用户名: 密码: 验证码:
瑶药四方藤(Cissus Pteroclada Hayata)和千斤拔(Flemingia philippinensis Merr.et Rolfe.)的化学成分及抗肿瘤活性研究
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
对瑶族植物药四方藤(Cissus Pteroclada Hayata)化学成分进行了较为系统的研究,从中分离和鉴定了9个单体化合物和1个混合物,分别是β-谷甾醇、豆甾醇和菜油甾醇的混合物(1),β-香树脂醇(2),白桦脂酸(3),β-谷甾醇(4),木栓酮(5),11-O-没食子酰岩白菜素(6),11-O-(4'-hydroxy benzoyl) bergenin(7),胡萝卜苷(8),没食子酸(9),岩白菜素(10)。除化合物10外,其余均为首次从该种植物中分离得到,化合物6、7为首次从该属植物中分离得到。
     采用水蒸气蒸馏(SD)法、超声萃取水蒸气蒸馏(UESD)法分别提取瑶药四方藤的挥发油,并应用GC-MS对所提取的挥发油进行分析比较。实验结果表明,水蒸气蒸馏法提取的挥发油鉴定了22种挥发性成分,鉴定的成分占挥发油总量的83.41%;超声萃取辅助水蒸气蒸馏法提取的挥发油鉴定出28种挥发性成分,鉴定的成分占挥发油总量的77.73%。两种方法相比,UESD法提取挥发油的得率约为SD法提取挥发油提取得率的2倍。
     从千斤拔(Flemingia philippinensis Merr.et Rolfe.)中分离并鉴定了5个单体化合物和1个黄酮混合物,分别是5-羟基-8-γ,γ-二甲代烯丙基-3',3'-二甲基-吡喃并[6,7]色酮(Eriosematin,11)、羽扇豆醇(12)、染料木黄酮(13)、赝靛黄素和刺芒柄花素的混合物(14),3’-甲氧基香豌豆苷元(15)、5,7,3’,4’,5’-五甲氧基黄酮(16)。其中化合物15、16及混合物14均为首次从该植物中分离得到。
     采用MTT法研究了四方藤醇提物各萃取部位及部分化合物的抗肿瘤活性。实验结果表明,四方藤乙酸乙酯萃取部位、正丁醇萃取部位、6、7、11、13、15以及混合物14具有一定的抗肿瘤活性,其他组分及化合物不具有抗肿瘤活性。四方藤乙酸乙酯萃取物对鼻咽癌细胞CNE和宫颈癌细胞Hela具有较好的活性,其IC50分别为35.55μg/mL和39.74μg/mL。11-O-(4'-hydroxy benzoyl) bergenin及11-O-没食子酰岩白菜素对结肠癌细胞HT-29抑制作用较强,IC50分别是12.36μg/mL和16.33μg/mL。Eriosematin对宫颈癌细胞Hela的生长具有较强的抑制作用,其IC50为12.22μg/mL,并且随着化合物浓度的增加,抑制肿瘤细胞的增殖作用逐渐增强。
The chemical constituents of Yao medicine Cissus Pteroclada Hayata were studied more systematically in this paper. Nine compounds and one mixture were isolated and identified to be the mixture ofβ-sitosterol, stigmasterol and campesterol(1), beta-amyrin(2), betulinic acid(3),β-sitosterol(4) friedelin(5),11-O-loylbergenin(6),11-O-(4'-hydroxy benzoyl) bergenin(7), daucosterol(8), gallic acid(9), bergenin(10). All the compounds had never been separated from this plant before except the compound 10. Compounds 6 and 7 were obtained from the plants of Cissus for the first time.
     Volatile oils were exacted by steam distillation(SD) method and ultrasound-assist-ted steam distillation(UESD) method from Yao medicine Cissus Pteroclada Hayata. The results showed that:22 volatile components were identified with the mothod of SD, which accounted for 83.41% of total essential oil.28 volatile components were identified with the mothod of UESD, which accounted for 77.73% of total essential oil. Compared two methods, the yield of volatile oil extracted by UESD was 2 times with its by SD.
     Five compounds and one mixture were isolated from Flemingia philippinensis Merr.et Rolfe and they were identified to be eriosematin(11), lupeol(12), genistein(13), the mixture of psedo-baptigenin and formononetin(14),3'-O-Methylorobol(15), 5,7,3',4',5'-pentamethoxyflavone(16). The compounds of 15,16 and mixture 14 were isolated from this plant for the first time.
