Studies On The Chemical Constituents And Biological Activities Of Ilex Hainanensis

English Abstract Studies on the Chemical Constituents and Biological Activities of Ilex hainanensisIlex hainanensis Merr. (Aquifoliaceae) is distributed mainly in the southern region of the People's Republic of China. Its leaves are used as a traditional tea product, known as "Shan-Lv-Cha". It is also used in the form of a traditional Chinese medicine as a diuretic, anti-hypertensive, antilipemic and anti-inflammatory agent. A literature search revealed that there were numerous reports on clinical research of "Shan-Lv-Cha" for treatment of hypertension. However, with regard to chemical constitutes and biological activities of Ilex hainanensis, there were few reports and only five compounds have been isolated. Therefore, we carried out phytochemical investigation systematically on llex hainanensis, and did some bio-activce screening of the part chemical constituents isolated from Ilex hainanensis.Studies on the chemical constituents of llex hainanensis: 81 componds have been isolated from the leaves of Ilex hainanensis. On the basis of their physiochemical and spectroscopic evidence, their chemical structures were elucidated as follows:20 flavonoids: eriodictyol (BF181), quercetin (BF191), dihydrokaempferol (BTB3165), (2R, 3R) -dihydroquercetagetin (BTB4121), hyperin (BTB954), querc- itrin (BTB855), quercitrin -3-O-β-D-glucopynanoside (BT551), kaermpferol-3 -O-α-L- rhamnopyranoside (BF1752), myricitrin (BTB9532), kaermpferol- 7-O-β-D- glucopynanoside (BTB955), quercitrin-7-O-β-D-glucopynanoside (BTB115b), luteolin-7-O-β-D glucopynanoside (BTBll5a), eriodictyol- 7-O-β-D-glucopynanosi -de (BT431), prunin (BT250922), rutin (BT2-45S-1), kaempferol -3 -O-β- robinob inoside (BT25143), Kaempferol -3-O -β-rutinoside (BT25144), isorhamnetin -3- O- [α-rhamopyranosyl- (1-6)-β-D- glucopyranoside (BT25145), 5,7-dihydroxychromone (BF171), 5,7-dihydroxy chromone -7 -O-β-D-glucopynanoside (BTB831). 10 compounds based on quinic acid: 3′, 5′-O- dicaffeoyl quinic acid (BT381), 3′, 5′-O-dicaffeoylquinic acid methyl ester (BTB734) , 3′, 5′-O- dicaffeoyl quinic acid ethyl ester (BTB408-8a), 3′, 5′-O-dicaffeoylquinic acid butyl ester (BTB408 11a), 4′, 5′-O-dicaffeoylquinic acid (BT383), 4′, 5′-O-dicaffeoylquinic acid methyl ester (BTB735), 4′, 5′-O-dicaffeoylquinic acid ethyl ester (BTB 408-8b), 4′, 5′-O- dicaffeoylquinic acid butyl ester (BTB408-11b), 3′, 4′-O- dicaffeoylquinic acid methyl ester (BTB641), 4′, 5′-O-tricaffeoylquinic acid butyl ester (BF1822).19 triterpenoids:α-amyrin (C-6113), ursolic acid (C724S), ilexgenin A (B70 E37), 3β, 30-dihydrexyurs-12-ene-24, 28-dioic acid (BF53210), 3β, 19α, 30- trihydro xyurs -12- ene- 24, 28-dioic acid (BF523), 3β, 19α, 20β-trihydroxyurs- 12-ene- 24, 28 -dioic acid (BF5324), 3β, 19α, 22α-trihydroxyurs- 12-ene- 24, 28-dioic acid (BF524), 3β, 19α-dihydrexy -11-oxo-urs- 12-ene- 24, 28-dioic acid (BF5323), rotundioic acid (BF5328), 19α- hydroxyasiatic acid (BF521), hydroxyasiatic acid (BF546), 2α, 3β, 19α-trihydroxyurs - 12-ene-23, 28-dioic acid (BF624a), 2α, 3β, 19α-trihydroxy olean -12-ene-23, 28-dioic acid (BF624b), 2α, 3β, 19α-trihydroxyurs -12-ene-24, 28-dioic acid (BF6522), 3β, 19α-dihydroxyolean -12-ene- 24, 28-dioic acid (B70E36), 3β, 29 -dihydroxyolean -12-ene-24, 28-dioic acid (BF5329), 3β, 19α, 23- -trihydroxyurs -12 -ene-24, 28-dioic acid (BF653a), 3β, 19α, 23-trihydroxyolean -12-ene-24, 28-dioic acid (BF653b), 3β, 19α, 23, 