亮叶围涎树根中具细胞毒活性的三萜苷成分研究少药八角根的化学成分及其生物活性研究
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摘要
本论文包括亮叶围涎根中具细胞毒活性的三萜苷成分研究和少药八角根中具有结构多样性的天然产物的发现及其生物活性研究两个部分。
亮叶围涎树(Pithecellobium lucidum Benth.),为豆科猴耳环属植物,分布于我国浙江、福建、台湾、广东、四川、云南等地。枝叶入药,有小毒,主治烫伤、风湿痛、跌打损伤。迄今为止,对其化学成分和生物活性未见研究报道。我们对亮叶围涎树根的95%乙醇提取物进行了活性筛选,发现其具有明显的细胞毒活性,通过活性追踪的方法从95%乙醇提取物的正丁醇部位分离得到7个三萜苷类化合物(1-7),通过波谱方法和化学方法确定了它们的结构,发现3个新的具有单萜烯酸取代的齐墩果烷型三萜苷pithelucoside A-C(1-3),以及4个已知化合物prosapogenin-10(4),julibroside J_(29)(5),julibroside A_2(6)和3-[(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oicacid(7),并初步总结了这些三萜苷抗肿瘤活性的构效关系,并进一步评价了它们的溶血活性。
少药八角(Illicium parvifolium subsp.oligandrum(Merr.et chun)Q.Lin)为木兰科(Magnoliaceae)八角属小叶八角(I.parvifolium Merr.et chun)的亚种,中国特有,主要分布于我国的广西和海南两省。树皮、叶和果实入药,有毒。主治风湿痹痛,跌打损伤。本课题组首次开展对少药八角的化学成分和生物活性的研究。前期从少药八角的果实和茎皮中共分离得到51个化合物,主要包括6个倍半萜内酯、13个木脂素(苷)及苯丙素(苷)、11个黄酮(苷)、9个异戊烯基取代的C_6-C_3类化合物(植物醌类),其中新化合物11个,包括3个为新骨架化合物。活性筛选发现:一些木脂素苷具有较强的抗炎活性;一些植物醌类化合物和倍半萜内酯具有潜在的阻滞特异性钾通道的作用。为了进一步寻找结构新颖的活性化合物,本论文作者对少药八角的另一组织部位——少药八角根,进行了较为系统的化学成分研究,从根的95%乙醇提取物中分离得到38个化合物。
通过波谱学方法,确定了上述38个化合物的结构分别为illoliganpyranone A-B(1-2),illoliganfunone A-C(3-5),illoliganone D-M(4-14,17),3a-allyl-5-(1-hydroxy-1-methyl-ethyl)-6a-methyl-tetrahydro-furo[2,3-b]furan-2-one(15),2-epimethylene-di-illifunoneD(16),2,2-dimethyl-6-allyl-7,8-methylene-dioxylchroman-3-ol(18),illioliganoside A(19),4-epi-illioliganoside A(20),2,5-二甲基-4-甲氧基-苯基α-L-阿拉伯呋喃糖基-(1→6)-β-D-葡萄糖苷(21),2,5-二甲基-4-甲氧基-苯基α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(22),5-烯丙基-2-羟基-3-甲氧基-苯基α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(23),3,5-二甲氧基-4-羟基-苯甲酸甲酯4-O-α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(24),methylene-di-illifunone D(25),4-allyl-4-(3-methylbut-2-enyl)-1,2-methylene-dioxycyclohexa-2,6-dien-5-one(26),4S-illicinone C(27),4S-illicinone B(28),11-epi-illicinone E(29),illifunone C(30),2,3-dehydroillifunone C(31),11-O-debenzoyl-11α-O-2-methylcyclopent-1-enecarboxyltashironin(32),tashironin(33),oplodiol(34),3-甲氧基-4-羟基-苯甲醛(35),benzyl 6-O-β-D-apiofuranosyl-β-D-glucopyranoside(36),8-acetyl harpagide(37),(-)-seco-isolariciresinol-9′-O-β-D-glucopyranoside(38)。这些化合物包括23个植物醌类化合物、3个倍半萜、2个倍半萜苷、4个酚苷和6个其它结构类型化合物。
从少药八角根中一共发现24个新化合物:包括16个植物醌类化合物(1-14,16-17)、1个具缩酮结构的内酯(15)、1个芳香化的植物醌(18)、2个倍半萜苷(19-20)和4个酚苷类化合物(21-24)。其中化合物1为新骨架化合物,化合物16为一对差向异构体的植物醌类化合物的二聚体。按异戊烯基与C_6-C_3基本骨架结合方式不同,将少药八角根中23个植物醌类化合物分为四类:①链状异戊烯基取代的C_6-C_3类化合物(6、7、8、9、10、11、26、27、28);②四氢呋喃型异戊烯基取代C_6-C_3类化合物(3、4、5、16、17、25、29、30、31);③四氢吡喃型异戊烯基取代的C_6-C_3类化合物(1、2);④桥型异戊烯基取代的C_6-C_3类化合物(12、13、14),其中第③和④类为两种新的结构类型。对上述4种结构类型的植物醌类化合物的生源途经进行了较深入的分析,提出了以5-烯丙基-1,2,4-苯三酚为前体的生源假说,为结构多样性的植物醌类化合物的形成以及仿生合成提供了理论依据。
活性筛选结果表明,少药八角根中植物醌类化合物(1,2,3,6,7,8,14,26,28,31)对脑内MAO酶具有较弱的抑制活性(抑制率,＜30.3%),而对脑内AchE活力无明显影响。采用MTT法的细胞毒活性筛选表明,植物醌类化合物(27、28,29)具有较强的细胞毒活性(IC_(50),0.30～3.02μM)。
The thesis included two parts of studies on the cytotoxic triterpenoid saponins from roots of Pithecellobium lucidum Benth.and new natural products with structure diversity and bioactivity from Roots of Illicium parvifolium Subsp.oligandrum.
