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Preparative Isolation of Piceatannol Derivatives from Passion Fruit (Passiflora edulis) Seeds by High-Speed Countercurrent Chromatography Combined with High-Performance Liquid Chromatography and Screening for α-Glucosidase Inhibitory Activities
- Source :
- Journal of Agricultural and Food Chemistry. 68:1555-1562
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- Passiflora edulis Sims (passion fruit) seeds are often discarded as byproducts during juice processing. In fact, the seeds are of considerable commercial value in the food and cosmetics industry because of their rich polyphenols, especially piceatannol. In this study, high-speed countercurrent chromatography (HSCCC) was applied for the separation of stilbene polyphenols from passion fruit seeds. The n-hexane-ethyl acetate-methanol-water (1:2:1:2.8, v/v) was found to be the optimum two-phase solvent for the preparation of two major stilbenes, scirpusin B (8) and piceatannol (9) with purities of 90.2% and 94.8%, respectively. In addition, a continuous semipreparative HPLC was applied to further purify the HSCCC fractions containing minor stilbenes and obtain four new piceatannol derivatives (1-4) along with three known ones (5-7). The structures of these new compounds were determined using spectroscopic methods, including NMR, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and circular dichroism (CD). The isolated compounds were evaluated for α-glucosidase inhibitory activities in vitro. The result suggested that all of them exhibited more significant activity than acarbose, and passiflorinol B (2) had the strongest activity, with a IC50 value of 1.7 μM.
- Subjects :
- 0106 biological sciences
Piceatannol
Circular dichroism
Chromatography
biology
Electrospray ionization
010401 analytical chemistry
General Chemistry
biology.organism_classification
01 natural sciences
High-performance liquid chromatography
0104 chemical sciences
Solvent
Passiflora
chemistry.chemical_compound
Countercurrent chromatography
chemistry
Polyphenol
General Agricultural and Biological Sciences
010606 plant biology & botany
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 68
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi...........113ebd5b08f5f422ae0dc137816e2a4f