24-tetrahydroxyurs -12-ene-28-oic acid (BF5326).7 triterpenoid saponins: ilexsaponin A1 (BF815), 3β, 19α-dihydroxyurs -12-ene-28-oic acid-3-O-β-D- glucopyranoside (BF631), 3β, 19α-dihydroxyolean -12 -ene- 24, 28-dioic acid-28- O-β-D-glucopyranoside (BFS14), 3β, 29-dthydroxy olean -12- ene- 24, 28- dioic acid-28-O-β-D-glucopyranoside (BF8213), 3β- hydroxyl urs -12, 18-alien-24, 28-dioic acid-28-O-β-D-glucopyranoside (BF643), (3β), 3, 30- di- hydroxyurs- 12, 19-alien-24, 28-dioic acid-28-O-β-D- glucopyranoside (BF8222), 3β, 19α-dihydroxyolean - 12-ene-24, 28-dioic acid-28-O-β-D-glucopy ranosyl -(1-6)-β- D -glucopyranoside (BF98272).11 componds based on hemiterpene: 2-hydroxymethyl-3-caffeoyloxy- 1-butene-4-ol (BT250621), 2-hydroxymethyl-4-caffeoyloxy-1-butene-3-ol (BT2506 22), 2- (caffeoyloxy) methyl -1- butane -3, 4-diol (BT250623), (2E) -2 -methyl -2 -butene-1, 4-diol-4-O-caffeic acid ester (BF1632a), (2E)-2-methyl-2-butene-1, 4-diol-1-O-caffeic acid ester (BF1632b), 2-(caffeoyloxy) methyl -3 - hydroxy -1- but ene-4- O-β-D-glucopy ranoside (BTBl134), 2- hydroxymethyl -3 -caffeoyloxy -1- butene-4-O-β-D- glucopyranoside (BTBI222), (2-hydroxymethyl -3-hydroxyl-1- butene -4-O-β-D- (6"-O-caffeoyl) -glucopy ranoside (BTBl132), (2E)-3- methyl -2-butene -1, 4-diol -4-O-β-D -(6"-O-caffeoyl) -glucopyranoside (BTB832), 1-O- caffeoyl -(2E) -3-methyl -2-butene -1, 4-diol-4-O-β-D-glucopyranoside (BTB833), 2- hydroxylmethyl-3 -caffeoyloxy -1-butene- 4-O-β-D- (6"'-O-caffeoyl) -glucopyra- noside (BTB932).14 other compounds: ellagic acid (BTB75), dibutyl phthalate (BS12), caffeic acid (BTB408-2), 4-hydroxycinnamic acid (BTB3153), hentriacontane (C4-2), tetracontane (C6111), 1-dotriacontanol (C4-30), 1-tetratfiacentanol (C5-1), hexadecaneicacid (BS131), glucose (BF811), (+)-olivil (BTB4062), breynioside A (BT250921), (2E)-3- (3-hydroxymethyl-phenyl) -2-propylene-1-o1 (BTB31621),β- sitosterol (C-62)。Among these compounds, 27 of which are new compounds: 10 triterpenoids : BF523, BF524, BF5323, BF5324, BF5326, BF5329, BF53210, B70E36, BF653a, BF653bb; 6 triterpenoid saponins : BF631, BF643, BF814, BF8213, BF8222, BF98272; 9 compounds based on herniterpene: BT250621, BT250622, BT250623, BTB1132, BTB932, BF1632a, BF1632b, BTB832, BTB833; 1 compound based on quinic acid: BF1822; 1 other compound: BTB31621. Other compounds expect C724S, BF814, BF815 are all isolated from the Ilex hainanensis for the frist time.Study on the screening of triterpenoids and triterpenoid saponins on anti-tumor: there is no positive results on the HL-60, GC-823, Bel-7402 and KB tumor cell when those compounds at the concentration of 10μmol/L.Study on the screening of triterpenoids and triterpenoid saponins on affecting the macrophage's absorption of LDA: some compounds BF631, B815, BF53210, BF6522, BF5324 and BF523 show some positive results on controlling macrophage's absorption of LDA, suggesting the potential activities on anti- atherosclerosis; while compounds BF8213, BF643, B70E37, B70E36, BF5326, BF653 show some promoting activities of macrophage's absorption of LDA. It can't be concluded the relationship between the structure and the activities from the present results, and need to be studied still.Advance in the studies on the chemical constituents and biological activities of Ilex hainanensis and the plants of genus Ilex were reviewed in this dissertation, also were concluded the structural and spectral characteristics of triterpenoids isolated from the plants of genus Ilex up to now.