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去甲二萜生物碱的1α-羟基-A环为扭船式构象。

The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers.

作者信息

Zeng Ziyu, Qasem Ashraf M A, Kociok-Köhn Gabriele, Rowan Michael G, Blagbrough Ian S

机构信息

Department of Pharmacy and Pharmacology, University of Bath Bath BA2 7AY UK

Material and Chemical Characterisation (MC2), University of Bath Bath BA2 7AY UK.

出版信息

RSC Adv. 2020 May 18;10(32):18797-18805. doi: 10.1039/d0ra03811c. eCollection 2020 May 14.

DOI:10.1039/d0ra03811c
PMID:35518334
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9053968/
Abstract

The skeletal conformations of naturally occurring norditerpenoid alkaloids fix their substituent functional groups in space, thereby directing their bioactivities. Solution conformations of the A-rings of 4 selected norditerpenoid alkaloid free bases: mesaconitine, karacoline (karakoline), condelphine, and neoline (bullatine B), were analysed by NMR spectroscopy and single-crystal X-ray crystallography. They adopt twisted-chair, twisted-boat, twisted-boat, twisted-boat conformations, respectively. That the A-ring is stabilised in a boat conformer by an intramolecular H-bond from 1α-OH to the -ethyl tertiary amine is also confirmed in the condelphine single crystal data. The conformations are a result of through-space repulsion between 12-H and atoms attached to C1 (in the equatorial positions). This causes the A-rings with 1α-OR always to be twisted whether in a chair or a boat conformation. The impact of these studies is in providing a detailed understanding of the shape of the A-ring of these important biologically active natural product alkaloids.

摘要

天然存在的去甲二萜生物碱的骨架构象在空间中固定其取代基官能团，从而指导它们的生物活性。通过核磁共振光谱和单晶X射线晶体学分析了4种选定的去甲二萜生物碱游离碱（中乌头碱、卡拉可林、中乌宁碱和新乌宁碱）A环的溶液构象。它们分别采用扭船式、扭椅式、扭船式、扭船式构象。在中乌宁碱的单晶数据中也证实了A环通过从1α-OH到乙基叔胺的分子内氢键稳定在船式构象中。这些构象是12-H与连接在C1（处于赤道位置）上的原子之间的空间排斥作用的结果。这使得带有1α-OR的A环无论处于椅式还是船式构象总是扭曲的。这些研究的意义在于详细了解这些重要的具有生物活性的天然产物生物碱A环的形状。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/53b06613dff5/d0ra03811c-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/f01a3e3c27f2/d0ra03811c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/17595cc9e6b3/d0ra03811c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/3abaee214121/d0ra03811c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/027648256abe/d0ra03811c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/43fbc3d21393/d0ra03811c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/a1a0979ff9fd/d0ra03811c-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/94569108857b/d0ra03811c-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/9425540ca437/d0ra03811c-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/53b06613dff5/d0ra03811c-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/f01a3e3c27f2/d0ra03811c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/17595cc9e6b3/d0ra03811c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/3abaee214121/d0ra03811c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/027648256abe/d0ra03811c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/43fbc3d21393/d0ra03811c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/a1a0979ff9fd/d0ra03811c-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/94569108857b/d0ra03811c-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/9425540ca437/d0ra03811c-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ec9/9053968/53b06613dff5/d0ra03811c-f9.jpg

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