Bi-2-(2-phenethyl)chromone derivatives from agarwood of Aquilaria filaria in the Philippines

Hong-Run Yang; Hao Wang; Pei Wang; Fang-Zheng Liu; Hong-Xing Chai; Cai-Hong Cai; Li Yang; Jing-Zhe Yuan; Bei Jiang; Wen-Li Mei; Hao-Fu Dai

doi:10.1016/j.phytochem.2024.114108

Bi-2-(2-phenethyl)chromone derivatives from agarwood of Aquilaria filaria in the Philippines

Phytochemistry. 2024 Jun:222:114108. doi: 10.1016/j.phytochem.2024.114108. Epub 2024 Apr 23.

Authors

Hong-Run Yang¹, Hao Wang², Pei Wang², Fang-Zheng Liu¹, Hong-Xing Chai¹, Cai-Hong Cai², Li Yang², Jing-Zhe Yuan², Bei Jiang³, Wen-Li Mei⁴, Hao-Fu Dai⁵

Affiliations

¹ International Joint Research Center of Agarwood, Haikou, 571101, PR China; Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan, Dali, 671000, PR China.
² International Joint Research Center of Agarwood, Haikou, 571101, PR China.
³ Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan, Dali, 671000, PR China.
⁴ National Key Laboratory for Tropical Crop Breeding, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, 571101, PR China; International Joint Research Center of Agarwood, Haikou, 571101, PR China. Electronic address: meiwenli@itbb.org.cn.
⁵ National Key Laboratory for Tropical Crop Breeding, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, 571101, PR China; International Joint Research Center of Agarwood, Haikou, 571101, PR China; Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan, Dali, 671000, PR China. Electronic address: daihaofu@itbb.org.cn.

PMID: 38663825
DOI: 10.1016/j.phytochem.2024.114108

Abstract

Twelve undescribed 2-(2-phenethyl)chromone dimers (1-12) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria in the Philippines, guided by a UHPLC-MS analysis. Their structures were elucidated by 1D NMR, 2D NMR, and HR-ESI-MS spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD spectra. Compounds 1, 2, 5 and 9-12 exhibited potent to moderate anti-inflammatory activity with IC₅₀ values in the range of 22.43 ± 0.86 to 53.88 ± 4.06 μM.

Keywords: 2-(2-Phenethyl)chromone dimers; Anti-inflammatory activity; Aquilaria filaria; Philippines; Thymelaeaceae.

MeSH terms

Animals
Chromones* / chemistry
Chromones* / isolation & purification
Chromones* / pharmacology
Crystallography, X-Ray
Dose-Response Relationship, Drug
Flavonoids
Mice
Molecular Structure
Philippines
Structure-Activity Relationship
Thymelaeaceae* / chemistry
Wood* / chemistry

Substances

Chromones
2-(2-phenylethyl)chromone
Flavonoids