丽江产玛咖的化学成分研究
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摘要
运用各种色谱分离方法对产自丽江的玛咖90%乙醇提取物进行化学成分研究,得到了11个化合物,其中包括8个苯丙素类化合物(1～8),1个二聚二氢苯并吡喃(9),1个亮氨酸衍生物(10)和1个吲哚衍生物(11).这些化合物的结构通过核磁共振波谱法进行了鉴定,化合物1～3,5～11等10个化合物均为首次从玛咖中分离得到.
Eleven compounds were isolated from the 90% alcohol extracts of Lepidium meyenii Walp cultivated in Lijiang by chromatographic methods, including eight phenylpropanoids, one bi-2H-benzopyran, one leucine derivative, and one indole derivative. The structures of these compounds were elucidated by NMR techniques. Ten of these compounds(1—3, 5—11) were isolated from this plant for the first time.
Eleven compounds were isolated from the 90% alcohol extracts of Lepidium meyenii Walp cultivated in Lijiang by chromatographic methods, including eight phenylpropanoids, one bi-2H-benzopyran, one leucine derivative, and one indole derivative. The structures of these compounds were elucidated by NMR techniques. Ten of these compounds(1—3, 5—11) were isolated from this plant for the first time.
引文
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[2]刘淼,黄莹莹,林梦雅,等.黑玛咖不同提取物的抗疲劳作用与谱效关系研究[J].中草药,2018,49(9):2 090-2 096.Liu M,Huang Y Y,Lin M Y,et al.Experimental studies on anti-fatigue effects and spectra-effect relationship of different extracts from black Lepidium meyenii(Maca)[J].Chinese Traditional and Herbal Drugs,2018,49(9):2 090-2 096.
[3]郑茜,张庆贺,卢丹,等.吉林产玛咖的化学成分研究[J].中草药,2014,45(17):2 457-2 460.DOI:10.7501/j.issn.0253-2670.2014.17.007.Zheng Q,Zhang Q H,Lu D,et al.Chemical constituents in Lepidium meyenii cultivated in Jilin[J].ChineseTraditional and Herbal Drugs,2014,45(17):2 457-2 460.
[4]Zhang L J,Zhao Q S,Wang L W,et al.Protective effect of polysaccharide from maca(Lepidium meyenii)on Hep-G2 cells and alcoholic liver oxidative injury in mice[J].International Journal of Biological Macromolecules,2017,99:63-70.DOI:10.1016/j.ijbiomac.2017.01.125.
[5]Tang W M,Jun L,Xie L H,et al.Structural characterization and antifatigue effect in vivo of Maca(Lepidium meyenii Walp)polysaccharide[J].Journal of Food Science,2017,82(3):757-764.DOI:10.1111/jfds.2017.82.issue-3.
[6]Tang Y,Zhu Z Y,Pan L C,et al.Structure analysis and anti-fatigue activity of a polysaccharide from Lepidium meyenii Walp[J].Natural Product Research,2018:1-10.
[7]Zha Z Q,Wang S Y,Chu W H,et al.Isolation,purification,structural characterization and immunostimulatory activity of water-soluble polysaccharides from Lepidium meyenii[J].Phytochemistry,2018,147:184-193.DOI:10.1016/j.phytochem.2018.01.006.
[8]Wang W,Zou Y,Li Q,et al.Immunomodulatory effects of a polysaccharide purified from Lepidium meyenii Walp.on macrophages[J].Process Biochemistry,2016,51(4):542-553.DOI:10.1016/j.procbio.2016.01.003.
[9]Zhang M M,Wang G,Lai F R,et al.Structural characterization and immunomodulatory activity of a novel polysaccharide from Lepidium meyenii[J].Journal of Agricultural and Food Chemistry,2016,64(9):1 921-1 931.DOI:10.1021/acs.jafc.5b05610.
[10]Zhang M M,Wu W J,Ren Y,et al.Structural characterization of a novel polysaccharide from Lepidium meyenii(maca)and analysis of its regulatory function in macrophage polarization in vitro[J].Journal of Agricultural and Food Chemistry,2017,65(6):1 146-1 157.DOI:10.1021/acs.jafc.6b05218.
