黄皮Clausena Lansium化学成分研究
摘要
芸香科(Rutacea)黄皮属植物黄皮(Clausena lansium)含有丰富的小分子化合物,并具有广泛的药理活性。本论文首先针对黄皮属植物中的生物碱和香豆素类成分进行了系统的文献综述,内容包括化合物结构类型、药理活性和光谱规律,为本课题化学成分的提取分离和结构鉴定工作打下坚实的基础。
本论文对黄皮干燥茎进行了系统化学成分研究,利用反复硅胶柱层析、Sephadex LH-20柱层析、制备薄层层析、制备高效液相等多种色谱技术,从黄皮茎二氯甲烷萃取部分分离得到了10个咔唑生物碱,1个吲哚生物碱,1个酰胺生物碱,6个呋喃香豆素和1个甾醇共计19个化合物。根据理化常数测定和波谱解析分别鉴定为:Claulansine-A(1),Claulansine-B(2),Claulansine-C(3),Clauseindole(4),Claulansitin(5),3-formylcarbazole(6),Methyl carbazole-3-carboxylate(7),O-demethylmurrayanine(8),3-formyl-6-methoxy carbazole(9),3-formyl-2-hydroxy-6-methoxy carbazole(10),Indizoline(11),1-hydroxy-3-formyl-4-prenylcarbazole(12),4-methoxy-1-methylquinolin-2-one(13),8-hydroxyfurocoumarin(14),Imperatorin(15),Alloisoimperatorin(16),Heraclenol(17),Wampetin(18),以及β-sitosterol(19),其中化合物-1,-2,-3,-4,-5为5个新化合物,化合物13为首次从本属中分离得到,化合物-10,-12,-17为首次从本种中分离得到。
为对黄皮化学成分进行初步的定性定量研究,本课题使用HPLC-UV法,对分离得到的化合物进行HPLC峰指认。进而以这些化合物为参照,对黄皮的不同植物部位茎、根、叶与叶柄的化学成分进行了比较,并选择化合物15作为指标成分研究其在茎和叶柄中含量。通过比较,发现黄皮的根和茎的化学成分具有很大的相似性,提示用药时它们之间具有很大的相互替代的可能性,对黄皮植物资源的保护具有重要意义。
Clausena lansium BURM.f.(Rutaceae) is known to abound with carbazoles and coumarins,and a variety of pharmacologic effects,such as anti-gastrointestinal inflammation,hepatoprotective,anti-tumor,etc.,have been reported for this plant.In order to support the research work,related literatures,including structure types,spectrum characteristics and bioactivities of these components from Clausena genus,were fully reviewed by this thesis.
The dichlormethane extract of the sun-dried stems was subjected successively to Si gel column,preparative TLC,preparative HPLC and Sephadex LH-20 column to give 19 compounds including 11 carbazole alkaloids,1 indole,1 amide,five furocoumarins and one sistol.By analysis of their physical-chemical characters and spectroscopic data (EI-MS,HR-ESI-MS,~1H-,~(13)C- NNR,H-H COSY,HSQC,TOCSY,HMBC),their structures were elucidated as:Claulansine-A(1),Claulansine-B(2),Claulansine-C (3),Clauseindole(4 ),Claulansitin(5 ),3-formylcarbazole(6 ),Methyl carbazole-3-carboxylate(7 ),O-demethylmurrayanine(8 ),3-formyl-6-methoxy carbazole (9),3-formyl-2-hydroxy-6-methoxy carbazole(10 ),Indizoline(11 ), 1-hydroxy-3-formyl-4-prenylcarbazole(12),4-methoxy-1-methylquinolin-2-one(13 ), 8-hydroxyfurocoumarin(14 ),Imperatorin(15 ),Alloisoimperatorin(16 ),Heraclenol (17),Wampetin(18),and sitosterol(19),.Five of them,including Compound-1, -2,-3,-4,-5 were identified as novel compounds,while Compound 13 was isolated from Clausena genus for the first time,and Compound-10,-12,-17 were isolated from the species of Clausena lansium for the first time.
Based on the chemical study,the HPLC profile of the stems,roots,leaves and petiolar part of the plant were compared to each other and to the reference compounds.A preliminary quantitative study of the content of Compound 15 was also performed. Results indicated that the chemical profile of the roots and stems were very similarity, there is possibility to use the stems as the substitute of the roots in some cases,which can be remarkably beneficial to the protection of plant resources.
本论文对黄皮干燥茎进行了系统化学成分研究,利用反复硅胶柱层析、Sephadex LH-20柱层析、制备薄层层析、制备高效液相等多种色谱技术,从黄皮茎二氯甲烷萃取部分分离得到了10个咔唑生物碱,1个吲哚生物碱,1个酰胺生物碱,6个呋喃香豆素和1个甾醇共计19个化合物。根据理化常数测定和波谱解析分别鉴定为:Claulansine-A(1),Claulansine-B(2),Claulansine-C(3),Clauseindole(4),Claulansitin(5),3-formylcarbazole(6),Methyl carbazole-3-carboxylate(7),O-demethylmurrayanine(8),3-formyl-6-methoxy carbazole(9),3-formyl-2-hydroxy-6-methoxy carbazole(10),Indizoline(11),1-hydroxy-3-formyl-4-prenylcarbazole(12),4-methoxy-1-methylquinolin-2-one(13),8-hydroxyfurocoumarin(14),Imperatorin(15),Alloisoimperatorin(16),Heraclenol(17),Wampetin(18),以及β-sitosterol(19),其中化合物-1,-2,-3,-4,-5为5个新化合物,化合物13为首次从本属中分离得到,化合物-10,-12,-17为首次从本种中分离得到。
为对黄皮化学成分进行初步的定性定量研究,本课题使用HPLC-UV法,对分离得到的化合物进行HPLC峰指认。进而以这些化合物为参照,对黄皮的不同植物部位茎、根、叶与叶柄的化学成分进行了比较,并选择化合物15作为指标成分研究其在茎和叶柄中含量。通过比较,发现黄皮的根和茎的化学成分具有很大的相似性,提示用药时它们之间具有很大的相互替代的可能性,对黄皮植物资源的保护具有重要意义。
Clausena lansium BURM.f.(Rutaceae) is known to abound with carbazoles and coumarins,and a variety of pharmacologic effects,such as anti-gastrointestinal inflammation,hepatoprotective,anti-tumor,etc.,have been reported for this plant.In order to support the research work,related literatures,including structure types,spectrum characteristics and bioactivities of these components from Clausena genus,were fully reviewed by this thesis.
