4-[2-O-11Z-Octadecenoyl-b-glucopyranosyl]-4,40-diapolycopene-4, 40-dioic acid and 4-[2-O-9Z-hexadecenoyl-b-glucopyranosyl]-4, 40-diapolycopene-4,40-dioic acid: new C30-carotenoids produced by Methylobacterium

A. Osawa, Y. Kaseya, N. Koue, J. Schrader, C. Knief, J. A. Vorholt, G. Sandmann, K. Shindo

During the course of screening for antioxidative carotenoids from bacteria, we isolated two novel C30 carotenoids, 4-[2-O-11Z-octadecenoyl-β-glucopyranosyl]-4,4′-diapolycopene-4,4′-dioic acid (1) and 4-[2-O-9Z-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 (1O2) quenching model, both 1 and 2 exhibited potent antioxidative activities (IC50: 3.2 and 3.6 μM, respectively).

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