Eudesmane-type and agarospirane-type sesquiterpenes from agarwood of Aquilaria agallocha. (December 2021)

• Record Type: Journal Article
• Authors: Xie, Yanqiao; Song, Leixin; Li, Chunge; Yang, Yingbo; Zhang, Siyu; Xu, Hong; Wang, Zhengtao; Han, Zhuzhen; Yang, Li
• Is Part Of: Phytochemistry. Volume 192(2021)
• Publication Date: 2021-12
• Subjects: Aquilaria agallocha Roxb. -- Thymelaeaceae -- Eudesmane-type sesquiterpenes -- Agarospirane-type sesquiterpenes -- Anti-inflammatory activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112920
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Eleven previously unreported sesquiterpenes, including nine eudesmane-type (agalleudesmanol A-I) and two agarospirane-type sesquiterpenes (agarospiranic aldehyde A-B), together with eight known sesquiterpenes, were isolated from the agarwood of Aquilaria agallocha Roxb. The structures were established based on extensive spectroscopic analyses, including infrared (IR), high-resolution electrospray ionisation mass spectrometry (HRESIMS), nuclear magnetic resonance (NMR), X-ray diffraction, quantum chemical calculations based on empirical electronic circular dichroism (ECD) data, and DP4+ probability analysis. The bioactivity of these undescribed compounds against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 cells was evaluated. Compounds 1 and 2 exhibited significant anti-inflammatory activities, with IC 50 values of 5.46–14.07 μ M (aminoguanidine as positive control, IC 50 20.33 ± 1.08 μ M). Graphical abstract: Image 1 Highlights: Eleven undescribed sesquiterpenes were isolated from Aquilaria agallocha Roxb . Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations were defined by X-ray crystallography and ECD calculation. Two compounds showed significant anti-inflammatory activities.