Dihydrochalcone Glycosides From Balanophora harlandii

Abstract

Dihydrochalcone class of compounds displays good performance in taste modulation on several natural non-caloric/low-caloric sweeteners. Compounds such as hesperetin dihydrochalcone (HDC) and hesperetin dihydrochalcone-4′- O-β-d-glucoside (HDCG) were reported to be found in nature. However, the evidence was not complete to support their natural presence. The Coca-Cola Company has been working on the identification of natural sources of reported dihydrochalcones, as well as the exploration of new natural dihydrochalcones. During the investigation on plant Balanophora harlandii, the natural presence of HDCG was confirmed, and 3 new analogs have been identified. In this paper, detailed structural elucidation of known HDCG and 3 new analogs have been described.

1, 2‐trans‐Stereoselective 7‐O‐Glycosylation of Flavonoids with Unprotected Pyranoses by Mitsunobu Reaction

“…The utility of our methodology was further demonstrated by accessing a wide range of natural flavonoid glycosides (Scheme 2). Thus, flavonoid glycosides such as diosmetin‐7‐ O ‐ β ‐D‐xylopyranoside ( 4 ), [29] naringenin‐7‐ O ‐ β ‐D‐xylopyrano‐side ( 5 ), [30] chrysin‐7‐ O ‐ β ‐D‐glucopyranoside ( 6 ), [31] hesperetin‐7‐ O ‐ β ‐D‐glucopyranoside ( 7 ), [32] phloretin‐4’‐ O ‐ β ‐D‐glucopy‐ranoside (trilobatin) ( 8 ), [33] and naringenin‐7‐ O ‐ β ‐D‐glucoside (prunin) ( 9) [34] were obtained in 42% to 76% yields from commercially available D‐xylose ( 1 d ), D‐glucose ( 1 f ), chrysin ( 2 a ), naringenin ( 2 b ), diosmetin ( 2 c ) hesperetin ( 2 d ), and phloretin ( 2 e ) in one step under Mitsunobu conditions.…”

“…The utility of our methodology was further demonstrated by accessing a wide range of natural flavonoid glycosides (Scheme 2). Thus, flavonoid glycosides such as diosmetin-7-O-β-D-xylopyranoside (4), [29] naringenin-7-O-β-D-xylopyrano-side (5), [30] chrysin-7-O-β-D-glucopyranoside (6), [31] hesperetin-7-O-β-D-glucopyranoside (7), [32] phloretin-4'-O-β-D-glucopy-ranoside (trilobatin) (8), [33] and naringenin-7-O-β-D-glucoside (prunin) (9) [34] were obtained in 42% to 76% yields from commercially Additionally, we also investigated the possibility to achieve regioselectivity among different types of hydroxyl groups on the glycosyl acceptors under Mitsunobu conditions (Scheme 3). Therefore, methyl 3,4-dihydroxybenzoate (10) with adjacent hydroxyl groups was employed as a glycosyl acceptor and…”

Products for Sportspeople Containing Constituents Derived from the Common Bean Phaseolus vulgaris L. (Fabaceae)—A Narrative Literature Review

“…A considerable number of nutritive compositions for sportspeople, such as bars [64], biscuits [65,66], cakes [67], chips [68], and frozen sweets [69], have been presented. Other scientists have patented nutritive sport drinks [70][71][72][73][74][75][76][77][78][79]. Smith, et al [80] patented a functional food paste, which can be used as a nougat-like filling for bars, cookies, and cupcakes, as well as a savoury filling for baked products (e.g., crackers, pretzels, or bread).…”

Microbial-Driven Synthesis and Hydrolysis of Neohesperidin Dihydrochalcone: Biotransformation Process and Feasibility Investigation

“…Our methods effectively overcame the disadvantages of harsh acidic reaction conditions or enzymatic methods with high costs in commonly used methods. , These achievements greatly encouraged us to further expand the accessible scope of microbial biotransformation for dihydrochalcone modifications. The application of whole-cell catalysts in the structural modification hydrolysis of NHDC contributes to the production of hydrolysis products, hesperetin dihydrochalcone-7- O -glucoside (HDC-G) and hesperetin dihydrochalcone (HDC) with high sweetness, enhanced solubility, and good biological activity, while retaining the basic skeleton of NHDC . This technology expands the application scope of NHDC in industrial production, allowing HDC-G and HDC to have the sensory characteristics and similar sweetness of NHDC, and they can be utilized as sweeteners or biologically active compounds in various fields such as food and pharmaceutical production.…”