The dichlormethane extract of the sun-dried stems was subjected successively to Si gel column,preparative TLC,preparative HPLC and Sephadex LH-20 column to give 19 compounds including 11 carbazole alkaloids,1 indole,1 amide,five furocoumarins and one sistol.By analysis of their physical-chemical characters and spectroscopic data (EI-MS,HR-ESI-MS,~1H-,~(13)C- NNR,H-H COSY,HSQC,TOCSY,HMBC),their structures were elucidated as:Claulansine-A(1),Claulansine-B(2),Claulansine-C (3),Clauseindole(4 ),Claulansitin(5 ),3-formylcarbazole(6 ),Methyl carbazole-3-carboxylate(7 ),O-demethylmurrayanine(8 ),3-formyl-6-methoxy carbazole (9),3-formyl-2-hydroxy-6-methoxy carbazole(10 ),Indizoline(11 ), 1-hydroxy-3-formyl-4-prenylcarbazole(12),4-methoxy-1-methylquinolin-2-one(13 ), 8-hydroxyfurocoumarin(14 ),Imperatorin(15 ),Alloisoimperatorin(16 ),Heraclenol (17),Wampetin(18),and sitosterol(19),.Five of them,including Compound-1, -2,-3,-4,-5 were identified as novel compounds,while Compound 13 was isolated from Clausena genus for the first time,and Compound-10,-12,-17 were isolated from the species of Clausena lansium for the first time.
Based on the chemical study,the HPLC profile of the stems,roots,leaves and petiolar part of the plant were compared to each other and to the reference compounds.A preliminary quantitative study of the content of Compound 15 was also performed. Results indicated that the chemical profile of the roots and stems were very similarity, there is possibility to use the stems as the substitute of the roots in some cases,which can be remarkably beneficial to the protection of plant resources.
引文
[1]中国科学院中国植物志编辑委员会.中国植物志[M],北京,1994,43(2):126.
[2]潘瑞乐,朱兆仪.黄皮属药用植物研究进展[J].国外医药:植物药分册,1990,5(6):243-247
[3]Bhattacharyya P,Biswas GK,Braua AK,etal.Clausenalene,a carbazole alkaloid from Clausena heptaphylla[J].Phytochemistry,1993,33(1):248-250.
[4]Chaicbantipyuth C,Pummangura S,Naowsarn K,et al.Two new bioactive carbazole alkaloids from the root bark of Clausena harmandiana[J].J Nat Prod,1988,51(6):1285-1288.
[5]Chavi Y,Somkrit S,Prachack S,et al.Coumarins and carbazoles with antiplasmodial activity from Clausena harmandiana [J]. Planta Med, 2000, 66(3):277-279.
[6] Liu GT, Li WX, Chen YY, et al. Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice [J]. Drug Develop Res, 1996, 39(2): 174-178.
[7] Wu CC, Ko FN, Wu TS, et al. Antiplatelet effects of Clausine-D isolated from Claulansine-Cxcavata [J]. Biochem Biophys Acta, 1994, 1201(1):1-6.
[8] Dhan Rakash, Kanwal Raj, Randhir S. Kapil, et al. Coumarins from Clausena Indica[J].Phytochemistry, 1978,17:1194-5.
[1]潘瑞乐,朱兆仪.黄皮属药用植物研究进展[J].国外医药:植物药分册,1990,5(6):243-247
[2]Khan NU,Naqvi SWI.Constituents of the genus Clausena[J].J Scient Ind Res,1988,47(3):543-546.
[3]Roy SP,Bhattacharyya P,Chakraborty DP.3-Methylcarbazole from Clausena heptaphylla[J].Phytochemistry,1974,13(2):1017.
[4]Li WS,Mcchesney JD,EI-Feraly FS.Carbazole alkaloids from Clausena lansium[J].Phytochemistry,1991,30(1 ):343-346.
[5]Wu TS,Huang SC,Wu PL,et al.Carbazole alkaloids from Claulansine-Cxcavata and their biological activity[J].Phytochemistry,1996,43(1 ):133-140.
[6]Ito C,Katsuno S,Ohta H.et al.Constituents of Claulansine-Cxcavate isolation and structural elucidation of new carbazole alkaloids[J].Chem.Pharm.Bull.,1997,45(1):48-52.
[7]Wu TS,Huang SC,Wu PL,et al.Alkaloidal and other constituents from the root bark of Claulansine-Cxcavate[J].Phytochemistry,1999,52(3):523-527.
[8]Chakraborty A,Chowdhury K,Bhattacharyya P.Clausenol and clausenine-two carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1995,40(1):295-298.
[9]Ngadjui BT,Ayafor JF,Sondengam BL,et al.Quinoione and carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1989,28(5):1517-1519.
[10]Chakraborty A,Saha C,Podder G,et al.Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla[J].Phytochemistry,1995,38(3):787-789.
[11]Wu TS,Huang SC,Wu PL.Carbazole alkaloids from stem bark of Claulansine-Cxcavata[J].Phytochemistry,1996,43(6):1427-1429.
