RESUMO
Two unusual polyketide-sesquiterpene metabolites, craterodoratins T (1) and U (2), along with the known compound craterellin A (3), were isolated from the higher fungus Craterellus odoratus. The structures of isolated compounds were characterized based on nuclear magnetic resonance (NMR) and mass spectrum (MS) spectroscopic analysis, while the absolute configuration of the compounds was determined by theoretical NMR and electronic circular dichroism (ECD) calculations. Compound 1 possessed a rare structure with two aromatic groups. Compounds 1 and 3 showed immunosuppressive activity with IC50 values ranging from 5.516 to 19.953 µM.
Assuntos
Basidiomycota , Estrutura Molecular , Basidiomycota/química , Fungos , Espectroscopia de Ressonância Magnética/métodos , Dicroísmo Circular , ImunossupressoresRESUMO
Seven new merosesquiterpenoids, trichothecrotocins D-J (1-7), two new trichothecene sesquiterpenoids, trichothecrotocins K (12) and L (13), and six known compounds (8-11, 14, and 15), were isolated from a potato-associated fungus, Trichothecium crotocinigenum. Compounds 5 and 6 were racemates which were further separated as pure enantiomers. Structures together with absolute configurations were established by extensive spectroscopic analysis, as well as quantum chemistry calculations on ECD and optical rotations. Compounds 1-4 are rare meroterpenoids featuring a seco-phenyl group, while 1 and 2 possessed a novel 6-6/5 fused ring system. Compounds 1-4, 8, 11, and 12 showed antifungal activity against four plant pathogens with MIC values of 8-128 µg/mL. It is suggested that the meroterpenoids produced by T. crotocinigenum may play an important role in the antifungal property of the fungus, thereby protecting the host plant, i.e., potato.
Assuntos
Antifúngicos/química , Antifúngicos/farmacologia , Hypocreales/química , Solanum tuberosum/microbiologia , Fermentação , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Rotação Ocular , Doenças das Plantas/microbiologia , EstereoisomerismoRESUMO
Fungi have traditionally been a very rewarding source of biologically active natural products, while diterpenoids from fungi, such as the cyathane-type diterpenoids from Cyathus and Hericium sp., the fusicoccane-type diterpenoids from Fusicoccum and Alternaria sp., the guanacastane-type diterpenoids from Coprinus and Cercospora sp., and the harziene-type diterpenoids from Trichoderma sp., often represent unique carbon skeletons as well as diverse biological functions. The abundances of novel skeletons, biological activities, and biosynthetic pathways present new opportunities for drug discovery, genome mining, and enzymology. In addition, diterpenoids peculiar to fungi also reveal the possibility of differing biological evolution, although they have similar biosynthetic pathways. In this review, we provide an overview about the structures, biological activities, evolution, organic synthesis, and biosynthesis of diterpenoids that have been specially produced by fungi from 2010 to 2020. We hope this review provides timely illumination and beneficial guidance for future research works of scholars who are interested in this area.
RESUMO
Fungi are widely distributed in the terrestrial environment, freshwater, and marine habitat. Only approximately 100,000 of these have been classified although there are about 5.1 million characteristic fungi all over the world. These eukaryotic microbes produce specialized metabolites and participate in a variety of ecological functions, such as quorum detection, chemical defense, allelopathy, and maintenance of symbiosis. Fungi therefore remain an important resource for the screening and discovery of biologically active natural products. Sesquiterpenoids are arguably the richest natural products from plants and micro-organisms. The rearrangement of the 15 high-ductility carbons gave rise to a large number of different skeletons. At the same time, abundant structural variations lead to a diversification of biological activity. This review examines the isolation, structural determination, bioactivities, and synthesis of sesquiterpenoids that were specially produced by fungi over the past five years (2015-2020).
RESUMO
The aim of this work was to comprehensively understand the chemical constituents of the edible mushroom Craterellus ordoratus and their bioactivity. A chemical investigation on this mushroom led to the isolation of 23 sesquiterpenoids including eighteen previously undescribed bergamotane sesquiterpenes, craterodoratins A-R (1-18), and one new victoxinine derivative, craterodoratin S (19). The new structures were elucidated by detailed interpretation of spectrometric data, theoretical nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) calculations, and single-crystal X-ray crystallographic analysis. Compounds 1 and 2 possess a ring-rearranged carbon skeleton. Compounds 3, 10, 12-15, 19, 20 and 23 exhibit potent inhibitory activity against the lipopolysaccharide (LPS)-induced proliferation of B lymphocyte cells with the IC50 values ranging from 0.67 to 22.68 µM. Compounds 17 and 20 inhibit the concanavalin A (ConA)-induced proliferation of T lymphocyte cell with IC50 values of 31.50 and 0.98 µM, respectively. It is suggested that C. ordoratus is a good source for bergamotane sesquiterpenoids, and their immunosuppressive activity was reported for the first time. This research is conducive to the further development and utilization of C. ordoratus.
