Sesquiterpenes from the fruits of Piper longum L. and their anti-inflammatory activity

Guanghui Gou; Nannan Xu; Hongliang Li; Jun Li; Haji Akber Aisa

doi:10.1016/j.fitote.2024.106260

Sesquiterpenes from the fruits of Piper longum L. and their anti-inflammatory activity

Fitoterapia. 2024 Dec:179:106260. doi: 10.1016/j.fitote.2024.106260. Epub 2024 Oct 15.

Authors

Guanghui Gou¹, Nannan Xu², Hongliang Li², Jun Li³, Haji Akber Aisa⁴

Affiliations

¹ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, China; University of Chinese Academy of Sciences, Beijing 100039, China.
² State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, China.
³ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, China; University of Chinese Academy of Sciences, Beijing 100039, China. Electronic address: lijun702@ms.xjb.ac.cn.
⁴ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, China; University of Chinese Academy of Sciences, Beijing 100039, China; College of Pharmacy, Xinjiang Medical University, Urumqi 830011, China. Electronic address: haji@ms.xjb.ac.cn.

PMID: 39413978
DOI: 10.1016/j.fitote.2024.106260

Abstract

The fruits of Piper longum are called long pepper, which are well-known culinary spice as well as traditional medicine. In present work, thirteen sesquiterpenes including four undescribed compounds were isolated from P. longum fruits. Compound 1 was a rare methylated bisabolane-type sesquiterpene. Compounds (-)-3 and (+)-3 were a pair of enantiomers of an uncommon humulane which were separated by chiral HPLC. The absolute configurations of compounds 1-3 were confirmed through the means of spectroscopic data analyses, ¹³C NMR calculations employing DP4+ probability analyses, and ECD calculations. Compounds 2 and 11 presented moderated inhibitory effect on the NO release in LPS-induced RAW264.7 cells with IC₅₀ values of 30.65 ± 0.90 and 38.48 ± 2.42 μM, respectively. Above results enriched the chemical information of P. longum fruits, and meanwhile provided scientific evidences for the anti-inflammatory function of P. longum fruits.

Keywords: Absolute configuration; Anti-inflammatory; Methylated bisabolane-type sesquiterpene; Piper longum L.; Sesquiterpenes.

MeSH terms

Animals
Anti-Inflammatory Agents* / chemistry
Anti-Inflammatory Agents* / isolation & purification
Anti-Inflammatory Agents* / pharmacology
China
Fruit* / chemistry
Mice
Molecular Structure
Nitric Oxide / metabolism
Phytochemicals* / isolation & purification
Phytochemicals* / pharmacology
Piper* / chemistry
RAW 264.7 Cells
Sesquiterpenes* / chemistry
Sesquiterpenes* / isolation & purification
Sesquiterpenes* / pharmacology

Substances

Anti-Inflammatory Agents
Sesquiterpenes
Phytochemicals
Nitric Oxide