Mangiterpenes A–C and 2′, 3′-seco-manginoid C, four sesquiterpene/monoterpene–shikimate–conjugated spirocyclic meroterpenoids from Guignardia mangiferae. (August 2019)

• Record Type: Journal Article
• Authors: Chen, Keliang; Chen, Chunmei; Guo, Jieru; Sun, Weiguang; Liu, Junjun; Yang, Jing; Liu, Xiulan; Wang, Jianping; Luo, Zengwei; Zhu, Hucheng; Zhang, Yonghui
• Is Part Of: Phytochemistry. Volume 164(2019)
• Page Start: 236
• Page End: 242
• Publication Date: 2019-08
• Subjects: Guignardia mangiferae -- Spirocyclic meroterpenoids -- Anti-inflammatory -- Nuclear factor-κB (NF-κB); Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.05.018
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Mangiterpenes A–C and 2′, 3′- seco -manginoid C, four undescribed sesquiterpene/monoterpene–shikimate–conjugated meroterpenoids with spiro ring systems, were isolated from Guignardia mangiferae . The structures and absolute configurations of these compounds were established by comprehensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Mangiterpenes A–C represent the first examples of sesquiterpene–shikimate-conjugated spirocyclic meroterpenoids, and 2′, 3′- seco -manginoid C features an unexpected 2′, 3′- seco -manginoids skeleton. Mangiterpene C strongly inhibited the production of NO inducted by LPS, with an IC50 value of 5.97 μ M. It showed an anti-inflammatory effect by means of blocking in the NF-κB signaling pathway and decreasing the expression of inflammatory mediators. Graphical abstract: Four undescribed sesquiterpene/monoterpene–shikimate–conjugated meroterpenoids with spiro ring systems were isolated from Guignardia mangiferae . Image 1 Highlights: Four undescribed meroterpenoids were isolated from Guignardia mangiferae. Mangiterpenes A–C are sesquiterpene–shikimate-conjugated spirocyclic meroterpenoids. Mangiterpene C strongly inhibited the production of NO inducted by LPS (IC50 = 5.97 μ M).