爪瓣山柑及锐尖山香圆叶化学成分的研究
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摘要
1.爪瓣山柑化学成分的研究
爪瓣山柑(Capparis himarayensis)为山柑科(Capparidaceae)山柑属(Capparis)植物,又称野西瓜、槌果藤等,在我国产于新疆和西藏。其根皮、叶及果实均可作药用。味辛苦,性温,具有祛风、除湿、通鼻窍、止瘀消肿、止痛活血之功效,在我国民间广泛用于治疗风湿性关节炎和疮毒等。野西瓜在土耳其、伊朗、约旦、印度、沙特、埃及、希腊和巴勒斯坦等国作为一种传统的草药用于滋补、抗炎、抗高血压、降血糖、通风、化痰、驱虫、利尿、通便等。该植物应用广泛,疗效确切,但国内外对其化学成分及药理作用的研究报道很少,因此,我们对其化学成分进行了系统的研究,以期阐明该植物的主要有效物质成分,从而为其更好的开发应用奠定基础。
综合运用多种现代分离方法和技术,从爪瓣山柑的乙醇提取物中分离得到29个化合物。综合运用现代波谱技术(包括IR,UV,~1H-NMR,~13C-NMR,HMQC,HMBC,EI-MS,FAB-MS,X-ray),结合经典的化学方法鉴定了27个化合物。包括6个吲哚类生物碱、2个蒽醌、2个甾醇、9个黄酮及其苷类成分、4个有机酸、1个多元酚、1个芳香醛、1个长链烷烃、1个甾体皂苷。其中有3个为新化合物,1个为新的天然产物,13个为本属中首次分离得到。
新化合物分别命名为爪瓣山柑碱A(3(S)6 methoxyl-2′-(methylthio)spiro[3H-indole-3,5′(4′H)thiazol]-2-on,CSP-10),爪瓣山柑碱B(6-methoxy-2-(methyl thio)-1H-indole-3-carbaldehyde,CSP-7),爪瓣山柑蒽醌A(2,6-dihydroxy-3-methyl anthra-9,10-quinone,CSP-15)。新的天然产物为6-甲氧基-2,3-吲哚二酮(CSP-8)。其余成分分别鉴定为β-谷甾醇(CSP-1),麦角甾醇(CSP-2),1-甲氧基-2-羟基-3-甲基-蒽醌(CSP-3),三十烷酸(CSP-4),对羟基苯甲醛(CSP-5),,汉黄芩素(CSP-6),2-醛基-4-羟基-吲哚(CSP-9,),苯甲酸(CSP-11),千层纸素A(CSP-12),6-甲氧基-吲哚-3-甲酸甲酯(CSP-13),香草酸(CSP-14),2-羟基-6-甲氧基-吲哚-3-甲基酮(CSP-16),对羟基苯甲酸(CSP-17),芹菜素(CSP-18),山柰酚(CSP-19),木犀草素(CSP-20),槲皮素(CSP-21),β-胡萝卜苷(CSP-22),焦没食子酸(CSP-23),正二十九烷(CSP-24),槲皮素-3-O-β-D-葡萄糖苷(CSP-25),山奈酚-3-O-β-D-葡萄糖苷(CSP-26),芦丁(CSP-27)。
对分离得到的2个生物碱进行了抗肿瘤活性的研究,结果表明爪瓣山柑碱B具有一定的抗肿瘤活性。
本文还对山柑属植物的化学和药理学研究进展进行了综述,为开发利用本属药用植物资源提供了依据。
2.锐尖山香圆叶化学成分的研究
锐尖山香圆(Turpinia arguta)为省沽油科(Staphyleaceae)山香圆属(Turpinia)植物,为落叶灌木。锐尖山香圆叶原系江西省安远县民间秘方,有悠久的应用历史,但历代本草均无记载,当地根据其用途取名为“蛾子药”,在我国主产于福建、江西、湖南、广东、广西、四川、贵州等省。锐尖山香圆叶用于治疗咽喉炎、扁桃体炎等,具有高效、速效的特点。目前对该植物的药理及化学研究很少,因该植物的成药制剂以水为提取溶剂,因此我们对其水提取物进行了研究,以期阐明其作用物质基础并为该植物的进一步研究开发奠定基础。
综合运用多种现代分离方法和技术,从锐尖山香圆叶的水提取物中分离得到13个化合物。综合运用现代波谱技术(包括IR,UV,~1H-NMR,~13C-NMR,HMQC,HMBC,EI-MS,FAB-MS)鉴定了它们的结构,包括6个黄酮及其苷:芹菜素(Sxy-4),木犀草素(Sxy-9),芹菜素-7-O-β-D-葡萄糖苷(Sxy-10),木犀草素-7-O-β-D-葡萄糖苷(Sxy-11),芹菜素-7-O-β-D-新橙皮糖苷(Sxy-12),芹菜素7-O-β-D-2′-鼠李糖基芸香糖苷(Sxy-13);5个酚酸类化合物:香草酸(Sxy-1),对羟基肉桂酸(Sxy-2),焦没食子酸(Sxy-5),没食子酸(Sxy-7),2-4′-羟基-苄基-2-羟基-丁二酸(Sxy-8):α-呋喃甲酸(Sxy-6)和丁二酸酐(Sxy-3)。上述化合物全部为该科中首次发现。
本文还对省沽油科植物的化学和药理学研究进展进行了综述,为开发利用该科药用植物资源提供了依据。
1.Studies on the chemical constituents of Capparis himalayensis
Capparis himalayensis Jsafri belongs to the Capparaceae family,Capparis genus.The plant is distributed in Xinjiang province and Tibet of China.The leaves,fruits,and root bark are used as medicinal materials.It is pungent and bitter in taste,warm in nature,has the effect of dispelling wind-damp,freeing nasal orifices,transforming stasis to reduce edema,relieving pain,quickening blood.It is widely used in the treatment of rheumatoid arthritis and sore-toxin among the people of china.
