紫玉盘的化学成分研究
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摘要
本课题研究了番荔枝科紫玉盘属植物紫玉盘(Uvaria microcarpa Champ.ex Benth.)茎枝的化学成分,采用多种现代色谱手段对紫玉盘茎枝的化学成分进行了系统的分离与纯化,并应用化学反应和光谱学方法进行结构鉴定。从该植物95%乙醇提取物中分离得到40个化合物,鉴定了34个化合物,其中1个新化合物,2个为首次从番荔枝科植物中分得,15个为首次从该植物中分得。
Studies on the Chemical Constituents of Uvaria microcarpa
Champ.ex Benth.
This article describes the chemical constituents of Uvaria microcarpa Champ.ex Benth.Fourty compounds have been isolated from 95%EtOH extract of the plant,and thirty-three chemicial structures of them were identified based on the chemical reaction and spectral analysis.Among them,there were 1 new compound,2 compounds were obtained from the family of Annonaceae for the first time,and 15 compounds were isolated from this plant for the first time.
Studies on the Chemical Constituents of Uvaria microcarpa
Champ.ex Benth.
This article describes the chemical constituents of Uvaria microcarpa Champ.ex Benth.Fourty compounds have been isolated from 95%EtOH extract of the plant,and thirty-three chemicial structures of them were identified based on the chemical reaction and spectral analysis.Among them,there were 1 new compound,2 compounds were obtained from the family of Annonaceae for the first time,and 15 compounds were isolated from this plant for the first time.
引文
[1]Jolad SD,Hoffmann JJ,Schram KH.Uvaricin,a new antitumor agent from Uvaria accuminata (Annonaceae)J.[J].J Org Chem,1982,47:3151.
[2]Priestap HA.Seven aristololactams from Atistolochia argentina.[J].Phytochemistry,1985,24(4):849-852.
[3]Desai SJ,Chaturvedi R and Mulchandani NB.Piperolactam D,a new aristolactam from India Piper Species.[J].Journal of Natural,Products,1990,53(2):496-497.
[4]Omar S,Leng C,Ahmad F,et al.Phenanthrene lactams from Goniothalamus,velutinus.[J].Phytochemistry,1992,31(12):4395-4397.
[5]余冬蕾等,紫玉盘中的新内酰胺,植物学报,1999,41(10):1104-1107.
[6]Mahmood K,Chan KC,Park MH,et al.Aristololactams of Orophea enterocarpa.[J].Phytochemistry,1986,25(4):965-967.
[7]许琼明等,瘤果紫玉盘中的酰胺类化学成分,药学学报,2007,42(4):405-407.
[8]Talapatra SK,Basu D,Chattopadhyay P,et al.Aristololactams of Goniothalamus sesquipedalis wall.Revised structures of the 2-oxygenated aristololactams.[J].Phytochemistry,1988,27(3):903-906.
[9]于德泉.分析化学手册.第七分册.北京:科学工业出版社,1999.20.
[10]张琳等,田基黄的化学成分研究,中国药学杂志,2007,42(5):341-344.
[11]Hirayama A,Kagami Y,Matsuyama K,et al.Preparation of inclusion compounds of hesperetin or naringenin with cyclodextrins,and foods and pharmaceuticals containing the inclusion compounds.Jpn.Kokai Tokkyo Koho(2006).
[12]Achenbach H,Lowel M,W,Waibel R,et al.New lignan glucosides from Stemmadenia minima.[J].Planta Med,1992,58(3):270-272.
[13]Shi SP,Dong CX,Jiang D,et al.Macrocyclic glucosides from Clematis mandshurica and Clematis hexapeta.[J].Blochemical Systematics,and Ecology,2007,35:57-70.
[14]Ankisetty S,ElSohly HN,Li XC,et al.Aromatic constituents of Uvaria grandiflora.[J].Journal,of Natural,Products,2006,69(4):692-694.
