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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Benzophenones and biflavonoids from Rheedia edulis
Ulyana Muñoz Acuña1, Mario Figueroa, Adam Kavalier
1Department of Biological Sciences, Lehman College and The Graduate Center, The City University of New York, New York 10468, United States.
Two new polyisoprenylated benzophenones were discovered in Rheedia edulis seeds and rinds. One compound demonstrated significant antioxidant activity, while the other was inactive.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Medicinal Chemistry
Background:
- Rheedia edulis is a plant species known for its potential medicinal properties.
- Polyisoprenylated benzophenones are a class of natural products with diverse biological activities.
Purpose of the Study:
- To isolate and characterize new and known compounds from Rheedia edulis.
- To evaluate the antioxidant potential of the isolated compounds.
Main Methods:
- Isolation of compounds using chromatographic techniques.
- Structure elucidation using 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy.
- Determination of absolute configurations via optical rotation, electronic circular dichroism (ECD), and DFT calculations.
Main Results:
- Two new polyisoprenylated benzophenones, 32-hydroxy-ent-guttiferone M and 6-epi-guttiferone J, were identified.
- Seven known compounds were also isolated: 6-epi-clusianone, guttiferone A, xanthochymol, guttiferone E, isoxanthochymol, (+)-volkensiflavone, and (+)-morelloflavone.
- 32-hydroxy-ent-guttiferone M exhibited significant antioxidant activity in DPPH and ABTS assays, while 6-epi-guttiferone J was inactive.
Conclusions:
- The study expands the knowledge of the chemical constituents of Rheedia edulis.
- 32-hydroxy-ent-guttiferone M is a promising antioxidant compound.
- Further research into the biological activities of these isolated compounds is warranted.
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