甘肃青龙衣（核桃青皮）化学成分的研究
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摘要
青龙衣(核桃青皮)为核桃和核桃楸的未成熟外果皮。青龙衣主要含有黄酮类化合物、萘醌类化合物、二芳基庚烷类化合物,同时还含有甾体、萜类、脂肪酸等成分。青龙衣具有清热解毒、祛风疗癣、止痛止痢的功效,现代医学研究表明青龙衣还具有显著的抗肿瘤活性,临床上主要用于治疗皮肤病、子宫脱垂、白细胞减少等症。为阐明该药用部位的物质基础,在综述其化学成分和药理作用的基础上,对其乙醇提取物化学成分进行了系统的研究。
以甘肃天水产青龙衣为原料,用95 %乙醇提取、浓缩得浸膏,浸膏混悬于水中,依次用石油醚、乙酸乙酯和正丁醇萃取,采用硅胶柱色谱、葡聚糖凝胶色谱和制备薄层色谱等分离纯化,通过1H、13C-核磁共振和质谱等手段鉴定了各组分的化学结构。
分离鉴定结果表明,本研究从甘肃产青龙衣中分离得到18个化合物,其结构分别为泰国树脂酸(siaresinolic acid,1),白桦脂酸(betulinic acid,2)、羽扇豆醇(lupeol, 3)、24-羟基-羽扇豆醇(24-hydroxy-lupeol, 4)、?-胡萝卜苷(?-daucosterin,5)、β-谷甾醇(β-sitosterol, 6)、2-丙氧基核桃醌(2-propoxy-juglon, 7)、核桃酮(regiolone, 8)、4-甲氧基-?-四氢萘醌-5-O-??-葡萄糖苷(4-methoxy-?-tetralone-5-O-?-glucopyranoside, 9)、4-乙氧基-8-羟基-?-四氢萘醌(4-ethoxy-8-hydroxy-?-tetralone, 10)、4, 5-二羟基-?-四氢萘醌(4,5-dihydroxy-?-tetralone , 11) , 5, 8-二羟基-4-甲氧基-?-四氢萘醌(5,8-dihydroxy-4-methoxy-?-tetralone, 12),4, 5, 8-三羟基-?-四氢萘醌(4, 5,8-trihydroxy-?-tetralone, 13) , 4, 5-O-异丙叉基-?-四氢萘醌(4,5-O-isopropylidene-?-tetralone, 14)、2,3-二羟基-1-(4-羟基取代苯基)-1-丙酮*(2,3-dihydroxy-1-(4-hydroxy-phenyl)-propan-1-one,15),琥珀酸(succinicacid,16)、丁香酸(syringic acid, 17)和二氢红花菜豆酸(dihydrophaseic acid, 18)。其中化合物15为新化合物,化合物1,2,9,10,14和18均为首次从该药用部位分离得到。
Qinglongyi (green walnut husks)is animmatureepicarpof walnut (Juglans regiaL.) and juglans ( Juglans mandshurica Maxim.). Its chemical components containflavonoids, naphthoquinones, diarylheptanoids, steroids, terpenes and fatty acids, etc.Qinglongyi has the medicine function such as clearing away pathogenic heat,removing the toxin, relieving rheumatic pains, treating ringworm, acesodyne andantidiarrheal. The prominent antineoplastic activity of Qinglongyi was also foundedby modern medicine. It was used for curing diseases such as dermatosis, uterineprolapse, leukopenia, etc. In order to elucidate the material basis of its drug parts, thechemical constitutions and the pharmacological action were reviewed, and studies onthe chemical constituents of Qinglongyi extracted by ethanol was elaborated in thisthesis.
Qinglongyi, supplied from walnut in Tianshui, Gansu province, was extracted byethanol (95%)and concentrated.The extractum was suspended inwaterandextractedbypetroleumether,ethylestateandn-butanol,respectively.Thechemicalconstituentswere isolated with silica gel chromatography, Sephadex LH-20 chromatography andpreparativeTLC.TheirstructureswereensuredbythemethodsofNMRand MS.Eighteen compounds were separated and identified as follows: assiaresinolic acid(1), betulinic acid (2), lupeol (3), 24-hydroxy-lupeol (4), ?-daucosterin (5),β-sitosterol (6), 2-propoxy-juglon (7), regiolone (8), 4-methoxy-?-tetralone-5-O-??-glucopyranoside(9),4-ethoxy-8-hydroxy-P-tetralone(10), 4,5-dihydroxy-?-tetralone(11), 5, 8-dihydroxy-4-methoxy-?-tetralone (12), 4, 5, 8-trihydroxy-?-tetralone (13),4,5-O-isopropylidene-?-tetralone(14),2,3-dihydroxy-1-(4-hydroxy-phenyl)-propan-1-one*(15), succinic acid (16), syringc acid (17), and dihydrophaseic acid (18),respectively.
Ofallthesecompounds,compound15isanewcompound,andcompoundsof1,2,9,10,14and18wereisolatedforthefirsttime.
