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A review of the state of sweeteners science: the natural artificial non-caloric sweeteners debate. and into the spotlight.
Crit Rev Biotechnol
September 2024
Institute of Food Science Research, CIAL (CSIC-UAM), Madrid, Spain.
The rapid increase in the worldwide prevalence of obesity and certain non-communicable diseases (NCDs), such as: cardiovascular diseases, cancers, chronic respiratory diseases, and diabetes, has been mainly attributed to an excess of sugar consumption. Although the potential benefits of the synergetic use of sweeteners have been known for many years, recent development based on synthesis strategies to produce sucrose-like taste profiles is emerging where biocatalyst approaches may be preferred to produce and supply specific sweetener compounds. From a nutritional standpoint, high-intensity sweeteners have fewer calories than sugars while providing a major sweet potency, placing them in the spotlight as valuable alternatives to sugar.
View Article and Find Full Text PDFMetabolism of Two Mogroside Isomers, Mogroside III and Mogroside IIIE, in Normal and Drug-Metabolizing Enzyme-Induced Rats.
J Agric Food Chem
December 2023
Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, No. 85, Yanshan Road, Yanshan District, Guilin 541006, China.
Mogrosides III () and IIIE () are two important bioactive cucurbitane-type triterpenoid triglycosides in the edible fruits of (Swingle), which are isomers and have only a minor difference in their structures. To clarify the effects of structural difference and drug-metabolizing-enzyme induction on their metabolism in vivo, their metabolites in normal rats and drug-metabolizing-enzyme-induced rats were tentatively identified and semiquantified by using the HPLC-DAD-ESI-IT-TOF-MS technique. Totally, 76, 78, 96, and 121 metabolites of mogrosides were identified in the NIII (normal rats orally administered with mogroside III), NIIIE (normal rats orally administered with mogroside IIIE), EIII (drug-metabolizing-enzyme-induced rats orally administered with mogroside III), and EIIIE (drug-metabolizing-enzyme-induced rats orally administered with mogroside IIIE) groups, respectively.
View Article and Find Full Text PDFProgress Toward the Asymmetric de Novo Synthesis of Lanostanes: A Counter Biomimetic Cucurbitane-to-Lanostane Type Transformation.
Tetrahedron
July 2023
Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, NH 03755, United States.
An oxidative rearrangement has been established that enables a cucurbitane-to-lanostane type rearrangement that is counter to known biomimetic transformations that proceed in an opposite direction by way of a lanostane-to-cucurbitane transformation. Here, an oxidative dearomatization/Wagner-Meerwein rearrangement with a substrate bearing the characteristic cucurbitane triad of quaternary centers at C9, C13 and C14, and possessing an alkene at C11-C12, proceeds in a manner that selectively shifts the methyl group at C9 to C10 in concert with the establishment of a sterically hindered allylic cation. The major product isolated from this transformation is formed by trapping of the allylic cation by addition of acetate to C12, rather than termination of the cascade by loss of a proton at C8.
View Article and Find Full Text PDFCucurbitane triterpenes from Hemsleya chinensis tubers and their anti-inflammatory activities.
Fitoterapia
April 2023
Henan University of Chinese Medicine, Zhengzhou, Henan 450046, PR China; Engineering Technology Research Center for Comprehensive Development and Utilization of Authentic Medicinal Materials in Henan Province, Zhengzhou, Henan 450046, PR China. Electronic address:
Six new cucurbitane-type triterpenes, hemchinins A-F (1-6), together with thirteen known ones (7-19) were isolated from ethyl acetate extraction of Hemsleya chinensis tubers. Compounds 1-2 were a group of cucurbitane triterpenes possessing an infrequent pentacyclic framework. Their structures were established by comprehensive UV, IR, HRMS, 1D/2D NMR, and ECD analyses.
View Article and Find Full Text PDFGeneral Enantioselective and Stereochemically Divergent Four-Stage Approach to Fused Tetracyclic Terpenoid Systems.
J Org Chem
March 2022
Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, New Hampshire 03755, United States.
Tetracyclic terpenoid-derived natural products are a broad class of medically relevant agents that include well-known steroid hormones and related structures, as well as more synthetically challenging congeners such as limonoids, cardenolides, lanostanes, and cucurbitanes, among others. These structurally related compound classes present synthetically disparate challenges based, in part, on the position and stereochemistry of the numerous quaternary carbon centers that are common to their tetracyclic skeletons. While de novo syntheses of such targets have been a topic of great interest for over 50 years, semisynthesis is often how synthetic variants of these natural products are explored as biologically relevant materials and how such agents are further matured as therapeutics.
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