Withanolides from Physalis coztomatl

Huaping Zhang; Cong-Mei Cao; Robert J Gallagher; Victor W Day; Kelly Kindscher; Barbara N Timmermann

doi:10.1016/j.phytochem.2014.10.012

Withanolides from Physalis coztomatl

Phytochemistry. 2015 Jan:109:147-53. doi: 10.1016/j.phytochem.2014.10.012. Epub 2014 Nov 8.

Authors

Huaping Zhang¹, Cong-Mei Cao¹, Robert J Gallagher¹, Victor W Day², Kelly Kindscher³, Barbara N Timmermann⁴

Affiliations

¹ Department of Medicinal Chemistry, School of Pharmacy, University of Kansas, Lawrence, KS 66045, USA.
² The Small-Molecule X-ray Crystallography Laboratory, University of Kansas, Lawrence, KS 66047, USA.
³ Kansas Biological Survey, University of Kansas, Lawrence, KS 66047, USA.
⁴ Department of Medicinal Chemistry, School of Pharmacy, University of Kansas, Lawrence, KS 66045, USA. Electronic address: btimmer@ku.edu.

PMID: 25457493
DOI: 10.1016/j.phytochem.2014.10.012

Abstract

Six withanolides (1-6), as well as two known withanolides (physachenolide D 7 and withanoside VI 8), were isolated from the aerial parts of Physalis coztomatl (Solanaceae). Structural elucidations of 1-6 were achieved through 2D NMR and other spectroscopic techniques, while the structure of 1 was confirmed by X-ray crystallographic analysis. In addition, the stereochemical orientation of the 17-hydroxy group in withanolides was discussed in relation to (13)C NMR shifts of C-12, 13, 14 and 16. Such analysis established that coagulansin A contains a 17α-hydroxy moiety rather than the reported 17β-hydroxy functionality, and has been revised accordingly.

Keywords: Coagulansin A; Physacoztolide; Physalis coztomatl; Solanaceae; Structure revision; Withanolide.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Molecular Structure
Physalis / chemistry*
Withanolides / chemistry*
Withanolides / isolation & purification

Substances

Withanolides

Abstract

Publication types

MeSH terms

Substances

Grants and funding