Twenty nine compounds were isolated from the ethanol extract of the plants of Capparis himalayensis collected in Xinjiang province using various modern chromatographic techniques.On the basis of classical chemical methods and modern spectrometric approaches,including IR,UV,~1H-NMR,~(13)C-NMR,HMQC,HMBC,EI-MS, FAB-MS,X-ray,etc.,the structures of twenty seven compounds were established.Among the twenty nine compounds twenty sewen were identified and three were found to be new compounds,one to be new natural product and thirteen were isolated from the genus for the first time.
The new compounds consisted of two indole alkaloids named as 3(S)6-methoxyl-2'-(methylthio) spiro[3H-indole-3,5'(4'H)thiazol]-2-on(CSP-7)、6-methoxy-2-(methylthio)-1 H-indole-3-carbaldehyde(CSP-10) and one anthraquinone named as 2,6-dihydroxy-3-methyl anthra-9,10-quinone(CSP-15).The twenty four known compounds were identified asβ-sitosterol(CSP-1),ergosterol(CSP-2),2-Hydroxy-1-methoxy-3-methyl-anthraquinone (CSP-3),Triacontanoic Acid(CSP-4),p-hydroxybenzaldehyde(CSP-5), wogonin(CSP-6),6-methoxyindoline-2,3-dione(CSP-8),4-hydroxy-1H-indole-2-carbaldehyde (CSP-9) benzoic acid(CSP-11),oroxylin A(CSP-12),6-methoxy-1H-indole-3-carboxylate (CSP-13),Vinillic acid(CSP-14),2-hydroxy-6-methoxy-1H-indol-3-ethanone (CSP-16),p-hydroxy-benzoic acid(CSP-17),apigenin(CSP-18), kaempferol(CSP-19),Luteolin(CSP-20),quercetin(CSP-21),β-daucosterol(CSP-22), Pyrogallic acid(CSP-23),n-Nonacosane(CSP-24),quercetin-3-O-β-D-glucoside (CSP-25),kaempferol-3-β-D-glucoside(CSP-26) and rutin(CSP-27),
In addition,advances in the research of chemical constituents and pharmacological activities of Capparis himalayensis were reviewed in this paper.
2.Studies on the chemical constituents of Turpinia arguta
Turpinia arguta was formerly folk secret recipe from Anyuan county of Jiangxi province,with a long history of the application,but it had not been recorded by Herbology of past ages.The plant is distributed in the provinces of Fujian,Jiangxi,Hunan, Guangdong,Guangxi,Sichuan,Guizhou in china and was used for the treatment of pharyngitis,tonsillitis.In order to elucidate the active constituents in the plants of Turpinia arguta,we made phytochemical studies on hydrosoluble part.