Pithecellobium lucidum Benth.belongs to the genus of Pithecellobium in the family Mimosaceae.Pithecellobium lucidum Benth.is widely distributed in Zhejiang,Fujiang, Taiwan,Guangdong,Sichuan,Yunnan Provinces,etc,in China.The leaves and stems have been used as Chinese folk medicine for the treatment of rheumatalgia and wounds. In our investigation,the EtOH extract of dried roots of P.lucidum showed significant cytotoxicity,bioassay-guided ffactionation led to the isolation of seven triterpenoid saponins(1-7).The structures of three new triterpenoid saponins(1-3) acylated with monoterpenic acid were established on the basis of extensive 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis,with four known compounds identified as prosapogenin-10(4),julibroside J_(29)(5),julibroside A_2(6),3-[(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)oxy]-16α-hydroxy-olean-12-en-28-oic acid(7),respectively.These triterpenoid saponins against tumor cell lines exhibited considerable structure-activity relationship in cytotoxic activity,and their hemolytic activities on rabbit erythrocytes were also evaluated.
Illicium parvifolium subsp,oligandrum(Merr.et chun ) Q.Lin is a toxic species of the genus Illicium in the family Magnoliaceae.This plant is only found in China,and mainly distributed in Guangxi and Hainan Provinces.Its leaves,stem barks and fruits have been used as Chinese folk medicine for the treatment of rheumatic arthralgia and wounds.Our study group have found 51 compounds from fruits and stem barks of the plant,which included sesquiterpene lactones,lignans,flavonoids,phenolics and prenylated C_6-C_3 compounds(phytoquinoids).Among them,there are eleven new compounds,and three of them possess new carbon skeletons.Some lignans showed significant anti-inflammatory activities,while some phytoquinoids and a sesquiterpene lactones exhibited potential activity of inhibiting potassium(K~+) channel.In order to find active compounds with unique structures,we continued to investigate roots of Illicium parvifolium subsp.Oligandrum.38 compounds were isolated from 95%alcohol extract of roots of the plant,including twenty-three phytoquinoids(1-14,16,17, 25-31),three sesquiterpenes(32-34),two sesquiterpene glycosides(19-20),four phenol glycosides(21-24) and other compounds(15,18,35-38).We found twenty-four new compounds which are consisted of eighteen phytoquinoids(1-18),two sesquiterpene glycosides(19-20),four phenol glycosides(21-24),Among them,one possesses new carbon skeleton(1) and one was a prenylated C_6-C_3 dimer(16).Based on the connective relations of isopentenyl-group and basic C_6-C_3 skeleton,the phytoquinoids can be classified into four structure types compounds(chain-form prenylated C_6-C_3 compounds, tetrahydrofuro-form prenylated C_6-C_3 compounds,tetrahydropyrano-form prenylated C_6-C_3 compounds and bridge-form prenylated C_6-C_3 compounds),and their biogenetic pathway with the precursor of 5-allyl-1,2,4-trihydroxybenzene were proposed.
On the basis of spectral analysis,the 38 compounds were elucidated as: illoliganpyranone A-B(1-2),illoliganfunone A-C(3-5),illoliganone D-M(4-14,17), 3a-allyl-5-(1-hydroxy-1-methyl-ethyl)-6a-methyl-tetrahydro-furo[2,3-b]furan-2- one (15),2-epi-methylene-di-illifunone D(16),2,2-dimethyl-6-allyl-7,8-methylene-dioxylchroman-3-ol (18),illioliganoside A(19),4-epi-illioliganoside A(20), 2,5-dimethy-4-methoxy-phenylα-L-arabino-furanosyl-(1→6)-β-D-glucopyranoside(21), 2,5-dimethy-4-methoxy-phenylα-L-rhamnopyranosyl-(1→6)-β-D-glucopyrano-side(22), 5-allyl-2-hydroxy-3-methoxy-phenylα-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (23),methyl syringate 4-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(24), methylene-di-illifunone D(25),4-allyl-4-(3-methylbut-2-enyl)-1,2-methylene-dioxycyclohexa-2, 6-dien-5-one(26),4S-illicinone C(27),4S-illicinone B(28), 11-epi-illicinone E(29),illifunone C(30),2,3-dehydroillifunone C(31), 11-O-debenzoyl- 11α-O-2-methylcyclopent-1-enecarboxyltashironin(32),tashironin (33),oplodiol(34),3-methoxy-4-hydroxy-benzaldehyde(35),benzyl 6-O-β-D-apiofuranosyl-β-D-glucopyranoside (36),8-acetyl harpagide(37),(-)-secoisolariciresinol-9'-O-β-D-glucopyranoside (38)。
Based on the results of activity screening,phytoquinoids(1,2,3,6,7,8,14,26,28, 31) showed weak inhibit-activity against monoamine oxidase,and exhibited no activity against AchE.Phytoquinoids(27,28,29) showed significant cytotoxic activity with IC_(50) values of 0.30-3.02μM.
