Further prenylated anthranoids from Harungana madagascariensis

Ya-Ping Huang; Yuan-Yu Zhao; Oluwatosin O Johnson; Jian Zhang; Ming Zhao; Chun-Tao Che; Zhi-Qi Yin

doi:10.1016/j.phytochem.2021.112711

Further prenylated anthranoids from Harungana madagascariensis

Phytochemistry. 2021 Jun:186:112711. doi: 10.1016/j.phytochem.2021.112711. Epub 2021 Mar 9.

Authors

Ya-Ping Huang¹, Yuan-Yu Zhao², Oluwatosin O Johnson³, Jian Zhang⁴, Ming Zhao⁵, Chun-Tao Che⁶, Zhi-Qi Yin⁷

Affiliations

¹ Department of TCMs Pharmaceuticals and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, People's Republic of China.
² Department of TCMs Pharmaceuticals and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, People's Republic of China; Laboratory of Translational Medicine, Affiliated Hospital of Integrated Traditional Chinese and Western Medicine, Nanjing University of Chinese Medicine, Nanjing, 210028, People's Republic of China.
³ Department of Pharmaceutical Chemistry, University of Lagos, CMUL Campus, Lagos, 100254, Nigeria; Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, Illinois, 60612, United States.
⁴ Laboratory of Translational Medicine, Affiliated Hospital of Integrated Traditional Chinese and Western Medicine, Nanjing University of Chinese Medicine, Nanjing, 210028, People's Republic of China.
⁵ Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, Illinois, 60612, United States; Traditional Chinese Medicine Resources Industrialization Process Collaborative Innovation Center, Nanjing University of Chinese Medicine, Nanjing, 210023, People's Republic of China.
⁶ Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, Illinois, 60612, United States.
⁷ Department of TCMs Pharmaceuticals and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, People's Republic of China. Electronic address: cpu-yzq@cpu.edu.cn.

PMID: 33711738
DOI: 10.1016/j.phytochem.2021.112711

Abstract

Ten undescribed anthranoids, including three anthraquinone acetals as racemic mixtures, (±)-kenganthranol G-I, and seven prenylated anthranols, (±)-kenganthranol J-M and harunganol G-I, together with thirteen known compounds, were isolated from the stem bark of Harungana madagascariensis. The structures of (±)-kenganthranol G and (±)-kenganthranol J were confirmed by X-ray crystallography. (±)-Kenganthranol G was separated into (+)-kenganthranol G and (-)-kenganthranol G by chiral HPLC and their absolute configurations were established by electronic circular dichroism. (±)-Kenganthranol L displayed α-glucosidase inhibitory activity with an IC₅₀ of 4.4 μM.

Keywords: Anthranoid; Harungana madagascariensis; Hypericaceae; Prenyl; α-Glucosidase inhibition.

MeSH terms

Anthraquinones
Clusiaceae*
Molecular Structure

Substances

Anthraquinones