紫红獐牙菜口山酮及环烯醚萜类化合物的研究

摘要/Abstract

摘要：

采用各种柱色谱法对紫红獐牙菜的石油醚和正丁醇部位进行分离纯化，从石油醚部位分离鉴定得到6个化合物，利用理化性质和波谱学方法分别鉴定为oleanolic acid（1），swerchirin（2），sweriaperenine（3），bellidifolin（4），gentiacaulein（5）和1,7,8-trihydroxy-3-methoxyxanthone（6）；从正丁醇部位分离鉴定得到9个化合物，分别鉴定为8-[(β-D-glucopyranosyl)oxy]-1,5-dihydroxy-3-methoxyxanthone（7），5-[(β-D-glucopyranosyl)oxy]-1,8-dihydroxy-3-methoxyxanthone（8），7-[(β-D-xylopyranosyl)oxy]-1,8-dihydroxy-3-methoxyxanthone（9），8-[(β-D-glucopyranosyl)oxy]-1,3,5-trimethoxyxanthone（10），swertiamarin（11），tetrahydrosertianolin（12），8-hydroxy-10-hydrosweroside（13），campestroside（14）以及uridine（15）。其中，化合物14和15首次从该属植物中得到，化合物9，10，12和13首次从该植物中分离得到。

关键词: 紫红獐牙菜, 石油醚部位, 正丁醇部位, 口山酮, 烯醚萜

Abstract:

The chemical constituents of Swertia punicea Hemsl. were isolated by various column chromatographic methods. Fifteen compounds were obtained and identified as oleanolic acid (1), swerchirin (2), sweriaperenine (3), bellidifolin(4), gentiacaulein (5), isobellidifolin (6), 8-[(β-D-glucopyranosyl)oxy]-1,5-dihydroxy-3-methoxyxanthone (7), 5-[(β-D-glucopyranosyl)oxy]-1,8-dihydroxy-3-methoxyxanthone (8), 7-[(β-D-xylopyranosyl)oxy]-1,8-dihydroxy-3-methoxyxanthone (9), 8-[(β-D-glucopyranosyl)oxy]-1,3,5- trimethoxyxanthone (10), swertiamarin (11), tetrahydrosertianolin (12), 8-hydroxy-10-hydrosweroside (13), campestroside (14), and uridine (15). Compounds 14 and 15 were isolated from this genus and 9，10，12，13 were obtained from this plant for the first time.

Key words: Swertia punicea Hemsl., petroleum ether fraction, n-butanol fraction, xanthonoids, iridoid glycosides

田峦鸢，陈家春，白雪，方进波. 紫红獐牙菜口山酮及环烯醚萜类化合物的研究[J]. 天然产物研究与开发, 2010, 23(6): 979-983.

TIAN Luan-Yuan, CHEN Jia-Chun, BAI Xue, FANG Jin-Bo. Xanthonoids and Iridoid Glycosides from Swertia punicea Hemsl.[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2010, 23(6): 979-983.

参考文献

1 Wan DR(万定容),Chen JC(陈家春),Yu HH(余汉华).Codex of Hubei Medicina Materials(湖北药材志).Wuhan: Hubei Science and Technology Publishing Company,2002.533.
2 Tian LY(田峦鸢),Hang FJ(黄凤娇),Zhang XQ(张秀桥).Inhibitory Ethyl Acetate Effect of the Extracts of Swertia Punicea Hemsl on Hepatitis B Virus in Vitro.J Hubei Coll Tradit Chin Medic(湖北中医学院学报),2006,8:5-7.
3 Wen L(文莉),Chen JC(陈家春).Hypoglycemic Activity of S.punicea Hemal Extracts in Streptozotocin Induced Hyperglycemic Mice.China Pharmacist(中国药师),2007,10:140-142.
4 Tan P(谭沛),Liu YL(刘永隆),Hou CY(侯翠英).Swertiapunimarin from Swertia Punicea Hemsl..Acta Pharm Sinica(药学学报),1993,28:522-525.
5 Fukamiya N,Okano M,Kondo K,et al.Xanthones from Swertia punicea.J Natl Prod,1990,53:1543-1547.
6 Tan P,Hou CY,Liu YL,et al.Swertipunicoside. The first bisxanthone C-glycoside.J Org Chem,1991,56:7130-7133.
7 Tan P(谭沛),Liu YL(刘永隆),Hou CY(侯翠英).Swertiapunisidefrom Swertia punicea Hemsl..Acta Pharm Sinica(药学学报),1992,27:476-479.
8 Tan P,Hou CY,Liu YL,et al.3-O-Demethylswertipunicoside from Swertia punicea.Phytochemistry, 1992,31:4313-4315. 9 Luo YH(罗跃华),Nie RL(聂瑞麟).The Secoiridoids Isolated from Swertia Punicea.Acta Bot Yunnan(云南植物研究),1993,15:97-100.
10 Kanamori H,Sakamoto I.The components of Swertia punicea.Hiroshima-ken Hoken Kankyo Senta Kenkyu Hokoku,1993,1:13-16.
11 Xin M,Qiu MH,Nie RL,et al.A new monoterpene glycoside from Swertia punicea.Chin Chem Let,2000,11:709-710.
12 Zhang XQ(张秀桥),Tian LY(田峦鸢),Chen JC(陈家春),et al.Constituents from Swertia Punicea Hemsl.. Chin Tradit Herb Drugs(中草药),2007,38:1153-1154.
13 Hajimehdipour H,Amanzadeh Y,Ebrahimi SES,et al.Three Tetraoxygenated Xanthones from Swertia longifolia.Pharm Biol,2003,41:497-99.
14 Bian QY(卞庆亚),Hou CY(侯翠英),Chen JM(陈建民).Chemical Constituents from Swertia Calycina Franch..Nat Prod Res Dev(天然产物研究与开发),1998,10:1-5.
15 Ji LJ(纪兰菊),Ding JY(丁经业),Fan SF(樊淑芬),et al.Study on Chemical Constituents of Gentianopsis Brabata var.Stennocalyx H.W.Li ex T.N.Ho.Acta Bot Sinica(植物学报),1992,34:203-207.
16 Zeng GY(曾光尧),Tan GS(谭桂山),Xu KP(徐康平),et al.Water-soluble Chemical Constituents of Swertia davidi Franch..Acta Pharm Sinica(药学学报),2004,39:351-353.
17 Sun HF(孙洪发),Hu BL(胡伯林),Ding JY(丁经业),et al.The Glucosides from Swertia Mussotii Franch.. Acta Bot Sinica(植物学报),1991,33:31-37.
18 Luo YH(罗跃华),Nie RL(聂瑞麟).Studies on Iridoid Glucosides from Swertia angustifolia. Acta Pharm Sinica(药学学报),l992,27:l25-l29.
19 Koji H, Shigetoshi K,Purusotam B,et al.Tetrahydroswertianolin:a potent hepatoprotective agent from Swertia japonica Makino.Chem Pharm Bull,1997,45:567-569.
20 Tan RX,Kong LD,Wei HX.Secoiridoid glycosides and an antifungal anthranilate derivative from Gentiana tibetica.Phytochemistry,1998,47:1223-1226.
21 Teodora J,Dijana K,Ivana A,et al.Xanthones and C-glucosides from the aerial parts of four species of Gentianella from Serbia and Montenegro.Biochem Syst Ecol,2005,33:729-735.
22 Yu DQ(于德泉),Yang JS(杨峻山).Analytic Chemistry Handbook. 2nd Ed.7th Subolume.(分析化学手册,第二版,第七分册).Beijin:Chemical Industry Press,1999:907.

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