1-甲基吡咯烷-2-乙酸不是托烷生物碱的前体。

1-Methylpyrrolidine-2-acetic Acid is not a Precursor of Tropane Alkaloids.

作者信息

Huang M N, Abraham T W, Kim S H, Leete E

机构信息

AgroEvo USA Company, Pikeville, NC 27863, USA.

出版信息

Phytochemistry. 1996 Feb;41(3):767-73. doi: 10.1016/0031-9422(95)00667-2.

DOI:10.1016/0031-9422(95)00667-2

PMID:8835455

Abstract

1-Methylpyrrolidine-2-acetic acid and related compounds were studied as precursors in the biosynthesis of the tropane alkaloids in Erythroxylum coca and Datura innoxia. (R,S)-[1',2-(13)C2,2-(14)C,(15)N]-1-methylpyrrolidine-2- acid, (R,S)-[1',2'-(13)C2,1'-(14)C]-1-methylpyrrolidine-2-acetic acid, (R,S) [1',2'-(13)C2,1-(14)C]-1-methylpyrrolidine-2-acetate, and (R,S)-+2'-(14)C] methylpyrrolidine-2-acetic acid N-acetylcysteamine thioester were synthesized an intact plants by leaf-planting or hydroponic-feeding. Specific incorporation of compounds into ( - )-hyoscyamine, ( - )-scopolamine, ( - )-cocaine and the biosynthetically related cuscohygrine were very low. These results indicate that 1-methylpyrrolidine acid is not an efficient precursor of tropane alkaloids.

摘要

研究了1-甲基吡咯烷-2-乙酸及相关化合物作为古柯和无刺曼陀罗中东莨菪烷生物碱生物合成前体的情况。通过叶插法或水培法在完整植株中合成了（R,S）-[1',2-(13)C2,2-(14)C,(15)N]-1-甲基吡咯烷-2-酸、（R,S）-[1',2'-(13)C2,1'-(14)C]-1-甲基吡咯烷-2-乙酸、（R,S）-[1',2'-(13)C2,1-(14)C]-1-甲基吡咯烷-2-乙酸酯以及（R,S）-[2'-(14)C]甲基吡咯烷-2-乙酸N-乙酰半胱氨酸硫酯。这些化合物向（-）-莨菪碱、（-）-东莨菪碱、（-）-可卡因以及生物合成相关的古豆碱中的特异性掺入率非常低。这些结果表明1-甲基吡咯烷酸不是东莨菪烷生物碱的有效前体。