Trechonolide A, a new withanolide type from Trechonaetes laciniata

David Lavie; Roberto Bessalle; Mauricio J. Pestchanker; Hugo E. Gottlieb; Felix Frolow; Oscar S. Giordano

doi:10.1016/s0031-9422(00)82290-6

Trechonolide A, a new withanolide type from Trechonaetes laciniata

David Lavie, Roberto Bessalle, Mauricio J. Pestchanker, Hugo E. Gottlieb, Felix Frolow, Oscar S. Giordano

Department of Chemistry

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

25 Scopus citations

Abstract

The structure of a new withanolide type isolated from Trechonaetes laciniata, having a hemiacetal ring system and a 5-member ring lactone has been elucidated by X-ray analysis as (23R)-5β,6β-epoxy-12β,17β-dihydroxy-1-oxo-12,22-hemiacetal-ergosta-2,24-dien-23,26-olide (trechonolide A). A second compound (trechonolide B) having at C-12 a β-methoxy group, has also been isolated and assumed to be an artifact since, by heating trechonolide A in methanol with a trace of acid, the methoxy derivative was produced.

Original language	English
Pages (from-to)	1791-1795
Number of pages	5
Journal	Phytochemistry
Volume	26
Issue number	6
DOIs	https://doi.org/10.1016/s0031-9422(00)82290-6
State	Published - 1987

Keywords

Solanaceae
Trechonaetes laciniata
X-ray structure
steroidal lactones
trechonolide A
trichloroacetyl isocyanate derivatives.
withanolides

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10.1016/s0031-9422(00)82290-6

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title = "Trechonolide A, a new withanolide type from Trechonaetes laciniata",

abstract = "The structure of a new withanolide type isolated from Trechonaetes laciniata, having a hemiacetal ring system and a 5-member ring lactone has been elucidated by X-ray analysis as (23R)-5β,6β-epoxy-12β,17β-dihydroxy-1-oxo-12,22-hemiacetal-ergosta-2,24-dien-23,26-olide (trechonolide A). A second compound (trechonolide B) having at C-12 a β-methoxy group, has also been isolated and assumed to be an artifact since, by heating trechonolide A in methanol with a trace of acid, the methoxy derivative was produced.",

keywords = "Solanaceae, Trechonaetes laciniata, X-ray structure, steroidal lactones, trechonolide A, trichloroacetyl isocyanate derivatives., withanolides",

author = "David Lavie and Roberto Bessalle and Pestchanker, {Mauricio J.} and Gottlieb, {Hugo E.} and Felix Frolow and Giordano, {Oscar S.}",

year = "1987",

doi = "10.1016/s0031-9422(00)82290-6",

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volume = "26",

pages = "1791--1795",

journal = "Phytochemistry",

issn = "0031-9422",

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T1 - Trechonolide A, a new withanolide type from Trechonaetes laciniata

AU - Lavie, David

AU - Bessalle, Roberto

AU - Pestchanker, Mauricio J.

AU - Gottlieb, Hugo E.

AU - Frolow, Felix

AU - Giordano, Oscar S.

PY - 1987

Y1 - 1987

N2 - The structure of a new withanolide type isolated from Trechonaetes laciniata, having a hemiacetal ring system and a 5-member ring lactone has been elucidated by X-ray analysis as (23R)-5β,6β-epoxy-12β,17β-dihydroxy-1-oxo-12,22-hemiacetal-ergosta-2,24-dien-23,26-olide (trechonolide A). A second compound (trechonolide B) having at C-12 a β-methoxy group, has also been isolated and assumed to be an artifact since, by heating trechonolide A in methanol with a trace of acid, the methoxy derivative was produced.

AB - The structure of a new withanolide type isolated from Trechonaetes laciniata, having a hemiacetal ring system and a 5-member ring lactone has been elucidated by X-ray analysis as (23R)-5β,6β-epoxy-12β,17β-dihydroxy-1-oxo-12,22-hemiacetal-ergosta-2,24-dien-23,26-olide (trechonolide A). A second compound (trechonolide B) having at C-12 a β-methoxy group, has also been isolated and assumed to be an artifact since, by heating trechonolide A in methanol with a trace of acid, the methoxy derivative was produced.

KW - Solanaceae

KW - Trechonaetes laciniata

KW - X-ray structure

KW - steroidal lactones

KW - trechonolide A

KW - trichloroacetyl isocyanate derivatives.

KW - withanolides

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SN - 0031-9422

VL - 26

SP - 1791

EP - 1795

JO - Phytochemistry

JF - Phytochemistry

IS - 6

ER -

Trechonolide A, a new withanolide type from Trechonaetes laciniata

Abstract

Keywords

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