[12]Ito C,Ohta H,Hugh TW,et al.Constituents of Claulansine-Cxcavata isolation and elucidation of seven new carbazole alkaloids and a new coumarin[J].Chem Pharm Bull,1996,44(2):2231-2235.
[13]Ito C,Katsuno S,Itoigawa M,et al.New carbazole alkaloids from Clauseindolenisata with antitumor promoting activity[J].J Nat Prod,2000,63(1):125-128.
[14]Kumar V,Vallipuram K,Adebajo AC,et al.2,7-Dihydrooxy-3-formyl- 1 -(3'-methyl-2'-butenyl)Carbazole from Clausena lansium[J].Phytochemistry,1995,40(5):1563-1565.
[15]Wu TS,Huang SC,Lan JS,et al.Chemical and antiplatelet aggregative investigation of the leaves of Claulansine-Cxcavata[J].Phytochemistry,1993,32(2):449-451.
[16]Bhattacharyya P,Chakraborty A.Heptazolicine,a carbazole alkaloid from Clausena heptaphylla [J].Phytochemistry,1984,23(10):2409-2410.
[17]Ito C,Katsuno S,Ruangrungsi N,et al.Structures of clausamine-A,B,C,three novel carbazole alkaloids from Clauseindolenisata[J].Chem Pharm Bull,1998,46(2):344-346.
[18]Wu TS,Huang SC,Wu PL,et al.Lactonic carbazole alkaloids from the root bark of Claulansine-Cxcavate[J].Chem Pharm Bull,1998,46(9):1459-1461.
[19]Wu TS,Huang SC,Wu PL,et al.Structure and synthesis of clausenaquinone- A,a novel carbazolequinone alkaloid and bioactive principle from Claulansine-Cxcavata[J].Bioorg Med Chem Lett,1994,4(20):2395-2398.
[20]Bhattacharyya P,Biswas GK,Braua AK,et al.Clausenalene,a carbazole alkaloid from Clausena heptaphylla[J].Phytochemistry,1993,33(1):248-250.
[21]Wu TS,Wu PL.Pyrano and furocarbazole alkaloids from the root bark of Claulansine-Cxcavate [J].Heterocycles,1997,45(5):969-973.
[22]Zhang A,Lin GQ.The first synthesis of Clausenamine-A and cytotoxic activities of three biscarbazole analogues against cancer[J].Bioorg Med Chem Lett,2000,10(10):1021 - 1023.
[23]Barbara R,Otmar H,Harald G.Tryptamine derived amides from Clausena indica[J].Phytochemistry,1997,45(2):337-341
[24]Mlner PH,Coates N J,Gilpin ML,et al.SB-204900,a novel oxirane carboxamide from Clausena lansium[J].J Nat Prod,1996,59(4):400-402
[25]Yang MH,Chen YY,Huang L.Three novel cyclic amides from Clausena lansium[J].Phytochemistry,1988,27(2):445-450.
[26]Liu GT,Li WX,Chen YY,et al.Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice[J].Drug Develop Res,1996,39(2):174-178.
[27]Lin JH.Cinnamamide derivatives from Clausena lansium[J].Phytochemistry,1989,28(2):621-622.
[28]Lakshmi V,Raj K,Kapil RS.Chemical constituents of Clausena lansium:Part Ⅲ- structure of lansamide-3 and 4[J].Indian J Chem See B,1998,37B:422-424.
[29]商立坚,文光裕,周俊,等.臭假黄皮中的新大环内酰胺[J].云南植物研究,1993,15(3):299-302.
[30]Kitamura T,Sugamoto M.Alkaloids of berberidaceous plant[J].Yakugakuzasshi,1961,81:154-261.
[31]Joshi BS,Kamat VN,Saksena AK,et al.Structure of heptaphylline,a carbazole alkaloid from Clausena heptaphylla[J].Tetra Lett,67(41):4019-4022.
[32]Mloody CJ.Synthesis of carbazole alkaloids[J].Synlett,1994,9:681-688.
[33]Brinhmann G.Ledermann A,Francois G.Dimeric murrayafoline-A,a potential bis-carbazole alkaloid:" biomimetic " systhesis,atropoisomer separation and antimalarial activity[J].Heterocycles,1995,40(1):293-300.
[34]Joshi BS,Kamat OH,Gawad DH,et al.Structure and synthesis of heptaphylline[J]. Phytochemistry,1972,11(3):2065-2071.
[35]Narasimhan NS,Paradkar MV,Gokhale AM.Synthses of grinimbine,mahanimbine &isomahanimbine[J].Indian J Chem,1976,7:329-331.
[36]Wu CC,Ko FN,Wu TS,et al.Antiplatelet effects of Clausine-D isolated from Claulansine-Cxcavata[J].Biochem Biophys Acta,1994,1201(1):1-6.
[37]Chaichantipyuth C,Pummangura S,Naowsarn K,et al.Two new bioactive carbazole alkaloids from the root bark of Ciausena harmandiana[J].J Nat Prod,1988,51(6):1285-1288.
[38]Chavi Y,Somkrit S,Prachack S,et al.Coumarins and carbazoles with antiplasmodial activity from Clausena harmandiana[J].Planta Med,2000,66(3):277-279.
[39]闫少羽.黑果黄皮Claulansine-Bunniana Levl.抗癌活性成分的研究.沈阳:沈阳药科大学,2001:
[40]Tian-Shung Wu,Shiow-Chyn Huang.Clausine-D and - F,Two New 4-Prenylcarbazole Alkaloids from Claulansine-Cxcavate.Chem.Pharm.Bull.,40(4):1069-71.