亮叶围涎树(Pithecellobium lucidum Benth.),为豆科猴耳环属植物,分布于我国浙江、福建、台湾、广东、四川、云南等地。枝叶入药,有小毒,主治烫伤、风湿痛、跌打损伤。迄今为止,对其化学成分和生物活性未见研究报道。我们对亮叶围涎树根的95%乙醇提取物进行了活性筛选,发现其具有明显的细胞毒活性,通过活性追踪的方法从95%乙醇提取物的正丁醇部位分离得到7个三萜苷类化合物(1-7),通过波谱方法和化学方法确定了它们的结构,发现3个新的具有单萜烯酸取代的齐墩果烷型三萜苷pithelucoside A-C(1-3),以及4个已知化合物prosapogenin-10(4),julibroside J_(29)(5),julibroside A_2(6)和3-[(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oicacid(7),并初步总结了这些三萜苷抗肿瘤活性的构效关系,并进一步评价了它们的溶血活性。
少药八角(Illicium parvifolium subsp.oligandrum(Merr.et chun)Q.Lin)为木兰科(Magnoliaceae)八角属小叶八角(I.parvifolium Merr.et chun)的亚种,中国特有,主要分布于我国的广西和海南两省。树皮、叶和果实入药,有毒。主治风湿痹痛,跌打损伤。本课题组首次开展对少药八角的化学成分和生物活性的研究。前期从少药八角的果实和茎皮中共分离得到51个化合物,主要包括6个倍半萜内酯、13个木脂素(苷)及苯丙素(苷)、11个黄酮(苷)、9个异戊烯基取代的C_6-C_3类化合物(植物醌类),其中新化合物11个,包括3个为新骨架化合物。活性筛选发现:一些木脂素苷具有较强的抗炎活性;一些植物醌类化合物和倍半萜内酯具有潜在的阻滞特异性钾通道的作用。为了进一步寻找结构新颖的活性化合物,本论文作者对少药八角的另一组织部位——少药八角根,进行了较为系统的化学成分研究,从根的95%乙醇提取物中分离得到38个化合物。
通过波谱学方法,确定了上述38个化合物的结构分别为illoliganpyranone A-B(1-2),illoliganfunone A-C(3-5),illoliganone D-M(4-14,17),3a-allyl-5-(1-hydroxy-1-methyl-ethyl)-6a-methyl-tetrahydro-furo[2,3-b]furan-2-one(15),2-epimethylene-di-illifunoneD(16),2,2-dimethyl-6-allyl-7,8-methylene-dioxylchroman-3-ol(18),illioliganoside A(19),4-epi-illioliganoside A(20),2,5-二甲基-4-甲氧基-苯基α-L-阿拉伯呋喃糖基-(1→6)-β-D-葡萄糖苷(21),2,5-二甲基-4-甲氧基-苯基α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(22),5-烯丙基-2-羟基-3-甲氧基-苯基α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(23),3,5-二甲氧基-4-羟基-苯甲酸甲酯4-O-α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖苷(24),methylene-di-illifunone D(25),4-allyl-4-(3-methylbut-2-enyl)-1,2-methylene-dioxycyclohexa-2,6-dien-5-one(26),4S-illicinone C(27),4S-illicinone B(28),11-epi-illicinone E(29),illifunone C(30),2,3-dehydroillifunone C(31),11-O-debenzoyl-11α-O-2-methylcyclopent-1-enecarboxyltashironin(32),tashironin(33),oplodiol(34),3-甲氧基-4-羟基-苯甲醛(35),benzyl 6-O-β-D-apiofuranosyl-β-D-glucopyranoside(36),8-acetyl harpagide(37),(-)-seco-isolariciresinol-9′-O-β-D-glucopyranoside(38)。这些化合物包括23个植物醌类化合物、3个倍半萜、2个倍半萜苷、4个酚苷和6个其它结构类型化合物。
从少药八角根中一共发现24个新化合物:包括16个植物醌类化合物(1-14,16-17)、1个具缩酮结构的内酯(15)、1个芳香化的植物醌(18)、2个倍半萜苷(19-20)和4个酚苷类化合物(21-24)。其中化合物1为新骨架化合物,化合物16为一对差向异构体的植物醌类化合物的二聚体。按异戊烯基与C_6-C_3基本骨架结合方式不同,将少药八角根中23个植物醌类化合物分为四类:①链状异戊烯基取代的C_6-C_3类化合物(6、7、8、9、10、11、26、27、28);②四氢呋喃型异戊烯基取代C_6-C_3类化合物(3、4、5、16、17、25、29、30、31);③四氢吡喃型异戊烯基取代的C_6-C_3类化合物(1、2);④桥型异戊烯基取代的C_6-C_3类化合物(12、13、14),其中第③和④类为两种新的结构类型。对上述4种结构类型的植物醌类化合物的生源途经进行了较深入的分析,提出了以5-烯丙基-1,2,4-苯三酚为前体的生源假说,为结构多样性的植物醌类化合物的形成以及仿生合成提供了理论依据。
活性筛选结果表明,少药八角根中植物醌类化合物(1,2,3,6,7,8,14,26,28,31)对脑内MAO酶具有较弱的抑制活性(抑制率,＜30.3%),而对脑内AchE活力无明显影响。采用MTT法的细胞毒活性筛选表明,植物醌类化合物(27、28,29)具有较强的细胞毒活性(IC_(50),0.30～3.02μM)。
The thesis included two parts of studies on the cytotoxic triterpenoid saponins from roots of Pithecellobium lucidum Benth.and new natural products with structure diversity and bioactivity from Roots of Illicium parvifolium Subsp.oligandrum.