以甘肃天水产青龙衣为原料,用95 %乙醇提取、浓缩得浸膏,浸膏混悬于水中,依次用石油醚、乙酸乙酯和正丁醇萃取,采用硅胶柱色谱、葡聚糖凝胶色谱和制备薄层色谱等分离纯化,通过1H、13C-核磁共振和质谱等手段鉴定了各组分的化学结构。
分离鉴定结果表明,本研究从甘肃产青龙衣中分离得到18个化合物,其结构分别为泰国树脂酸(siaresinolic acid,1),白桦脂酸(betulinic acid,2)、羽扇豆醇(lupeol, 3)、24-羟基-羽扇豆醇(24-hydroxy-lupeol, 4)、?-胡萝卜苷(?-daucosterin,5)、β-谷甾醇(β-sitosterol, 6)、2-丙氧基核桃醌(2-propoxy-juglon, 7)、核桃酮(regiolone, 8)、4-甲氧基-?-四氢萘醌-5-O-??-葡萄糖苷(4-methoxy-?-tetralone-5-O-?-glucopyranoside, 9)、4-乙氧基-8-羟基-?-四氢萘醌(4-ethoxy-8-hydroxy-?-tetralone, 10)、4, 5-二羟基-?-四氢萘醌(4,5-dihydroxy-?-tetralone , 11) , 5, 8-二羟基-4-甲氧基-?-四氢萘醌(5,8-dihydroxy-4-methoxy-?-tetralone, 12),4, 5, 8-三羟基-?-四氢萘醌(4, 5,8-trihydroxy-?-tetralone, 13) , 4, 5-O-异丙叉基-?-四氢萘醌(4,5-O-isopropylidene-?-tetralone, 14)、2,3-二羟基-1-(4-羟基取代苯基)-1-丙酮*(2,3-dihydroxy-1-(4-hydroxy-phenyl)-propan-1-one,15),琥珀酸(succinicacid,16)、丁香酸(syringic acid, 17)和二氢红花菜豆酸(dihydrophaseic acid, 18)。其中化合物15为新化合物,化合物1,2,9,10,14和18均为首次从该药用部位分离得到。
Qinglongyi (green walnut husks)is animmatureepicarpof walnut (Juglans regiaL.) and juglans ( Juglans mandshurica Maxim.). Its chemical components containflavonoids, naphthoquinones, diarylheptanoids, steroids, terpenes and fatty acids, etc.Qinglongyi has the medicine function such as clearing away pathogenic heat,removing the toxin, relieving rheumatic pains, treating ringworm, acesodyne andantidiarrheal. The prominent antineoplastic activity of Qinglongyi was also foundedby modern medicine. It was used for curing diseases such as dermatosis, uterineprolapse, leukopenia, etc. In order to elucidate the material basis of its drug parts, thechemical constitutions and the pharmacological action were reviewed, and studies onthe chemical constituents of Qinglongyi extracted by ethanol was elaborated in thisthesis.
Qinglongyi, supplied from walnut in Tianshui, Gansu province, was extracted byethanol (95%)and concentrated.The extractum was suspended inwaterandextractedbypetroleumether,ethylestateandn-butanol,respectively.Thechemicalconstituentswere isolated with silica gel chromatography, Sephadex LH-20 chromatography andpreparativeTLC.TheirstructureswereensuredbythemethodsofNMRand MS.Eighteen compounds were separated and identified as follows: assiaresinolic acid(1), betulinic acid (2), lupeol (3), 24-hydroxy-lupeol (4), ?-daucosterin (5),β-sitosterol (6), 2-propoxy-juglon (7), regiolone (8), 4-methoxy-?-tetralone-5-O-??-glucopyranoside(9),4-ethoxy-8-hydroxy-P-tetralone(10), 4,5-dihydroxy-?-tetralone(11), 5, 8-dihydroxy-4-methoxy-?-tetralone (12), 4, 5, 8-trihydroxy-?-tetralone (13),4,5-O-isopropylidene-?-tetralone(14),2,3-dihydroxy-1-(4-hydroxy-phenyl)-propan-1-one*(15), succinic acid (16), syringc acid (17), and dihydrophaseic acid (18),respectively.
Ofallthesecompounds,compound15isanewcompound,andcompoundsof1,2,9,10,14and18wereisolatedforthefirsttime.
引文
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[2]李淑芳,孙光春,鲍淑娟,等.核桃皮酊剂毒性试验研究[J].贵阳医学院学报,1997,4(22):356-358.
[3]刘薇,季宇彬.青龙衣毒性作用及体内抗肿瘤作用的实验研究[J].哈尔滨商业大学学报(自然科学版),2004,20(1):4-10.
[4] Alkhawajah AM. Studies on the antimicrobial activityof Juglans regia[J].Am.J.Clin.Med,1997,25(2):175-180.
[5]杜旭,李玉文,倪雁.中药青核桃镇痛作用研究与展望[J].中国中药杂志,2000,25(1):7-10.
[6] Liu J X, Di D L, Huang X Y, Li C. Two new diarylheptanoids from the pericarpsofJuglansregiaL.[J].ChineseChemicalLetters,2007,18(8):943-946.
[7]张洪娟,桑树荣,高奎滨.用青龙衣制剂治疗肿瘤用药经验[J] .黑龙江省中医药,2000,2:64-65.
[8]杜旭,倪雁.青龙衣粉针与十全大补汤合用抗肿瘤作用的实验研究[J].中国中医药科技1998,5(3):149-150.
[9]陈静岚,张国屏,孙玉波.复方青龙衣配合化疗治疗急性白血病23例[J].黑龙江中医药,2000,6(7):26-27.
[10]全国中草药汇编编写组.全国中草药汇编[M].北京:人民卫生出版社,1978.
[11] Bender R G, Benson M E, Flath R A. Eight-1, 4- naphthoquinones fromJuglans[J].Phytochemistry,1989,28(10):2799-2801.
[12] Pardha S, Babu M H. A new bisjuglone from Juglans regia root bark [J].Phytochemistry,1978,17:2042-2043.
[13].Hirakawa K, Ogiuee, Motoyoshiya J, et al. Naphthoquinones fromJuglandaceae[J].Phytochemistry,1986,25(6):1494-1495.
[14] Kim S H, Lee K S, Son J K, et al. Cytotoxic compounds from the roots ofJuglans mandshurica[J].J.Nat.Prod.,1998,61(5):643-645.
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