2. Academic Validation
  3. Leucoflavonine, a new bioactive racemic flavoalkaloid from the leaves of Leucosceptrum canum

Leucoflavonine, a new bioactive racemic flavoalkaloid from the leaves of Leucosceptrum canum

  • Bioorg Med Chem. 2019 Jan 15;27(2):442-446. doi: 10.1016/j.bmc.2018.12.023.
Ling Feng 1,  Yu Zhang 2,  Yan-Chun Liu 2,  Yan Liu 2,  Shi-Hong Luo 2,  Chun-Shuai Huang 2,  Sheng-Hong Li 3
Affiliations

Affiliations

  • 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Forestry School, Southwest Forestry University, Kunming 655024, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.
  • 2 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, PR China.
  • 3 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, PR China. Electronic address: shli@mail.kib.ac.cn.
PMID: 30579802 DOI: 10.1016/j.bmc.2018.12.023
Abstract

A new flavoalkaloid racemate, leucoflavonine (1), together with its flavonoid precursor pectolinarigenin (2), was isolated from the leaves of Leucosceptrum canum collected from Tibet. Its structure was established by comprehensive spectroscopic analysis. Chrial separation of the enantiomers of 1 was achieved, and their absolute configurations were determined as S-(+)- and R-(-)-leucoflavonines ((+)-1a and (-)-1b) by comparison of their computational and experimental optical rotations. Biological assays indicated that both (+)-1a and (-)-1b exhibited inhibitory activity against acetylchlorinesterase (AChE) in vitro (IC50 = 68.0 ± 8.6 and 18.3 ± 1.8 μM, respectively). Moreover, (-)-1b displayed cytotoxicity against human hepatoma cells HepG2 (IC50 = 52.9 ± 3.6 μM), and inhibited the production of interleukelin-2 (IL-2) in Jurkat cells (IC50 = 16.5 ± 0.9 μM), while (+)-1a showed no obvious activity in these assays.

Keywords

Biological activities; Flavoalkaloid; Lamiaceae; Leucoflavonine; Leucosceptrum canum.

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