化合物13 白色粉末;ESI-MS m/z 523[M+H]+;[α]25D+5.5(c 0.6,CH3OH); 1H,13C-NMR數據。數據與文獻[22]報道基本一致,化合物13鑒定為(+)-5,5′-二甲氧基落葉鬆脂素 4′-O-β-D-葡萄糖苷。
化合物14 白色粉末;ESI-MS m/z 575[M+Na]+;[α]25D -20.1(c 0.4,CH3OH); 1H,13C-NMR數據。數據與文獻[23]報道基本一致,化合物14鑒定為(-)-5,5′-二甲氧基落葉鬆脂素 4′-O-β-D-葡萄糖苷。
化合物15 白色粉末;ESI-MS m/z 521[M+H]+。[α]25D -36.7(c 0.6,CH3OH); 1H,13C-NMR數據。數據與文獻[22]報道基本一致,化合物15鑒定為(-)-鬆脂醇 4′-O-β-D-葡萄糖苷。
化合物16 白色粉末;ESI-MS m/z 605[M+Na]+;[α]25D 0(c 0.9,CH3OH); 1H,13C-NMR數據。數據與文獻[22]報道基本一致,化合物16鑒定為(±)-5,5′-二甲氧基落葉鬆脂素 9′-O-β-D-葡萄糖苷。
[參考文獻]
[1] Calway T, Du G J, Wang C Z, et al. Chemical and pharmacological studies of Oplopanax horridus, a north American botanical[J]. J Nat Med, 2012, 66(2):249.
[2] Huang W H, Zhang Q W, Yuan C S, et al. Chemical constituents of the plants from genus Oplopanax[J]. Chem Biodivers, 2014, 11(2):181.
[3] Lantz T C, Swerhun K, Turner N J. Devil′s club(Oplopanax horridus):an ethnobotanical review[J]. Herbal Gram, 2004, 62(10):33.
[4] McCutcheon A R, Roberts T E, Gibbons E, et al. Antiviral screening of British Columbian medicinal plants[J]. J Ethnopharmacol, 1995, 49(2):101.
[5] Gottesfeld L M J. The importance of bark products in the aboriginal economies of northwestern british-columbia, Canada[J]. Econ Bot, 1992, 46(2):148.
[6] Gottesfeld L M J. Wet′Suwet′en ethnobotany:traditional plant uses[J]. J Ethnobiol, 1994, 14(6):185.
[7] Huang W H, Yang J, Zhao J, et al. Quantitative analysis of six polyynes and one polyene in Oplopanax horridus and Oplopanax elatus by pressurized liquid extraction and on-line SPE-HPLC[J]. J Pharm Biomed Anal, 2010, 53(4):906.
[8] Huang W H, Zhang Q W, Meng L Z, et al. Oplopanphesides A-C, three new phenolic glycosides from the root barks of Oplopanax horridus[J]. Chem Pharm Bull, 2011, 59(5):676.
[9] Huang W H, Zhang Q W, Wang C Z, et al. Isolation and identification of two new polyynes from a north American ethnic medicinal plant——Oplopanax horridus(Smith)Miq[J]. Molecules, 2010, 15(2):1089.
[10] 陳亮, 王磊, 張慶文, 等.黃連非生物堿類化學成分研究[J]. 中國中藥雜誌, 2012, 37(9):1241.
[11] 李從軍, 陳迪華, 肖培根. 中藥升麻的化學成分(Ⅴ)[J]. 中草藥, 1995, 26(6):288.
[12] 張彬鋒, 侴桂新, 王崢濤. 鉤吻非生物堿類化學成分研究[J]. 中國中藥雜誌, 2009, 34(18):2334.
[13] Ushiyama M, Furuya T. Glycosylation of phenolic compounds by root culture of Panax ginseng[J]. Phytochemistry, 1989, 28(11):3009.
[14] Ageta M, Ishimaru K, Nonaka G I, et al. Tannins and related compounds. LXIV. :six new phenol glucoside gallates from Castanopsis cuspidata var. sieboldii NAKAI.(2)[J]. Chem Pharm Bull, 1988, 36(3):870.
[15] Steeves V, Frster H, Pommer U, et al. Coniferyl alcohol metabolism in conifers——I. Glucosidic turnover of cinnamyl aldehydes by UDPG:coniferyl alcohol glucosyltransferase from pine cambium[J]. Phytochemistry, 2001, 57(7):1085.
[16] Sugiyama M, Nagayama E, Kikuchi M. Lignan and phenylpropanoid glycosides from Osmanthus asiaticus[J]. Phytochemistry, 1993, 33(5):1215.
[17] Wu Y, Qu W, Geng D. et al. Phenols and flavonoids from the aerial part of Euphorbia hirta[J]. Chin J Nat Med, 2012, 10(1):40.
[18] 崔鳳俠, 章宸, 薑勇, 等. 新疆一枝蒿乙酸乙酯部位化學成分研究[J]. 中國中藥雜誌, 2013, 38(11):1757.
[19] Bellino A, Venturella P, Luisa-Marino M, et al. Coumarins from Seseli bocconi[J]. Phytochemistry, 1986, 25(5):1195.
[20] Latté K P, Kaloga M, Schfer A, et al. An ellagitannin, n-butyl gallate, two aryltetralin lignans, and an unprecedented diterpene ester from Pelargonium reniforme[J]. Phytochemistry, 2008, 69(3):820.
[21] Dou D Q, Hu X Y, Zhao Y R, et al. Studies on the anti-psoriasis constituents of Oplopanax elatus Nakai[J]. Nat Prod Res, 2009, 23(4):334.
[22] Ida Y, Satoh Y, Ohtsuka M, et al. Phenolic constituents of Phellodendron amurense bark[J]. Phytochemistry, 1993, 35(1):209.
[23] Fan C Q, Zhu X Z, Zhan Z J, et al. Lignans from Saussurea conica and their NO production suppressing activity[J]. Planta Med, 2006, 72(7):590.
[24] Matsunami K, Otsuka H, Kondo K, et al. Absolute configuration of(+)-pinoresinol 4-O-[6″-O-galloyl]-β-D-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tanarius[J]. Phytochemistry, 2009, 70(10):1277.
[25] Ono M, Mishima K, Yamasaki T, et al. A new lignan glucoside from the stems of Callicarpa japonica Thunb. var. luxurians Rehd[J]. J Nat Med, 2009, 63(1):86.