Zhong-Yu Zhou

Pigments of fungi (macromycetes)

This review surveys the chemical, biological and mycological literature dealing with the isolation, structure elucidation, biological activities, and synthesis of pigments manufactured by those fungi that produce conspicuous fruiting bodies (macromycetes).

Evidence for the Natural Toxins from the Mushroom Trogia venenata as a Cause of Sudden Unexpected Death in Yunnan Province, China

National Basic Research Program of China (973 Program)[2009CB522300]; National Natural Sciences Foundation of China[30830113, U1132607]; Ministry of Health[200802002]

Sesquiterpenes and aliphatic diketones from cultures of the basidiomycete Conocybe siliginea

Five new tremulane-type sesquiterpenes, 11,12-dihydroxy-1-tremulen-5-one (1), 11,12-epoxy-12beta-hydroxy-1-tremulen-5-one (2), 5alpha,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (3), 2alpha,11-dihydroxy-1(10)-tremulen-5,12-olide (4), and 10beta,11-dihydroxy-5,6- seco-1,6(13)-tremuladien-5,12-olide (5), as well as three new aliphatic diketones, 2,3-dihydroxydodecane-4,7-dione (9 and 10) and 1-hydroxydecane-2,5-dione (11), together with three known sesquiterpene analogues, tremulenediol A (6), conocenol B (7), and conocenolide A (8), were isolated from cultures of the basidiomycete Conocybe siliginea.

Bioactive Quinic Acid Derivatives from Ageratina adenophora

A novel quinic acid derivative, 5-O-trans-o-coumaroylquinic acid methyl ester (1), together with three known ones, chlorogenic acid methyl ester (2), macranthoin F (3) and macranthoin G (4), were isolated from the aerial parts of the invasive plant Ageratina adenophora (Spreng.). The structure of new compound 1 was elucidated on the basis of extensive spectroscopic analysis, including 1D- and 2D-NMR techniques. Compounds 2–4 were isolated from plant A. adenophora for the first time. All the compounds showed in vitro antibacterial activity toward five assayed bacterial strains, especially 3 and 4, which showed in vitro antibacterial activity against Salmonella enterica with MIC values of 7.4 and 14.7 μM, respectively. Compound 1 was further found to display in vitro anti-fungal activity against spore germination of Magnaporthe grisea with an IC50 value 542.3 µM. These four compounds were also tested for their antioxidant activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical.

Phenolics from Ageratina adenophora roots and their phytotoxic effects on Arabidopsis thaliana seed germination and seedling growth.

A bioassay-directed phytochemical study was conducted to investigate potential allelochemicals in the roots of the invasive plant Ageratina adenophora. Eleven phenolic compounds, including seven new ones, 7-hydroxy-8,9-dehydrothymol 9-O-trans-ferulate (1), 7-hydroxythymol 9-O-trans-ferulate (2), 7,8-dihydroxythymol 9-O-trans-ferulate (3), 7,8-dihydroxythymol 9-O-cis-ferulate (4), methyl (7R)-3-deoxy-4,5-epoxy-D-manno-2-octulosonate 8-O-trans-p-coumarate (5), methyl (7R)-3-deoxy-4,5-epoxy-D-manno-2-octulosonate 8-O-cis-p-coumarate (6), and 3-(2-hydroxyphenyl)propyl methyl malonate (7), were isolated from a bioactive subfraction of the ethanol extract of the roots of A. adenophora. The new structures were established on the basis of detailed spectroscopic analysis. The potential phytotoxic effects of these compounds on the germination of Arabidopsis thaliana seeds were tested by a filter paper assay. Compound 7 and known compounds 3-(2-hydroxyphenyl)-1-propanol (8) and o-coumaric acid (9) remarkably showed inhibition activity against Arabidopsis seed germination at a concentration of 1.0 mM. Compounds 1, 2, 5, 6, and 10 showed slight inhibitory activity at the test concentration after treatment for 3 days, while the other compounds showed no obvious inhibitory effects. Moreover, 7-9 were further found to show obvious inhibitory activity on retarding the seedling growth of Ar. thaliana cultured in soil medium.

