well as chemical degradations and X-ray crystallography. The results are concluded as follows:1. Fusaroside (1), a unique trehalose-containing glycolipid composed of the 4-hydroxyl group of a trehalose unit attached to the carboxylic carbon of a long-chain fatty acid, was isolated from the organic extract of fermentation broths of an endophytic fungus, Fusarium sp. LN-11 isolated from the leaves of Melia azedarach. Nine known compounds, phalluside-1 (2), (9R*,10R*,7E)-6,9,10-trihydroxyoctadec-7-enoic acid (3), porrigenic acid (4), (9Z)-2,3-dihydroxypropyl octadeca-9-enoate (5), cerevisterol (6), ergokonin B (7), ergosterol peroxide (8), 22E,24S)-24-methyl-5α-cholesta-7,22-diene-3β, 5α, 6β, 9α- tetraol (9), 4’,5,7-Trihydroxyisoflavone (10), were also isolated from this fungus. The metabolites 1-5 were shown to be moderate to weak active toward brine shrimp larvae at a concentration of 10μg·mL-1 with mortality rates of 47.6%, 64.8%, 26.2%, 20.9% and 18.7%, respectively.2. A new isocoumarin derivative named fusariumin (1), together with 11 known metabolites Aigialomycins D (2), Pochonin N (3), Asperamides B (4), Cerebroside B (5), ergosterol (6), ergosta-7,22-dien-3β-ol (7), ergosterol peroxide (8), ergokonin B (9), cerevisterol (10), 3β,5α,9α-trihydroxy-6β-methoxyergosta-7,22-dien (11), cyclosporin A (12), has been isolated from the cultures of Fusarium sp. LN-10, an endophytic fungus originated from the leaves of Melia azedarach. Compounds 1–3 displayed significant growth inhibitory activity against the brine shrimp (Artemia salina) at a concentration of 10μg·mL-1 with mortality rates of 78.2%、76.7% and 82.8%, respectively.3. A novel quaternary isoquinoline alkaloid 4-methyl-3-isobutyl -2-hydroxyethyl-7 -carboxyl-6,8-dihydroxyisoquinoline (1), and a new azaphilones derivative named fusarone (2), combine with 12 known compounds 4-hydroxy-phenylethyl alcohol (3), cinnamic acid (4), p-hydroxypenylpropionic acid (5), fusaric acid (6), 9,10-dehydrofusaric acid (7), ergosterol (8), ergosterol peroxide (9), Ergosta-7, 22-dien-6β-methoxy-3β,5α-diol (10), ergosta-4,6,8(14),22-tetraen-3-one (11), 25-hydroxy-ergosta-4,6,8(14),22-tetraen-3-one (12), and beauvericin (13), has been isolated from the cultures of Fusarium sp. LN-12, an endophytic fungus originated from the leaves of Melia azedarach. The metabolite 1 was found to be inactive in the agar diffusion test at a concentration of 40μg/paper disk against Escherichia coli, Bacillus subtilis, Streptomyces viridochromogenes, Staphylococcus aureus, Candida albicans, Mucor miehei, and brine shrimps (Artemia salina). The absolute configuration of fusarone (2) was established by means of TDDFT calculations of electronic CD spectrum and comparison with the experimental one.4. 13 known compounds ergosterol (1), ergosterol peroxide (2), ergosta-4,6,8(14), 22- tetraen-3-one (3), H1-A (4), 3β, 15β-dihydroxyl-(22E, 24R)-ergosta-5, 8(14), 22-trien-7-one (5), 3β, 15α-dihydroxyl-(22E, 24R)-ergosta-5, 8(14), 22-trien-7-one (6), (3β, 5α, 6β, 22E)-6-methoxyergosta-7, 22-diene-3, 5-diol (7), (22E)-24-ethyl-4α-methyl-5α-cholest-22-en -3β-ol (8), allantoin (9), indole-3- carboxylic acid (10), Tenuazonic acid (11), Cerebroside A (12), and Cerebroside C (13), have been obtanied from the cultures of Fusarium sp. LN-12, an endophytic fungus originated from the leaves of Melia azedarach.5. A new rare 20-membered macrocyclic lactam incorporating a diene conjugated olefin, designated sannastatin (1), together with 13 known compounds Vicenistatin (2), Vicenistatin M (3), stigmast-5-en-3-O-β-D-glucopyranoside (4), thymidine (5), 7,8-dimethylalloxazine (6), uracil (7), 3-methyl-2,5-piperazinedione (8), pyrrole-2-carboxylic acid (9), p-hydroxybenzonic acid (10), anthranilic acid (11), indole-3- carboxylic acid (12), Ethanone (13), Indole-3-lactic acid (14), has been isolated from the culturesof Streptomyces sannanensis, a bacteria found in the feces of Ailuropoda melanoleuca. Compounds 1–3 displayed significant growth inhibitory activity against the brine shrimp (Artemia salina) at a concentration of 10μg·mL-1 with mortality rates of 82.4%, 89.8% and 72.9%, respectively.6. 17 identified compounds Emodin (1), Aloeemodin (2), Chrysophanol (3), Clarithromycin (4), 7,4′-dihydroxyisoflavone (5), genistein (6), 3,4,5-Trihydroxy benzoic acid (7), 4-methyl-2,6-dihydroxybenzaldehyde (8), 2-Hydroxyphenyl-acetamide (9), uracil (10), thymine (11), E-1-(4’-hydroxyphenyl)-buten-3-one (12), N-[2-(4-hydroxy-phenyl)ethyl] acetamide (13),β-carboline (14), 1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid (15), Arbutin (16), and 3-sec-butyl-6-isopropylpiperazine-2,5-dione (17), have been isolated from the cultures of Streptomyces SP. YIM100520, a bacteria found in the feces of Taurdragus oryx. 7. A new highly oxygenated lanostane triterpene, designated ganodermacetal (1), together with 17 related known compounds, Methyl ganoderate C (2), Ganoderic acid P (3), Ganoderic acid DM (4), 15-Hydroxy-ganoderic acid S (5), 3β,15α,22-trihydroxylanosta-7,9 (11),24-trien-26-oic acid (6) (22E,24S)-24-methyl-5α-cholesta-7,22-diene-3β,5α,6β,9α-tetraol (7), Cerevisterol (8), Methyl ganoderate E (9), Ganodermanontriol (10), Ganoderic acid D (11), Ganoderic acid H (12), Ganodermatriol (13), Ganoderiol F (14), Methyl ganoderate B (15), Ganoderic acid H (16), lanosta-7,9( 11), 24-trien-3β,15α,22β-triacetoxy -26-oic acid (17), and Ganoderic acid N (18), has been isolated from the fruiting bodies of the basidiomycetous fungus Ganoderma amboinense. Ganodermacetal (1) possesses an uncommon 7,15-acetonide unit. Among the test compounds, only compounds 1, 2, 8, 12, 14, and 15 showed moderate to strong toxicity toward the brine shrimp larvae at a concentration of 10μg·mL-1 with mortality rates of 70.3 %, 75.8 %, 91.5 %, 81.8 %, 45.7% and 29.8%, respectively. |
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