[15]Wang S,Chen RY,Yu SS,et al.Uvamalols D-G:Novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla.[J].Journal,of Asian Natural Products Research,2003,5(1):17-23.
[16]周耘,假马齿苋活性成分研究,第二军医大学博士论文,2005.
[17]轧霁,张晓琦,叶文才等,广东桑种子的化学成分,中国药科大学学报,2006,37(4): 301-303.
[18]Khan IA.,Clemens AJ,Sticher O,et al.New phenolic glucosides from the leaves of Eurya tigang.[J].Journal of Natural Products,1992,55(9):1270-1274.
[19]张薇,张卫东,李廷钊等,毛瑞香化学成分研究,中国中药杂志,2005,30(7):513-515.
[20]Zhang YJ,Kong M,Chen RY,et al.Alkaloids from the roots of goniothalamus griffithii.[J].Journal of Natural Products,1999,62(7):1050-1052.
[21]张海玲,番荔枝科植物大叶紫玉盘抗肿瘤化学成分研究,中国协和医科大学硕士论文,2001.
[22]Hussain SR,Gozler B,Shamma M,et al.Feruloyltyramine from Hypecoum.[J].Phytochemistry,1982,21(12):2979-2980.
[23]DellaGreca M,Previtera L,Purcaro R,et al.Cinnamic acid amides and lignanamides from Aptenia cordifolia.[J].Tetrahedron,2006,62,2877-2882.
[24]张治针,小池一男,滇白珠化学成分研究(Ⅱ),中草药,1999,30(3):167-169.
[25]柴兴云,窦静,贺清辉等,山银花中酚酸类成分研究,中国天然药物,2004,2(6):339-340.
[26]卢汝梅,何翠薇,潘英.紫玉盘挥发油化学成分的分析,世界科学技术—中医药现代化,2006,8(6):40-42.
[27]卢汝梅,何翠薇.紫玉盘叶脂溶性成分的气相色谱—质谱联用分析,时珍国医国药,2005,16(8):713-714.
[28]Nonaka,G.et al.Tannins and related compounds.XV.A new class of dimericflavanaol gallates,Theasinensins A and B,and proanthocyanidin gallates from Green Tea Leaf.[J].Chem.Pharm.Bull.,1983,31:3904-3906.
[29]张雯洁,刘玉清,李兴从等,云南“生态茶”的化学成分,云南植物研究,1995,17(2):204-208.
1.中国医学科学院中国植物志编辑委员会.中国植物志(第三十卷第二分册)[M].北京:科学出版社,1979:14.
2.Jolad SD,Hoffmann JJ,Schram KH.Uvaricin,a new antitumor agent from Uvaria accuminata(Annonaceae)[J].J Org Chem,1982,47:3151-3153.
3.Chiu HF,Chih TT,Hsian YM,et al.Bullatacin,a potent antitumor Annonaceous acetogenin,induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells[J].Biochemical Pharmacology,2003,65(3):319.
4.Yuan SSF,Chang HL,Chen HW,et al.Selective cytotpxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-,Bad-,and caspase-3-ralated pathways.[J].Life Sciences,2006,78(8):869.
5.Hattori Y,Konno H,Abe M,et al.Synthesis,determination of the absolute configuration of tonkinelin,and inhibitoy action with bovine heart mitochondrial complex I[J].Bioorganic＆Medicinal Chemistry,2007,15(8):3026.
6.Waterman PG,Mohammad I.Chemistry of the annonaceae.Structures of uvarindoles A-D,four new benzylated indole alkaloids from Uvaia angolensis[J].Chem.Soc.,Chem.Commun.,1984,1280.
7.Panichpol K,Waigh RD,and Waterman PG.Chondrofoline from Uvaria ovata[J].Phytochemistry,1977,16(5):621.
8.杨小江,徐丽珍,孙南君,等.番荔枝化学成分研究[J].药学学报,1992,27(3):185.