     The anti-tumor activity of extract in Cissus Pteroclada Hayata and some compounds were studied by MTT method. The results showed that:ethyl acetate extract and butanol extract of Cissus Pteroclada Hayata together with compounds of 6, 7,11,13,15 and mixture 14 had some anti-tumor activity. But other compounds did not have anti-tumor activity. Ethyl acetate extract of Cissus Pteroclada Hayata had better activity in the inhibition of CNE and Hela cells. The IC50 values reached to 35.55μg/mL and 39.74μg/mL.11-O-(4'-hydroxy benzoyl) bergenin and 11-O-galloyl-bergenin showed apparent effect on the growth of cancer cells HT-29, its IC50 values reached to 12.36μg/mL and 16.33μg/mL. Eriosematin inhibitting the growth of cervical cancer Hela was outstanding, its IC50 value reached to 12.22μg/mL. And with increasing concentrations of Eriosematin, inhibition of tumor cells gradually increased.
引文
[1]林翠梧,蒋林斌,赵树凯.天然药物的研究与开发[J].广西大学学报(自然科学版),2001,26(3):162.
    [2]戴斌,丘翠嫦.瑶药资源及其开发利用研究进展[J].中国民族民间医药杂志.2003(65):314-318.
    [3]罗金裕,草显玉.瑶族医药概述[J].中国民族民间医药杂.1994,10:1-4.
    [4]广西僮族自治区卫生厅编著.广西中药志[S].第二辑.广西人民出版社,1963:138.
    [5]潘保强,濮全龙.四方藤化学成分研究简报[J].中草药,1981,12(8):54.
    [6]张叶青,谢一辉,黄丽萍.白粉藤属植物化学成分及生理活性的研究进展[J].时珍国医国药,2006,17(1):107-108.
    [7]Al-Said MS, Khalifa AS, Al-Azizi MM. Flavonoids from Cissus digitata[J]. International Journal of Pharmacognosy,1991,29(4):281-283.
    [8]Thakur A, Jain, V, Hingorani L. Phytochemical studies on Cissus quadrangularis Linn[J]. Pharmacognosy Research,2009,1(4):213-215.
    [9]Saifah E, Kelley CJ, Leary JD. Constituents of the leaves of Cissus rheifolia[J]. Journal of Natural Products,1983,46(3):353-358.
    [10]Toledo MCF, Reyes FGR, Iaderoza M, etal. Anthocyanins from anti trepador(Cis-sus sicyoides, Linn.)[J]. Journal of Food Science,1983,48(4):368-1369.
    [11]Beltrame FL, Ferreira AG, Cortez AG. Coumarin glycoside from Cissus sicyoide-s[J]. Natural Product Letters,2002,16(4):213-216.
    [12]Ahmadu AA, Onanuga A, Aquino R. Flavonoid glycosides from the leaves of Ci-ssus ibuensis Hook(Vitaceae)[J]. African Journal of Traditional, Complementa-ry and Alternative Medicines,2010,7(3):225-230.
    [13]Xu Fengming, Matsuda Hisashi, Hata Hiroki, etal. Structures of new flavonoids and benzofuran-type stilbene and degranulation inhibitors of rat basophilic leuke-mia cells from the Brazilian herbal medicine Cissus sicyoides[J]. Chemical & Pharmaceutical Bulletin,2009,57(10):1089-1095.
    [14]Bhutani KK, Kapoor R, Atal CK. Investigations of medicinal plants. Part Ⅱ. Two unsymmetric tetracyclic triterpenoids from Cissus quadrangularis[J]. Phytochemi-stry(Elsevier),1984,23(2):407-410.
    [15]Wang Yuehu, Zhang Zhongkai, He Hongping, etal. Lignans and triterpenoids fro-m Cissus repens(Vitaceae)[J]. Yunnan Zhiwu Yanjiu,2006,28(4):433-437.
    [16]Gupta MM, Verma RK. Unsymmetric tetracyclic triterpenoid from Cissus quadra-ngularis[J]. Phytochemistry,1990,29(1):336-337.
    [17]Gupta MM, Verma RK. Lipid constituents of Cissus quadrangularis[J]. Phytoche-mistry,1991,30(3):875-878.
    [18]谢一辉,邓鹏,张叶青,等.安痛藤化学成分研究[J].中药材,2009,32(2):210-213.
    [19]杨连春,王峰,刘敏,等.红背丝绸拮抗内皮素有效成分的提取分离和鉴定[J].空军总医院学报,1997,13(14):205-208.
