北枳椇树干中的化学成分研究Constituents from the stems of Hovenia dulcis Thunb.
徐方方,吴烦,杨建展,蔡婉娜,张晓琦,刘博
XU Fangfang,WU Fan,YANG Jianzhan,CAI Wanna,ZHANG Xiaoqi,LIU Bo
摘要(Abstract):
目的 对北枳椇(Hovenia dulcis Thunb.)树干的化学成分开展研究。方法 采用硅胶、ODS、Sephdex LH-20等色谱技术对北枳椇树干中的化学成分进行分析分离,利用NMR、LC/MS、IR、UV和旋光波谱仪等技术并结合文献对单体化合物的结构进行确证,利用CCK-8法测定化合物的抗肿瘤活性。结果 从北枳椇树干体积分数70%乙醇提取物中得到15个成分,分别鉴定为羽扇豆醇(1)、白桦脂酸(2)、麦珠子酸(3)、3β-O-trans-p-coumaroyl alphitolic acid(4)、β-谷甾醇(5)、柚皮素(6)、根皮素(7)、5,7-dihydroxy-2-[2-(4-hydroxyphenyl) ethyl]chromone(8)、(+)-阿夫儿茶精(9)、(-)-表阿夫儿茶精(10)、儿茶素(11)、墨沙酮(12)、4-羟基苯戊酸(13)、(-)-杜仲树脂酚(14)、7,10-二羟基硬脂酸(15)。结论化合物1、8、14和15为首次从枳椇属中分离得到,化合物13为首次得到的天然产物,化合物4表现出一定的抗肿瘤作用。
Objective The chemical compounds from the stems of Hovenia dulcis Thunb. were studied. Methods The compounds were purified by many separation methods including silica gel,ODS,and Sephadex LH-20. The structures were elucidated by spectral data including NMR,LC/MS,IR,UV and ORD,combined with literature references. The CCK-8 method was used to evaluated the anticancer activities of the isolated constituents. Results Fifteen compounds were identified as lupeol (1),betulinic acid (2),alphitolic acid (3),3β-O-trans-p-coumaroyl alphitolic acid (4),β-sitosterol (5),naringenin (6),phloretin (7),5,7-dihydroxy-2-[2-(4-hydroxyphenyl) ethyl]chromone (8), (+)-afzelechin (9),(-)-epiafzelechin (10),catechin (11),maesopsin (12),4-hydroxybenzenepentanoic acid (13),(-)-medioresinol (14),7,10-dihydroxyoctadecanoic acid (15). Conclusion Compounds 1,8,14 and 15 are firstly isolated from genus Hovenia and compound 13 is firstly obtained as a natural product. Compound 4 shows the anti-tumor effects.
关键词(KeyWords):
北枳椇;化学成分;萜类;黄酮;抗肿瘤作用
Hovenia dulcis Thunb.;chemical constituent;triterpenoid;flavonoid;anti-tumor effect
基金项目(Foundation): 国家自然科学基金项目(82173700,82474216);; 广东省科技计划项目(2023B1212060062,2023B1212060063);; 广州市科技局项目(2024A04J9997,2025A03J4085,2023A03J0240)
作者(Author):
徐方方,吴烦,杨建展,蔡婉娜,张晓琦,刘博
XU Fangfang,WU Fan,YANG Jianzhan,CAI Wanna,ZHANG Xiaoqi,LIU Bo
DOI: 10.14066/j.cnki.cn21-1349/r.2024.0657
参考文献(References):
- [1]Editorial Board of Flora of China Chinese Academy of Sciences.Flora of China(中国植物志)[M].Beijing:Science Press,1982:88.
- [2]KANG K B,JUN J B,KIM J W,et al.Ceanothane-and lupanetype triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cell[J].Phytochemistry,2017,142:60-67.
- [3]XU F F,XU S M,CAI W N,et al.Isolation identification of chemical constituents from the seeds of Hovenia dulcis Thunb[J].Journal of Shenyang Pharmaceutical University(沈阳药科大学学报),2022,39(4):375-379.