Pithecellobium lucidum Benth.belongs to the genus of Pithecellobium in the family Mimosaceae.Pithecellobium lucidum Benth.is widely distributed in Zhejiang,Fujiang, Taiwan,Guangdong,Sichuan,Yunnan Provinces,etc,in China.The leaves and stems have been used as Chinese folk medicine for the treatment of rheumatalgia and wounds. In our investigation,the EtOH extract of dried roots of P.lucidum showed significant cytotoxicity,bioassay-guided ffactionation led to the isolation of seven triterpenoid saponins(1-7).The structures of three new triterpenoid saponins(1-3) acylated with monoterpenic acid were established on the basis of extensive 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis,with four known compounds identified as prosapogenin-10(4),julibroside J_(29)(5),julibroside A_2(6),3-[(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)oxy]-16α-hydroxy-olean-12-en-28-oic acid(7),respectively.These triterpenoid saponins against tumor cell lines exhibited considerable structure-activity relationship in cytotoxic activity,and their hemolytic activities on rabbit erythrocytes were also evaluated.
Illicium parvifolium subsp,oligandrum(Merr.et chun ) Q.Lin is a toxic species of the genus Illicium in the family Magnoliaceae.This plant is only found in China,and mainly distributed in Guangxi and Hainan Provinces.Its leaves,stem barks and fruits have been used as Chinese folk medicine for the treatment of rheumatic arthralgia and wounds.Our study group have found 51 compounds from fruits and stem barks of the plant,which included sesquiterpene lactones,lignans,flavonoids,phenolics and prenylated C_6-C_3 compounds(phytoquinoids).Among them,there are eleven new compounds,and three of them possess new carbon skeletons.Some lignans showed significant anti-inflammatory activities,while some phytoquinoids and a sesquiterpene lactones exhibited potential activity of inhibiting potassium(K~+) channel.In order to find active compounds with unique structures,we continued to investigate roots of Illicium parvifolium subsp.Oligandrum.38 compounds were isolated from 95%alcohol extract of roots of the plant,including twenty-three phytoquinoids(1-14,16,17, 25-31),three sesquiterpenes(32-34),two sesquiterpene glycosides(19-20),four phenol glycosides(21-24) and other compounds(15,18,35-38).We found twenty-four new compounds which are consisted of eighteen phytoquinoids(1-18),two sesquiterpene glycosides(19-20),four phenol glycosides(21-24),Among them,one possesses new carbon skeleton(1) and one was a prenylated C_6-C_3 dimer(16).Based on the connective relations of isopentenyl-group and basic C_6-C_3 skeleton,the phytoquinoids can be classified into four structure types compounds(chain-form prenylated C_6-C_3 compounds, tetrahydrofuro-form prenylated C_6-C_3 compounds,tetrahydropyrano-form prenylated C_6-C_3 compounds and bridge-form prenylated C_6-C_3 compounds),and their biogenetic pathway with the precursor of 5-allyl-1,2,4-trihydroxybenzene were proposed.