    [20]Quilez AM, Saenz MT, Garcia MD, etal. Phytochemical analysis and antiallergic study of Agave intermixta Trel.and Cissus sicyoides L.[J]. Journal of Pharmacy and Pharmacology,2004,56(9):1185-1189.
    [21]Adesanya SA, Nia R, Martin MT, etal. Stilbene derivatives from Cissus quadrang-ularis[J]. Journal of Natural Products,1999,62(12):1694-1695.
    [22]Wang YH, Zhang ZK, He HP, etal. Stilbene C-glucosides from Cissus repens[J]. Journal of Asian Natural Products Research,2007,9(7):631-636.
    [23]Yang Lianchun, Wang Feng. Extraction of stilbene derivatives from Cissus assa-mica as endothelin antagonists[J]. Faming Zhuanli Shenqing Gongkai Shuo min-gshu,1998.
    [24]Mehta M, Kaur N, Bhutani KK. Determination of marker constituents from Cissu-s quadrangularis Linn. and their quantitation by HPTLC and HPLC[J]. Phytoche-mical Analysis,2001,12(2):91-95.
    [25]Chidambara MK, Vanitha A, Mahadeva SM, etal. Antioxidant and antimicrobial activity of Cissus quadrangularis[J].Journal of medicinal food,2003,6(2):99-105.
    [26]Moody JO, Ojo OO, Omotade OO, etal. Anti-sickling potential of a Nigerian herbal formula(ajawaron HF) and the major plant component (Cissus populnea L. CPK)[J]. Phytotherapy research,2003,17(10):1173-1176.
    [27]江苏省植物研究所,中国医学科学院药物研究所,中国科学院昆明植物所.新华本草纲要,第3册[M].上海科学技术出版杜,1991:164.
    [28]黄丽萍,谢一辉,肖百全,等.安痛藤对大鼠佐剂性关节炎的实验研究[J].时珍国医国药,2006,17(11):2139-2140.
    [29]黄立中,莫新民,雷晓明,等.安痛藤口服液对小鼠镇痛抗炎作用的实验究[J].湖南中医杂志,2000,16(4):53.
    [30]王峰,杨连春,刘敏,等.抗蛇毒中草药拮抗ET-1和S6b作用的初步研究[J].空军总医院学报,1996,12(3):128-130.
    [31]王峰,杨连春,刘敏,等.抗蛇毒中草药拮抗ET-1和S6b作用的初步初步[J].中国中药杂志研,1997,22(10):621-622.
    [32]杨连春,王峰,刘敏,等.抗蛇毒中草药红背丝绸对内皮素-1的拮抗作用[J].中国新药杂志,2000,9(7):455-458.
    [33]Jainu M, Devi CS, Shyamala. Effect of Cissus quadrangularis on gastric mucosal defensive factors in experimentally induced gastric ulcer-a comparative study with sucralfate[J]. Journal of medicinal food,2004,7(3):372-376.
    [34]Shirwaikar A, Khan S, Malini S. Antiosteoporotic effect of ethanol extract of Cis-sus quadrangularis Linn. on ovariectomized rat[J]. Journal of ethnopharmacolo-gy,2003,89(2-3):245-250.
    [35]Kone WM, Atindehou KK, Terreaux C, etal. Traditional medicine in north Cote-d'Ivoire:screening of 50 medicinal plants for antibacterial activity[J]. Journal of ethnopharmacology,2004,93(1):43-49.
    [36]Saenz MT, Garcia MD, Quilez A, etal. Cytotoxic activity of Agave intermixta L. (Agavaceae) and Cissus sicyoides L. (Vitaceae)[J]. Phytotherapy research:PTR, 2000,14(7):552-554.
    [37]Opoku AR, Geheeb KM, Lin J, etal. Preliminary screening of some traditional Zulu medicinal plants for antineoplastic activities versus the HepG2 cell line[J]. Phytotherapy research:PTR,2000),14(7),534-537.
    [38]Garcia X, Cartas HL, LJ Marte, etal. Vasoconstrictor effect of Cissus sicyoides on guinea Pig aortic rings[J]. General Pharmacology,1997,29(3):457-462.
    [39]Balachandran B, Sivaswamy SN, Sivaramakrishnan VM. Genotoxic effects of some foods & food components in Swiss mice[J]. The Indian journal of medical research,1991(94),378-383.
    [40]林朝展,祝晨蔯,邓贵华,等.枇杷叶紫珠化学成分研究[J].中药材.2010,33(6):897-900.
