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Structure-Acaricidal Activity Relationship of Protopine and Allocryptopine from Macleaya Microcarpa

Author: LiXiaoZuo
Tutor: ZhouLe
School: Northwest University of Science and Technology
Course: Applied Chemistry
Keywords: protopine allocryptopine acaricidal activity Macleaya microcarpa structure-activity relationship
CLC: TQ454
Type: Master's thesis
Year: 2009
Downloads: 51
Quote: 1
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Abstract


Protopines are one kind of alkaloids which were researched most early. They are widely distributed in lots of plants, and have intensive clinic applied value. At present, the research of protopines primarily focus on their clinic value, but not their acaricidal activity and structure-activity relationship. So, two main compounds of protopines (protopine and allocryptopine) are chosen as parent compounds to modify. Meanwhile, the SARs with acaricidal activities is preliminary investigated by determinating and evaluating acaricidal activities.The reductive derivatives of Compounds (Pro-1, Pro-2 andα-1) were prepared from protopine and allocryptopine by using of NaBH4 as the reducing agent. The cyclized derivatives of Pro-3 andα-3 were obtained from protopine and allocryptopine by using of (COCl)2 as the cyclized reagent. The other cyclized derivative (α-2) was obtained fromα-1 by using of CF3CO2H. Based on the analysis of their spectral data (IR, ESI-MS, 1H NMR, 13C NMR), the six derivatives were identified as dihydroprtopine(P-1), dihydrocryptopine(Pro-2), dihydroallocryptopine(α-1), N-Methyl-13,14-dehydrostylopine(P-3), N-Methyl-13,14-dehy- dro-protoberberine(α-3) and N-Methylprotoberberine(α-2), respectively.The acaricidal activity of protopine, allocryptopine and their six derivatives and abamectin were tested with impregnation method in vitro against wheaten red mite. Analysising acaricidal activity of them, it was concluded that Pro-1 andα-1 have better acaricidal activity, and other derivants′acaricidal activity are not changed compared with protopine and allocryptopine.These results provide some theoretical basis for futher knowing about the modification and structure- acaricidal activity of protopines.

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