Fusaroside, a unique glycolipid from Fusarium sp., an endophytic fungus isolated from Melia azedarach

Abstract

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. Six known compounds, phalluside (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) and ergokonin B (7), were also isolated from this fungus. The glycolipid contains a rare branched long-chain fatty acid (C(20:4)) with a conjugated diene moiety and a conjugated ketone moiety. The structure of the new compound 1 was elucidated by spectroscopic methods (1D and 2D NMR experiments, MS) and chemical degradations. The metabolites 1-5 were shown to have moderate to weak active against the brine shrimp larvae. To our knowledge, this is the first report of isolation of the first representative of a new family of glycolipids from natural sources.

Three cyclic pentapeptides and a cyclic lipopeptide produced by endophytic Fusarium decemcellulare LG53

“…Notably, a plethora of plants residing in varied ecological niches harbor Fusarium species exhibiting an endophytic lifestyle and concomitantly, providing certain ecological tness benets. For instance, on the one hand, the plant Melia azedarach was shown to harbor different endophytic Fusarium species capable of producing fusariumin, 14 fusarimine, 15 fusaroside, 16 fusarone, 17 and other bioactive compounds unrelated to the host plant with plausible implications in aiding the host chemical defense. On the other hand, an endophytic strain of F. solani inhabiting the Chinese medicinal plant Camptotheca acuminata was shown to be capable of biosynthesizing the important anticancer compound camptothecin, also produced by the host plant, by means of a plant-endophyte cross-species biosynthetic pathway.…”

Chaetoglobosin Vb from Endophytic Chaetomium Globosum: Absolute Configuration of Chaetoglobosins

“…7,8 Endophytic fungi have been proven to be a rich source of novel structural compounds with interesting biological activities and a high level of biodiversity. [9][10][11] In our continuing search for novel bioactive metabolites from plant-derived endophytic fungi, [12][13][14][15][16] on the basis of the "OSMAC" (one strain many compounds) approach, 17 we investigated secondary metabolites obtained from a culture of an endophytic strain of Chaetomium globosum, associated with the plant Ginkgo biloba. Incubation of this fungus using Sabouraud's medium, instead of the previously employed potato dextrose agar (PDA) and modified PDA medium, 12,13 led to the production of a new cytochalasan alkaloid, chaetoglobosin V b (1), together with two previously described congeners, chaetoglobosins V (2) and G (3).…”

Absolute Configuration of Fusarone, a New Azaphilone from the Endophytic Fungus Fusarium sp. Isolated from Melia azedarach, and of Related Azaphilones

“…5 This plant produces a class of modified oxygenated triterpenoids, also known as limonoids. 6,7 In previous articles, some of us reported the isolation and structural elucidation of new metabolites from the endophytes harbored inside the healthy tissues of M. azedarach, [8][9][10] including Fusarium sp. Among the natural products afforded by the same endophyte is the recently reported fusarisetin A, a compound endowed with very interesting biological properties.…”