[1]W.L.Stanley,S.H.Vannier.Chemical Composition of Lemon Oil.I.Isolation of a Series of Substituted Coumarins[J].Journal of the American Chemical Society,1957,79(13):3488-91.
[2]B.S.Joshi,V.N.Kamat,D.H.Gawad.Structure of Ciausindine,a new coumarin from Clausena indica Oliv.[J].Specialia,1974,15(3):223
[3]Falak Anwer,A.Shoeb,R.S.Kapil.Clausarin-a novel coumarin from Clausena pentaphylla(Roxb.) DC.[J].Specialia,1977,15(4):412-3.
[4]Von I.Mester,K.Szendrei,J.Reisch.Constituents ofClauseindolenisata(Willd.) Oliv.(Rutaceae)I.Coumarins from the root bark[J].Planta medica,1977,32:81-85.
[5]Dhan Rakash,Kanwal Raj,Randhir S.Kapil,et al.Coumarins from Clausena Indica[J].Phytochemistry,1978,17:1194-5.
[6]Tian-Shung Wu,Hiroshi Furukawa.Biological and Phytochemical Investigation of Claulansine-Cxcavata[J].J.Nat.Prod.,1982,45(6):718-20.
[7]Nizam U.Khan,S.W.I.Naqvi,Khwaja Ishratullah.Wampetin,a furocoumarin from Clausena Wampi[J].Phytochemistry,1983,22(11):2264-5.
[8]Vijai Lakshmi,Dhan Parkash,Kanwal Raj,et al.Monoterpenoid Furanocoumarin from Clauseindolenisata[J].Phytochemistry,1984,23(11):2629-31.
[9]J.D.Wangboonskul,S.Pummangura,C.Chaichantipyuth.Five Coumarins and a Carbazole Alkaloids from the Root Bark of Clausena harmandiana[J].J.Nat.Prod.,1984,47(6):1058-9.
[10]Laura R.Coassini Lokar,Sergio Delben.Photoactive furocoumarins in two populations of Seseli Elatum[J].Phytochemistry,1988,27(4):1073-77.
[11]Chihiro Ito,Miyuki Matsuoka,Toyoko Mizuno,et al.New Coumarins from Some Citrus Plants[J].Chem.Pharm.Bull.,1988,36(10):3805-10.
[12]Bonaventure T.Ngadjui,Johnson F.Ayafor,Beibam L.Sondengam,et al.Coumarins from Clauseindolenisata[J]. Phytochemistry, 1989,28(2): 585-9.
[13] Bonaventure T. Ngadjui, Johnson F. Ayafor, Beibam L. Sondengam. Prenylated Coumarins from the Leaves of Clauseindolenisata[J]. Journal of Natural Products, 1989, 52(2):243-7.
[14] Bonaventure T. Ngadjui, S. M. Mouncherou, Johnson F. Ayafor, et al. Geranyl Coumarins from Clauseindolenisata[J]. Phytochemistry, 1991,30(8): 2809-11.
[15] Vijay Kumar, Kayalvily Vallipuram, Adeleke C. Adebajo, et al.2,7-Dihydroxy-3-Formyl-1-(3'-Methyl-2'-Butenyl)Carbazole from Clausena Lansium[J].Phytochemistry, 1995,40(5): 1563-65.
[16] Shiow-Chyn Huang, Pei-Lin Wu, Tian-Shung Wu. Two Coumarins from the Root Bark of Clausean Excavata[J]. Phytochemistry, 1997,44(1): 179-81.
[17] Chihiro Ito, Shinya Katsuno, Hiroshi Furukawa. Structures of Lansiumarin-A, -B, -C, Three New Furocoumarins from Clausena lansium[J]. Chem. Pharm. Bull., 1998,46(2):341-3.
[18] Keiko Nakamura, Yuko Takemura, Motoharu Ju-ichi, et al. Three New Coumarins from Claulansine-Cxcavata[J]. Heterocycles, 1998, 48(3):549-553.
[19] Trinh Thi Thuy, Helmut Ripperger, Andrea Porzel, et al. Coumarins, limonoids and an alkaloid from Claulansine-Cxcavate[J]. Phytochemistry, 1999,52: 511-16.
[20] Chihiro Ito, Masataka Itoigawa, Shinya Katsuno, et al. Chemical Constituents of Claulansine-Cxcavate: Isolation and Structure Elucidation of Novel Furano-Coumarins with Inhibitory Effects for Tumor-Promotion[J]. Journal of Natural Products, 2000,63(9): 1218-24.
[21] Mohammad H. Sohrab, Choudhury M. Hasan, Mohammad A. Rashid. Clausmarin-A from the leaves of Clausena heptaphylla[J]. Biochemical Systematics and Ecology, 2000,28:91-93.
[22] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. O-Terpenoidal Coumarins from Claulansine-Cxcavata[J]. Heterocycles, 2000, 53(8):1807-10.
[23] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. Six New O-Terpenoidal Coumarins,Excavacoumarins B-G from Claulansine-Cxcavata[J]. Heterocycles, 2000, 53(9):2067-70.
[24] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. Two New O-Terpenoidal Coumarins,Excavacoumarin A and B from Claulansine-Cxcavata[J]. Chinese Chemical Letters, 2000,11(6):539-42.
[25] Yuko Takemura, Keiko Nakamura, Chihiro Ito, et al. Four New Furano-Coumarins from Claulansine-Cxcavata[J]. Chem. Pharm. Bull.,2000,48(4):582-4.
[26] Nam-In Baek, Eun-Mi Ahn, Hae-Yeong Kim, et al. Furanocoumarins from the Root of Angelica dahurica[J]. Arch. Pharm. Res., 2000,23(5):467-70.
[27] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. A Novel Dimeric Coumarin from Clausena lenis[J]. Chinese Chemical Letters, 2003,14(11):1150-53.
