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

• Published in: Phytochemistry (Oxford) Vol. 69; no. 5; pp. 1242 - 1249
• Main Authors: Yodsaoue, Orapun, Cheenpracha, Sarot, Karalai, Chatchanok, Ponglimanont, Chanita, Chantrapromma, Suchada, Fun, Hoong-Kun, Kanjana-Opas, Akkharawit
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-03-2008; Elsevier
• Subjects: Analytical, structural and metabolic biochemistry; Anticancer activity; anticarcinogenic activity; Biological and medical sciences; Caesalpinia - chemistry; Caesalpinia sappan; Caesalpinia sappan Linn; cassane diterpenes; Cassane-type diterpenes; Chemical constitution; chemical structure; Crystallography, X-Ray; cultured cells; cytotoxicity; Diterpenes - chemistry; Diterpenes - isolation & purification; diterpenoids; Fundamental and applied biological sciences. Psychology; Glycoproteins; humans; Leguminosae; Magnetic Resonance Spectroscopy - methods; Magnetic Resonance Spectroscopy - standards; medicinal plants; medicinal properties; Models, Molecular; Molecular Conformation; phanginin; Phanginin A–K; Plant physiology and development; Proteins; Reference Standards; seeds; Seeds - chemistry; spectral analysis; stereochemistry; Stereoisomerism; Thailand; Caesalpinia sappan Linn; Leguminosae; Cassane-type diterpenes; Phanginin A–K; Anticancer activity; Terpenoid; Seeds; Ether; Molecular structure; Phanginin A-K; Dicotyledones; KB cell line; Seed; Angiospermae; Diterpene; Isolation; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2007.11.013

Eleven cassane-type diterpenes, named phanginin A–K (
1–
11), were isolated from the seeds of
Caesalpinia sappan Linn. The structure of
1 was confirmed by X-ray diffraction technique.
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 IC
50 value of 4.4
μg/ml.