Lupane-Triterpene Esters from the Leaves of Ceriops decandra (Griff.) Ding Hou

Abstract

Two novel triterpene esters were isolated from the leaves of Ceriops decandra in addition to 16 known triterpenes: lupenone 3, lupeol 4, betulinaldehyde 5, 3β-Z-coumaroyllupeol 6, 3β-E-coumaroyllupeol 7, 3-epi-betulinic acid 8, betulin 9, betulinic acid 10, 3β-E-feruloylbetulin 11, 30-nor-lup-3β-ol-20-one 12, 3β-E-caffeoyllupeol 13, lup-20(29)-en-3β,30-diol 14, 3β-hydroxylupan-29-oic acid 15, 3β,20-dihydroxylupane 16, and a mixture of oleanolic and ursolic acid 17 and 18. The new compounds were determined by spectroscopic methods to be 3β-E-feruloyllupeol 1 and 3β-Z-feruloyllupeol 2. Compounds 3 and 5–16 were reported for the first time as metabolites of C. decandra.

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

“…Reviews on anticancer properties of betulinic acid (5) and its derivatives have been provided [25][26][27][28][29][30]. A review on the anticancer and chemopreventive potential of betulin (4) in vitro and in vivo has also been provided [31].…”

“…Another study reported that the leaf extracts afforded α-amyrin, β-amyrin, lupeol, oleanolic acid, and ursolic acid [5]. The bark of C. decandra yielded decandrins A-K [6]; 2-(9-hydroxy-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-1-yl) propanoic acid (3β-hydroxylupan-29-oic acid) [7]; d-catechin, leucoanthocyanidins [4]; procyanidin [8]; decandrinin [9]; (-)-syringaresinol, (-)-pinoresinol, β-sitosterol, stigmasterol, palmitic acid, and 3,4-dihydroxybenzoic acid Et ester [10]; and 7,13-abietadien-3β-ol, 7-oxodehydro-abietinol, margocin, 3β-hydroxy-abieta-8,11,13-trien-7-one, 15,18-dihydroxyabieta-8,11,13-trien-7-one, 7β,18-dihydroxy dehydroabietanol, 4-epitriptobezene L, 7α, 18-dihydroxydehydroabietanol, sabiperone E, 13β,18-dihydroxy-abiet-8(14)-ene-7-one, ent-labd-8(17),13E-dien-15-ol, ent-8(14)-pimarene-15R,16-diol, and (5S*,8S*,9S*,10R*,13S*)-3-hydroxy-16-nor-2-oxodolar-3-ene-15-oic acid [11]. Furthermore, the wood extract of C. decandra yielded 3β,13β-dihydroxy-8-abietaen-7-one and 3β-hydroxy-8,13-abietadien-7-one [12].…”

“…Several studies were reported on the chemical constituents of C. decandra. The leaves of C. decandra yielded lupenone, lupeol, betulinaldehyde, 3β-Z-coumaroyllupeol, 3β-E-coumaroyllupeol, 3-epi-betulinic acid, betulin, betulinic acid, 3β-E-feruloylbetulin, 30-nor-lup-3β-ol-20-one, 3β-E-caffeoyllupeol, lup-20(29)-en-3β,30-diol, 3β-hydroxylupan-29-oic acid, 3β,20-dihydroxylupane, oleanolic acid, ursolic acid, and 3β-E-feruloyllupeol and 3β-Z-feruloyllupeol [4] which are of relevance to our present report. Another study reported that the leaf extracts afforded α-amyrin, β-amyrin, lupeol, oleanolic acid, and ursolic acid [5].…”

Chemical Constituents and Some Biological Activities of Plants from the Genus Ceriops

“…ent-3,16-Dihydroxydolabr-3-ene-2,15-dione (11) and tagalsin S (15) have a 2-hydroxyacetyl group at C(13), whereas tagalsins T and U (16 and 17, resp. ), ent-dolabr-3-ene-15,16-diol (18), ent-dolabr-4(18)-ene-15,16-diol (19), and erythroxydiol Y (20) possess a 1,2-dihydroxyethyl group instead. The relative configuration of tagalsin S (15) was confirmed by means of singlecrystal X-ray diffraction analysis in 2010 [11].…”

Isolation of a lupane triterpene fatty acid ester with antibacterial activity from the leaves of Finlaysonia obovata

“…This compound was first isolated from Koelpinia linearis [12]. There are several reports on the isolation of triterpene esters from mangrove plants [13,14], but this is the first report of all spectral characterization of lup-20(29)-ene-3-tetradecanoate and the first report from a latex-exuding mangrove plant.…”