- [4]XU F F,LIU B,ZHANG X Q.Research progress on chemical constituents and pharmacological activities of Hovenia[J].China Journal of Chinese M ateria M edcia(中国中药杂志),2020,45(20):4827-4835.
- [5]BI J D,MU H Y,ZHANG Y Y,et al.Study on chemical constituents of chlorophyll non-saponifable matter in Faeces Bombycis[J].Journal of Sichuan University(Natural Science Edition)[四川大学学报(自然科学版)],2022,59(3):163-168.
- [6]JIANG C,WANG W Z,LIAO X J,et al.Chemical constituents and cytotoxicity assay research in small polar substances from Vitis thunbergii var.taiwaniana[J].China Journal of Chinese M ateria M edcia(中国中药杂志),2015,40(15):2999-3004.
- [7]YOKOSUKA A,KAWAKAMI S,HARAGUCHI M,et al.Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum[J].Phytochem Lett,2011,4:259-266.
- [8]SIDDIQUI B S,FARHAT N,BEGUM S,et al.Isolation and structural elucidation of acylated pentacyclic triterpenoids from the leaves of Eucalyptus camaldulensis var.Obtusa[J].Planta M ed,1997,63:47-50.
- [9]DUAN Z H,LI W Y,YANG M C,et al.Chemical constituents of Bothrocaryum controversum[J].Journal of Hainan Normal University(Natural Science)[海南师范大学学报(自然科学版)],2019,32(2):128-131.
- [10]CHA X J,SHI Q,SHAO F,et al.Chemical constituents of Euphorbia helioscopia[J].Chinese Traditional and Herbal Drugs(中草药),2021,52(2):341-348.
- [11]LIU Y,YAO J H,MEI Y,et al.Chemical consituents of Rhodiola crenulata[J].Chinese Traditional and Herbal Drugs(中草药),2024,55(9):2875-2886.
- [12]QIN X,XING Y F,ZHOU Z,et al.Dihydrochalcone compounds isolated from crabapple leaves show ed anticancer effects on human cancer cell lines[J].M olecules,2015,20(12):21193-21203.
- [13]IBRAHIM,SABRIN R M.New 2-(2-phenylethyl) chromone derivatives from the seeds of Cucumis melo L var.reticulatus[J].Nat Prod Commun,2010,5(3):403-406.
- [14]SAIJYO J,SUZUKI Y,OKUNO Y,et al.Alpha-glucosidase inhibitor from Bergenia ligulata[J].J Oleo Sci,2008,57(8):431-435.
- [15]ZHANG N,HE J,DING K,et al.Chemical constituents from Stellera chamaejasme Linn[J].China Journal of Chinese M ateria M edcia(中国中药杂志),2020,55(10):799-805.
- [16]LIU H X,LIU Z X,JIANG Q H,et al.Phenolic constituents of w hole plant of Agrimonia pilosa Ledeb[J].Journal of Shenyang Pharmaceutical University(沈阳药科大学学报),2010,27(4):286-289,298.
- [17]LI X C,CAI L,WU C D.Antimicrobial compounds from Ceanothus americanus against oral pathogens[J].Phytochemistry,1997,46(1):97-102.
- [18]PHAM V C,JOSSANG A,SEVENET T,et al.Cytotoxic acylphenols from Myristica maingayi[J].Tetrahedron,2000,56:1707-1713.
- [19]DORN H,TREIBS W.Synthesen mit Dicarbons?uren,XII.M itteil.:über die Friessche Verschiebung an Adipins?ure-und Glutars?ure-diphenylester[J].Chem Ber,1955,88:834-843.
- [20]ZHANG S L,LIAO H B,LIANG D.Chemical constitutes from Clerodendrum japonicum[J].China Journal of Chinese M ateria M edcia(中国中药杂志),2018,43(13):2732-2739.
- [21]KNOTHE G,BAGBY M O,PETERSON R E,et al.7,10-Dihydroxy-8(E)-octadecenoic acid:stereochemistry and a novel derivative,7,10-dihydroxyoctadecanoic acid[J].J Am Oil Chem Soc,1992,69:367-371.