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Benzophenones and biflavonoids from Rheedia edulis.

Journal of natural products (2010-10-30)
Ulyana Muñoz Acuña, Mario Figueroa, Adam Kavalier, Nikola Jancovski, Margaret J Basile, Edward J Kennelly
ABSTRACT

Two new polyisoprenylated benzophenones, 32-hydroxy-ent-guttiferone M (1) and 6-epi-guttiferone J (2), along with seven known compounds, 6-epi-clusianone (3), guttiferone A (4), xanthochymol (5), guttiferone E (6), isoxanthochymol (7), (+)-volkensiflavone (8), and (+)-morelloflavone (9), were identified from the seeds and rinds of Rheedia edulis. Compounds 1-3 and 5-9 have been isolated and identified from this species for the first time. The structures of the new compounds were elucidated mainly by analysis of their 1D and 2D NMR spectroscopic data, and their absolute configurations were determined by comparison of their experimental optical rotation and electronic circular dichroism measurements with those values predicted by DFT calculations. Compound 1 showed significant antioxidant activity in both DPPH and ABTS free radical scavenging assays, whereas compound 2 was inactive.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Gallic acid, 97.5-102.5% (titration)
Sigma-Aldrich
Gallic acid monohydrate, ≥99% (HPLC)
Sigma-Aldrich
Gallic acid monohydrate, ACS reagent, ≥98.0%