RESUMO
The chemical constituents and their biological activities of the mushroom Pyropolyporus fomentarius were investigated in this study. Two previously undescribed pentacyclic lupane-type triterpenes, 3-formyloxybetulin and 3-formyloxybetulinic acid, two rare degraded ergosterols, pyropolincisterols A and B, along with ten known triterpenoids and four known ergosterols were isolated from the fruiting bodies of P. fomentarius. Their chemical structures were determined using a combination of spectroscopic analysis. Nine compounds exhibited certain cytotoxicities to human cancer cell lines, while polyporenic acid showed significant cytotoxicities to SMMC-7721 and A-549 with IC50 values less than 10 µM. Four compounds showed inhibitory activities against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages with IC50 values of 36.3, 25.1, 21.4, and 34.2 µM, respectively. The results of this assessment suggested that the lanostane triterpenoids and ergosterols in fruiting bodies of P. fomentarius played key roles in its folk usages.
Assuntos
Agaricales , Triterpenos , Carpóforos , Macrófagos , Estrutura Molecular , Óxido Nítrico , Esteroides , Triterpenos/farmacologiaRESUMO
Melodinines Y1-Y4 (1-4), four undescribed alkaloids were isolated from Melodinus henryi. Their structures were elucidated by extensive NMR, mass spectroscopic analyses, theoretical NMR and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of bisindole alkaloids possessing an eburnamine-leuconoxine combination. Compound 3 is a rare 2,3-seco pleiocarpamine type monoterpene indole alkaloid. Compound 1 showed cytotoxic activities against six human cancer cell lines with IC50 values of 0.5-15.2 µM.
RESUMO
To comprehensively understand the chemical constituents of the edible mushroom Agrocybe salicacola and their biological functions, a phytochemical separation of the cultural broth of A. salicacola led to the isolation of four new illudane sesquiterpenoids, agrocybins H-K (1-4), along with 10 known analogues (5-14). Compounds 2-4 were racemates of which 2 and 3 were further separated into single enantiomers as 2a/2b and 3a/3b. All new structures with absolute configurations were elucidated on the basis of an extensive spectroscopic analysis and quantum chemistry calculations. Compound 1 possesses a new carbon skeleton that might be derived from the protoilludane backbone. Compounds 1, 5, 8, and 9 show a certain degree of cytotoxicity to five human cancer cell lines. Compound 1 shows a mild inhibitory effect on nitric oxide production with an IC50 value of 31.4 µM. It is concluded that A. salicacola is rich in illudin derivatives with potential bioactivity prospects, which would make A. salicacola a good material of medicine and food homology.
RESUMO
Two undescribed triterpenes, tricholimbrins A and B, three undescribed steroids, tricholimbrins CâE, one undescribed 4-chromanone derivative, along with 27 known compounds were isolated from fruiting bodies of the mushroom Tricholoma imbricatum. Tricholimbrins A and B are two polycyclic triterpenoids with a carbon degradation, while tricholimbrin C is a ring-rearranged steroid containing an aromatic moiety that might be derived from an ergosterol. Isocyathisterol, 3ß,15α-dihydroxyl-(22E,24R)-ergosta-5,8(14),22-trien-7-one, demethylincisterol A3, and volemolide showed cytotoxicities to six human cancer cell lines. 3ß-Hydroxyl-(22E,24R)-ergosta-5,8,22-trien-7,15-dione and 3ß-hydroxyl-(22E,24R)-ergosta-5,8,22-trien-7-one showed preferable cytotoxicities against HL-60 while chaxine C and volemolide showed preferable cytotoxicities against A-549, with IC50 values less than 10 µM.
Assuntos
Ascomicetos , Rodófitas , Tricholoma , Triterpenos , Humanos , Estrutura Molecular , EsteroidesRESUMO
Four new alkaloids, melodinines W1-W4 (1-4), together with twenty one known alkaloids (5-25) were isolated from Melodinus henryi. The structures with absolute configurations were elucidated by extensive MS and NMR spectroscopic methods, as well as the single crystal X-ray diffraction and ECD calculations. All compounds were evaluated for their cytotoxicities to five human cancer cell lines. Many compounds showed certain cytotoxicities to five human cancer cell lines with an IC50 range of 1.4-29.4⯵M.