On the basis of spectral analysis,the 38 compounds were elucidated as: illoliganpyranone A-B(1-2),illoliganfunone A-C(3-5),illoliganone D-M(4-14,17), 3a-allyl-5-(1-hydroxy-1-methyl-ethyl)-6a-methyl-tetrahydro-furo[2,3-b]furan-2- one (15),2-epi-methylene-di-illifunone D(16),2,2-dimethyl-6-allyl-7,8-methylene-dioxylchroman-3-ol (18),illioliganoside A(19),4-epi-illioliganoside A(20), 2,5-dimethy-4-methoxy-phenylα-L-arabino-furanosyl-(1→6)-β-D-glucopyranoside(21), 2,5-dimethy-4-methoxy-phenylα-L-rhamnopyranosyl-(1→6)-β-D-glucopyrano-side(22), 5-allyl-2-hydroxy-3-methoxy-phenylα-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (23),methyl syringate 4-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(24), methylene-di-illifunone D(25),4-allyl-4-(3-methylbut-2-enyl)-1,2-methylene-dioxycyclohexa-2, 6-dien-5-one(26),4S-illicinone C(27),4S-illicinone B(28), 11-epi-illicinone E(29),illifunone C(30),2,3-dehydroillifunone C(31), 11-O-debenzoyl- 11α-O-2-methylcyclopent-1-enecarboxyltashironin(32),tashironin (33),oplodiol(34),3-methoxy-4-hydroxy-benzaldehyde(35),benzyl 6-O-β-D-apiofuranosyl-β-D-glucopyranoside (36),8-acetyl harpagide(37),(-)-secoisolariciresinol-9'-O-β-D-glucopyranoside (38)。
Based on the results of activity screening,phytoquinoids(1,2,3,6,7,8,14,26,28, 31) showed weak inhibit-activity against monoamine oxidase,and exhibited no activity against AchE.Phytoquinoids(27,28,29) showed significant cytotoxic activity with IC_(50) values of 0.30-3.02μM.
引文
[1]朱相云.中国豆科植物分类系统概览[J].植物研究.2004,24(1):1-6.
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[3]Gomes,Denise de Castro Ferreira;Alegrio,Leila Vilela.Acyl steryl glycosides from Pithecellobium cauliflorum[J].Phytochemistry.1998,49(5):1365-1367.
[4]Gunasekera,Sarath P.;Cordell,Geoffrey A.;Farnsworth,Norman R..Constitutents of Pithecellobium multiflorum[J].J.Nat.Prod.1982,45(5):651.
[5]Bhargava.K.P.,Gupta.B.M.and Mitra C.R..Anti-inflammatory activity of saponins and other natural products[J].Indian J Med.Res.1970,58(6):724-730.
[6]Saxena,V.K.;Singhal,Madhuri.Bioactive flavonoidal constituents from PithecelIobium dulce (leaves)[J].Journal of the Institution of Chemists,1998,70(5):168-171.
[7]李药兰,李克明,苏妙贤,梁锦堂,陈玉武,张永文.猴耳环抗病毒有效成分研究[J].中国中药杂志,2006,31(5):397-400.
[8]Mondhe,O.S.;Rao,J.T..Studies on nonconventional oil seeds:a new source of edible and industrial oils[J].Asian J.Chem.,1993,5(2):247-252.
[9]Mohamed,Suhaila;Rahman,Mohamed Shamsuddin A.;Sulaiman,Sabturiah;Abdullah,Fauziah.Some nutritional and antinutritional components in jering(Pithecellobium jeringa),keredas(Pithecellobium microcarpum) and petai(Parkia speciosa)[J].Pertanika,1987,10(1):61-68.
[10]Nigam,S.K.;Gopal,Misra;Uddin,Rais;Yoshikawa,Kazuko;Kawamoto,Miwako;Arihara,Shigenobu.Pithedulodides A-D,oleanane glycosides from Pithecellobium dulce[J]. Phytochemistry,1997,44(7):1329-1334.
[11]Ripperger,Helmut;Preiss,Alfred;Schmidt,Juergen.O(3)-(2-Acetylamino-2-deoxy-β-D-glucopyranosyl)oleanolic acid,a novel triterpenoid glycoside from two Pithecellobium species [J].Phytochemistry,1981,20(10):2434-2435.
[12]Niranjan P.Sahu and Shashi B.Mahato.Anti-inflammatory triterpene saponins of Pithecellobium dulce:characterization of an echinocystic acid bisdesmoside[J].Phytochemistry,1994,37(5):1425-1427.
[13]Khan,Ikhlas A.;Clark,Alice M.;Mcchesney,James D..Antifungal activity of a new triterpenoid glycoside from Pithecellobium racemosum(M.)[J].Pharmaceutical Research,1997,14(3):358-361.
[14]Yoshikawa,Kazuko;Suzaki,Yuki;Tanaka,Masami;Arihara,Shigenobu and Nigam,S.K..Three acylated saponins and a related compound from Pithecellobium dulce[J].J.Nat.Prod.1997,60(12):1269-1274.
[15]Lee,Min Won;Morimoto,Satoshi;Nonaka,Genichiro;Nishioka,Itsuo.Tannins and related compounds.Ⅲ.Flavan-3-ol gallates and proanthocyanidins from Pithecellobium lobatum[J].Phytochemistry,1992,31(6):2117-2120.