Bioactive 30-Noroleanane Triterpenes from the Pericarps of Akebia trifoliata

Two new 30-noroleanane triterpenes, 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid (1), 2α,3β-dihydroxy-23-oxo-30-norolean-12,20(29)-dien-28-oic acid (2), were isolated from the pericarps of Akebia trifoliata, together with four known ones, 3β-akebonoic acid (3), 2α,3β-dihydroxy-30-noroleana-12,20(29)-dien-28-oic acid (4), 3α-akebonoic acid (5) and quinatic acid (6). Their structures were established on the basis of detailed spectroscopic analysis, and they were all isolated from the pericarps of A. trifoliata for the first time. Compounds 3−6 showed in vitro bacteriostatic activity against four assayed Gram-positive bacterial strains. In particular 3 showed antibacterial activity toward MRSA with a MIC value 25 μg/mL, which was more potent than kanamycin (MIC 125 μg/mL). No compounds showed antibacterial activity toward the three Gram-negative bacteria tested. Compounds 4 and 5 showed interesting in vitro growth inhibitory activity against human tumor A549 and HeLa cell lines, with IC50 values ranging from 8.8 and 5.6 μM, respectively. Compounds 1, 2, 5 and 6 were further revealed to show significant in vitro α-glucosidase inhibitory activity with IC50 values from 0.035 to 0.367 mM, which were more potent than the reference compound acarbose (IC50 0.409 mM).

Gallicynoic acids A-I, acetylenic acids from the basidiomycete Coriolopsis gallica.

Nine new acetylenic acids, gallicynoic acids A-I ( 1- 9), have been isolated from a culture of the basidiomycete Coriolopsis gallica. The structures of 1- 9 were elucidated on the basis of spectroscopic and chemical means.

Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata

Three new oleanane triterpenoids, 2α,3β,29-trihydroxyolean-12-en-28-oic acid (1), 2α,3β-dihydroxy-23-oxo-olean-12-en-28-oic acid (2) and 2α,3β,21β,22α-tetrahydroxyolean-12-en-28,29-dioic acid (3), and ten known ones, maslinic acid (4), arjunolic acid (5), oleanolic acid (6), 3-epi-oleanolic acid (7), stachlic acid A (8), serratagenic acid (9), gypsogenic acid (10), 2α,3β-dihydroxyol-ean-13(18)-en-28-oic acid (11), mesembryanthemoidigenic acid (12) and 12α-hydroxy-δ-lactone (13), were isolated from the pericarps of Akebia trifoliata, a new valued fruit crop in China. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compounds 8, 10, 11 and 13 were isolated for the first time from the genus Akebia. All the compounds were tested for their antimicrobial activity against five bacterial strains. Compounds 4, 6 and 11 showed significant antibacterial activity toward all the assayed microorganisms with MIC values ranging from 0.9 to 15.6μg/mL, which were close or even more potent than the reference compound Kanamycin (MIC values ranging from 1.9 to 3.9μg/mL).

Phytoecdysteroids from the roots of Achyranthes bidentata Blume.

Two new phytoecdysteroids, (25S)-20,22-O-(R-ethylidene)inokosterone (1) and 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone (2), together with six known phytoecdysteroids 3–8 were isolated from the roots of Achyranthes bidentata Blume. The new structures were established on the basis of spectroscopic studies and chemical evidences. The absolute configuration at C-25 in the structure of known compound 3 was determined by chemical and spectroscopic means.

Facile and Efficient One-Pot Synthesis of β-Carbolines

Initial formation of tetrahydrocarboline 3 from tryptophan methyl ester 1 and aldehyde 2 by Pictet–Spengler reaction, followed by treatment with trichlorocyanuric acid, provides a facile and efficient route for a one-pot synthesis of β-carbolines with excellent yields.