[28] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. New OTerpenoidal Coumarins from Claulansine-Cxcavata[J].Heterocycles,2004,63(9):2087-90.
[29]Yun-Song Wang,Hong-Pin He,Xiaojiang Hao,et al.New Monoterpenoid Coumarins from Clauseindolenisum-olens[J].Molecules,2008,13:931-7.
[30]Yun-Song Wang,Rong Huang,Liang Li,et al.O-Terpenoidal Coumarins from Clauseindolenisum-olens[J].Biochemical Systematics and Ecology,2008,36:801-3.
[31]Zhen-Qiang Xin,Jing-Jian Lu,Yang Ye,et al.Constituents from Claulansine-Cxcavate[J].Chem.Pharm.Bull.,2008,56(6):827-30.
[32]Yun-Song Wang,Hong-Yi Xu,Jing-Hua Yang,et al.A New O-Terpenoidal Coumarin from Clauseindolenisum-olens Merr.[J].Molecules,2009,14,771-6.
[33]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:563.
[1]Von I.Mester,K.Szendrei,J.Reisch.Constituents of Clauseindolenisata(Willd.)Oliv.(Rutaceae) Ⅰ.Coumarins from the root bark[J].Planta medica,1977,32:81-85.
[2]Nizam U.Khan,S.W.I.Naqvi,Khwaja Ishratullah.Wampetin,a furocoumarin from Clausena Wampi[J].Phytochemistry,1983,22(11 ):2264-5.
[3]Harkar S.,Razdan T.K.,Waight E.S..Steroids,chromone,and coumarins from Angelica officinalis[J].Phytochemistry,1984,23(2):419-26.
[4]Razdan T.K.,Qadri B.,Harkar S.,et al.Chromones and coumarins from Skimmia laureola[J].Phytochemistry,1987,26(7):2063-9.
[5]Ngadjui BT,Ayafor JF,Sondengam BL,et al.Quinolone and carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1989,28(5):1517-1519.
[6]Li WS,Mcchesney JD,EI-Feraly FS.Carbazole alkaloids from Clausena lansium[J].Phytochemistry,1991,30(1):343-346.
[7]Tian-Shung Wu,Shiow-Chyn Huang.Clausine-D and -F,Two New 4-Prenylcarbazole Alkaloids from Claulansine-Cxcavate[J].Chem.Pharm.Bull.,1992,40(4):1069-71.
[8]Wu TS,Huang SC,Wu PL,et al.Carbazole alkaloids from Claulansine-Cxcavata and their biological activity[J].Phytochemistry,1996,43(1 ):133-140.
[9]Camarda L.,Di Stefano V.,Lentini F.,et al.Coumarins from the fruits of Magydaris pastinacea[J].Fitoterapia,1996,67(3):282.
[10]Maricely J.U.,Muller Adolfo H.,Arruda Mara S.E,et al[J].Phytochemistry,1997,45(4):851-853.
[11]闫少羽.黑果黄皮Claulansine-Bunniana Levl,抗癌活性成分的研究[D].沈阳: 沈阳药科大学,2001.
[12]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:103.
[13]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:563.
[1]B.Kongkaship,N.Kongkathip,A.Sunthitikawinsakul,et al.Anti-HIV-1 Constituents from Claulansine-Cxcavate:Part Ⅱ.Carbazoles and a Pyranocoumatin[J].Phytotherapy Research,2005,19:728-731.
[2]A.Sunthitikawinsakul,N.Kongkathip,B.Kongkaship,et al.Coumarins and Carbazoles from Claulansine-Cxcavate Exhibited Antimycobacterial and Antifungal Activities[J].Planta Med,2003,69:155-157.
[3]Chihito Ito,Masataka Itoigawa,Shinya Katsuno,et al.Chemical Constituents of Claulansine-Cxcavate:Isolation and Structure Elucidation of Novel Furanone-Coumarins with Inhibitory Effects for Tumor-Promotion[J].Journal of Natural Product,2000,63(9):1218-24.
[4]A.C.Adebajo,E.O.Iwalewa,E.M.Obuotor.Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark[J].Journal of Ethnopharmacology,2009,122:10-19.
[2]潘瑞乐,朱兆仪.黄皮属药用植物研究进展[J].国外医药:植物药分册,1990,5(6):243-247
[3]Bhattacharyya P,Biswas GK,Braua AK,etal.Clausenalene,a carbazole alkaloid from Clausena heptaphylla[J].Phytochemistry,1993,33(1):248-250.
[4]Chaicbantipyuth C,Pummangura S,Naowsarn K,et al.Two new bioactive carbazole alkaloids from the root bark of Clausena harmandiana[J].J Nat Prod,1988,51(6):1285-1288.
[5]Chavi Y,Somkrit S,Prachack S,et al.Coumarins and carbazoles with antiplasmodial activity from Clausena harmandiana [J]. Planta Med, 2000, 66(3):277-279.
[6] Liu GT, Li WX, Chen YY, et al. Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice [J]. Drug Develop Res, 1996, 39(2): 174-178.
[7] Wu CC, Ko FN, Wu TS, et al. Antiplatelet effects of Clausine-D isolated from Claulansine-Cxcavata [J]. Biochem Biophys Acta, 1994, 1201(1):1-6.
[8] Dhan Rakash, Kanwal Raj, Randhir S. Kapil, et al. Coumarins from Clausena Indica[J].Phytochemistry, 1978,17:1194-5.
[1]潘瑞乐,朱兆仪.黄皮属药用植物研究进展[J].国外医药:植物药分册,1990,5(6):243-247
[2]Khan NU,Naqvi SWI.Constituents of the genus Clausena[J].J Scient Ind Res,1988,47(3):543-546.
