红花水提取物的化学成分研究

赫军, , 陈钟, 杨桠楠, 姜建双, 冯子明, 张培成*

中国药学杂志 ›› 2014, Vol. 49 ›› Issue (6) : 455-458.

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中国药学杂志 ›› 2014, Vol. 49 ›› Issue (6) : 455-458. DOI: 10.11669/cpj.2014.06.004
论 著

红花水提取物的化学成分研究

  • 赫军1, 2, 陈钟1, 杨桠楠1, 姜建双1, 冯子明1, 张培成1*
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Chemical Constituents from Aqueous Extract of Carthamus tinctorius

  • HE Jun1, 2, CHEN Zhong1, YANG Ya-nan1, JIANG Jian-shuang1, FENG Zi-ming1, ZHANG Pei-cheng1*
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摘要

目的 对红花水提取物中的化学成分进行研究。方法 通过大孔吸附树脂、Sephadex LH-20、反相HPLC等多种色谱进行分离纯化, 根据理化性质和波谱数据进行鉴定。结果 从红花水提物中分离得到了12个化合物, 分别为(2E, 8E)-12R-tetradecadiene-4, 6-diyne-1, 12, 14-triol(1), (8Z)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside(2), (8E)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside(3), (2S)-4′, 5, 6, 7-四羟基二氢黄酮 6-O-β-D-吡喃葡萄糖苷(4), 对羟基苯甲酸(5), 异香草酸(6), dihydrophaseic acid methyl ester-3-O-β-D-glucoside(7), dihydrophaseic acid methyl ester(8), 对羟基苯甲醛(9), N, N′-dicoumaroyl-putrescine(10), 4-(4′-羟基苯基)-丁-3-烯-2-酮(11), 对羟基苯乙酮(12)。结论 化合物1, 3~4, 6, 8, 10为首次从红花中分离得到, 并首次报道化合物1的绝对构型及碳谱数据。

Abstract

OBJECTIVE To study the chemical constituents of the aqueous extract of Carthamus tinctorius. METHODS Compounds were isolated by a combination of various chromatographic techniques including column chromatography on macroporous resin and Sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by physiochemical properties and spectral analysis. RESULTS Twelve compounds were isolated and identified as(2E, 8E)-12R- tetradecadiene-4, 6-diyne-1, 12, 14-triol(1), (8Z)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside(2), (8E)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside(3), (2S)-4′, 5, 6, 7-tetrahydroxyflavavone 6-O-β- D-glucoside(4), p-hydroxybenzoic acid(5), 3-hydroxy-4-methoxybenzoic acid(6), dihydrophaseic acid methyl ester-3-O-β-D-glucoside(7), dihydrophaseic acid methyl ester(8), 4-hydroxy benzaldehyde(9), N, N′-dicoumaroyl-putrescine(10), 4-(4′-hydroxyphenyl)but-3-en-2-one(11) and 4-hydroxyacetophenone(12).CONCLUSION Compounds 1, 3-4, 6, 8, and 10 are isolated from this plant for the first time. The absolute configuration and 13C-NMR data of compound 1 are for the first time reported.

关键词

红花 / 水提物 / (2E / 8E)-12R-tetradecadiene-4 / 6-diyne-1 / 12 / 14-triol / (8Z)-decaene-4 / 6-diyn-1-O-β-D-glucopyranoside / (8E)-decaene-4 / 6-diyn-1-O-β-D-glucopyranoside / 结构鉴定

Key words

Carthamus tinctorius / aqueous extract / (2E, 8E)-12R-tetradecadiene-4, 6-diyne-1, 12, 14-triol / (8Z)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside / (8E)-decaene-4, 6-diyn-1-O-β-D-glucopyranoside / structural identification

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导出引用
赫军, , 陈钟, 杨桠楠, 姜建双, 冯子明, 张培成*. 红花水提取物的化学成分研究[J]. 中国药学杂志, 2014, 49(6): 455-458 https://doi.org/10.11669/cpj.2014.06.004
HE Jun, , CHEN Zhong, YANG Ya-nan, JIANG Jian-shuang, FENG Zi-ming, ZHANG Pei-cheng*. Chemical Constituents from Aqueous Extract of Carthamus tinctorius[J]. Chinese Pharmaceutical Journal, 2014, 49(6): 455-458 https://doi.org/10.11669/cpj.2014.06.004
中图分类号: R284.1   

