Two new cytotoxic cytochalasins from Xylaria obovata

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

doi:10.1016/S0040-4020(01)85632-5

Two new cytotoxic cytochalasins from Xylaria obovata

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

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

Abstract

Two new cytotoxic cytochalasins were isolated by brine shrimp bioassay-guided fractionation from a culture of the wood inhabiting fungus, Xylaria obovata. Their structures were determined as 19,20-epoxycytochalasin Q (1) and its deacetyl analog 2 by the application of spectroscopic techniques and chemical correlation with cytochalasin R. Acetylation of 2 yielded 1. Both 1 and 2 were cytotoxic but were found to be inactive in an HIV-protease inhibitory assay and a mechanism-based DNA damaging yeast assay.

Original language	English (US)
Pages (from-to)	5615-5620
Number of pages	6
Journal	Tetrahedron
Volume	50
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4020(01)85632-5
State	Published - 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)85632-5

Cite this

@article{270a169f9f304905a0d5f4ba799c6c34,

title = "Two new cytotoxic cytochalasins from Xylaria obovata",

abstract = "Two new cytotoxic cytochalasins were isolated by brine shrimp bioassay-guided fractionation from a culture of the wood inhabiting fungus, Xylaria obovata. Their structures were determined as 19,20-epoxycytochalasin Q (1) and its deacetyl analog 2 by the application of spectroscopic techniques and chemical correlation with cytochalasin R. Acetylation of 2 yielded 1. Both 1 and 2 were cytotoxic but were found to be inactive in an HIV-protease inhibitory assay and a mechanism-based DNA damaging yeast assay.",

author = "Ermias Dagne and Gunatilaka, \{A. A.Leslie\} and Senait Asmellash and Dawit Abate and Kingston, \{David G.I.\} and Hofmann, \{Glenn A.\} and Johnson, \{Randall K.\}",

note = "Funding Information: This work wasf undedb y grantsf rom theN ationalC ancerI nstituteu ndera NationalC ooperativeD rug DiscoveryG roup awardedt o theU niversityo f Virginia (Dr. S. M. Hecht,P rincipal Investigator)f,r om the InternationalF oundation for Science (awardedt o D.A.), and from the Swedish Agency for Research Cooperationin DevelopingC ountries( awardedto E.D.). The visit of E.D. to V.P.I. \& S.U. wass upportebdy a fellowshipo f theF ulbright-HaysF oundation.W e thankD r. T. Laessoe( Kew GardensL, ondon,U .K.) for identifyingt hef ungus;P rof. R. L. Edwards( Universityo f Bradford,U .K.) for a sampleo f cyclochalasinR ; Mr. T. Glass (V.P.I. \& S.U.) for assistancien obtainings omeN MR spectraa; nd Mr. Kim Harich (V.P.I. \& S.U.) andt heM idwestC enterf or MassS pectrometrwyi th partials upporbt y theN ationalS cienceF oundation BiologyD ivision (GrantN o. DIR 9017262f)o r MS.",

year = "1994",

doi = "10.1016/S0040-4020(01)85632-5",

language = "English (US)",

volume = "50",

pages = "5615--5620",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "19",

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T1 - Two new cytotoxic cytochalasins from Xylaria obovata

AU - Dagne, Ermias

AU - Gunatilaka, A. A.Leslie

AU - Asmellash, Senait

AU - Abate, Dawit

AU - Kingston, David G.I.

AU - Hofmann, Glenn A.

AU - Johnson, Randall K.

N1 - Funding Information: This work wasf undedb y grantsf rom theN ationalC ancerI nstituteu ndera NationalC ooperativeD rug DiscoveryG roup awardedt o theU niversityo f Virginia (Dr. S. M. Hecht,P rincipal Investigator)f,r om the InternationalF oundation for Science (awardedt o D.A.), and from the Swedish Agency for Research Cooperationin DevelopingC ountries( awardedto E.D.). The visit of E.D. to V.P.I. & S.U. wass upportebdy a fellowshipo f theF ulbright-HaysF oundation.W e thankD r. T. Laessoe( Kew GardensL, ondon,U .K.) for identifyingt hef ungus;P rof. R. L. Edwards( Universityo f Bradford,U .K.) for a sampleo f cyclochalasinR ; Mr. T. Glass (V.P.I. & S.U.) for assistancien obtainings omeN MR spectraa; nd Mr. Kim Harich (V.P.I. & S.U.) andt heM idwestC enterf or MassS pectrometrwyi th partials upporbt y theN ationalS cienceF oundation BiologyD ivision (GrantN o. DIR 9017262f)o r MS.

PY - 1994

Y1 - 1994

N2 - Two new cytotoxic cytochalasins were isolated by brine shrimp bioassay-guided fractionation from a culture of the wood inhabiting fungus, Xylaria obovata. Their structures were determined as 19,20-epoxycytochalasin Q (1) and its deacetyl analog 2 by the application of spectroscopic techniques and chemical correlation with cytochalasin R. Acetylation of 2 yielded 1. Both 1 and 2 were cytotoxic but were found to be inactive in an HIV-protease inhibitory assay and a mechanism-based DNA damaging yeast assay.

AB - Two new cytotoxic cytochalasins were isolated by brine shrimp bioassay-guided fractionation from a culture of the wood inhabiting fungus, Xylaria obovata. Their structures were determined as 19,20-epoxycytochalasin Q (1) and its deacetyl analog 2 by the application of spectroscopic techniques and chemical correlation with cytochalasin R. Acetylation of 2 yielded 1. Both 1 and 2 were cytotoxic but were found to be inactive in an HIV-protease inhibitory assay and a mechanism-based DNA damaging yeast assay.

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DO - 10.1016/S0040-4020(01)85632-5

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AN - SCOPUS:0028359789

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VL - 50

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EP - 5620

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Two new cytotoxic cytochalasins from Xylaria obovata

Abstract

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