Two antibacterial and xanthine oxidase inhibitory cerebrosides, one of which is chemically new, were characterized from the chloroform-methanol (1∶1) extract of Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis. By means of chemical and spectral methods [IR, electrospray ionization MS (ESI-MS), tandem ESI-MS, 1H and 13C NMR, distortionless enhancement by polarization transfer, COSY, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond correlation, and 2-D nuclear Overhauser effect correlation spectroscopy], the structure of the new metabolite named fusaruside was established as (2S,2′R,3R,3′E,4E,8E,10E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8,10-sphingatrienine, and the structure of the other was identified as (2S,2′R,3R,3′E,4E,8E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine. Both new and known cerebrosides, although inactive to Trichophyton rubrum and Candida albicans, showed strong antibacterial activities against Bacillus subtilis, Escherichia coli, and Pseudomonas fluorescens, with their minimum inhibitory concentrations being 3.9, 3.9, and 1.9 μg/mL, and 7.8, 3.9, and 7.8 μg/mL, respectively. Furthermore, both metabolites were inhibitory to xanthine oxidase, with the IC50 value of fusaruside being 43.8±3.6 μM and the known cerebroside being 55.5±1.8 μM.

Antibacterial and xanthine oxidase inhibitory cerebrosides from Fusarium sp. IFB-121, and endophytic fungus in Quercus variabilis

Fungal meroterpenoids are secondary metabolites from mixed terpene-biosynthetic origins. Their intriguing chemical structural diversification and complexity, potential bioactivities, and pharmacological significance make them attractive targets in natural product chemistry, organic synthesis, and biosynthesis. This review provides a systematic overview of the isolation, chemical structural features, biological activities, and fungal biodiversity of 1585 novel meroterpenoids from 79 genera terrestrial and marine-derived fungi including macrofungi, Basidiomycetes, in 441 research papers in 2009-2019. Based on the nonterpenoid starting moiety in their biosynthesis pathway, meroterpenoids were classified into four categories (polyketide-terpenoid, indole-, shikimate-, and miscellaneous-) with polyketide-terpenoids (mainly tetraketide-) and shikimate-terpenoids as the primary source. Basidiomycota produced 37.5% of meroterpenoids, mostly shikimate-terpenoids. The genera of Ganoderma, Penicillium, Aspergillus, and Stachybotrys are the four dominant producers. Moreover, about 56% of meroterpenoids display various pronounced bioactivities, including cytotoxicity, enzyme inhibition, antibacterial, anti-inflammatory, antiviral, antifungal activities. It's exciting that several meroterpenoids including antroquinonol and 4-acetyl antroquinonol B were developed into phase II clinically used drugs. We assume that the chemical diversity and therapeutic potential of these fungal meroterpenoids will provide biologists and medicinal chemists with a large promising sustainable treasure-trove for drug discovery.

The chemistry and biology of fungal meroterpenoids (2009-2019).

Isolation of three new meroterpenoids and seven known compounds from Albatrellus yasudae and their Aβ-aggregation inhibitory activity.

A new grifolin derivative, named grifolene (1), together with grifolin (2), neogrifolin (3) and grifolic acid (4) was isolated from the fruiting bodies of the fungus Albatrellus yasuda. The structure of 1 was elucidated on the basis of extensive spectroscopic analysis.

A New Grifolin Derivative from the Mushroom Albatrellus yasuda (Polyporaceae)

Fifteen known compounds,cerebroside B(1),psicofuranine(2),uridic triphosphate(3),uracil(4),adenine(5),3β-acteoxy-(22E,24R)-24-methyl-5α-cholest-7,22-diene-5,6β-diol(6),(22E)-27-nor-24-methyl-5α-cholesta-7,22-diene-3β,5,6β-triol(7),3β-hydroxy-5α,8α-epidioxy-24ξ-methylcholesta-6-en(8)(22?mg),3β-O-glucopyranosyl-5α,6β-dihydroxyergosta-7,22-diene(9),(24S)-ergosta-4,6,8(14),22-tetraen-3-one(10),(22E,24R)-24-methylergosta-7,22-diene-3β,5α,6β-triol(11),(22E,24S)-24-methyl-5α-cholest-7,22-diene-3β,5,6β-triol(12).3β-hydroxy-5α,8α-epidioxyergosta-6,22-diene (13),3β-hydroxyergosta-5,7,22-triene(14) and D-allitol(15)loene isolated from the fresh fruiting bodies of Sarcodon aspratum (Berk.) S.Ito,and their structures were identified by means of spectroscopy.All the compounds are reported firstly in genus Sarcodon ?

Dong Ze

Papers

A New Grifolin Derivative from the Mushroom Albatrellus yasuda (Polyporaceae)

The Chemical Constituents from Basidiocarps of Sarcodon aspratum