魚針草化學成分及其生物活性之研究

從魚針草之甲醇萃取物分離純化得到31個化合物，包含七個雙萜類化合物：ovatodiolide (1)、4,5-epoxovatodiolide (2)、4??-hydroxy-5-enovatodiolide (3)、4??-hydroxy-5-enovatodiolide (4)、4-methylene-5??-hydroxyovatodiolide (5)、4-methylene-5??- hydroxyovatodiolide (6)及4-methylene-5-oxovatodiolide (7)；七個黃酮類化合物：apigenin (8)、terniflorin (9)、apigenin 7-O-??-D-(6′′-cis-p-coumaroyl) glucoside (10)、5,8,4′-trihydroxy-7,3′- dimethoxyflavone (11)、anisofolin A (12)、anisofolin B (12)及prunin-6′′-p-coumarate (13)；四個三萜類化合物：masmalic acid (15)、3-O-trans-p-coumaroylmaslinic acid (16)、hederagenin (17)及arjumolic acid (18)；三個indole類化合物：indole-3-carboxylic acid (19)、indole-3-carboxylic acid methyl ester (20)及indole-3- carbaldehyde (21)；五個芳香環類化合物：p-hydroxybenzoic methyl ester (22)、p-hydroxybenzoic acid (23)、p-hydroxycinnamic methyl ester (24)、3,4-dihydroxycinnamic methyl ester (25)及anisovatodside (26)；及五個固醇類化合物：6’-(β-sitostery-3- O-β-D-glucopyranosidyl)-hexadecanoate (27)、β-sitosteryl (28)與β-sitigmasteryl glucoside (29)混合物及β-sitosterol (30)與β-sitigmasterol (31)混合物。其中化合物3~5、7和10為新化合物，而11、15~22、25及27為首次在魚針草分離而得之化合物。經活性試驗，化合物1~7對於癌症細胞株有細胞毒殺作用以及有抗血小板凝集效果。化合物1、8及11~14具抗發炎活性。

關鍵字

魚針草；唇形科；細胞毒殺

並列摘要

Thirty-one compounds were isolated from the MeOH extracts of Anisomeles Indica. These include seven diterpenoids: ovatodiolide (1), 4,5-epoxovatodiolide (2), 4??-hydroxy-5-enovatodiolide (3), 4??-hydroxy-5-enovatodiolide (4), 4-methylene-5??- hydroxyovatodiolide (5), 4-methylene-5??-hydroxyovatodiolide (6) and 4-methylene-5-oxovatodiolide (7); seven flavonoids: apigenin (8), terniflorin (9), apigenin 7-O-??-D-(6′′-cis-p-coumaroyl) glucoside (10), 5, 8, 4′-trihydroxy-7, 3′-dimethoxyflavone (11), anisofolin A (12), anisofolin B (13) and prunin-6′′-p-coumarate (14); four triterpenoids: masmalic acid (15), 3-O-trans-p-coumaroylmaslinic acid (16), hederagenin (17) and arjumolic acid (18); three indoles: indole-3-carboxylic acid (19), indole-3-carboxylic acid methyl ester (20) and indole-3-carbaldehyde (21); five benzenoids: p-hydroxybenzoic methyl ester (22), p-hydroxybenzoic acid (23), p-hydroxycinnamic methyl ester (24), 3,4-dihydroxycinnamic methyl ester (25) and anisovatodside (26); five steroids: 6′-(β-sitostery-3-O-β-D-glucopyranosidyl)-hexadecanoate (27), the mixture of β-Sitosteryl (28) and β-sitigmasteryl glucoside (29) and the mixture of β-Sitosterol (30) and β-sitigmasterol (31). Among them, 3~5, 7 and 10 are new compounds; 11, 15~22, 25 and 27 are isolated for the first time from this plant. In biological tests, the diterpenoids 1~7 showed cytotoxicity against several cancer cell lines and inhibitory effect on platelet aggregation. Furthermore, 1, 8, and 11~14 showed anti-inflammation activity.

並列關鍵字

Anisomeles indica ； Labiatae ； Cytotoxicity

參考文獻

1. Boufford, D. E.; Hsieh, C. F.; Huang, T. C.; Lowry, P. P.; Ohashi, H.; Peng, C. I., 台灣植物誌- Flora of Taiwan. second edition; Vol. 4, p432-717, 1998.