Isosteroidal alkaloids from the bulbs of Fritillaria tortifolia

Zhu Hu; Jian-Fa Zong; Abulimiti Yili; Mei-Hua Yu; Haji Akber Aisa; Ai-Jun Hou

doi:10.1016/j.fitote.2018.10.019

Isosteroidal alkaloids from the bulbs of Fritillaria tortifolia

Fitoterapia. 2018 Nov:131:112-118. doi: 10.1016/j.fitote.2018.10.019. Epub 2018 Oct 16.

Authors

Zhu Hu¹, Jian-Fa Zong¹, Abulimiti Yili², Mei-Hua Yu¹, Haji Akber Aisa³, Ai-Jun Hou⁴

Affiliations

¹ Department of Pharmacognosy, School of Pharmacy, State Key Laboratory of Medical Neurobiology, Fudan University, Shanghai 201203, PR China.
² Key Laboratory of Plant Resources and Chemistry in Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China.
³ Key Laboratory of Plant Resources and Chemistry in Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China. Electronic address: haji@ms.xjb.ac.cn.
⁴ Department of Pharmacognosy, School of Pharmacy, State Key Laboratory of Medical Neurobiology, Fudan University, Shanghai 201203, PR China. Electronic address: ajhou@shmu.edu.cn.

PMID: 30336193
DOI: 10.1016/j.fitote.2018.10.019

Abstract

Three new isosteroidal alkaloids, frititorines A-C (1-3), were isolated from the bulbs of Fritillaria tortifolia, together with ten known ones (4-13). Their structures were elucidated by extensive spectroscopic analyses, chemical methods, and single-crystal X-ray crystallographic analysis. Compound 1 is the first 5β-cevanine alkaloid with a cis A/B ring junction from the Fritillaria genus. Compound 2 is the first example of glycosylated isosteroidal alkaloid N-oxide. Compound 1 showed significant relaxant effect on Ach-induced tracheal contraction with pA₂ and EC₅₀ values equivalent to those of aminophylline.

Keywords: Fritillaria tortifolia; Frititorines A-C; Isosteroidal alkaloids; Tracheal relaxant effect.

MeSH terms

Alkaloids / isolation & purification*
Animals
China
Fritillaria / chemistry*
In Vitro Techniques
Molecular Structure
Phytochemicals / isolation & purification
Plant Roots / chemistry*
Rats, Sprague-Dawley
Trachea / drug effects*

Substances

Alkaloids
Phytochemicals