9.余冬莆.紫玉盘抗肿瘤化学成分研究[D].北京:中国医学科学院—中国协和医科大学,1998.
10.许琼明,刘艳丽,赵葆华,等.瘤果紫玉盘中的酰胺类化学成分[J].药学学报,2007,42(4):405.
11.廖永红,徐丽珍,杨世林,等.紫玉盘属植物化学成分研究进展[J].国外医学中医中药分册,1995,17(6):9.
12.Huang L,Wall ME,Wani MC,et al.New compounds with DNA strand-scission activity from the combined leaf and stem of Uvaria hamiltonii[J].J Nat Prod,1998,61(4):446.
13.张海玲,王嗣,陈若芸,等.大叶紫玉盘化学成分研究[J].药学学报,2002,37(2):124.
14.王嗣,戴胜军,张培成,等.景红哥纳香和大叶紫玉盘化学成分研究[J].化学学报,2003,61(7):1090.
15.许琼明,石峰,徐丽珍,等.瘤果紫玉盘叶中的黄酮类成分[J].沈阳药科大学学报,2006,23(5):277.
16.Wang S,Chen RY,Yu SS,et al.Uvamalols D-G:novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla.[J].Journal of Asian Natural Products Research,2003,5(1):17.
17.Liu A,Zou ZM,Xu LZ,et al.A new cyclohexene oxide from Uvaria tonkinesis var.subglabra[J].Chinese Chemical Letters,2003,14(11):1144.
18.许琼明,刘艳丽,赵葆华,等.HPLC法从瘤果紫玉盘叶中分离制备紫玉盘醇和大花紫玉盘醇G[J].中草药,2007,38(11):1654.
19.周光雄,张沿军,陈若芸,等.刺果紫玉盘的化学成分研究[J].天然产物研究与开发,2007,19:433.
20.Raynaud S,Fourneau C,Hocquemiller R,et al.Acetogenins from the bark of Uvaria pauci-ovulata.[J].Phytochemistry,1997,46(2):321.
21.戴支凯等,紫玉盘茎叶石油醚部位抗肿瘤作用的研究[J].中国现代医学杂志,2008,18(11):47.
22.Nakatani N,Ichimaru M,Moriyasu M,et al.Induction of apoptosis in human promyelocytic leukemia cell line HL-60 by C-benzylated dihydrochalcones,uvaretin,isouvaretin and diuvaretin.[J].Bio Pharm Bull,2005,28(1):83.
23.Philipov S,Ivanovska N,Istatkova R.et al.Phytochemical study and cytotoxic activity of alkaloids from Uvaria chamaeP.Beauv[J].Pharmazie,2000,55(9):688.
24.Asha KN,Chowdhury R,Hasan CM,et al.Antibacterial activity and cytotoxicity of extractives from Uvaria hamiltonii stem bark[J].Fitoterapia,2003,74(1/2):159.
25.Akendengue B,Ngou-Milama E,Roblot F,et al.Antiplasmodial activity of Uvaria klaineana[J].Planta Medica,2002,68(2):167.
26.Raynaud S,Fourneau C,Laurens A,et al.Squamocin and benzyl benzoate,acaricidal components of Uvaria pauci-ovulata bark extracts[J].Planta Medica,2000,66(2):173.
