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

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.

Selective Extraction of Piceatannol from Passiflora edulis by-Products: Application of HSPs Strategy and Inhibition of Neurodegenerative Enzymes

“…Two studies using P. edulis reported trans-resveratrol in ethanolic seed extracts [53] and resveratrol, with the use of acetone extraction assisted by the ultrasound of P. edulis by-products [34]. Other stilbenes identified in this work were classified as piceatannol derivatives, and were recently found in P. edulis by Pan et al [43], named passiflorinol C/D-type isomers, cyperusphenol B, passiflorinol A/B-type isomers, cyperusphenol D, and cassigarol D. The same authors elucidate the potential of such compounds as hypoglycemic agents due to the promising results in α-glucosidase inhibitory activities, where passiflorinol B exhibited the best results, achieving an IC 50 = 1.7 µM. It is worth noting that this stilbene has rarely been cited in literature.…”

Rapid enrichment and separation of two novel minor phenols from Malus hupehensis utilizing liquid–liquid extraction with three‐phase solvent system and high‐speed counter‐current chromatography based on the polarity parameter

“…As well known, the preparation of minor compounds is the challenge for various conventional solid sorbent-based chromatography techniques. HSCCC has been extensively applied for the separation of various natural compounds, and provided a nice candidate [8][9][10][11][12]. The selection of solvent system with "sweet point" (K = 1.0) is the foremost operation before the HSCCC separation.…”

“…The structural diversity of phenols produced by this genus have prompted researchers to examine their characteristics and minor components. Owing to irreversible adsorption on a solid support, enriching and separating minor components through conventional solid sorbent-based chromatography techniques using silica gel columns and RP HPLC columns are difficult [8][9][10].…”

Lesser Investigated Natural Ingredients for the Management of Obesity

“…In a pilot clinical study C. rotundus extract showed bodyweight reduction, a significant decrease in waist circumference, and BMI with no adverse events [104]. Piceatannol and its dimer Scirpusin B are also found in passion fruit (Passiflora edulis) seeds in larger amounts [105,106]. Piceatannol has been shown to inhibit adipogenesis of preadipocytes 3T3-L1, especially in the first 24 h of adipogenesis by inhibiting the cell cycle progression of preadipocytes.…”