Phytochemical studies in the present study were carried out using modern chromatographic techniques and had led to the isolation of 13 conpounds from the H_2O extract of leaves of Turpinia arguta collected in Jiangxi province.Subsequently,the structures of these compounds were established on the basis of classical chemical methods and modern spectrometric approaches,including IR,UV,~1H-NMR,~(13)C-NMR,HMQC, HMBC,EI-MS,FAB-MS,etc.They were Vanillic acid(Sxy-1),E-p-hydroxoy-cinnamic acid(Sxy-2),Butanedioic andydride(Sxy-3),Apigenin(Sxy-4),Pyrogallic acid(Sxy-5), 2-furoic acid(Sxy-6),Gallic acid((Sxy-7),2-(4-Hydroxybenzyl)malic acid(Sxy-8), luteolin(Sxy-9),Apigenin-7-O-β-D-glucoside(Sxy-10),Luteolin-7-O-β-D-glucoside (Sxy-11),Apigenin-7-O-β-D-neohesperidoside(Sxy-12) and Apigenin-7-O-β-D-(2",6"-di-α-rhamnopyran-osyl) -glucopyranoside(Sxy-13).All compounds were isolated from the family for the first time.
The thesis also reviewed the research advances of the chemical and pharmacological studies of Staphyleceae family.
爪瓣山柑(Capparis himarayensis)为山柑科(Capparidaceae)山柑属(Capparis)植物,又称野西瓜、槌果藤等,在我国产于新疆和西藏。其根皮、叶及果实均可作药用。味辛苦,性温,具有祛风、除湿、通鼻窍、止瘀消肿、止痛活血之功效,在我国民间广泛用于治疗风湿性关节炎和疮毒等。野西瓜在土耳其、伊朗、约旦、印度、沙特、埃及、希腊和巴勒斯坦等国作为一种传统的草药用于滋补、抗炎、抗高血压、降血糖、通风、化痰、驱虫、利尿、通便等。该植物应用广泛,疗效确切,但国内外对其化学成分及药理作用的研究报道很少,因此,我们对其化学成分进行了系统的研究,以期阐明该植物的主要有效物质成分,从而为其更好的开发应用奠定基础。
综合运用多种现代分离方法和技术,从爪瓣山柑的乙醇提取物中分离得到29个化合物。综合运用现代波谱技术(包括IR,UV,~1H-NMR,~13C-NMR,HMQC,HMBC,EI-MS,FAB-MS,X-ray),结合经典的化学方法鉴定了27个化合物。包括6个吲哚类生物碱、2个蒽醌、2个甾醇、9个黄酮及其苷类成分、4个有机酸、1个多元酚、1个芳香醛、1个长链烷烃、1个甾体皂苷。其中有3个为新化合物,1个为新的天然产物,13个为本属中首次分离得到。
新化合物分别命名为爪瓣山柑碱A(3(S)6 methoxyl-2′-(methylthio)spiro[3H-indole-3,5′(4′H)thiazol]-2-on,CSP-10),爪瓣山柑碱B(6-methoxy-2-(methyl thio)-1H-indole-3-carbaldehyde,CSP-7),爪瓣山柑蒽醌A(2,6-dihydroxy-3-methyl anthra-9,10-quinone,CSP-15)。新的天然产物为6-甲氧基-2,3-吲哚二酮(CSP-8)。其余成分分别鉴定为β-谷甾醇(CSP-1),麦角甾醇(CSP-2),1-甲氧基-2-羟基-3-甲基-蒽醌(CSP-3),三十烷酸(CSP-4),对羟基苯甲醛(CSP-5),,汉黄芩素(CSP-6),2-醛基-4-羟基-吲哚(CSP-9,),苯甲酸(CSP-11),千层纸素A(CSP-12),6-甲氧基-吲哚-3-甲酸甲酯(CSP-13),香草酸(CSP-14),2-羟基-6-甲氧基-吲哚-3-甲基酮(CSP-16),对羟基苯甲酸(CSP-17),芹菜素(CSP-18),山柰酚(CSP-19),木犀草素(CSP-20),槲皮素(CSP-21),β-胡萝卜苷(CSP-22),焦没食子酸(CSP-23),正二十九烷(CSP-24),槲皮素-3-O-β-D-葡萄糖苷(CSP-25),山奈酚-3-O-β-D-葡萄糖苷(CSP-26),芦丁(CSP-27)。
对分离得到的2个生物碱进行了抗肿瘤活性的研究,结果表明爪瓣山柑碱B具有一定的抗肿瘤活性。
本文还对山柑属植物的化学和药理学研究进展进行了综述,为开发利用本属药用植物资源提供了依据。
2.锐尖山香圆叶化学成分的研究
锐尖山香圆(Turpinia arguta)为省沽油科(Staphyleaceae)山香圆属(Turpinia)植物,为落叶灌木。锐尖山香圆叶原系江西省安远县民间秘方,有悠久的应用历史,但历代本草均无记载,当地根据其用途取名为“蛾子药”,在我国主产于福建、江西、湖南、广东、广西、四川、贵州等省。锐尖山香圆叶用于治疗咽喉炎、扁桃体炎等,具有高效、速效的特点。目前对该植物的药理及化学研究很少,因该植物的成药制剂以水为提取溶剂,因此我们对其水提取物进行了研究,以期阐明其作用物质基础并为该植物的进一步研究开发奠定基础。
