Spiralosides A-C, Three New C27-Steroidal Glycoalkaloids from the Fruits of Solanum spirale

Dan Li; Yun-Li Zhao; Xu-Jie Qin; Lu Liu; Xing-Wei Yang; Ying-Ying Chen; Bei Wang; Xin Wei; Ya-Ping Liu; Xiao-Dong Luo

doi:10.1007/s13659-016-0103-9

Spiralosides A-C, Three New C27-Steroidal Glycoalkaloids from the Fruits of Solanum spirale

Nat Prod Bioprospect. 2016 Aug;6(4):225-31. doi: 10.1007/s13659-016-0103-9. Epub 2016 Jun 18.

Authors

Dan Li^{1

2}, Yun-Li Zhao¹, Xu-Jie Qin¹, Lu Liu^{1

2}, Xing-Wei Yang¹, Ying-Ying Chen^{1

2}, Bei Wang^{1

2}, Xin Wei^{1

2}, Ya-Ping Liu³, Xiao-Dong Luo⁴

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.
² University of Chinese Academy of Sciences, Beijing, 100039, China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China. liuyaping@mail.kib.ac.cn.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China. xdluo@mail.kib.ac.cn.

Abstract

Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods. On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively. The total alkaloids of S. spirale have been screened for their antitussive and expectorant effects in intact animal model.

Keywords: Solanaceae; Solanum spirale; Spiralosides A–C.