Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn

Orapun Yodsaoue; Sarot Cheenpracha; Chatchanok Karalai; Chanita Ponglimanont; Suchada Chantrapromma; Hoong-Kun Fun; Akkharawit Kanjana-Opas

doi:10.1016/j.phytochem.2007.11.013

Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn

Phytochemistry. 2008 Mar;69(5):1242-9. doi: 10.1016/j.phytochem.2007.11.013.

Authors

Orapun Yodsaoue¹, Sarot Cheenpracha, Chatchanok Karalai, Chanita Ponglimanont, Suchada Chantrapromma, Hoong-Kun Fun, Akkharawit Kanjana-Opas

Affiliation

¹ Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

PMID: 18178229
DOI: 10.1016/j.phytochem.2007.11.013

Abstract

The first chemical study on the seeds of Caesalpinia sappan Linn. led to isolation of 11 cassane-type diterpenes, named phanginin A-K (1-11). The skeleton present in compounds 1-8 is rather unusual, consisting of a cassane-type diterpene with an ether bridge between C-19/C-20 in compounds 1-6 and C-11/C-20 in compounds 7 and 8. Their structures were elucidated on the basis of spectroscopic techniques. In addition, the X-ray structure of phanginin A (1) is reported. Only phanginin I (9) exhibited cytotoxic effect against KB cell line with IC50 value of 4.4 microg/ml.

Publication types

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

MeSH terms

Caesalpinia / chemistry*
Crystallography, X-Ray
Diterpenes / chemistry*
Diterpenes / isolation & purification
Magnetic Resonance Spectroscopy / methods
Magnetic Resonance Spectroscopy / standards
Models, Molecular
Molecular Conformation
Reference Standards
Seeds / chemistry*
Stereoisomerism

Substances

Diterpenes