综合运用多种现代分离方法和技术,从锐尖山香圆叶的水提取物中分离得到13个化合物。综合运用现代波谱技术(包括IR,UV,~1H-NMR,~13C-NMR,HMQC,HMBC,EI-MS,FAB-MS)鉴定了它们的结构,包括6个黄酮及其苷:芹菜素(Sxy-4),木犀草素(Sxy-9),芹菜素-7-O-β-D-葡萄糖苷(Sxy-10),木犀草素-7-O-β-D-葡萄糖苷(Sxy-11),芹菜素-7-O-β-D-新橙皮糖苷(Sxy-12),芹菜素7-O-β-D-2′-鼠李糖基芸香糖苷(Sxy-13);5个酚酸类化合物:香草酸(Sxy-1),对羟基肉桂酸(Sxy-2),焦没食子酸(Sxy-5),没食子酸(Sxy-7),2-4′-羟基-苄基-2-羟基-丁二酸(Sxy-8):α-呋喃甲酸(Sxy-6)和丁二酸酐(Sxy-3)。上述化合物全部为该科中首次发现。
本文还对省沽油科植物的化学和药理学研究进展进行了综述,为开发利用该科药用植物资源提供了依据。
1.Studies on the chemical constituents of Capparis himalayensis
Capparis himalayensis Jsafri belongs to the Capparaceae family,Capparis genus.The plant is distributed in Xinjiang province and Tibet of China.The leaves,fruits,and root bark are used as medicinal materials.It is pungent and bitter in taste,warm in nature,has the effect of dispelling wind-damp,freeing nasal orifices,transforming stasis to reduce edema,relieving pain,quickening blood.It is widely used in the treatment of rheumatoid arthritis and sore-toxin among the people of china.
Twenty nine compounds were isolated from the ethanol extract of the plants of Capparis himalayensis collected in Xinjiang province using various modern chromatographic techniques.On the basis of classical chemical methods and modern spectrometric approaches,including IR,UV,~1H-NMR,~(13)C-NMR,HMQC,HMBC,EI-MS, FAB-MS,X-ray,etc.,the structures of twenty seven compounds were established.Among the twenty nine compounds twenty sewen were identified and three were found to be new compounds,one to be new natural product and thirteen were isolated from the genus for the first time.
The new compounds consisted of two indole alkaloids named as 3(S)6-methoxyl-2'-(methylthio) spiro[3H-indole-3,5'(4'H)thiazol]-2-on(CSP-7)、6-methoxy-2-(methylthio)-1 H-indole-3-carbaldehyde(CSP-10) and one anthraquinone named as 2,6-dihydroxy-3-methyl anthra-9,10-quinone(CSP-15).The twenty four known compounds were identified asβ-sitosterol(CSP-1),ergosterol(CSP-2),2-Hydroxy-1-methoxy-3-methyl-anthraquinone (CSP-3),Triacontanoic Acid(CSP-4),p-hydroxybenzaldehyde(CSP-5), wogonin(CSP-6),6-methoxyindoline-2,3-dione(CSP-8),4-hydroxy-1H-indole-2-carbaldehyde (CSP-9) benzoic acid(CSP-11),oroxylin A(CSP-12),6-methoxy-1H-indole-3-carboxylate (CSP-13),Vinillic acid(CSP-14),2-hydroxy-6-methoxy-1H-indol-3-ethanone (CSP-16),p-hydroxy-benzoic acid(CSP-17),apigenin(CSP-18), kaempferol(CSP-19),Luteolin(CSP-20),quercetin(CSP-21),β-daucosterol(CSP-22), Pyrogallic acid(CSP-23),n-Nonacosane(CSP-24),quercetin-3-O-β-D-glucoside (CSP-25),kaempferol-3-β-D-glucoside(CSP-26) and rutin(CSP-27),
In addition,advances in the research of chemical constituents and pharmacological activities of Capparis himalayensis were reviewed in this paper.