[3]Roy SP,Bhattacharyya P,Chakraborty DP.3-Methylcarbazole from Clausena heptaphylla[J].Phytochemistry,1974,13(2):1017.
[4]Li WS,Mcchesney JD,EI-Feraly FS.Carbazole alkaloids from Clausena lansium[J].Phytochemistry,1991,30(1 ):343-346.
[5]Wu TS,Huang SC,Wu PL,et al.Carbazole alkaloids from Claulansine-Cxcavata and their biological activity[J].Phytochemistry,1996,43(1 ):133-140.
[6]Ito C,Katsuno S,Ohta H.et al.Constituents of Claulansine-Cxcavate isolation and structural elucidation of new carbazole alkaloids[J].Chem.Pharm.Bull.,1997,45(1):48-52.
[7]Wu TS,Huang SC,Wu PL,et al.Alkaloidal and other constituents from the root bark of Claulansine-Cxcavate[J].Phytochemistry,1999,52(3):523-527.
[8]Chakraborty A,Chowdhury K,Bhattacharyya P.Clausenol and clausenine-two carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1995,40(1):295-298.
[9]Ngadjui BT,Ayafor JF,Sondengam BL,et al.Quinoione and carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1989,28(5):1517-1519.
[10]Chakraborty A,Saha C,Podder G,et al.Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla[J].Phytochemistry,1995,38(3):787-789.
[11]Wu TS,Huang SC,Wu PL.Carbazole alkaloids from stem bark of Claulansine-Cxcavata[J].Phytochemistry,1996,43(6):1427-1429.
[12]Ito C,Ohta H,Hugh TW,et al.Constituents of Claulansine-Cxcavata isolation and elucidation of seven new carbazole alkaloids and a new coumarin[J].Chem Pharm Bull,1996,44(2):2231-2235.
[13]Ito C,Katsuno S,Itoigawa M,et al.New carbazole alkaloids from Clauseindolenisata with antitumor promoting activity[J].J Nat Prod,2000,63(1):125-128.
[14]Kumar V,Vallipuram K,Adebajo AC,et al.2,7-Dihydrooxy-3-formyl- 1 -(3'-methyl-2'-butenyl)Carbazole from Clausena lansium[J].Phytochemistry,1995,40(5):1563-1565.
[15]Wu TS,Huang SC,Lan JS,et al.Chemical and antiplatelet aggregative investigation of the leaves of Claulansine-Cxcavata[J].Phytochemistry,1993,32(2):449-451.
[16]Bhattacharyya P,Chakraborty A.Heptazolicine,a carbazole alkaloid from Clausena heptaphylla [J].Phytochemistry,1984,23(10):2409-2410.
[17]Ito C,Katsuno S,Ruangrungsi N,et al.Structures of clausamine-A,B,C,three novel carbazole alkaloids from Clauseindolenisata[J].Chem Pharm Bull,1998,46(2):344-346.
[18]Wu TS,Huang SC,Wu PL,et al.Lactonic carbazole alkaloids from the root bark of Claulansine-Cxcavate[J].Chem Pharm Bull,1998,46(9):1459-1461.
[19]Wu TS,Huang SC,Wu PL,et al.Structure and synthesis of clausenaquinone- A,a novel carbazolequinone alkaloid and bioactive principle from Claulansine-Cxcavata[J].Bioorg Med Chem Lett,1994,4(20):2395-2398.
[20]Bhattacharyya P,Biswas GK,Braua AK,et al.Clausenalene,a carbazole alkaloid from Clausena heptaphylla[J].Phytochemistry,1993,33(1):248-250.
[21]Wu TS,Wu PL.Pyrano and furocarbazole alkaloids from the root bark of Claulansine-Cxcavate [J].Heterocycles,1997,45(5):969-973.
[22]Zhang A,Lin GQ.The first synthesis of Clausenamine-A and cytotoxic activities of three biscarbazole analogues against cancer[J].Bioorg Med Chem Lett,2000,10(10):1021 - 1023.
[23]Barbara R,Otmar H,Harald G.Tryptamine derived amides from Clausena indica[J].Phytochemistry,1997,45(2):337-341
[24]Mlner PH,Coates N J,Gilpin ML,et al.SB-204900,a novel oxirane carboxamide from Clausena lansium[J].J Nat Prod,1996,59(4):400-402
[25]Yang MH,Chen YY,Huang L.Three novel cyclic amides from Clausena lansium[J].Phytochemistry,1988,27(2):445-450.
[26]Liu GT,Li WX,Chen YY,et al.Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice[J].Drug Develop Res,1996,39(2):174-178.
[27]Lin JH.Cinnamamide derivatives from Clausena lansium[J].Phytochemistry,1989,28(2):621-622.
[28]Lakshmi V,Raj K,Kapil RS.Chemical constituents of Clausena lansium:Part Ⅲ- structure of lansamide-3 and 4[J].Indian J Chem See B,1998,37B:422-424.
[29]商立坚,文光裕,周俊,等.臭假黄皮中的新大环内酰胺[J].云南植物研究,1993,15(3):299-302.
[30]Kitamura T,Sugamoto M.Alkaloids of berberidaceous plant[J].Yakugakuzasshi,1961,81:154-261.
[31]Joshi BS,Kamat VN,Saksena AK,et al.Structure of heptaphylline,a carbazole alkaloid from Clausena heptaphylla[J].Tetra Lett,67(41):4019-4022.
[32]Mloody CJ.Synthesis of carbazole alkaloids[J].Synlett,1994,9:681-688.
[33]Brinhmann G.Ledermann A,Francois G.Dimeric murrayafoline-A,a potential bis-carbazole alkaloid:" biomimetic " systhesis,atropoisomer separation and antimalarial activity[J].Heterocycles,1995,40(1):293-300.