[1]Jonathan Addae-Kyereme,Simon L.Croft,et al.[J].Ethnopharmacology 76,99-103(2001)
[2]Cloudhury.M.Hasan,Kamrun N.et al.Aristolactams from the stem bark of Uvaria hamiltonii[J].Biochemical Systematics and Ecology 29,207-208(2001)
[3]SIRAJ OMAR,CHANG LENG CHEE,et al.Phenanthrene Lactams from Goniothalamus Velutintis.[J].Phytochemistry,31,4395-4397(1992)
[4]Mahmood K,Chan KC,ParKMH,et al.Aristolactams of Orophea enterocarpa[J].Phytochemistry,25,965-967(1986)
[5]Talapatra,Sunil K;Basu,Dipankar;Chattopadhyay,Pratap;Talapatra,Baniv[J].Phytochemistry,27,No3,903-906(1988)
[6]Priestap H A.Seven aristololactams from Atistolochia argentina.Phytochemistry,24,849-852(1985)
[7]YU Dong-Lei,LIAo Jian-Guo.et al.Uvarilactam,a New Lactam from Uvaria microcarpa (Annonaceae)[J].Acta Botanica Sinica,41,No.10,1104-1107(1999)
[8]XU Qiong-ming,LIU Yan-li,ZHAO Bao-hua,XU Li-zhen.Amides from the stems of Uvaria kweichowensis[J].Acta Pharmaceutica Sinica,42,No.4,405-407(2007)
[1]Shi SP,Dong CX,Jiang D,et al.Macrocyclic glucosides from Clematis mandshurica and Clematis hexapetala.[J].Biochemical Systematics and Ecology,2007,35:57-70.
[2]H Achenbach,M Lowel,R Waibel,et al.New lignan glucosides from Stemmadenia minima.[J].Planta Med,1992,58(3):270-272.
[3]S Ankisetty,HN ElSohly,X Li,et al.Aromatic constituents of Uvaia grandiflora. [J].J.Nat.Prod.,2006,69(4):692-694.
[4]Wang S,Chen RY,Yu SS,et al.Uvamalols D-G:Novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla.[J].Journal of Asian Natural Products Research,2003,5(1):17-23.
[5]K Mahmood,KC Chan,MH Park,et al.Aristolactams of Orophea enterocarpa.[J].Phytochemistry,1986,25(4):965-967.
[6]SJ Desai,R Chaturvedi,NB Mulchandani.Piperolactam D,a new aristolactam from India Piper Species.[J].J.Nat.Prod,1990,53 (2):496-497.
[7]Zhang YJ,Kong M,Chen RY,et al.Alkaloids from the roots of goniothalamus griffithii.[J].J.Nat.Prod,1999,62(7):1050-1052.
[2]Priestap HA.Seven aristololactams from Atistolochia argentina.[J].Phytochemistry,1985,24(4):849-852.
[3]Desai SJ,Chaturvedi R and Mulchandani NB.Piperolactam D,a new aristolactam from India Piper Species.[J].Journal of Natural,Products,1990,53(2):496-497.
[4]Omar S,Leng C,Ahmad F,et al.Phenanthrene lactams from Goniothalamus,velutinus.[J].Phytochemistry,1992,31(12):4395-4397.
[5]余冬蕾等,紫玉盘中的新内酰胺,植物学报,1999,41(10):1104-1107.
[6]Mahmood K,Chan KC,Park MH,et al.Aristololactams of Orophea enterocarpa.[J].Phytochemistry,1986,25(4):965-967.
[7]许琼明等,瘤果紫玉盘中的酰胺类化学成分,药学学报,2007,42(4):405-407.
[8]Talapatra SK,Basu D,Chattopadhyay P,et al.Aristololactams of Goniothalamus sesquipedalis wall.Revised structures of the 2-oxygenated aristololactams.[J].Phytochemistry,1988,27(3):903-906.
[9]于德泉.分析化学手册.第七分册.北京:科学工业出版社,1999.20.
[10]张琳等,田基黄的化学成分研究,中国药学杂志,2007,42(5):341-344.
[11]Hirayama A,Kagami Y,Matsuyama K,et al.Preparation of inclusion compounds of hesperetin or naringenin with cyclodextrins,and foods and pharmaceuticals containing the inclusion compounds.Jpn.Kokai Tokkyo Koho(2006).
[12]Achenbach H,Lowel M,W,Waibel R,et al.New lignan glucosides from Stemmadenia minima.[J].Planta Med,1992,58(3):270-272.