2.Studies on the chemical constituents of Turpinia arguta
Turpinia arguta was formerly folk secret recipe from Anyuan county of Jiangxi province,with a long history of the application,but it had not been recorded by Herbology of past ages.The plant is distributed in the provinces of Fujian,Jiangxi,Hunan, Guangdong,Guangxi,Sichuan,Guizhou in china and was used for the treatment of pharyngitis,tonsillitis.In order to elucidate the active constituents in the plants of Turpinia arguta,we made phytochemical studies on hydrosoluble part.
Phytochemical studies in the present study were carried out using modern chromatographic techniques and had led to the isolation of 13 conpounds from the H_2O extract of leaves of Turpinia arguta collected in Jiangxi province.Subsequently,the structures of these compounds were established on the basis of classical chemical methods and modern spectrometric approaches,including IR,UV,~1H-NMR,~(13)C-NMR,HMQC, HMBC,EI-MS,FAB-MS,etc.They were Vanillic acid(Sxy-1),E-p-hydroxoy-cinnamic acid(Sxy-2),Butanedioic andydride(Sxy-3),Apigenin(Sxy-4),Pyrogallic acid(Sxy-5), 2-furoic acid(Sxy-6),Gallic acid((Sxy-7),2-(4-Hydroxybenzyl)malic acid(Sxy-8), luteolin(Sxy-9),Apigenin-7-O-β-D-glucoside(Sxy-10),Luteolin-7-O-β-D-glucoside (Sxy-11),Apigenin-7-O-β-D-neohesperidoside(Sxy-12) and Apigenin-7-O-β-D-(2",6"-di-α-rhamnopyran-osyl) -glucopyranoside(Sxy-13).All compounds were isolated from the family for the first time.
The thesis also reviewed the research advances of the chemical and pharmacological studies of Staphyleceae family.
引文
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17.Pelotto Juan P.,Del Pero Martinez,Maria A,Flavonoid aglycons from Argentinian Capparis species(Capparaceae),Biochemical Systematics and Ecology,1998,26(5):577-580.
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28.C A
29.Oliveira Antonio F.M.,Salatino Antonio,Major constituents of the foliar epicuticular waxes of species from the Caatinga and Cerrado,Zeitschrift fuer Naturforschung,C:Journal of Biosciences,2000,55(9/10):688-692.
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31.Calis Ihsan,Kuruuzum-Uz Ayse,Lorenzetto Piergiorgio A.,Ruedi Peter,(6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits Phytochemistry,2002 59(4):451-457.
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38.MAHASNEH A.M.,ELOQLAH A.A.,Antimicrobial activity of extracts of herbal plants used in the traditional medicine of Jordan,J Ethnopharm,1999,64:271-276.
39.ADEL M.M.,Screening of Some Indigenous Qatari medicinal plants for antimicrobial activity,Phytother.Res,2002,16:751-753.
40.WU Jiu-hong,CHANG Fang-rong,HAYASHI K.,et al.Antitumor agents:Cappamensin A,a new in vitro anticancerprinciple,from Capparis sikkimensis,Bioorganic&Medicinal Chemistry Letters,2003,13(13):2223-2225.
41.DHAR D.,TEWARI R P.,TRIPATHI R.D.,et al.Chemical examination of Capparis decidua,Proc Nat Acad Sci Indian Sect A,1972,42(1):24-27.
42.AL-SAID M.S.,ABDELSATTAR E.A.,KHALIFA SI,et al.Isolation and identification of an anti-inflammatory principle from Capparis spinosa,Pharmazie,1988,43(9):640-641.
43.RASHID S.,LODHI F.,AHMAD M.,Preliminary cardiovascular activity evaluation of capparidisine,a spermidine alkaloid from Capparis decidua,Pak.J.Pharmacol,1989,6,(1/2):61-66.
44.ALTYMYSHEV A.A.,DRPZOV M.A.,VARVASJ-TUAN V.M.,et al.Comparative action of rutin and flavonoids from the common Caper on the course of radiation sickness an d indexes of the blood coagulation system in rats,Izv Akad Nauk Kirg SSR,1981(5):60-63.
45.GADGOLI C,MISHRA S H.Antihepatotoxic activity of P-methoxy benzoic acid from Capparis spinosa,J.Ethnopharmacol,1999,66(2):187-192.
46.ANGELO D.,CATAN1A S.,Evaluation of extracts and isolated fraction from Capparis spinosa L.buds as an antioxidant source[J].J.Agric.Food.Chem.,2002,50(5):1168-1171.
47.ONINA F.,PUGLIA C.,In vitro antioxidant and in vivo photoprotective effects of a lyophilized extract of Capparis spinosa L buds,Cosmet.Sci.,2002,53(6):321-335.
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