[34]Joshi BS,Kamat OH,Gawad DH,et al.Structure and synthesis of heptaphylline[J]. Phytochemistry,1972,11(3):2065-2071.
[35]Narasimhan NS,Paradkar MV,Gokhale AM.Synthses of grinimbine,mahanimbine &isomahanimbine[J].Indian J Chem,1976,7:329-331.
[36]Wu CC,Ko FN,Wu TS,et al.Antiplatelet effects of Clausine-D isolated from Claulansine-Cxcavata[J].Biochem Biophys Acta,1994,1201(1):1-6.
[37]Chaichantipyuth C,Pummangura S,Naowsarn K,et al.Two new bioactive carbazole alkaloids from the root bark of Ciausena harmandiana[J].J Nat Prod,1988,51(6):1285-1288.
[38]Chavi Y,Somkrit S,Prachack S,et al.Coumarins and carbazoles with antiplasmodial activity from Clausena harmandiana[J].Planta Med,2000,66(3):277-279.
[39]闫少羽.黑果黄皮Claulansine-Bunniana Levl.抗癌活性成分的研究.沈阳:沈阳药科大学,2001:
[40]Tian-Shung Wu,Shiow-Chyn Huang.Clausine-D and - F,Two New 4-Prenylcarbazole Alkaloids from Claulansine-Cxcavate.Chem.Pharm.Bull.,40(4):1069-71.
[1]W.L.Stanley,S.H.Vannier.Chemical Composition of Lemon Oil.I.Isolation of a Series of Substituted Coumarins[J].Journal of the American Chemical Society,1957,79(13):3488-91.
[2]B.S.Joshi,V.N.Kamat,D.H.Gawad.Structure of Ciausindine,a new coumarin from Clausena indica Oliv.[J].Specialia,1974,15(3):223
[3]Falak Anwer,A.Shoeb,R.S.Kapil.Clausarin-a novel coumarin from Clausena pentaphylla(Roxb.) DC.[J].Specialia,1977,15(4):412-3.
[4]Von I.Mester,K.Szendrei,J.Reisch.Constituents ofClauseindolenisata(Willd.) Oliv.(Rutaceae)I.Coumarins from the root bark[J].Planta medica,1977,32:81-85.
[5]Dhan Rakash,Kanwal Raj,Randhir S.Kapil,et al.Coumarins from Clausena Indica[J].Phytochemistry,1978,17:1194-5.
[6]Tian-Shung Wu,Hiroshi Furukawa.Biological and Phytochemical Investigation of Claulansine-Cxcavata[J].J.Nat.Prod.,1982,45(6):718-20.
[7]Nizam U.Khan,S.W.I.Naqvi,Khwaja Ishratullah.Wampetin,a furocoumarin from Clausena Wampi[J].Phytochemistry,1983,22(11):2264-5.
[8]Vijai Lakshmi,Dhan Parkash,Kanwal Raj,et al.Monoterpenoid Furanocoumarin from Clauseindolenisata[J].Phytochemistry,1984,23(11):2629-31.
[9]J.D.Wangboonskul,S.Pummangura,C.Chaichantipyuth.Five Coumarins and a Carbazole Alkaloids from the Root Bark of Clausena harmandiana[J].J.Nat.Prod.,1984,47(6):1058-9.
[10]Laura R.Coassini Lokar,Sergio Delben.Photoactive furocoumarins in two populations of Seseli Elatum[J].Phytochemistry,1988,27(4):1073-77.
[11]Chihiro Ito,Miyuki Matsuoka,Toyoko Mizuno,et al.New Coumarins from Some Citrus Plants[J].Chem.Pharm.Bull.,1988,36(10):3805-10.
[12]Bonaventure T.Ngadjui,Johnson F.Ayafor,Beibam L.Sondengam,et al.Coumarins from Clauseindolenisata[J]. Phytochemistry, 1989,28(2): 585-9.
[13] Bonaventure T. Ngadjui, Johnson F. Ayafor, Beibam L. Sondengam. Prenylated Coumarins from the Leaves of Clauseindolenisata[J]. Journal of Natural Products, 1989, 52(2):243-7.
[14] Bonaventure T. Ngadjui, S. M. Mouncherou, Johnson F. Ayafor, et al. Geranyl Coumarins from Clauseindolenisata[J]. Phytochemistry, 1991,30(8): 2809-11.
[15] Vijay Kumar, Kayalvily Vallipuram, Adeleke C. Adebajo, et al.2,7-Dihydroxy-3-Formyl-1-(3'-Methyl-2'-Butenyl)Carbazole from Clausena Lansium[J].Phytochemistry, 1995,40(5): 1563-65.
[16] Shiow-Chyn Huang, Pei-Lin Wu, Tian-Shung Wu. Two Coumarins from the Root Bark of Clausean Excavata[J]. Phytochemistry, 1997,44(1): 179-81.
[17] Chihiro Ito, Shinya Katsuno, Hiroshi Furukawa. Structures of Lansiumarin-A, -B, -C, Three New Furocoumarins from Clausena lansium[J]. Chem. Pharm. Bull., 1998,46(2):341-3.
[18] Keiko Nakamura, Yuko Takemura, Motoharu Ju-ichi, et al. Three New Coumarins from Claulansine-Cxcavata[J]. Heterocycles, 1998, 48(3):549-553.
[19] Trinh Thi Thuy, Helmut Ripperger, Andrea Porzel, et al. Coumarins, limonoids and an alkaloid from Claulansine-Cxcavate[J]. Phytochemistry, 1999,52: 511-16.
[20] Chihiro Ito, Masataka Itoigawa, Shinya Katsuno, et al. Chemical Constituents of Claulansine-Cxcavate: Isolation and Structure Elucidation of Novel Furano-Coumarins with Inhibitory Effects for Tumor-Promotion[J]. Journal of Natural Products, 2000,63(9): 1218-24.
