Bioactive ent-clerodane diterpenoids from the aerial parts of Baccharis gaudichaudiana

Yuanqiang Guo; Yushan Li; Jing Xu; Ryuichi Watanabe; Yasukatsu Oshima; Tohru Yamakuni; Yasushi Ohizumi

doi:10.1021/np050276q

Bioactive ent-clerodane diterpenoids from the aerial parts of Baccharis gaudichaudiana

J Nat Prod. 2006 Feb;69(2):274-6. doi: 10.1021/np050276q.

Authors

Yuanqiang Guo¹, Yushan Li, Jing Xu, Ryuichi Watanabe, Yasukatsu Oshima, Tohru Yamakuni, Yasushi Ohizumi

Affiliation

¹ Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 980-8578, Japan.

PMID: 16499330
DOI: 10.1021/np050276q

Abstract

Three new ent-clerodane diterpenes (1-3) were isolated from the aerial parts of Baccharis gaudichaudiana, and their structures were elucidated as 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (1), 13-epi-15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (2), and 7-oxo-16-hydroxy-ent-clerod-3-en-15-oic acid methyl ester-18,19-olide (3), on the basis of spectroscopic data analysis. A known compound, 7-oxo-ent-clerod-3-en-15,16:18,19-diolide, was also identified. Compounds 1 and 2 showed enhancing activity of nerve growth factor (NGF)-induced neurite outgrowth in PC 12D cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Baccharis / chemistry*
Diterpenes, Clerodane / chemistry
Diterpenes, Clerodane / isolation & purification*
Diterpenes, Clerodane / pharmacology*
Molecular Structure
Nerve Growth Factor / pharmacology*
Neurites / drug effects*
PC12 Cells
Plants, Medicinal / chemistry*
Rats
Stereoisomerism

Substances

13-epi-15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid
15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid
7-oxo-16-hydroxy-ent-clerod-3-en-15-oic acid methyl ester-18,19-olide
Diterpenes, Clerodane
Nerve Growth Factor