Meroterpenoids with diverse structures and anti-inflammatory activities from Rhododendron anthopogonoides. (December 2020)

• Record Type: Journal Article
• Authors: Shi, Qing; Li, Teng-Teng; Wu, Yong-Mei; Sun, Xin-Yu; Lei, Chun; Li, Jing-Ya; Hou, Ai-Jun
• Is Part Of: Phytochemistry. Volume 180(2020)
• Publication Date: 2020-12
• Subjects: Rhododendron anthopogonoides Maxim. -- Ericaceae -- Meroterpenoids -- Anthoponoids A−I -- Daurichromene D -- Anti-inflammation; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112524
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Eight pairs of meroterpenoid enantiomers and four achiral meroterpenoids were isolated from Rhododendron anthopogonoides Maxim. Seventeen of them, named (+)-/(−)-anthoponoids A−G, (+)-daurichromene D, and anthoponoids H and I, are undescribed compounds with structural diversity. Their structures were characterized herein by a combined application of spectroscopic techniques, X-ray crystallographic analysis, ECD calculation, and the modified Mosher's method. (+)-/(−)-Anthoponoid A and anthoponoid I are the first Rhododendron meroterpenoids found to possess a hexahydroxanthene motif and a diterpene unit, respectively. Some isolates were identified as NF- κ B pathway inhibitors, and (+) - anthoponoid E, (−)-anthoponoid G, and anthoponoid H showed suppressive effects on LPS-induced inflammatory responses in RAW 264.7 macrophages. Graphical abstract: Eight pairs of meroterpenoid enantiomers and four achiral meroterpenoids were isolated from Rhododendron anthopogonoides, including seventeen undescribed compounds with structural diversity. Some of the meroterpenoids showed significant anti-inflammatory activities. Image 1 Highlights: Twenty meroterpenoids were isolated from Rhododendron anthopogonoides. Eight pairs of meroterpenoid enantiomers were resolved by chiral-phase HPLC . Seventeen meroterpenoids with structural diversity are undescribed. Some of the meroterpenoids showed significant anti-inflammatory activities.