[關(guān)鍵詞]
[摘要]
目的 研究離舌橐吾Ligularia veitchiana花和種子中的倍半萜類化學(xué)成分及其細(xì)胞毒活性。方法 綜合運(yùn)用正、反相硅膠柱色譜、薄層制備色譜、Sephadex LH-20凝膠柱色譜及高效液相色譜等多種色譜技術(shù)對(duì)離舌橐吾花和種子中倍半萜類化學(xué)成分進(jìn)行分離純化,采用現(xiàn)代波譜學(xué)技術(shù)鑒定單體化合物的結(jié)構(gòu);采用MTT法對(duì)單體化合物進(jìn)行體外細(xì)胞毒活性評(píng)價(jià)。結(jié)果 從離舌橐吾花和種子中分離得到了14個(gè)倍半萜類化合物,分別鑒定為10β-氫-8α,12-環(huán)二氧艾里莫酚-7(11)-烯-8β-醇(1)、8β-羥基艾里莫酚-7(11)-烯-12,8α-內(nèi)酯(2)、艾里莫酚-7(11),9-二烯-8-酮(3)、isopetasol(4)、neopetasane(5)、6,9-二烯-8-羰基艾里莫酚-12-去甲基-11-酮(6)、1β-羥基艾里莫酚-7(11),9(10)-二烯-8-酮(7)、11-羥基艾里莫酚-6(7),9(10)-二烯-8-酮(8)、rel-[(4S,5S)-1β,11-二羥基艾里莫酚-6,9-二烯-8-酮](9)、phacadinane E(10)、platyphyllide(11)、liguhodgsonal(12)、ligudentatin A(13)、7-methoxylplatyphyllide(14);體外細(xì)胞毒活性評(píng)價(jià)結(jié)果表明,化合物1對(duì)人胃癌HCG-27細(xì)胞、人肝癌HepG2細(xì)胞的半數(shù)抑制濃度(median inhibition concentration,IC50)值分別為(13.46±1.93)、(14.79±1.45)µg/mL;化合物12對(duì)HepG2細(xì)胞的IC50值為(28.65±2.08)µg/mL。結(jié)論 化合物1、4~10和14均為首次從該植物中分離得到;化合物10為首次從橐吾屬植物中分離得到。化合物1對(duì)HCG-27細(xì)胞、HepG2細(xì)胞具有較顯著的細(xì)胞毒活性。
[Key word]
[Abstract]
Objective To study the sesquiterpenoids from flowers and seeds of Ligularia veitchiana and their cytotoxic activities in vitro. Methods Various chromatographic techniques such as normal and reversed-phase silica gel column chromatography, precipitation thin-layer chromatography (PTLC), Sephadex LH-20 gel column chromatography, and HPLC were used to isolate and purify the sesquiterpenoids from flowers and seeds of L. veitchiana, and combined with the spectroscopic techniques such as NMR and MS for the structural characterization. The MTT method was used for evaluating cytotoxic activities of the compounds in vitro. Results Fourteen sesquiterpenoids were isolated from the flowers and seeds of L. veitchiana and identified as 10βH-8α,12-epidioxyeremophil-7(11)-en-8β-ol (1), 8β-hydroxy-eremophil-7(11)-en-12,8α-olide (2), eremophil-7(11),9-dien-8-one (3), isopetasol (4), neopetasane (5), 6,9-dien-8-oxoeremophil-12-nor-11-ketone (6), 1β-hydroxyeremophil-7(11),9(10)-dien-8-one (7), 11- hydroxyeremophil-6(7),9(10)-dien-8-one (8), rel-[(4S,5S)-1β,11-dihydroxy-eremophil-6,9-dien-8-one] (9), phacadinane E (10), platyphyllide (11), liguhodgsonal (12), ligudentatin A (13) and 7-methoxylplatyphyllide (14). The half maximal inhibitory concentration (IC50) value of compound 1 against human gastric cancer cell line HCG-27 and human liver cancer cell line HepG2 were (13.46 ±1.93) and (14.79 ±1.45) μg/mL, respectively; Compound 12 showed certain cytotoxic activity against human liver cancer cells HepG2 with an IC50 value of (28.65 ±2.08) µg/mL. Conclusion Compounds 1, 4—10 and 14, were isolated from this plant for the first time. Compound 10 was isolated from Ligularia genus for the first time. Compound 1 has significant cytotoxic activity against human gastric cancer cells HCG-27 and human hepatocellular carcinoma cells HepG2
[中圖分類號(hào)]
R284.1
[基金項(xiàng)目]
國家自然科學(xué)基金資助項(xiàng)目(22207063);高等學(xué)校學(xué)科創(chuàng)新引智計(jì)劃(111計(jì)劃,D20015);湖北省教育廳科學(xué)技術(shù)研究項(xiàng)目(Q20161207)