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Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum
Chen, QB (Chen, Qi-Bin); Gao, J (Gao, Jie); Zou, GA (Zou, Guo-An); Xin, XL (Xin, Xue-Lei); Aisa, HA (Aisa, Haji Akber)
2018
Source PublicationJOURNAL OF NATURAL PRODUCTS
ISSN0163-3864
Volume81Issue:6Pages:1474-1482
Abstract

Fifteen new piperidine derivatives, pyracyclumines A-J (1-10), including five pairs of enantiomers, (+)-1/(-)-1 to (+)-5/(-)-5, together with three known compounds, agrocybenine (11), 4,6,6-trimethyl-5,6-dihydro-2(1H)-pyridone (12), and 3,5,5-trimethyl-1,5-dihydro-2H-pyrrol-2-one (13), were isolated from the roots of Anacyclus pyrethrum. Pyracyclumines A, B, and H (1, 2, and 8) possess a novel 6/5/6/6 dimeric piperidine skeleton, a unique 6/5/6 dimeric piperidine skeleton, and a 1,4,6-triazaindan skeleton, respectively. Pyracyclumine C (3) is based on a rare cyclopentane-piperidine framework. The structures of the isolated compounds were established by analysis of their NMR and HRESIMS data. The racemic pyracyclumines A-E (1-5) were further separated by chiral HPLC to give the enantiomers (+)-1/ (-)-1 to (+)-5/(-)-5, for which the absolute configurations were determined by comparison of their experimental and calculated ECD spectra. The plausible biogenetic pathways of these piperidine alkaloids were proposed starting from the basic units of compounds 12 and 13. All of the isolated compounds were tested for their inhibitory effects on menin-mixed lineage leukemia 1 protein-protein interaction.

DOI10.1021/acs.jnatprod.8b00239
Indexed BySCI
WOS IDWOS:000436527100021
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5479
Collection省部共建新疆特有药用资源利用重点实验室
资源化学研究室
Corresponding AuthorAisa, HA (Aisa, Haji Akber)
Affiliation1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zone, Urumqi 830011, Peoples R China
2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, State Key Lab Basis Xinjiang Indigenous Med Plant, Urumqi 830011, Peoples R China
Recommended Citation
GB/T 7714
Chen, QB ,Gao, J ,Zou, GA ,et al. Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum[J]. JOURNAL OF NATURAL PRODUCTS,2018,81(6):1474-1482.
APA Chen, QB ,Gao, J ,Zou, GA ,Xin, XL ,&Aisa, HA .(2018).Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum.JOURNAL OF NATURAL PRODUCTS,81(6),1474-1482.
MLA Chen, QB ,et al."Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum".JOURNAL OF NATURAL PRODUCTS 81.6(2018):1474-1482.
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