[13]Shi SP,Dong CX,Jiang D,et al.Macrocyclic glucosides from Clematis mandshurica and Clematis hexapeta.[J].Blochemical Systematics,and Ecology,2007,35:57-70.
[14]Ankisetty S,ElSohly HN,Li XC,et al.Aromatic constituents of Uvaria grandiflora.[J].Journal,of Natural,Products,2006,69(4):692-694.
[15]Wang S,Chen RY,Yu SS,et al.Uvamalols D-G:Novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla.[J].Journal,of Asian Natural Products Research,2003,5(1):17-23.
[16]周耘,假马齿苋活性成分研究,第二军医大学博士论文,2005.
[17]轧霁,张晓琦,叶文才等,广东桑种子的化学成分,中国药科大学学报,2006,37(4): 301-303.
[18]Khan IA.,Clemens AJ,Sticher O,et al.New phenolic glucosides from the leaves of Eurya tigang.[J].Journal of Natural Products,1992,55(9):1270-1274.
[19]张薇,张卫东,李廷钊等,毛瑞香化学成分研究,中国中药杂志,2005,30(7):513-515.
[20]Zhang YJ,Kong M,Chen RY,et al.Alkaloids from the roots of goniothalamus griffithii.[J].Journal of Natural Products,1999,62(7):1050-1052.
[21]张海玲,番荔枝科植物大叶紫玉盘抗肿瘤化学成分研究,中国协和医科大学硕士论文,2001.
[22]Hussain SR,Gozler B,Shamma M,et al.Feruloyltyramine from Hypecoum.[J].Phytochemistry,1982,21(12):2979-2980.
[23]DellaGreca M,Previtera L,Purcaro R,et al.Cinnamic acid amides and lignanamides from Aptenia cordifolia.[J].Tetrahedron,2006,62,2877-2882.
[24]张治针,小池一男,滇白珠化学成分研究(Ⅱ),中草药,1999,30(3):167-169.
[25]柴兴云,窦静,贺清辉等,山银花中酚酸类成分研究,中国天然药物,2004,2(6):339-340.
[26]卢汝梅,何翠薇,潘英.紫玉盘挥发油化学成分的分析,世界科学技术—中医药现代化,2006,8(6):40-42.
[27]卢汝梅,何翠薇.紫玉盘叶脂溶性成分的气相色谱—质谱联用分析,时珍国医国药,2005,16(8):713-714.
[28]Nonaka,G.et al.Tannins and related compounds.XV.A new class of dimericflavanaol gallates,Theasinensins A and B,and proanthocyanidin gallates from Green Tea Leaf.[J].Chem.Pharm.Bull.,1983,31:3904-3906.
[29]张雯洁,刘玉清,李兴从等,云南“生态茶”的化学成分,云南植物研究,1995,17(2):204-208.
1.中国医学科学院中国植物志编辑委员会.中国植物志(第三十卷第二分册)[M].北京:科学出版社,1979:14.
2.Jolad SD,Hoffmann JJ,Schram KH.Uvaricin,a new antitumor agent from Uvaria accuminata(Annonaceae)[J].J Org Chem,1982,47:3151-3153.
3.Chiu HF,Chih TT,Hsian YM,et al.Bullatacin,a potent antitumor Annonaceous acetogenin,induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells[J].Biochemical Pharmacology,2003,65(3):319.
4.Yuan SSF,Chang HL,Chen HW,et al.Selective cytotpxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-,Bad-,and caspase-3-ralated pathways.[J].Life Sciences,2006,78(8):869.
5.Hattori Y,Konno H,Abe M,et al.Synthesis,determination of the absolute configuration of tonkinelin,and inhibitoy action with bovine heart mitochondrial complex I[J].Bioorganic＆Medicinal Chemistry,2007,15(8):3026.