[16]Li,Yaolan;Leung,Kam-Tong;Yao,Fenghe;Ooi,Linda S.M.;Ooi,Vincent E.C..Antiviral flavans from the leaves of Pithecellobium clypearia[J].J.Nat.Prod.2006,69(5):833-835.
[17]Morita,Naokata;Arisawa,Munehisa;Nagaes,Machiko;Hsu,Hong-Yen;Chen,Yuh-Pan.Studies on the constituents of Formosan leguminosae.Ⅲ.Flavonoids from Leucaena glauca (L.) Benth,Cassia fistula L.,and 8 other varieties[J].Shoyakugaku Zasshi,1977,31(2):172-174.
[18]Zapesochnaya,G.G.;Yarosh,E.A.;Svanidze,N.V.;Yarosh,G.I.Flavonoids from Pithecellobium dulce leaves[J].Khim.Prir.Soedin.,1980,2:252-253.
[19]Dan,Mrs.S.;Dan,S.S.;Mukhopadhayay,P..Chemical examination of three indigenous plants [J].J.Indian Chem.Soc.,1982,59(3):419-420.
[20]Gupta,H.M.;Saxena,N.K.A novel saponin stigmasta-7,16,25(26)-triene-3-O-β-D-glucopyranosyl-(1→5)-O-β-D-xylofuranoside isolated and identified from the stem of Pithecellobium dulce[J].Asian Journal of Chemistry,2003,15(3 & 4):1817-1818.
[21]王永刚,淡墨,李咏华,苏薇薇.猴耳环化学成分的研究[J].中药材,2005,28(9):774-775.
[22]Lajts,Nordin N.;Khan,Mohammad Niyaz.Extraction.identification and spectrophotometric determination of second ionization constant of methyl gallate,a constituent present in the fruit shells of Pithecellobium jiringa[J].Indian J.Chem.,Sect.B:Org.Chem.Incl.Med.Chem.,1994,33b(6):609-612.
[23]Mondhe,O.S.;Rao,J.T..Phytochemical investigation of Pithecellobium dulce seed oil[J].J.Inst.Chem.,1991,63(4):136.
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[26]Felker,Peter;Bandurski,Robert S.Protein and amino acid composition of tree legume seeds[J].J.Sci.Food Agric.,1977,28(9):791-797.
[27]Areekul,Suvit;Kirdudom,Pimphan.Studies on the chemical components and toxic substances in niang beans[J].J.Med.Assoc.Thailand,1977,60(1):3-8.
[28]Barrera-Necha,L.;Bautista-Banos,S.;Bravo-Luna,L.;Bermudez-Torres,K.;Garcia-Suarez,E;Jimenez-Estrada,M.;Reyes-Chilpa,R..Antifungal activity against postharvest fungi by extracts and compounds of Pithecellobium dulce seeds(Huamuchil).Acta Horticulturae,628(Vol.2,Proceedings of the 26th International Horticultural Congress,2002,Volume 2),2003:761-766.
[29]程兆盛,王坤根,林志南,等主编.现代中成药[M].江西,江西科技出版社,1997:78.
[30]福建省科学技术委员会编.福建植物志[M].福州,福建科学技术出版社,1982:95.
[1]江苏新医学院,中药大辞典[M].上海,上海科学技术出版社.1999:1183.
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[3]Ikeda,T.;Fujiwara,S.;Araki,K.;Kinjo,J.;Nohara,T.;Miyoshi,T.,Cytotoxic glycosides fromAlbizia julibrissin[J].J.Nat.Prod.1997,60,(2),102-107.
[4]Kiuchi,F.;Gafur,M.A.;Obata,T.;Tachibana,A.;Tsuda,Y.,Acacia concinna saponins.Ⅱ.Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction[J].Chem.Pharm.Bull.1997,45,807-812.
[5]Zheng,L.;Zheng,J.;Zhao,Y.;Wang,B.;Wu,L.;Liang,H.,Three anti-tumor saponins fromAlbizia julibrissin[J].Bioorg.Med.Chem.Lett.2006,16,(10),2765-2768.
[6]Marc,M.;Clement,O.A.;Kurt,H.,New Triterpenoid N-acetylglycosides with molluscicidalactivity from Tetrapleura tetraptera Taub[J].Helv.Chim.Acta 1989,72,(4),668.
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[5]Sato,S.;Obara,H.;Kumazawa,T.;Onodera,J.-i.;Furuhata,K.,Synthesis of(+),(-)-model compounds and absolute configuration of carthamin;A red pigment in the flower petals of Safflower[J].Chem.Lett.1996,10,833-834.
[6]Fukuyama,Y.;Shida,N.;Sakurai,T.;Kodama,M.,Prenylated C6-C3 compounds from Illicium tashiroi[J].Phytochemistry 1992,31,(11),3975-3979.
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[2]陈冀胜,郑硕.中国有毒植物[M].北京,科学出版社,1987:189.
