Limonoids and tirucallane derivatives from the seeds of a krishna mangrove, Xylocarpus moluccensis.
Six new phragmalins, moluccensins H-M (1-6), two new andirobin-type limonoids, moluccensins N and O (7, 8), and two new tirucallane derivatives, moluccensins P and Q (9, 10), were isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, together with the known compound 3beta,22S-dihydroxytirucalla-7,24-dien-23-one. The structures of these compounds were established on the basis of spectroscopic data. Moluccensins H-L were phragmalins with a C-30 carbonyl group, and moluccensin M was a unique ring-D-opened 16-norphragmalin. Moluccensins H-J possess conjugated Delta(8,9) and Delta(14,15) double bonds, moluccensins K and L contain a Delta(8,14) double bond, and moluccensin M has a characteristic C(15)-C(30) linked five-membered lactone ring. Moluccensins H and I showed moderate insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L.
Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, People's Republic of China. wwujun2003@yahoo.com
Jun
J
Wu
Sheng-Xin
SX
Yang
Min-Yi
MY
Li
Gang
G
Feng
Jian-Yu
JY
Pan
Qiang
Q
Xiao
Jari
J
Sinkkonen
Tirumani
T
Satyanandamurty
D000818:Animals; D001517:Coleoptera / Q000187:drug effects; D007814:Larva / Q000187:drug effects; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D043982:Rhizophoraceae / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D036701:Limonins; D014315:Triterpenes; C514393:tirucallane