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Planta Med 2022; 88(11): 913-920
DOI: 10.1055/a-1585-5877
Biological and Pharmacological Activity
Original Papers

Flavanols and Flavanes from Crinum asiaticum and Their Effects on LPS Signaling Pathway Through the Inhibition of NF-κB Activation

Kiep Minh Do
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
,
Min-Kyoung Shin
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
,
Takeshi Kodama
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
,
Nwet Nwet Win
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
,
Prema Prema
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
2   Department of Chemistry, University of Yangon, Yangon, Myanmar
,
Hien Minh Nguyen
3   Faculty of Pharmacy, Ton Duc Thang University, Ho Chi Minh City, Vietnam
,
Yoshihiro Hayakawa
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
,
Hiroyuki Morita
1   Institute of Natural Medicine, University of Toyama, Toyama, Japan
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Abstract

Three new flavanols, (2R,3S)-7-methoxy-flavan-3-ol (1), (2R,3S)-7-hydroxy-flavan-3-ol (2), and (2R,3S)-2′-hydroxy-7-methoxy-flavan-3-ol (3), together with two known flavans (4 and 5), were isolated from the chloroform extract of Crinum asiaticum. Their structures were elucidated by various spectroscopic methods, including 1D and 2D NMR, HR-ESI-MS, and CD data. The isolated compounds 1 and 3−5 showed inhibitory activity toward LPS-induced nitric oxide (NO) production. Further investigation of the NF-κB pathway mechanisms indicated that 1 and 3−5 inhibited the LPS-induced IL-6 production and p65 subunit phosphorylation of NF-κB in RAW264.7 cells, with an effective dose of 10 µM.

Key words

Crinum asiaticum - flavans - flavanols - NO inhibition - NF-κB pathway

Supporting Information

    Spectra (1D and 2D NMR, HR-ESI-MS) of compounds 1–3 and LC-MS/MS analysis of C. asiaticum extracts are available as Supporting Information.

  • Supporting Information


Publication History

Received: 15 March 2021

Accepted after revision: 03 August 2021

Article published online:
02 September 2021

© 2021. Thieme. All rights reserved.

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