[3]Gomes,Denise de Castro Ferreira;Alegrio,Leila Vilela.Acyl steryl glycosides from Pithecellobium cauliflorum[J].Phytochemistry.1998,49(5):1365-1367.
[4]Gunasekera,Sarath P.;Cordell,Geoffrey A.;Farnsworth,Norman R..Constitutents of Pithecellobium multiflorum[J].J.Nat.Prod.1982,45(5):651.
[5]Bhargava.K.P.,Gupta.B.M.and Mitra C.R..Anti-inflammatory activity of saponins and other natural products[J].Indian J Med.Res.1970,58(6):724-730.
[6]Saxena,V.K.;Singhal,Madhuri.Bioactive flavonoidal constituents from PithecelIobium dulce (leaves)[J].Journal of the Institution of Chemists,1998,70(5):168-171.
[7]李药兰,李克明,苏妙贤,梁锦堂,陈玉武,张永文.猴耳环抗病毒有效成分研究[J].中国中药杂志,2006,31(5):397-400.
[8]Mondhe,O.S.;Rao,J.T..Studies on nonconventional oil seeds:a new source of edible and industrial oils[J].Asian J.Chem.,1993,5(2):247-252.
[9]Mohamed,Suhaila;Rahman,Mohamed Shamsuddin A.;Sulaiman,Sabturiah;Abdullah,Fauziah.Some nutritional and antinutritional components in jering(Pithecellobium jeringa),keredas(Pithecellobium microcarpum) and petai(Parkia speciosa)[J].Pertanika,1987,10(1):61-68.
[10]Nigam,S.K.;Gopal,Misra;Uddin,Rais;Yoshikawa,Kazuko;Kawamoto,Miwako;Arihara,Shigenobu.Pithedulodides A-D,oleanane glycosides from Pithecellobium dulce[J]. Phytochemistry,1997,44(7):1329-1334.
[11]Ripperger,Helmut;Preiss,Alfred;Schmidt,Juergen.O(3)-(2-Acetylamino-2-deoxy-β-D-glucopyranosyl)oleanolic acid,a novel triterpenoid glycoside from two Pithecellobium species [J].Phytochemistry,1981,20(10):2434-2435.
[12]Niranjan P.Sahu and Shashi B.Mahato.Anti-inflammatory triterpene saponins of Pithecellobium dulce:characterization of an echinocystic acid bisdesmoside[J].Phytochemistry,1994,37(5):1425-1427.
[13]Khan,Ikhlas A.;Clark,Alice M.;Mcchesney,James D..Antifungal activity of a new triterpenoid glycoside from Pithecellobium racemosum(M.)[J].Pharmaceutical Research,1997,14(3):358-361.
[14]Yoshikawa,Kazuko;Suzaki,Yuki;Tanaka,Masami;Arihara,Shigenobu and Nigam,S.K..Three acylated saponins and a related compound from Pithecellobium dulce[J].J.Nat.Prod.1997,60(12):1269-1274.
[15]Lee,Min Won;Morimoto,Satoshi;Nonaka,Genichiro;Nishioka,Itsuo.Tannins and related compounds.Ⅲ.Flavan-3-ol gallates and proanthocyanidins from Pithecellobium lobatum[J].Phytochemistry,1992,31(6):2117-2120.
[16]Li,Yaolan;Leung,Kam-Tong;Yao,Fenghe;Ooi,Linda S.M.;Ooi,Vincent E.C..Antiviral flavans from the leaves of Pithecellobium clypearia[J].J.Nat.Prod.2006,69(5):833-835.
[17]Morita,Naokata;Arisawa,Munehisa;Nagaes,Machiko;Hsu,Hong-Yen;Chen,Yuh-Pan.Studies on the constituents of Formosan leguminosae.Ⅲ.Flavonoids from Leucaena glauca (L.) Benth,Cassia fistula L.,and 8 other varieties[J].Shoyakugaku Zasshi,1977,31(2):172-174.
[18]Zapesochnaya,G.G.;Yarosh,E.A.;Svanidze,N.V.;Yarosh,G.I.Flavonoids from Pithecellobium dulce leaves[J].Khim.Prir.Soedin.,1980,2:252-253.
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[20]Gupta,H.M.;Saxena,N.K.A novel saponin stigmasta-7,16,25(26)-triene-3-O-β-D-glucopyranosyl-(1→5)-O-β-D-xylofuranoside isolated and identified from the stem of Pithecellobium dulce[J].Asian Journal of Chemistry,2003,15(3 & 4):1817-1818.
[21]王永刚,淡墨,李咏华,苏薇薇.猴耳环化学成分的研究[J].中药材,2005,28(9):774-775.
[22]Lajts,Nordin N.;Khan,Mohammad Niyaz.Extraction.identification and spectrophotometric determination of second ionization constant of methyl gallate,a constituent present in the fruit shells of Pithecellobium jiringa[J].Indian J.Chem.,Sect.B:Org.Chem.Incl.Med.Chem.,1994,33b(6):609-612.
