Two new cytotoxic cytochalasins from Xylaria obovata

Dagne, Ermias; Gunatilaka, A. A. Leslie; Asmellash, Senait; Abate, Dawit; Kingston, David G. I.; Hofmann, Glenn A.; Johnson, Randall K.

doi:10.1016/s0040-4020(01)85632-5

Cited by 53 publications

(26 citation statements)

References 10 publications

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“…The macrocyclic moiety is an octaketide derived from the headto-tail condensation of eight acetate units to construct an unbranched C 16 -polyketide moiety.…”

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confidence: 99%

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An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Rukachaisirikul

Khamthong

Sukpondma

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new [11]cytochalasin derivative, xylarisin (1), was isolated from the marine-derived fungus Xylaria sp. PSU-F100 along with six known metabolites: three mellein derivatives (2-4), one pyrone derivative (5) and two carboxylic acids (6,7). The structure and stereochemistry of 1 were determined by NMR and X-ray diffraction analyses. All isolated compounds showed mild antibacterial activity against standard Staphylococcus aureus ATCC 25923 and methicillin-resistant strain.

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“…The macrocyclic moiety is an octaketide derived from the headto-tail condensation of eight acetate units to construct an unbranched C 16 -polyketide moiety.…”

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confidence: 99%

“…12) The plausible biogenetic pathway would involve the attachment of L-leucine, not Lphenylalanine which was incorporated in all cytochalasins isolated from the genus Xylaria, 1,4,[14][15][16][17][18] to the C 16 -polyketide unit. The isolation of RKS-1778, a key intermediate of the [11]cytochalasin group from a soil fungus Phoma sp.…”

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confidence: 99%

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Rukachaisirikul

Khamthong

Sukpondma

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Many unique secondary metabolites have been found in the fungi of this genus. During the study of Xylaria sp., various new metabolites had been discovered, including cytochalasins [2,3], globoscin [4], lactones [5], maldoxin [6], sesquiterpenoids [7,8], xylaramide [9], xylarin [10], and xyloketals [11]. As a part of our search for naturally occurring bioactive metabolites of the higher fungi in Yunnan province [12], we have carried out a detailed chemical investigation on the fungus Xylaria euglossa Fr.…”

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confidence: 99%

Xylactam, a New Nitrogen-containing Compound from the Fruiting Bodies of Ascomycete Xylaria euglossa

2005

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A novel nitrogen-containing compound, named xylactam (1), was isolated from the fruiting bodies of ascomycete Xylaria euglossa together with two known compounds penochalasin B2 and neoechinulin A. Their structures were elucidated on the basis of spectral data. Fruiting bodies of Xylaria euglossa were collected at Ailao mountain of Yunnan province, P. R. China, in July, 2002 and identified by Prof. Mu Zang, Kunming Institute of Botany, the Chinese Academy of Sciences. The voucher specimen was deposited in the Herbarium of the Kunming Institute of Botany, the Chinese Academy of Sciences. The air-dried fruiting bodies of X. euglossa (0.5 kg) were crushed and extracted with chloroform/methanol (1/1, v/v) four times at room temperature. The combined extracts were concentrated in vacuo to give a syrup (25 g), which was partitioned between chloroform and water. The chloroform soluble part (17 g) was subjected to silica gel column chromatography employing a gradient elution with chloroform/methanol (from 100 : 0 to 85 : 15, v/v) to give six fractions. Fraction II (100 : 1, v/v) was chromatographed on silica gel (petroleum ether/acetone 85 : 15), yielding penochalasin B2 (30 mg). Fraction III (98 : 2, v/v) was rechromatographed through silica gel, eluting with petroleum ether/acetone 80 : 20 (v/v) to give neoechinulin A (5 mg). Fraction VI (85 : 15, v/v) was passed through Sephadex LH-20, eluting with chloroform/methanol (1 : 1, v/v). A fraction exhibited strong yellow and white-blue fluorescence at 254 nm and was further purified on silica gel in petroleum ether/acetone (7 : 3, v/v) to afford compound 1 (8 mg). KeywordsXylactam (1) was obtained as a white powder. Its molecular formula was determined as C 23 H 31 NO 6 from the quasi-molecular ion peak at m/z 418.2211 ([MϩH] ϩ , calcd. 418.2229) in the positive-ion HR-ESI-MS. Twenty-three signals in the 13 C-NMR (DEPT) spectra of 1 were recognized (9ϫC, 2ϫCH, 11ϫCH 2 , 1ϫCH 3 ), including three carbonyl C-atoms (d 172.4, 173.5 and 204.0) and six aromatic quartery C-atoms (d 102.5, 120.8, 125.9, 128.2, 155.0, 164.8). To fulfill the molecular formula of

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“…Xylaria species are known for their medicinal value and produce a variety of bioactive compounds (e.g. alkaloids, antifungal metabolites, cytochalasins, cell-degrading enzymes, exopolysaccharides, xylaramide, xylarin and xyloketals) (Dagne et al 1994, Schneider et al 1995, 1996, Boonphong et al 2001, Lin et al 2001, Ramesh et al 2012a, Ma et al 2013b, Rajulu et al 2013, Latha et al, 2015. Investigations in the Western Ghat region including this study (in the States of Maharashtra, Karnataka, Kerala and Tamil Nadu) revealed occurrence of 24 Xylaria species with a highest, 17 species in Maharashtra followed by 10 species in Karnataka, 7 species in Kerala and 1 species in Tamil Nadu ( Table 1).…”

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confidence: 99%

Xylaria complex in the South Western India

Karun¹

2015

PPQ

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Nine species of Xylaria (X. escharoidea, X. filiformis, X. hypoxylon, X. longipes, X. multiplex, X. nigripes, X. obovata, X. polymorpha and X. symploci) were recorded during an inventory of various habitats of the Western Ghats and west coast of India. Xylaria escharoidea, X. hypoxylon and X. longipes were common to the Western Ghats and west coast, while five (X. filiformis, X. multiplex, X. obovata, X. polymorpha and X. symploci) and one (X. nigripes) species were confined to the Western Ghats and west coast regions, respectively. Xylaria longipes, X. multiplex, X. obovata and X. polymorpha grew on dead logs/stubs, X. escharoidea, X. nigripes and X. symploci preferred to grow on soil/termite mound/soil embedded with wood, X. hypoxylon preferred to grow on pods/kernels/twigs/humus/wood pieces and X. filiformis exclusively grew on leaves. Xylaria filiformis and X. multiplex recorded for the first time from the Western Ghats. Based on the occurrence on different substrates, a dichotomous key has been given for identification of nine species recorded in this survey. Including this survey, a total of 24 species of Xylaria has been reported from the Western Ghats and west coast regions of Maharashtra, Karnataka, Kerala and Tamil Nadu.

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Two new cytotoxic cytochalasins from Xylaria obovata

Cited by 53 publications

References 10 publications

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Xylactam, a New Nitrogen-containing Compound from the Fruiting Bodies of Ascomycete Xylaria euglossa

Xylaria complex in the South Western India

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