Chemical Constituents from an Endophytic Fungus Chaetomium Globosum Z1

Abstract

A new ergosterol, 15β-hydroxyl-(22E,24R)-ergosta-3,5,8,22-tetraen-one (1), along with three known ergosterols, two known cytochalasins, and two known azapholines were isolated from Chaetomium globosum Z1. The structures of these compounds were elucidated on the basis of spectroscopic methods (HR-ESI-MS, 1D NMR, and 2D NMR). Compound 6 showed significant cytotoxic activity against A-549 and MG-63 cell lines with IC₅₀ values of 6.96 and 1.73 μg/mL, respectively.

Keywords

Constituents Chaetomium globosum Ergosterol

References

(a) Sun

P.X.

, Zheng

C.J.

, Li

W.C.

, Jin

G.L.

, Huang

, Qin

L.P.

(2011) Trichodermanin A, a novel diterpenoid from endophytic fungus culture. Journal of Natural Medicines, 65, 381–384;(b) Wu LS, Hu CL, Han T, Zheng CJ, Ma XQ, Rahman K, Qin LP. (2012) Cytotoxic metabolites from Perenniporia tephropora, an endophytic fungus from Taxus chinensis var. mairei. Applied Microbiology and Biotechnology, 97, 305–315; (c) Zheng CJ, Sun PX, Jin GL, Qin LP. (2011) Sesquiterpenoids from Trichoderma atroviride, an endophytic fungus in Cephalotaxus fortunei. Fitoterapia, 82, 1035–1038.

Jiao

R.H.

, Xu

, Liu

J.Y.

, Ge

H.M.

, Ding

, Xu

, Zhu

H.L.

, Tan

R.X.

(2006) Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Organic Letters, 8, 5709–5712.

(a) Wang

F.Z.

, Fang

Y.C.

, Zhang

, Lin

A.Q.

, Zhu

T.J.

, Gu

Q.Q.

, Zhu

W.M.

(2008) Six new ergosterols from the marine-derived fungus Rhizopus sp. Steroids, 73, 19–26;(b) Shirane N, Takenaka H, Ueda K, Hashimoto Y, Katoh K, Ishii H. (1996) Sterol analysis of DMI-resistant and -sensitive strains of Venturia inaequalis. Phytochemistry, 41, 1301–1308; (c) Krzyczkowski W, Malinowska E, Suchocki P, Kleps J, Olejnik M, Herold F. (2009) Isolation and quantitative determination of ergosterol peroxide in various edible mushroom specie. Food Chemistry, 113, 351–355.

Sekita

, Yoshihira

, Natori

(1983) Chaetoglobosins, cytotoxic 10-(indol-3-yl)-(13) cytochalasans from Chaetomium spp. IV. super (13) C-nuclear magnetic resonance spectra and their application to a biosynthetic study. Chemical and Pharmaceutical Bulletin, 31, 490–498.

(a) Muroga

, Yamada

, Numata

, Tanaka

(2010) 11- and 4′-epimers of chaetomugilin A, novel cytostatic metabolites from marine fish-derived fungus Chaetomium globosum. Helvetica Chimica Acta, 93, 542–549;(b) Kingsland SR, Barrow RA. (2009) Identification of chaetoviridin E from a cultured microfungus, Chaetomium sp. and structural reassignment of chaetoviridins B and D. Australian Journal of Chemistry, 62, 269–274.

(a) Adler

J.H.

, Young

, Nes

W.R.

(1977) Determination of the absolute configuration at C-20 and C-24 of ergosterol in ascomycetes and basidiomycetes by proton magnetic resonance spectroscopy. Lipids, 12, 364–366;(b) Sright J, Mcinnes A, Shimizu S, Smith D, Walter J, Idler D, Khalil W. (1978) Identification of C-24 alkyl epimers of marine sterols by ¹³C nuclear magnetic resonance spectroscopy. Canadian Journal of Chemistry, 56, 1898–1903.

Guo

L.D.

, Huang

G.R.

, Wang

, He

W.H.

, Zheng

W.H.

, Hyde

K.D.

(2003) Molecular identification of white morphotype strains of endophytic fungi from Pinus tabulaeformis. Mycological Research, 107, 680–688.

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