Undescribed sesquiterpene-diterpene heterodimers from the fruits of Aphanamixis polystachya selectively modulate inflammatory markers in RAW 264.7 cells

Bui Huu Tai; Ngo Anh Bang; Pham Hai Yen; Duong Thi Hai Yen; Nguyen Thi Cuc; Duong Thi Dung; Phan Thi Thanh Huong; Do Thi Trang; Nguyen Xuan Nhiem; Nguyen The Cuong; Phan Van Kiem

doi:10.1016/j.phytochem.2024.113997

Undescribed sesquiterpene-diterpene heterodimers from the fruits of Aphanamixis polystachya selectively modulate inflammatory markers in RAW 264.7 cells

Phytochemistry. 2024 Apr:220:113997. doi: 10.1016/j.phytochem.2024.113997. Epub 2024 Jan 19.

Affiliations

¹ Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
² Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam; Graduate University of Science and Technology, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
³ Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
⁴ Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam. Electronic address: phankiem@yahoo.com.

PMID: 38244960
DOI: 10.1016/j.phytochem.2024.113997

Abstract

Aphanapolystachones A-C (1-3), three undescribed sesquiterpene-diterpene heterodimers, were obtained from the fruits of Aphanamixis polystachya. Their structures and absolute configurations were identified by extensive analysis of HR-ESI-MS, NMR, experimental and TD-DFT calculated ECD spectra. The biosynthetic pathway of them was also proposed, which is produced by key intermolecular Diels-Alder [4 + 2]-cycloaddition reaction between a guaiane sesquiterpene and an acyclic diterpene. Compounds 1-3 inhibited NO production in LPS activated RAW 264.7 cells with the IC₅₀ values of 1.7 ± 0.2, 3.0 ± 0.3, 5.3 ± 0.3 μM, respectively, lower than that of the positive control L-NMMA (31.5 ± 2.6 μM). In addition, compounds 1-3 significantly reduced IL-6 secretion at diluted concentration of 0.4 μM.

Keywords: Anti-inflammatory activity; Aphanamixis polystachya; Aphanapolystachone; Meliaceae; Sesquiterpene-diterpene heterodimer.

MeSH terms

Animals
Diterpenes* / chemistry
Fruit / chemistry
Magnetic Resonance Spectroscopy
Meliaceae* / chemistry
Mice
Molecular Structure
RAW 264.7 Cells
Sesquiterpenes* / analysis
Sesquiterpenes* / pharmacology

Substances

Diterpenes
Sesquiterpenes