4-[2-O-11Z-Octadecenoyl-β-glucopyranosyl]-4, 4′-diapolycopene-4, 4′-dioic acid and 4-[2-O-9Z-hexadecenoyl-β-glucopyranosyl]-4, 4′-diapolycopene-4, 4′-dioic acid: new C30-carotenoids produced by Methylobacterium. Issue 21 (20th May 2015)

• Record Type: Journal Article
• Authors: Osawa, Ayako; Kaseya, Yui; Koue, Nao; Schrader, Jens; Knief, Claudia; Vorholt, Julia A.; Sandmann, Gerhard; Shindo, Kazutoshi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 21(2015)
• Page Start: 2791
• Page End: 2794
• Publication Date: 2015-05-20
• Subjects: Carotenoid -- 4, 4′-Diapolycopenedioic acid -- Methylobacterium -- Singlet oxygen quenching activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.042
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: During the course of screening for antioxidative carotenoids from bacteria, we isolated two novel C30 carotenoids, 4-[2- O -11 Z -octadecenoyl-β-glucopyranosyl]-4, 4′-diapolycopene-4, 4′-dioic acid (1 ) and 4-[2- O -9 Z -hexadecenoyl-β-glucopyranosyl]-4, 4′-diapolycopene-4, 4′-dioic acid (2 ), from Methylobacterium strains. These compounds possessed the common structure 'β-d -glucosyl 4, 4′-diapolycopene-4, 4′-dioic acid', while the fatty acid attached at the C-2 position of glucose differed. In the singlet oxygen ( 1 O2 ) quenching model, both1 and2 exhibited potent antioxidative activities (IC50 : 3.2 and 3.6 μM, respectively).