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Withanolides from Aureliana fasciculata var. fasciculata
Author(s) -
AlmeidaLafetá Rita C.,
Ferreira Marcelo J. P.,
Emerenciano Vicente P.,
Kaplan Maria A. C.
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000126
Subject(s) - chemistry , dept , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , phytochemical , solanaceae , biochemistry , gene
In the first phytochemical study of the Aureliana genus (Solanaceae), two new withanolides, 1 and 2 , together with two known sterols, were isolated from the MeOH extract of the leaves of Aureliana fasciculata var. fasciculata. The structures were established as (4 S ,22 R )‐16 α ‐acetoxy‐5 β ,6 β ‐epoxy‐4 β ,17 α ‐dihydroxy‐1‐oxowitha‐2,24‐dienolide (aurelianolide A) and (4 S ,22 R )‐16 α ‐acetoxy‐4 β ,17 α ‐dihydroxy‐1‐oxowitha‐2,5,24‐trienolide (aurelianolide B). The new compounds possessed the unusual 16 α ,17 α ‐dioxygenated group and were fully characterized by spectroscopic techniques, including 1 H‐ and 13 C‐NMR (DEPT), as well as 2D‐NMR (HMBC, HMQC, 1 H, 1 H‐COSY, NOESY) experiments, and HR‐MS.