Study On The Chemical Constituents From Two Species Of The Genus Trichilia

Trichilia sinensis and T. connaroides var. microcarpa belong to the genus of Trichilia (Meliaceae). Domestic and international phytochemical studies on the plants of this genus indicated that the main chemical constituents were limonoids, which are highly oxygenated, structurally diversified with significant biological activities. In order to search for more novel limonoids, chemical constituents from the genus of Trichilia were studied, which were collected from Hainan. Together with the cytotoxicities, anti-feeding and contact toxicity of extracts and some compounds were tested. This study provided the basis for research and development these plants resources.63compounds in total were acquired from the ethanol extracts of those two plants by column chromatography, and their structures were identified by physicochemical and organic spetra (IR, UV, MS and NMR, etc). These compounds were characterized as twenty-four limonoids, seven tirucallane-type triterpenoids, one lupine-type triterpenoid, sixteen steroids, four flavonoids and glycosides, three sesquiterpenoids, three aromatic derivatives, two ceramides and three other compounds. Among them,19compounds were new.Forty-two compounds were isolated from the roots of T. sinensis, which were identified as trichiliton B (1), trichiliton C (2), trisinenmalin A (3), trisinenmalin B (4), trisinenmalin C (5),15-Acetyltrichagmalin C (6), trichinenlide U (7), trichinenlide V (8), trichinenlide W (9), trichinenlide X (10), humilin B (11), trichisinlin A (12), trichisinlin B (13), trichisinlin C (14), trichisinlin D (15), trichisinlin E (16), trichisinlin F (17), meliatoxin B1(18), meliatoxin B2(19), aphanastatin (20),12-O-deacetyltrichilin H (21), trisinlin A (22), trichilinoid A (23),3β-hydroxy-4a-acetylpregnane-16-one (24), stigmastane-3β,6α-diol (25), schleicheol1(26),3β-hydroxy-stigmasta-5-en-7-one (27),3α,16β,20,22-tetrahydroxyergosta-5,24(28)-diene (28),3β4α-dihydroxypregnan-16-one (29), ekebergin B (30),21α-methylmelianodiol (31), hispidol B (32), piscidinol A (33), odoratone (34),24-epi-piscidinol A (35),24β,25-dihydroxy-melianone lactone (36),(4E,8E)-2[2’-hydroxyhexadecanoyl amino]-4,8-octadecadiene-1,3-diol (37), methyl syringate (38),4-hydroxy-3,5-dimethoxy-benzaldehyde (39), lasiodiplodin (40), tran.s-4-hydroxymellein (41),9-octadecenoic acid-2’,3’-dihydroxypropyl ester (42). Among them, eighteen were new:seventeen new limonoids (1～5、7～10、12～17、22～23), one new steroid (24).Eighteen compounds were isolated from the leaves of T. connaroides var. microcarpa, which were identified as3β,4β,20β-trihydroxyergosta-5,24(28)-dien-16-one (1), β-sitosterol (2),(3β,23S)-ergosta-5,24(28)-diene-3,23-diol (3), ergosta-5,24(28)-diene-3β-diol (4), stigmast-5-ene-3β,7α-diol (5), sitoindoside (6), stigmast-3β,5α,6β-triol (7),3β,4α,20β-trihydroxypregnan (8), daucosterol (9),1β,11-dihydroxy-5-eudesmene (10), aromadendrane-4β,10β-diol (11), caryolane-1,9β-diol (12), betulin (13), kaempferol (14), luteolin (15), kaempferol-3-O-β-D-glucopyranoside (16), quercetin-3-O-β-D-glucopyranoside (17),4-Hydroxybenzoic acid (18). Among them, one was new:steroid (1).Four compounds were isolated from the fruits of T. connaroides var. microcarpa, which were identified as sitoindoside I (1), limocin A and B (2), apicatin (3),1-O-β-D-Glucopyranosyl-(2S,3R,4E,8Z)-2-N-(2’-hydroxypalmitoyl)octadecasphinga-4,8-di enine (4).The cytotoxicities of compound1,3-8,10-18from the leaves of T. connaroides var. microcarpa were evaluated in vitro using the MTT method. Compound1,3and4showed inhibitory activities towards human hepatoma (BEL-7402) cell lines. Anti-feeding and contact toxicity of extracts against three instar larvae of Plutella xylostella were assessed by immersion methods. All extracts showed anti-feeding activity against three instar larvae of P. xylostella. Only Pet. Ext. and n-BuOH Ext. from the roots of T. sinensis showed48h and72h the mortality rate more than15%against three instar larvae of P. xylostella.