A new monosesquiterpene diacetylgliocladic acid (1), a new dimeric sesquiterpene divirensol H (9), and two exceptionally novel trimeric sesquiterpene trivirensols A and B (11 and 12), together with another eight known congeners, were purified from an endophytic fungus Trichoderma virens FY06, derived from Litchi chinensis Sonn. whose fruit is a delicious and popular food. All of them were identified by comprehensive spectroscopic analysis, combined with biosynthetic considerations. Trivirensols A and B are unprecedented trimers of which three subunits are connected by two ester bonds of the sesquiterpene class. Relative to the positive control triadimefon, all the tested metabolites showed strong inhibitory activities against at least one phytopathogenic fungus among Penicillium italicum, Fusarium oxysporum, Fusarium graminearum, Colletotrichum musae, and Colletotrictum gloeosporioides. Notably, as metabolites of the endophytic fungus from L. chinensis, they all presented strong antifungal activities against C. gloeosporioides which causes anthracnose in L. chinensis.
Two novel cyclic hexadepsipeptides, fusarihexin A (1: ) and fusarihexin B (2: ), and two known compounds, cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Val) (3: ) and cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Ile) (4: ), were isolated from the marine mangrove endophytic fungus sp. R5. Their chemical structures were elucidated on the basis of spectroscopic data and Marfey's analysis. In an bioassay, fusarihexin A (1: ) remarkably inhibited three plant pathogenic fungi: (Penz.) Sacc., which causes anthracnose in many fruits and vegetables, (Berk. and M. A. Curtis) Arx, which causes crown rot and anthracnose in bananas, and Schlecht. f. sp. lycopersici (Sacc.) W. C. Snyder et H. N. Hansen, which causes Fusarium wilt and fruit rot in tomatoes. Fusarihexin B (2: ) strongly inhibited and . The compounds were more potent than carbendazim, which is widely used as an agricultural and horticultural fungicide worldwide.
Five
new carotane sesquiterpenoids (asperalacids A–E (1–5)), one new tricyclic sesquiterpenoid
(4-hydroxy-5(6)-dihydroterrecyclic acid A (6)), and two
known analogues (7–8) were obtained
from a seagrass-derived fungus Aspergillus alabamensis, which was speculated to be a phytopathogenic fungus, isolated from
the necrotic leaves of Enhalus acoroides. The structures of 1–6 were established
by a combination of spectroscopic methods, including comprehensive
NMR analysis, mass spectrometry, conformational analysis, NMR computational
methods, and ECD calculations. Compound 4, with higher
inhibitory activity on wheat (Triticum aestivum L.) root and shoot elongation than the positive control terbutryn,
a broad-spectrum systemic herbicide, is a new natural plant growth
inhibitor. Compound 5, belonging to the rare glycosylated
sesquiterpenoid class, represents the first example of glycosylated
carotane sesquiterpenoid whose sugar moiety was identified as α-d-glucose. Compounds 1–4 and 6 displayed weak to potent antimicrobial activity against
the plant pathogenic fungi Fusarium oxysporum, Fusarium graminearum, and Penicillium italicum and the Gram-positive bacteria Bacillus subtilis and Staphylococcus
aureus.
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