[11]Li S F,Hao L M,Kang Q Z,et al.Purification,characterization and biological activities of a polysaccharide from Lepidium meyenii leaves[J].International Journal of Biological Macromolecules,2017,103:1 302-1 310.DOI:10.1016/j.ijbiomac.2017.05.165.
[12]Wang W,Zhang F M,Li Q,et al.Structure characterization of one polysaccharide from Lepidium meyenii Walp.,and its antioxidant activity and protective effect against H2O2-induced injury RAW264.7 cells[J].International Journal of Biological Macromolecules,2018,118:816-833.DOI:10.1016/j.ijbiomac.2018.06.117.
[13]Tian X X,Peng X R,Yu M Y,et al.Hydantoin and thioamide analogues from Lepidium meyenii[J].Phytochemistry Letters,2018,25:70-73.DOI:10.1016/j.phytol.2018.03.011.
[14]Yu M Y,Qin X J,Peng X R,et al.Macathiohydantoins B-K,novel thiohydantoin derivatives from Lepidium meyenii[J].Tetrahedron,2017,73:4 392-4 397.DOI:10.1016/j.tet.2017.05.096.
[15]Bai N S,He K,Roller M,et al.Flavonolignans and other constituents from Lepidium meyenii with activities in anti-inflammatory and human cancer cell lines[J].Journal of Agricultural and Food Chemistry,2015,63(9):2 458-2 463.DOI:10.1021/acs.jafc.5b00219.
[16]Cui B L,Zheng B L,He K,et al.Imidazole alkaloids from Lepidium meyenii[J].Journal of Natural Products,2003,66(8):1 101-1 103.DOI:10.1021/np030031i.
[17]Piacente S,Carbone V,Plaza A,et al.Investigation of the tuber constituents of Maca(Lepidium meyenii Walp.)[J].Journal of Agricultural and Food Chemistry,2002,50(20):5 621-5 625.DOI:10.1021/jf020280x.
[18]Xia C,Chen J,Deng J L,et al.Novel macamides from maca(Lepidium meyenii Walpers)root and their cytotoxicity[J].Phytochemistry Letters,2018,25:65-69.DOI:10.1016/j.phytol.2018.03.001.
[19]Hajdu Z,Nicolussi S,Rau M,et al.Identification of endocannabinoid system-modulating N-alkylamides from Heliopsis helianthoides var.scabra and Lepidium meyenii[J].Journal of Natural Products,2014,77(7):1 663-1 669.DOI:10.1021/np500292g.
[20]Lin L Z,Huang J Y,Sun-Waterhouse D X,et al.Maca(Lepidium meyenii)as a source of macamides and polysaccharide in combating of oxidative stress and damage in human erythrocytes[J].International Journal of Food Science and Technology,2017,53(2):304-312.
[21]Gan J,Feng Y,He Z,et al.Correlations between antioxidant activity and alkaloids and phenols of Maca(Lepidium meyenii)[J].Journal of Food Quality,2017(3):1-10.
[22]Chen J J,Zhao Q S,Wang L W,et al.Physicochemical and functional properties of dietary fiber from maca(Lepidium meyenii Walp.)liquor residue[J].Carbohydrate Polymers,2015,132:509-512.DOI:10.1016/j.carbpol.2015.06.079.
[23]Bramara B V B,Vasavi H S,Sudeep H V,et al.Hydroalcoholic extract from Lepidium meyenii(black maca)root exerts wound healing activity in streptozotocin-induced diabetic rats[J].Wound Medicine,2017,19:75-81.DOI:10.1016/j.wndm.2017.10.003.
[24]臧贞,雷泽,朱洪友,等.玛咖的化学成分研究[J].云南化工,2014,41(4):37-39.DOI:10.3969/j.issn.1004-275X.2014.04.010.Zang Z,Lei Z,Zhu H Y,et al.Chemical constituentsfrom Maca(Lepidium meyenii)[J].Yunnan ChemicalTechnology,2014,41(4):37-39.
[25]肖蒙蒙,王燕,邓君.云南产玛卡乙酸乙酯部位化学成分研究[J].西南师范大学学报:自然科学版,2017,42(2):59-63.Xiao M M,Wang Y,Deng J.On chemical constituents of ethyl acetate fraction from Lepidium meyenii[J].Journal of Southwest China Normal University:Natural Science Edition,2017,42(2):59-63.
