Angustifolinoid A, a macrocyclic flavonoid glycoside from Elaeagnus angustifolia flowers. Issue 26 (27th June 2018)

• Record Type: Journal Article
• Authors: Chen, Xiaoyu; Liu, Yushuang; Chen, Guangying; Gong, Chi; Li, Shengge; Hua, Huiming; Yuan, Tao
• Is Part Of: Tetrahedron letters. Volume 59:Issue 26(2018)
• Page Start: 2610
• Page End: 2613
• Publication Date: 2018-06-27
• Subjects: Angustifolinoid -- Flavonoid glycoside -- Elaeagnus angustifolia -- Oxidative coupling -- Cyclooxygenase; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.074
• Languages: English
• ISSNs: 0040-4039

Abstract

Highlights: A novel macrocyclic flavonoid glycoside, angustifolinoid A (1 ), was isolated from Elaeagnus angustifolia flowers. Angustifolinoid A (1 ) was determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. Angustifolinoid A (1 ) is baring an unprecedented 13-membered heterocyclic ring framework. Graphical abstract: Abstract: A novel macrocyclic flavonoid glycoside, angustifolinoid A (1 ), featuring an unprecedented 13-membered heterocyclic ring moiety, along with a known flavonoid glycoside, tiliroside (2 ), were isolated from Elaeagnus angustifolia flowers. Their structures were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. Biosynthesis analysis indicated that compound 1 might be derived from compound 2 via a key enzymatic intramolecular oxidative coupling. Compounds 1 and 2 showed inhibitory activities against cyclooxygenases, COX-1 and COX-2.