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

22 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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@article{7c8a378608424f49aefc260b0f6df009,

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",

month = dec,

day = "1",

doi = "10.1021/jo00888a006",

language = "English",

volume = "41",

pages = "4078--4081",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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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%.

UR - https://www.scopus.com/pages/publications/0017314922

U2 - 10.1021/jo00888a006

DO - 10.1021/jo00888a006

M3 - Article

C2 - 1003262

AN - SCOPUS:0017314922

SN - 0022-3263

VL - 41

SP - 4078

EP - 4081

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

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

Abstract

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