广藿香中非挥发性化学成分研究

Non-volatile chemical constituents from Pogostemon cablin

目的对刺蕊草属植物广藿香Pogostemon cablin中的非挥发性化学成分进行研究。方法采用硅胶、DM130大孔树脂、ODS、Sephadex LH-20、TLC、半制备HPLC等多种色谱技术对其化学成分进行分离纯化,依据理化性质、MS、1D NMR和2DNMR等波谱数据鉴定化合物结构。结果从广藿香95%乙醇提取物中共分离得到25个化合物,分别鉴定为2α,3β,19α,23α,30β-五羟基齐墩果-12-烯-28-酸(1)、2α,3β,19α,23α,29α-五羟基齐墩果-12-烯-28-酸(2)、齐墩果酸(3)、无羁萜酮(4)、β-谷甾醇(5)、豆甾醇(6)、豆甾-4-烯-3,6-二酮(7)、6-羟基豆甾-4-烯-3-酮(8)、6-羟基豆甾-4,22-二烯-3-酮(9)、5-羟基-7,3′,4′-三甲氧基-二氢黄酮(10)、5,4′-二羟基-7,3′-二甲氧基-二氢黄酮(11)、5-羟基-7,4′-二甲氧基-二氢黄酮(12)、圣草酚(13)、3,3′,4′,7-四甲氧基-5-羟基黄酮(14)、3,5,3′,4′-四羟基-7-甲氧基黄酮(15)、5-羟基-3,7,4′-三甲氧基黄酮(16)、3,5-二羟基-7,4′-二甲氧基黄酮(17)、木犀草素(18)、3-甲氧基槲皮素(19)、7,3′,4′-三甲氧基槲皮素(20)、10-二十碳烯酸(21)、13-十八碳烯酸乙酯(22)、二十二烷酸(23)、天师酸(24)、9(S),12(S),13(S)-三羟基十八烷-10(E),15(Z)-二烯酸(25)。结论化合物1和2为新的齐墩果烷型五环三萜化合物,分别命名为30β-羟基阿江榄仁素和29α-羟基阿江榄仁素。化合物1、2、7、8、19、24、25为首次从刺蕊草属植物中分离得到。

Objective To study the non-volatile chemical constituents from Guanghuoxiang(Pogostemon cablin(Blanco) Benth). Methods The chemical constituents were isolated and purified by various chromatographic techniques such as silica gel, DM130 macroporous resin, ODS, Sephadex LH-20, TLC, semi-preparative HPLC and their structures were identified based on physicochemical properties, MS, 1 D NMR and 2 D NMR spectral data. Results Twenty-five compounds were isolated from the 95% ethanol extract of P. cablin, which were identified as 2α,3β,19α,23α,30β-pentahydroxyolean-12-en-28 oic acid(1), 2α,3β,19α,23α,29α-pentahydroxyolean-12-en-28 oic acid(2), oleanolic acid(3), friedelin(4), β-sitosterol(5), stigmasterol(6), stigmast-4-ene-3,6-dione(7), 6-hydroxystigmast-4-en-3-one(8), 6-hydroxystigmasta-4,22-dien-3-one(9), 5-hydroxy-7,3′,4′-trimethoxyflavanone(10), 5,4′-dihydroxy-7,3′-dimethoxyflavanone(11), 5-hydroxy-7,4′-dimethoxyflavanone(12), eriodictyol(13), 3,3′,4′,7-tetramethoxy-5-hydroxyflavone(14), 3,5,3′,4′-tetrahydroxy-7-methoxyflavone(15), 5-hydroxy-3,7,4′-trimethoxyflavone(16), 3,5-dihydroxy-7,4′-dimethoxyflavone(17), luteolin(18), 3-O-methylquercetin(19), 7,3′,4′-trimethylquercetin(20), 10-eicosenoic acid(21), 13-octadecenoic acid ethyl ester(22), behenic acid(23), tianshic acid(24), and 9(S),12(S),13(S)-trihydroxyoctadeca-10(E),15(Z)-dienoic acid(25). Conclusion Compounds 1 and 2 are new oleanane type pentacyclic triterpenes named 30β-hydroxyarjungenin and 29α-hydroxyarjungenin respectively. Compounds 1-2, 7-8, 19, and 24-25 are isolated from Pogostemon genus for the first time.