Isolation and Structure Determination of the Second Toxic Constituent from Tetradymia glabrata

Paul W. Jennings; Jerome C. Hurley; S. K. Reeder; Andrij Holian; Pauthon Lee; Charles N. Caughlan; Raymond D. Larsen

doi:10.1021/jo00888a006

Isolation and Structure Determination of the Second Toxic Constituent from Tetradymia glabrata

Paul W. Jennings, Jerome C. Hurley, S. K. Reeder, Andrij Holian, Pauthon Lee, Charles N. Caughlan, Raymond D. Larsen

Montana State University

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

21 Scopus citations

Abstract

A new furanoeremophilane has been isolated and a derivative of it analyzed by x-ray crystallography. The two compounds are 10β-hydroxy-6β-isobutyrylfuranoeremophilane (II) and 6β,10β-dihydroxyfuranoeremophilane (III). Both have been shown to be hepatotoxins, LD₅₀IP₄₀₀ and 113 mg/kg, respectively. Physical data are included in the publication with particular emphasis on NMR spectra correlation with x-ray structure. Compound III crystallized in a space group P2₁2₁2₁ with cell dimensions a = 21.322 (7) Å,b = 7.593 (2) Å,c= 8.387 (1) Å, with Z = 4. Counter data were refined by full-matrix least squares to a residual of 4.7%.

Original language	English
Pages (from-to)	4078-4081
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	41
Issue number	26
DOIs	https://doi.org/10.1021/jo00888a006
State	Published - Dec 1 1976

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title = "Isolation and Structure Determination of the Second Toxic Constituent from Tetradymia glabrata",

abstract = "A new furanoeremophilane has been isolated and a derivative of it analyzed by x-ray crystallography. The two compounds are 10β-hydroxy-6β-isobutyrylfuranoeremophilane (II) and 6β,10β-dihydroxyfuranoeremophilane (III). Both have been shown to be hepatotoxins, LD50IP400 and 113 mg/kg, respectively. Physical data are included in the publication with particular emphasis on NMR spectra correlation with x-ray structure. Compound III crystallized in a space group P212121 with cell dimensions a = 21.322 (7) {\AA},b = 7.593 (2) {\AA},c= 8.387 (1) {\AA}, with Z = 4. Counter data were refined by full-matrix least squares to a residual of 4.7%.",

author = "Jennings, {Paul W.} and Hurley, {Jerome C.} and Reeder, {S. K.} and Andrij Holian and Pauthon Lee and Caughlan, {Charles N.} and Larsen, {Raymond D.}",

year = "1976",

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doi = "10.1021/jo00888a006",

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volume = "41",

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TY - JOUR

T1 - Isolation and Structure Determination of the Second Toxic Constituent from Tetradymia glabrata

AU - Jennings, Paul W.

AU - Hurley, Jerome C.

AU - Reeder, S. K.

AU - Holian, Andrij

AU - Lee, Pauthon

AU - Caughlan, Charles N.

AU - Larsen, Raymond D.

PY - 1976/12/1

Y1 - 1976/12/1

N2 - A new furanoeremophilane has been isolated and a derivative of it analyzed by x-ray crystallography. The two compounds are 10β-hydroxy-6β-isobutyrylfuranoeremophilane (II) and 6β,10β-dihydroxyfuranoeremophilane (III). Both have been shown to be hepatotoxins, LD50IP400 and 113 mg/kg, respectively. Physical data are included in the publication with particular emphasis on NMR spectra correlation with x-ray structure. Compound III crystallized in a space group P212121 with cell dimensions a = 21.322 (7) Å,b = 7.593 (2) Å,c= 8.387 (1) Å, with Z = 4. Counter data were refined by full-matrix least squares to a residual of 4.7%.

AB - A new furanoeremophilane has been isolated and a derivative of it analyzed by x-ray crystallography. The two compounds are 10β-hydroxy-6β-isobutyrylfuranoeremophilane (II) and 6β,10β-dihydroxyfuranoeremophilane (III). Both have been shown to be hepatotoxins, LD50IP400 and 113 mg/kg, respectively. Physical data are included in the publication with particular emphasis on NMR spectra correlation with x-ray structure. Compound III crystallized in a space group P212121 with cell dimensions a = 21.322 (7) Å,b = 7.593 (2) Å,c= 8.387 (1) Å, with Z = 4. Counter data were refined by full-matrix least squares to a residual of 4.7%.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Isolation and Structure Determination of the Second Toxic Constituent from Tetradymia glabrata

Abstract

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