Premium
Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.
Author(s) -
Baloch Imam Bakhsh,
Baloch Musa Kaleem,
Najam us Saqib Qazi
Publication year - 2005
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.200590254
Subject(s) - chemistry , diterpene , homonuclear molecule , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , nuclear magnetic resonance spectroscopy , organic chemistry , molecule
Tumor‐promoting characteristics of seven esters, 1 – 7 , obtained from the latex of Euphorbia cauducifolia L. was appraised by carrying out NMRI mice back skin. The structures of 1 – 7 were elucidated by spectroscopic techniques like 1 H‐ and 13 C‐NMR, 2D‐NMR (HMQC, HMBC, HOHAHA (homonuclear Hartmann–Hahn ), NOESY, and NOE), FT‐IR, UV, and MS as esters of 17‐hydroxyingenol, namely 17‐[(2 Z ,4 E ,6 Z )‐deca‐2,4,6‐trienoyloxy]ingenol ( 1 ), 3‐ O ‐angeloyl‐17‐[(2 Z ,4 E ,6 Z )‐deca‐2,4,6‐trienoyloxy]ingenol ( 2 ), 3‐ O ‐acetyl‐20‐ O ‐angeloyl‐17‐hydroxyingenol ( 3 ), 17‐(acetyloxy)‐3‐ O ‐angelyl‐ingenol ( 4 ), 20‐ O ‐acetyl‐3‐ O ‐angeloyl‐17‐hydroxyingenol ( 5 ), 3‐ O ‐angelyl‐17‐(benzoyloxy)ingenol ( 6 ) and 20‐ O ‐acetyl‐3‐ O ‐angelyl‐17‐(benzoyloxy)ingenol ( 7 ). Compounds 1 – 4 were isolated for the first time, whereas 5 – 7 are known metabolites but detected for the first time in this plant. Biological investigations revealed that these compounds are tumor promoters.