Chemical Study on the Indole Alkaloids from Plant Tissue Cultures

植物组织培养物中吲哚生物碱的化学研究

• 批准号: 01044025
• 负责人: SAKAI Shin-ichiro
• 金额: $ 7.3万
• 依托单位: Chiba University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for international Scientific Research
• 财政年份: 1989
• 资助国家: 日本
• 起止时间: 1989 至 1991
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-01044025/
• 关键词: Plant Tissue Cultures; Indole Alkaloids; Structure Elucidation; Rauwolfia serpentina Benth; Biotransformation of ajmaline; Raumaclines; Aspidosperma quebracho blanco; Aspidochibine.; Raumacline; 化学変換; アジマリン; Aspidasperma queblacho blanco; Aspi

The joint research among Chiba University (Japan), Chulalongkorn University (Thailand) and Mainz University (Germany) supported by a grant under the Monbusho International Scientific Research brought about many successful results on the subject "The Chemical Study on the Indole Alkaloids from Plant Tissue Cultures".The technology of plant cell suspension cultures was employed for three medicinal plants originally producing the indole alkaloids.I. Biotransformation of Ajmaline in Plant Cell Cultures of Rauwolfia serpentina Benth.From the methanol extracts of the plant cell suspension cultures of R. serpentina, which have been cultivated in the alkaloid-production medium after feeding of ajmaline, four new indole alkaloids, raumacline, N_b-methylraumacline, 19(S)-hydroxy-N_b-methylraumacline, and 6alpha-hydroxyraumacline were isolated. These structures first elucidated by the spectroscopic analysis were unambiguously determined by the biomimetically chemical synthesis from ajmaline. These new compounds are the first examples of the macroline-type indole alkaloids having the trans relationship between the C15 and C16 positions.II. Isolation of Novel Indole Alkaloids from Cell Cultures of Aspidosperma quebracho blanco Schlecht.From the cell suspension cultures of A. quebracho blanco, three novel monoterpenoid indole alkaloids, aspidochibine, 3-oxo-14, 15-dehydrorhazinilam, and 11-hydroxytubotaiwine were isolated, though the production amounts of them were very low at this stage. The structure elucidation and the stereochemical analysis were made by mainly 2D NMR technique. Aspidochibine, bearing a characteristic ten membered lactone, is a completely new structural class of the quebrachamine series.III. Investigation of the Alkaloidal Components in the Cell Culture of Uncaria gambir.No alkaloidal constituent was detected from the cell cultures of Uncaria gambir

日本千叶大学、泰国朱拉隆功大学和德国美因茨大学在蒙布绍国际科学研究基金资助下，联合开展了“植物组织培养中吲哚生物碱的化学研究”课题，取得了多项成果。蛇根萝芙木细胞培养物中阿娇的生物转化。serpentina中分离到四种新的吲哚生物碱：raumacline、N_b-甲基raumacline、19（S）-羟基-N_b-甲基raumacline和6 α-羟基raumacline。这些结构首先通过光谱分析阐明，明确确定了生物仿生化学合成从ajapine。这些新化合物是在C15和C16位置之间具有反式关系的大环内酯型吲哚生物碱的第一个例子。从白坚木（Aspidosperma quebracho布兰科Schlecht）细胞培养物中分离新的吲哚生物碱。从白坚木布兰科中分离出三种新的单萜吲哚生物碱：aspidochibine、3-oxo-14，15-dichorhazinilam和11-hydroxytubotaiwine，尽管它们在该阶段的产量很低。用二维核磁共振技术进行了结构鉴定和立体化学分析。Aspidochibine是一种具有特征性十元内酯的全新结构类型的白坚木碱。钩藤细胞培养物中生物碱成分的研究从钩藤细胞培养物中未检测到生物碱成分

项目成果

L.Polz: "Biotransformation of Ajmaline in Plant Cell Cultures of Rauwolfia serpentina Benth.The New Indole Alkaloids,Raumacline and N_b-Methylraumacline." Tetrahedron Letters. 31. 6693-6696 (1990)

L.Polz：“Ajmaline 在 Rauwolfia serpentina Benth 植物细胞培养物中的生物转化。新的吲哚生物碱、Raumacline 和 N_b-Mmethylraumacline。”

S.Endress: "Isolation,Identification and Chemical Synthesis of 6α-Hydroxyraumacline,a novel Alkaloid from cultivated Rauwolfia serpentina Cells." Planta Medica.

S.Endress：“6α-Hydroxyraumacline 的分离、鉴定和化学合成，这是一种来自培养的蛇形萝芙木细胞的新型生物碱。”

H.Takayama: "Structure and Synthesis of a new Indole Alkaloid,19(S)-Hydroxy-N_b-methylraumacline,obtained by the Biotransformation of Ajmaline in Plant Cell Cultures of R.serpentina." Tetrahedron.

H.Takayama：“一种新型吲哚生物碱 19(S)-Hydroxy-N_b-methylraumacline 的结构和合成，通过在蛇纹藻植物细胞培养物中对 Ajmaline 进行生物转化而获得。”

H.Takayama: "Partial Synthesis of Rauwolfia Alkaloids,Vomilenine and 19Z-Vomilenine,and Their Relative Thermodynamic Stability as Revealed by Their Transformation into Perakine." Chem.Pharm.Bull.39. 266-269 (1991)

H.Takayama：“萝芙木生物碱、Vomilenine 和 19Z-Vomilenine 的部分合成，以及通过转化为 Perakine 所揭示的相对热力学稳定性。”

N.Aimi: "Three Novel Metabolites in Cultured Cells of Aspidosperma quebrachoーblanco" in preparation.

N.Aimi：“白坚木培养细胞中的三种新型代谢物”正在准备中。