目的 为提高朝鲜族药材万年蒿的质量标准,分离纯化质量研究用对照品。方法 采用硅胶、ODS开放柱和半制备液相色谱等多种色谱方法,对万年蒿的体积分数95%乙醇提取物进行分离纯化,根据质谱和核磁共振等波谱学技术鉴定化合物的结构。结果 分离得到14个化合物,分别鉴定为1α-acetoxyeudesm-4-en-6β,11βH-12,6-olide(1)、(11S)-3-oxoeudesma-1,4(15)-dieno-12,6α-lactone(2)、1-epi-dehydroisoerivanin(3)、11-epitaurin(4)、chrysanthemolide(5)、1α-acetyl-gallicadiol(6)、erivanin(7)、1α, 4α-dihydroxyeudesm-2-en-5α,6β, 11βH-12, 6-olide(8)、vulgarin(9)、(+)-dehydrovomifoliol(10)、isoevodionol(11)、(+)-表松脂素(12)、落叶松脂醇-4'-O-β-D-葡萄糖苷(13)和落叶松脂醇-4-O-β-D-葡萄糖苷(14)。结论 化合物1～14均为从该植物中首次分离得到,为该药材的质量标准提高奠定了基础。
Abstract
OBJECTIVE To isolate and purify the reference compounds and improve the quality standard of Korean medicinal Herba Artemisiae sacrorum. METHODS The chemical constituents were isolated from the aerial parts of Korean medicinal herb Artemisia sacrorum by silica gel, ODS column chromatography and preparative HPLC, and the structures were identified by NMR and MS. RESULTS Fourteen known compounds were isolated and identified as follows:1α-acetoxyeudesm-4-en-6β,11βH-12,6-olide(1),(11S)-3-oxoeudesma-1,4(15)-dieno-12,6α-lactone(2), 1-epi-dehydroisoerivanin(3), 11-epi-taurin(4), chrysanthemolide(5), 1α-acetyl-gallicadiol(6), erivanin(7), 1α, 4α-dihydroxyeudesm-2-en-5α, 6β, 11βH-12, 6-olide(8), vulgarin(9),(+)-dehydrovomifoliol(10), isoevodionol(11),(+)-epi-pinoresinol(12), lariciresinol-4'-O-β-D-glucopyranoside(13), and lariciresinol-4-O-β-D-glucopyranoside(14). CONCLUSION All compounds are obtained from this plant for the first time. These compounds can be used as reference substances for the quality control of this ethnic medicine.
关键词
万年蒿 /
蒿属 /
倍半萜内酯 /
落叶松脂醇-4'-O-β-D-葡萄糖苷 /
落叶松脂醇-4'-O-β-D-葡萄糖苷
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Key words
Artemisia sacrorum /
Artemisia /
chemical constituent /
sesquiterpenoid /
lariciresinol-4'-O-β-D-glucopyranoside /
lariciresinol-4-O-β-D-glucopyranoside
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中图分类号：
R284
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参考文献
[1] Editorial Committee of Flora of China. Flora of China(中国植物志) [M]. Beijing:Science Press, 1991, 76(2):44.
[2] HUANG X M, GUAN Y H, JIANG Y Z. Pharmacognostical study on national medicine Artemisia sacrorum Ledeb [J].J Med Sci Yanbian Univ(延边大学医学学报),2016,39(1):35-37.
[3] Jilin Provincial Department of Health. Drug Standards of Jilin Province(1977)(吉林省药品标准1977年版) [S]. 1977:251.
[4] WANG X X, JIN G Z. Research progress on chemical constituents and pharmacological activities of Artemisia sacrorum [J]. J Chin Med Mater(中药材),2010,33(5):831-834.
[5] LIU C, DUGU J X, JIN L L. Chemical constituents of petroleum ether extract from the Artemisia sacrorum Ledeb [J]. J Med Sci Yanbian Univ(延边大学医学学报), 2013,36(1):27-28.
[6] MACRO J A, SANZ-CERVERA J F, PAREJA J M, et al. Sesquiterpene lactones from north African Artemisia species[J]. Phytochemistry, 1994, 37(2):477-485.
[7] HIGUCHI Y, SHIMAMA F, KOYANAGI R, et al. Synthetic approach to exo-endo cross-conjugated cyclohexadienones and its application to the syntheses of dehydrobrachylaenolide, isodehydrochamaecynone, and trans-isodehydrochamaecynone [J]. J Nat Prod, 2003, 66(5):588-594.
[8] RUSTAIYAN A, SIGARI H, JAKUPOVIC J, et al. A sesquiterpene lactone from Artemisia diffusa [J]. Phytochemistry, 1989, 28(10):2723-2725.
[9] HASHIMOTO T, NOMA Y, ASAKAWA Y. Biotransformation of terpenoids from the crude drugs and animal origin by microorganisms [J]. Heterocycyles, 2001, 54(1):529-559.
[10] SANZ J F, CASTELLANO G, MARCO J A. Sesquiterpene lactones from Artemisia herba-alba [J]. Phytochemistry, 1990, 29(2):541-545.
[11] MENGI N, TANEJA S C, MAHAJAN V P, et al. Eudesmanolides from Senecio chrysanthemoides [J]. Phytochemistry, 1991, 30(7):2329-2330.
[12] MARCO J A, SANZ-CERVERA J F, PAREJA J M, et al. Sesquiterpene lactones from North African Artemisia species [J]. Phytochemistry, 1994, 37(2):477-485.
[13] BORIKY D, BERRADA M, TALBINAYA M, et al. Eudesmanolides from Artemisia herba-alba [J]. Phytochemistry, 1996, 43(1):309-311.
[14] MARCO J A, SANZ J F, SANCENON F, et al. Sesquiterpene lactones from Artemisia species [J]. Phytochemistry, 1993, 32(2):460-462.
[15] METWALLY M A, JAKUPOVIC J, YOUNS M I, et al. Eudesmanolides from Artemisia judaica [J]. Phytochemistry, 1985, 24(5):1103-1104.
[16] HISAHIRO K, MASAKI B, TORU O. Two new megastigmanes from the leaves of Cucumis sativus [J]. Chem Pharm Bull, 2007, 55(1):133-136.
[17] LEE Y R, WANG X, XIA L K. An efficient and rapid synthetic route to biologically interesting pyranochalcone natural products [J]. Molecules, 2007, 12(7):1420-1429.
[18] EMI O, KUNIHARU S, MIKIO Y. Harmacologically active components of Todopon Puok(Fagraea racemosa), a medicinal plant from Borneo [J]. Chem Pharm Bull, 1995, 43(12):2200-2204.
[19] SHOEB M, JASPARS M, STEPHEN M, et al. Epoxylignans from the seeds of Centaurea cyanus(Asteraceae) [J]. Biochem Syst Ecol, 2004, 32(12):1201-1204.
[20] SUGIYAMA M, KIKUCHI M. Characterization of lariciresinol glucosides from Osmanthus asiaticus [J]. Heterocycles, 1993, 36(1):117-121.
[21] SHI Y P. Monoterpene and Sesquiterpene Chimistry(单萜和倍半萜化学) [M]. Beijing:Chemical Industry Press,2010:203-205.
[22] WANG J, ZHANG Y P, LIU Y. Content determination of hydroxyacetophenone in Artemisia capillaries from different collection time by HPLC [J]. Chin Med J Res Prac(现代中药研究与实践), 2011, 25(3):7-10.
[23] SHI J G. Lignan Chemistry(木脂素化学) [M]. Beijing:Chemical Industry Press,2010:199-200.
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