[23]Mondhe,O.S.;Rao,J.T..Phytochemical investigation of Pithecellobium dulce seed oil[J].J.Inst.Chem.,1991,63(4):136.
[24]Hosamani,Kallappa M.J..Studies on glycolipids of Kenaf,English walnut,Myrobalan and Manila tamarind seeds of the Vidarbha region(India)[J].Am.Oil Chem.Soc.,1995,72(4):489-492.
[25]Sotelo,A.;Contreras,E.;Flores,S..Nutritional value and content of antinutritional compounds and toxics in ten wild legumes of Yucatan Peninsula[J].Plant Foods Hum.Nutr.(Dordrecht,Neth.),1995,47(2):115-123.
[26]Felker,Peter;Bandurski,Robert S.Protein and amino acid composition of tree legume seeds[J].J.Sci.Food Agric.,1977,28(9):791-797.
[27]Areekul,Suvit;Kirdudom,Pimphan.Studies on the chemical components and toxic substances in niang beans[J].J.Med.Assoc.Thailand,1977,60(1):3-8.
[28]Barrera-Necha,L.;Bautista-Banos,S.;Bravo-Luna,L.;Bermudez-Torres,K.;Garcia-Suarez,E;Jimenez-Estrada,M.;Reyes-Chilpa,R..Antifungal activity against postharvest fungi by extracts and compounds of Pithecellobium dulce seeds(Huamuchil).Acta Horticulturae,628(Vol.2,Proceedings of the 26th International Horticultural Congress,2002,Volume 2),2003:761-766.
[29]程兆盛,王坤根,林志南,等主编.现代中成药[M].江西,江西科技出版社,1997:78.
[30]福建省科学技术委员会编.福建植物志[M].福州,福建科学技术出版社,1982:95.
[1]江苏新医学院,中药大辞典[M].上海,上海科学技术出版社.1999:1183.
[2]Yoshikawa,K.;Suzaki,Y.;Tanaka,M.;Arihara,S.;Nigam,S.K.,Three acylated saponins and a related compound from Pithecellobium dulce[J].J.Nat.Prod.1997,60,(12),1269-1274.
[3]Ikeda,T.;Fujiwara,S.;Araki,K.;Kinjo,J.;Nohara,T.;Miyoshi,T.,Cytotoxic glycosides fromAlbizia julibrissin[J].J.Nat.Prod.1997,60,(2),102-107.
[4]Kiuchi,F.;Gafur,M.A.;Obata,T.;Tachibana,A.;Tsuda,Y.,Acacia concinna saponins.Ⅱ.Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction[J].Chem.Pharm.Bull.1997,45,807-812.
[5]Zheng,L.;Zheng,J.;Zhao,Y.;Wang,B.;Wu,L.;Liang,H.,Three anti-tumor saponins fromAlbizia julibrissin[J].Bioorg.Med.Chem.Lett.2006,16,(10),2765-2768.
[6]Marc,M.;Clement,O.A.;Kurt,H.,New Triterpenoid N-acetylglycosides with molluscicidalactivity from Tetrapleura tetraptera Taub[J].Helv.Chim.Acta 1989,72,(4),668.
[1]黄建梅;杨春澍,八角科植物化学成分和药理研究概况[J].中国药学杂志1998,33,(6),321-327.
[2]杨春澍;孙建宁;黄建梅,细辛属和八角属中药研究与应用[M].北京,人民卫生出版社.2006:234.
[3]Baeckstr(o|¨),E;Koutek,B.;Saman,D.;Vrkoc,J.,A convenient synthesis of trans-sabinene hydrate from(-)-3-thujol via a highly selective ene reaction of singlet oxygen[J].Biorg.Med.Chem.1996,4,(3),419-421.
[4]Sato,S.;Nojiri,T.;Onodera,J.-i.,Studies on the synthesis of saffiomin-A,a yellow pigment in safflower petals:oxidation of 3-C-[beta]-d-glucopyranosyl-5-methylphloroacetophenone[J].Carbohydr.Res.2005,340,(3),389-393.
[5]Sato,S.;Obara,H.;Kumazawa,T.;Onodera,J.-i.;Furuhata,K.,Synthesis of(+),(-)-model compounds and absolute configuration of carthamin;A red pigment in the flower petals of Safflower[J].Chem.Lett.1996,10,833-834.
[6]Fukuyama,Y.;Shida,N.;Sakurai,T.;Kodama,M.,Prenylated C6-C3 compounds from Illicium tashiroi[J].Phytochemistry 1992,31,(11),3975-3979.
[7]Kouno,I.;Shimamoto,S.;Jiang,Z.-H.;Tanaka,T.,Prenylated C6-C3 compounds from root bark of Illicium anisatum[J].Phytochemistry 1997,46,(8),1389-1392.
[8]Fukuyama,Y.;Shida,N.;Hata,Y.;Kodama,M.,Prenylated C6-C3 compounds from Illicium tashiroi[J].Phytochemistry 1994,36,(6),1497-1503.
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