[21] Mohammad H. Sohrab, Choudhury M. Hasan, Mohammad A. Rashid. Clausmarin-A from the leaves of Clausena heptaphylla[J]. Biochemical Systematics and Ecology, 2000,28:91-93.
[22] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. O-Terpenoidal Coumarins from Claulansine-Cxcavata[J]. Heterocycles, 2000, 53(8):1807-10.
[23] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. Six New O-Terpenoidal Coumarins,Excavacoumarins B-G from Claulansine-Cxcavata[J]. Heterocycles, 2000, 53(9):2067-70.
[24] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. Two New O-Terpenoidal Coumarins,Excavacoumarin A and B from Claulansine-Cxcavata[J]. Chinese Chemical Letters, 2000,11(6):539-42.
[25] Yuko Takemura, Keiko Nakamura, Chihiro Ito, et al. Four New Furano-Coumarins from Claulansine-Cxcavata[J]. Chem. Pharm. Bull.,2000,48(4):582-4.
[26] Nam-In Baek, Eun-Mi Ahn, Hae-Yeong Kim, et al. Furanocoumarins from the Root of Angelica dahurica[J]. Arch. Pharm. Res., 2000,23(5):467-70.
[27] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. A Novel Dimeric Coumarin from Clausena lenis[J]. Chinese Chemical Letters, 2003,14(11):1150-53.
[28] Hongping He, Yuemao Shen, Xiaojiang Hao, et al. New OTerpenoidal Coumarins from Claulansine-Cxcavata[J].Heterocycles,2004,63(9):2087-90.
[29]Yun-Song Wang,Hong-Pin He,Xiaojiang Hao,et al.New Monoterpenoid Coumarins from Clauseindolenisum-olens[J].Molecules,2008,13:931-7.
[30]Yun-Song Wang,Rong Huang,Liang Li,et al.O-Terpenoidal Coumarins from Clauseindolenisum-olens[J].Biochemical Systematics and Ecology,2008,36:801-3.
[31]Zhen-Qiang Xin,Jing-Jian Lu,Yang Ye,et al.Constituents from Claulansine-Cxcavate[J].Chem.Pharm.Bull.,2008,56(6):827-30.
[32]Yun-Song Wang,Hong-Yi Xu,Jing-Hua Yang,et al.A New O-Terpenoidal Coumarin from Clauseindolenisum-olens Merr.[J].Molecules,2009,14,771-6.
[33]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:563.
[1]Von I.Mester,K.Szendrei,J.Reisch.Constituents of Clauseindolenisata(Willd.)Oliv.(Rutaceae) Ⅰ.Coumarins from the root bark[J].Planta medica,1977,32:81-85.
[2]Nizam U.Khan,S.W.I.Naqvi,Khwaja Ishratullah.Wampetin,a furocoumarin from Clausena Wampi[J].Phytochemistry,1983,22(11 ):2264-5.
[3]Harkar S.,Razdan T.K.,Waight E.S..Steroids,chromone,and coumarins from Angelica officinalis[J].Phytochemistry,1984,23(2):419-26.
[4]Razdan T.K.,Qadri B.,Harkar S.,et al.Chromones and coumarins from Skimmia laureola[J].Phytochemistry,1987,26(7):2063-9.
[5]Ngadjui BT,Ayafor JF,Sondengam BL,et al.Quinolone and carbazole alkaloids from Clauseindolenisata[J].Phytochemistry,1989,28(5):1517-1519.
[6]Li WS,Mcchesney JD,EI-Feraly FS.Carbazole alkaloids from Clausena lansium[J].Phytochemistry,1991,30(1):343-346.
[7]Tian-Shung Wu,Shiow-Chyn Huang.Clausine-D and -F,Two New 4-Prenylcarbazole Alkaloids from Claulansine-Cxcavate[J].Chem.Pharm.Bull.,1992,40(4):1069-71.
[8]Wu TS,Huang SC,Wu PL,et al.Carbazole alkaloids from Claulansine-Cxcavata and their biological activity[J].Phytochemistry,1996,43(1 ):133-140.
[9]Camarda L.,Di Stefano V.,Lentini F.,et al.Coumarins from the fruits of Magydaris pastinacea[J].Fitoterapia,1996,67(3):282.
[10]Maricely J.U.,Muller Adolfo H.,Arruda Mara S.E,et al[J].Phytochemistry,1997,45(4):851-853.
[11]闫少羽.黑果黄皮Claulansine-Bunniana Levl,抗癌活性成分的研究[D].沈阳: 沈阳药科大学,2001.
[12]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:103.
[13]杨世林,杨学东,刘江云.天然产物化学研究[M].北京:科学出版社,2009:563.
[1]B.Kongkaship,N.Kongkathip,A.Sunthitikawinsakul,et al.Anti-HIV-1 Constituents from Claulansine-Cxcavate:Part Ⅱ.Carbazoles and a Pyranocoumatin[J].Phytotherapy Research,2005,19:728-731.
[2]A.Sunthitikawinsakul,N.Kongkathip,B.Kongkaship,et al.Coumarins and Carbazoles from Claulansine-Cxcavate Exhibited Antimycobacterial and Antifungal Activities[J].Planta Med,2003,69:155-157.
[3]Chihito Ito,Masataka Itoigawa,Shinya Katsuno,et al.Chemical Constituents of Claulansine-Cxcavate:Isolation and Structure Elucidation of Novel Furanone-Coumarins with Inhibitory Effects for Tumor-Promotion[J].Journal of Natural Product,2000,63(9):1218-24.
[4]A.C.Adebajo,E.O.Iwalewa,E.M.Obuotor.Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark[J].Journal of Ethnopharmacology,2009,122:10-19.