6.Waterman PG,Mohammad I.Chemistry of the annonaceae.Structures of uvarindoles A-D,four new benzylated indole alkaloids from Uvaia angolensis[J].Chem.Soc.,Chem.Commun.,1984,1280.
7.Panichpol K,Waigh RD,and Waterman PG.Chondrofoline from Uvaria ovata[J].Phytochemistry,1977,16(5):621.
8.杨小江,徐丽珍,孙南君,等.番荔枝化学成分研究[J].药学学报,1992,27(3):185.
9.余冬莆.紫玉盘抗肿瘤化学成分研究[D].北京:中国医学科学院—中国协和医科大学,1998.
10.许琼明,刘艳丽,赵葆华,等.瘤果紫玉盘中的酰胺类化学成分[J].药学学报,2007,42(4):405.
11.廖永红,徐丽珍,杨世林,等.紫玉盘属植物化学成分研究进展[J].国外医学中医中药分册,1995,17(6):9.
12.Huang L,Wall ME,Wani MC,et al.New compounds with DNA strand-scission activity from the combined leaf and stem of Uvaria hamiltonii[J].J Nat Prod,1998,61(4):446.
13.张海玲,王嗣,陈若芸,等.大叶紫玉盘化学成分研究[J].药学学报,2002,37(2):124.
14.王嗣,戴胜军,张培成,等.景红哥纳香和大叶紫玉盘化学成分研究[J].化学学报,2003,61(7):1090.
15.许琼明,石峰,徐丽珍,等.瘤果紫玉盘叶中的黄酮类成分[J].沈阳药科大学学报,2006,23(5):277.
16.Wang S,Chen RY,Yu SS,et al.Uvamalols D-G:novel polyoxygenated seco-cyclohexenes from the roots of Uvaria macrophylla.[J].Journal of Asian Natural Products Research,2003,5(1):17.
17.Liu A,Zou ZM,Xu LZ,et al.A new cyclohexene oxide from Uvaria tonkinesis var.subglabra[J].Chinese Chemical Letters,2003,14(11):1144.
18.许琼明,刘艳丽,赵葆华,等.HPLC法从瘤果紫玉盘叶中分离制备紫玉盘醇和大花紫玉盘醇G[J].中草药,2007,38(11):1654.
19.周光雄,张沿军,陈若芸,等.刺果紫玉盘的化学成分研究[J].天然产物研究与开发,2007,19:433.
20.Raynaud S,Fourneau C,Hocquemiller R,et al.Acetogenins from the bark of Uvaria pauci-ovulata.[J].Phytochemistry,1997,46(2):321.
21.戴支凯等,紫玉盘茎叶石油醚部位抗肿瘤作用的研究[J].中国现代医学杂志,2008,18(11):47.
22.Nakatani N,Ichimaru M,Moriyasu M,et al.Induction of apoptosis in human promyelocytic leukemia cell line HL-60 by C-benzylated dihydrochalcones,uvaretin,isouvaretin and diuvaretin.[J].Bio Pharm Bull,2005,28(1):83.
23.Philipov S,Ivanovska N,Istatkova R.et al.Phytochemical study and cytotoxic activity of alkaloids from Uvaria chamaeP.Beauv[J].Pharmazie,2000,55(9):688.
24.Asha KN,Chowdhury R,Hasan CM,et al.Antibacterial activity and cytotoxicity of extractives from Uvaria hamiltonii stem bark[J].Fitoterapia,2003,74(1/2):159.
25.Akendengue B,Ngou-Milama E,Roblot F,et al.Antiplasmodial activity of Uvaria klaineana[J].Planta Medica,2002,68(2):167.
26.Raynaud S,Fourneau C,Laurens A,et al.Squamocin and benzyl benzoate,acaricidal components of Uvaria pauci-ovulata bark extracts[J].Planta Medica,2000,66(2):173.
[1]Jonathan Addae-Kyereme,Simon L.Croft,et al.[J].Ethnopharmacology 76,99-103(2001)
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