参考文献

[1] Editorial Board of Compendium Traditionan Herbal Drugs. Compendium of Chinese Traditional Herbal Drugs(全国中草药汇编). Vol 2. Beijing:People′s Health Press, 1992:386.[2] ZHENG H Z, DONG Z H, SHE J. Moderm Study of Traditional Chinese Medicine(中药现代研究与应用). Vol 3. Beijing:Xue Yuan Press, 1998:2057.[3] JIANG J S, XIA P F, FENG Z M, et al. Chemical constituents from flowers of Carthamus tinctorius. China J Chin Mater Med(中国中药杂志), 2008, 33(24):2911-2913.[4] JIANG J S, LV L, YANG Y N, et al. New spermidines from the florets of Carthamus tintorius. J Asia Nat Prod Res, 2008, 10(5):447-451.[5] JIANG J S, HE J, FENG Z M, et al. Two new quinochalcones from the florets of the Carthamus tinctorius. Org Lett, 2010, 12(6):1196-1199.[6] HE J, SHEN Y, JIANG J S, et al. New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities. Carbohy Res, 2011, 346(13):1903-1908.[7] JIANG J S, CHEN Z, YANG Y N, et al. Two new glycosides from the florets of Carthamus tintorius. J Asia Nat Prod Res, 2013, 15(5):427-432.[8] JENTE R, BOHLMANN F, SCHONEWEISS S. Weitere acetylenverbindungen aus Centaurea Ruthenica. Phytochemistry, 1979, 18(5):829-837.[9] GERARDS M, SNATZKE G. Circular dichroism, xcⅢ1 determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their “in situ” complexes with. Tetrahedron:Asymmetry, 1990, 1(4):221-236. FRELEK J, SZCZEPAK W J. as an auxiliary chromophore in chiroptical studies on steroidal alcohols. Tetrahedron:Asymmetry, 1999, 10(8):1507-1520. FRELEK J, JAGODZINSKI J, FIGGER H M, et al. Chiroptical properties of binuclear rhodium complexes of lanostane alcohols. Chirality, 2001, 13(6):313-321. LI S, KUANG H X, OKADA Y, et al. New acetylenic glucoside from Bidens bipinnata Linne. Chem Pharm Bull, 2004, 52(4):439-440. WANG C Z, YU D Q. Lignan and acetylenic glycosides from Aster auriculatus. Phytochemistry, 1998, 48(4):711-717. PRESCOTT A G, STAMFORD N P J, WHEELER G, et al. In vitro properties of a recombinant flavonol synthase from Arabidopsis yhaliana. Phytochemistry, 2002, 60(6):589-593. ZHAO M B, ITO Y, TU P F. Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorius(Honghua)by high-speed counter-current chromatography. J Chromatogr A, 2005, 1090(1-2):193-196. WANG M F, KIKUZAKI H, ZHU N Q, et al. Isolation and structural elucidation of two new glycosides from Sage(Salvia offoconalis L.). J Agric Food Chem, 2000, 48(2):235-238. ZHANG Q Y, ZHAO Y Y, LIU X H, et al. Studies on chemical constituents of Stelmatocrypton khasianum(Benth.)H.Bail. China J Chin Mater Med(中国中药杂志), 2000, 25(2):101-102. HIRAI N, KOSHIMIZU K. A new conjugate of dihydrophaseic acid from Acocado fruit. Agric Bio Chem, 1983, 47(2):365-371. LUO C, ZHANG W N. Chemical constituents of Opuntia Milpa(Ⅰ). Chin Tradit Herb Drugs(中草药), 2011, 42(3):437-439. CHOI S W, LEE S K, KIM E O, et al. Antioxidant and antimelanogenic activities of polyamine conjugates from corn bran and related hydroxycinnamic acids. J Agric Food Chem, 2007, 55(10):3920-3925. JULIUS S, HARRI N, AANN M K, et al. A modification of the hammett equation for predicting ionization constants of p-vinyl phenols. Eur J Pharm Sci, 2005, 25(4-5):417-425. ALADESANMI A J. The stem constituents of dysoxylum lenticellare. Tetrahedron, 1988, 44(12):3749-3756.

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“重大新药创制”科技重大专项(2012ZX09301002-001003)
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