    [41]张军民,石晓峰,李冲,等.雪松松针化学成分研究[J].中药材,33(2):215-218.
    [42]毛士龙,桑圣民,劳爱娜,等.宝兴卫矛中三萜成分研究[J].中草药,2000,31(10):729-730.
    [43]Reiko S, Genichiro N, Itsuo N. Gallic acid esters of bergenin and norbergenin from Mallotus japonicus[J]. Phytochemistry,1990,29(1):267-270.
    [44]章为,徐康平,曾光尧,等.两色紫金牛化学成分研究[J].中国药学杂志,2007,42(9):656-658.
    [45]Masayuki F, Yukinori M, Tsuyoshi T. Studies on Nepalese crude drugs ⅩⅫ. On the phenolic constituents of the rhizome of Bergenia ciliate(Haw.) Sternb[J]. Nat-ural Medicines,1996,50(6):404-407.
    [46]谢一辉,邓鹏,张叶青,等.安痛藤化学成分研究[J].中药材,2009,32(2):210-213.
    [47]焦启扬,吴立军,黄建,等.板栗总苞化学成分的分离与鉴定[J].沈阳药科大学学报,2009,26(1):23-26.
    [48]陈萍,杨峻山.小叶云实化学成分的研究[J].中国药学杂志,2008,43(24):1852-1855.
    [49]刘因华.中药挥发油的研究现状[J].现代中医药,2009,29(1):68-70.
    [50]管燕红,曾君,张丽霞.千斤拔制剂研究概况及在傣医中的应用[J].中国民族医药杂志.2008,14(10):39-40.
    [51]李华,杨美华,斯建勇,等.千斤拔化学成分研究[J].中草药.2009,40(04):512-516.
    [52]Li H, Yang M, Miao J, etal. Prenylated isoflavones from Flemingia philippinensis[J]. Magnetic Resonance of Chemistry.2008,46(12):1203-1207.
    [53]李华,杨美华,马小军.千斤拔黄酮类化学成分研究[J].中国中药杂志.2009,34(06):724-726.
    [54]Ahn E, Nakamura N, Akao T, et al. Prenylated flavonoids from Moghania philippinensis.[J]. Phytochemistry (Elsevier).2003,64(08):1389-1394.
    [55]Chen M, Lou S, Chen J. Two isoflavones from Flemingia philippinensis[J]. Phytochemistry.1991,30(11):3842-3844.
    [56]陈敏,罗思齐,陈钧鸿.蔓性千斤拔化学成分的研究[J].药学学报.1990,26(01):42-48.
    [57]孙琳,李占林,韩国华,等.千斤拔化学成分研究[J].中国药物化学杂志.2009,19(05):364-367.
    [58]陈一,李开双,黄凤娇.千斤拔的镇痛和抗炎作用[J].广西医学.1993,15(02):77-79.
    [59]刘玉鹏,刘梅,刘俊英,等.30种中草药的抗氧化活性研究[J].烟台大学学报:自然科学与工程版,2000,13(1):71-73.
    [60]张明秋,关铭,年晓莉,等.千斤拔黄酮抑制血栓形成机制研究[J].中国老年学杂志.2009,29(16):2074-2076.
    [61]袁建新,倪立新,冯凯,等.千斤拔、人参茎叶皂甙对Wistar大鼠坐骨神经损伤保护作用的实验研究[J].中国煤炭工业医学杂志.2002,5(4):405.
    [62]王学勇.千斤拔中的天然雌激素[J].国际中医中药杂志.2006,28(03):150.
    [63]韦丽君,陈惠民,王建慧.壮药千斤拔饮对去卵巢大鼠免疫内分泌影响的研究[J].广西中医药.2009,32(06):46-49.
    [64]张慧,裴志东,李春雪,等.乌骨藤的化学成分研究[J].中国中药杂志.2010,35(23):3175-3177.
    [65]王栋,杨欢,戴衍鹏,等.镰形棘豆的化学成分研究[J].中国药学杂志.2008,43(17):1192-1194.
    [66]王晓中,马彦冬,李绪文,等.九里香叶中甲氧基黄酮类化合物的NMR研究[J].波谱学杂志.2007,24(3):341-346.
    [67]Arfan M, Amin H, Khan N, etal. Analgesic and anti-inflammatory activities of 11-O-galloylbergenin. Journal of Ethnopharmacology[J].2010,131(2),502-504.
    [68]王刚,麻兵继.岩白菜素的研究概况[J].安徽中医学院报.2002,21(6):59-61.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700