Unusual immunosuppressive pyridine-containing bisnor- (c23), tetranor- (c21) and pentanor- (c20) sesterterpenoids from Tibetan Leucosceptrum canum

Man Li; Ling Feng; Han Zhang; Yan-Chun Liu; Ting-Ting Zhou; Yu Zheng; Kai Guo; Yan Liu; Sheng-Hong Li

doi:10.1039/D4OB00334A

Unusual immunosuppressive pyridine-containing bisnor- (c₂₃), tetranor- (c₂₁) and pentanor- (c₂₀) sesterterpenoids from Tibetan Leucosceptrum canum†

Man Li,‡^ad Ling Feng,‡^ac Han Zhang,‡^ad Yan-Chun Liu,^ad Ting-Ting Zhou,^ad Yu Zheng,^a Kai Guo,*^b Yan Liu^b and Sheng-Hong Li

*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China
E-mail: shli@mail.kib.ac.cn, shli@cdutcm.edu.cn

^b State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China
E-mail: guokai@cdutcm.edu.cn

^c School of Forestry, Southwest Forestry University, Kunming 650224, P. R. China

^d University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Abstract

An unusual pyridine-containing sesterterpenoid, leucosceptrodine (1), and five new nor-leucosceptrane sesterterpenoids, including bisnor- (C₂₃, 2), tetranor- (C₂₁, 3) and pentanor- (C₂₀, 4–6) skeletons, were isolated from the leaves of Tibetan Leucosceptrum canum. Their structures including their absolute configurations were determined by extensive spectroscopic analyses and quantum chemical calculations. A single crystal of one epimer (5) was crystallized from a pair of inseparable epimers, and its structure including its absolute configuration was determined by X-ray crystallographic analysis. The immunosuppressive activities of compounds 1–4 with different potencies were evaluated by inhibiting the secretion of cytokines TNF-α and IL-6 in LPS-induced RAW264.7 macrophages.

Supplementary files

Article information

DOI: https://doi.org/10.1039/D4OB00334A
Article type: Paper
Submitted: 01 Mar 2024
Accepted: 21 Mar 2024
First published: 21 Mar 2024

Download Citation

Org. Biomol. Chem., 2024,22, 3019-3024

Permissions

Request permissions

Unusual immunosuppressive pyridine-containing bisnor- (c₂₃), tetranor- (c₂₁) and pentanor- (c₂₀) sesterterpenoids from Tibetan Leucosceptrum canum

M. Li, L. Feng, H. Zhang, Y. Liu, T. Zhou, Y. Zheng, K. Guo, Y. Liu and S. Li, Org. Biomol. Chem., 2024, 22, 3019 DOI: 10.1039/D4OB00334A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Organic & Biomolecular Chemistry

Unusual immunosuppressive pyridine-containing bisnor- (c₂₃), tetranor- (c₂₁) and pentanor- (c₂₀) sesterterpenoids from Tibetan Leucosceptrum canum†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Unusual immunosuppressive pyridine-containing bisnor- (c₂₃), tetranor- (c₂₁) and pentanor- (c₂₀) sesterterpenoids from Tibetan Leucosceptrum canum

Social activity

Search articles by author

Spotlight

Advertisements

Organic & Biomolecular Chemistry