[26]赵雪飞,马宁,杨尚军,等.玛咖化学成分研究[J].食品与药品,2018,20(2):93-97.DOI:10.3969/j.issn.1672-979X.2018.02.004.Zhao X F,Ma N,Yang S J,et al.Chemical constituents of Lepidium Meyenii Walp[J].Food and Drug,2018,20(2):93-97.
[27]梁文娟,许洪波,杨彩艳,等.玛咖化学成分的研究[J].中国中药杂志,2015,40(23):4 531-4 535.Liang W J,Xu H B,Yang C Y,et al.Chemical constituents of Lepidium meyenii[J].China Journal of Chinese Materia Medica,2015,40(23):4 531-4 535.
[28]刘艳梅,赵德,肖蒙蒙,等.鹤庆产黄玛咖抗骨质疏松活性部位的化学成分研究[J].药学学报,2017,52(6):943-947.Liu Y M,Zhao D,Xiao M M,et al.Studies on the chemical constituents of the anti-osteoporotic part of Lepidium meyenii Walp.produced in Heqing[J].Acta Pharmaceutica Sinica,2017,52(6):943-947.
[29]Zhou M,Zhang R Q,Chen Y J,et al.Three new pyrrole alkaloids from the roots of Lepidium meyenii[J].Phytochemistry Letter,2018,23:137-140.DOI:10.1016/j.phytol.2017.12.002.
[30]Zhou M,Ma H Y,Liu Z H,et al.(+)-Meyeniins A-C,novel hexahydroimidazo[J].Journal of Agricultural and Food Chemistry,2017,65(9):1 887-1 892.DOI:10.1021/acs.jafc.6b05805.
[31]Zhou M,Ma H Y,Xing H H,et al.Biomimetic synthesis of macahydantoins A and B from Lepidium meyenii,and structure revision of macahydantoin B as a class of thiohydantoin with a 4-methyl-hexahydropyrrolo[J].Organic Letters,2017,19(18):4 952-4 955.DOI:10.1021/acs.orglett.7b02433.
[32]Brader G,Vajrodaya S,Greger H,et al.Bisamides,lignans,triterpenes,and insecticidal cyclopenta[b]benzofurans from Aglaia Species'[J].Journal of Natural Products,1998,61(12):1 482-1 490.DOI:10.1021/np9801965.
[33]Chang C I,Hsu C M,Li T S,et al.Constituents of the stem of Cucurbita moschata exhibit antidiabetic activities through multiple mechanisms[J].Journal of Functional Foods,2014,10:260-273.DOI:10.1016/j.jff.2014.06.017.
[34]乔立瑞,杨林,张德武,等.瑞香狼毒细胞培养物的化学成分研究[J].中国中药杂志,2011,36(24):3 457-3 462.Qiao L R,Yang L,Zhang D W,et al.Studies on chemical constitutes from callus cultures of Stellera chamaejasme[J].China Journal of Chinese Materia Medica,2011,36(24):3 457-3 462.
[35]In S J,Seo K H,Song N Y,et al.Lignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity[J].Archives of Pharmacal Research,2015,38(1):26-34.DOI:10.1007/s12272-014-0358-9.
[36]Xu W,Jin H,Zhang W,et al.Studies on the chemical constituents of Daphne pedunculata[J].Chemistry of Natural Compounds,2008,44(6):771-772.DOI:10.1007/s10600-009-9176-6.
[37]Katayama T,Davin L B,Chu A,et al.Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia[J].Phytochemistry,1993,33(3):581-591.DOI:10.1016/0031-9422(93)85452-W.
[38]Chiang Y M,Liu H K,Lo J M,et al.Cytotoxic constituents of the leaves of Calocedrus formosana[J].Journal of the Chinese Chemical Society,2003,50(1):161-166.DOI:10.1002/jccs.v50.1.
[39]孙照翠,郑庆霞,吴海峰,等.猫须草水溶性化学成分的研究[J].中国药学杂志,2014,49(1):22-25.Sun Z C,Zheng Q X,Wu H F,et al.Water-soluble constituents of Clerodendranthus spicatus[J].Chinese Pharmaceutical Journal,2014,49(1):22-25.
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