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Flavan-3-ols and 2-diglycosyloxybenzoates from the leaves of Averrhoa carambola. 2020

Yue Yang, and Haihui Xie, and Yueming Jiang, and Xiaoyi Wei
Guangdong Provincial Key Laboratory of Applied Botany, Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, and South China Branch of Innovation Academy for Drug Discovery and Development, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China; University of Chinese Academy of Sciences, Beijing 100049, China.

Averrhoa carambola L. (Oxalidaceae) was widely cultivated for fruits (star fruit), whereas the value of leaves remains to be discovered. Our study on the leaves yielded five flavan-3-ols (1-5) and two 2-diglycosyloxybenzoates. Their structures were determined by spectroscopic and chemical methods. Epicatechin-(5,6-bc)-4β-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (1) and benzyl 2-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranosyloxybenzoate (6) were new structures. 6-(S-2-Pyrrolidinone-5-yl)epicatechin (4) and 6-(R-2-pyrrolidinone-5-yl)epicatechin (5) were obtained as monomeric diastereomer for the first time and their absolute configurations were determined by electronic circular dichroism (ECD) computation. Epicatechin-(7,8-bc)-4α-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (2), epicatechin-(7,8-bc)-4β-(p-hydroxyphenyl)-dihydro-2(3H)-pyranone (3), and methyl 2-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranosyloxybenzoate (7) were not previously reported from the genus Averrhoa. Compounds 1-5 showed more potent 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities and ferric reducing antioxidant power (FRAP) than l-ascorbic acid. Meanwhile 1 and 3 exhibited lipase and α-glucosidase inhibitory activities, respectively. The results clarified the structures of flavan-3-ols and 2-diglycosyloxybenzoates in the leaves and their antioxidant, lipase, and α-glucosidase inhibitory activities.

UI MeSH Term Description Entries
D008049 Lipase An enzyme of the hydrolase class that catalyzes the reaction of triacylglycerol and water to yield diacylglycerol and a fatty acid anion. It is produced by glands on the tongue and by the pancreas and initiates the digestion of dietary fats. (From Dorland, 27th ed) EC 3.1.1.3. Triacylglycerol Lipase,Tributyrinase,Triglyceride Lipase,Acid Lipase,Acid Lipase A,Acid Lipase B,Acid Lipase I,Acid Lipase II,Exolipase,Monoester Lipase,Triacylglycerol Hydrolase,Triglyceridase,Triolean Hydrolase,Hydrolase, Triacylglycerol,Hydrolase, Triolean,Lipase A, Acid,Lipase B, Acid,Lipase I, Acid,Lipase II, Acid,Lipase, Acid,Lipase, Monoester,Lipase, Triglyceride
D002681 China A country spanning from central Asia to the Pacific Ocean. Inner Mongolia,Manchuria,People's Republic of China,Sinkiang,Mainland China
D005419 Flavonoids A group of phenyl benzopyrans named for having structures like FLAVONES. 2-Phenyl-Benzopyran,2-Phenyl-Chromene,Bioflavonoid,Bioflavonoids,Flavonoid,2-Phenyl-Benzopyrans,2-Phenyl-Chromenes,2 Phenyl Benzopyran,2 Phenyl Benzopyrans,2 Phenyl Chromene,2 Phenyl Chromenes
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D001565 Benzoates Derivatives of BENZOIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxybenzene structure. Benzoate,Benzoic Acids,Acids, Benzoic
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018515 Plant Leaves Expanded structures, usually green, of vascular plants, characteristically consisting of a bladelike expansion attached to a stem, and functioning as the principal organ of photosynthesis and transpiration. (American Heritage Dictionary, 2d ed) Plant Leaf,Leaf, Plant,Leave, Plant,Leaves, Plant,Plant Leave
D064209 Phytochemicals A broad range of biologically active compounds which occur naturally in plants having important medicinal and nutritional properties. Dietary Phytochemical,Plant Bioactive Compound,Plant Biologically Active Compound,Plant-Derived Chemical,Plant-Derived Compound,Bioactive Coumpounds, Plant,Biologically Active Coumpounds, Plant,Dietary Phytochemicals,Phytochemical,Phytonutrient,Phytonutrients,Plant Bioactive Compounds,Plant Biologically Active Compounds,Plant-Derived Chemicals,Plant-Derived Compounds,Bioactive Compound, Plant,Bioactive Compounds, Plant,Chemical, Plant-Derived,Chemicals, Plant-Derived,Compound, Plant Bioactive,Compound, Plant-Derived,Compounds, Plant Bioactive,Compounds, Plant-Derived,Coumpounds, Plant Bioactive,Phytochemical, Dietary,Phytochemicals, Dietary,Plant Bioactive Coumpounds,Plant Derived Chemical,Plant Derived Chemicals,Plant Derived Compound,Plant Derived Compounds
D065089 Glycoside Hydrolase Inhibitors Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. alpha-Glucosidase Inhibitor,alpha-Glucosidase Inhibitors,Intestinal alpha-Amylase Inhibitors,Pancreatic alpha-Amylase Inhibitors,alpha-Amylase Inhibitors, Pancreatic,Hydrolase Inhibitors, Glycoside,Inhibitor, alpha-Glucosidase,Inhibitors, Glycoside Hydrolase,Inhibitors, Intestinal alpha-Amylase,Inhibitors, Pancreatic alpha-Amylase,Inhibitors, alpha-Glucosidase,Intestinal alpha Amylase Inhibitors,Pancreatic alpha Amylase Inhibitors,alpha Amylase Inhibitors, Pancreatic,alpha Glucosidase Inhibitor,alpha Glucosidase Inhibitors,alpha-Amylase Inhibitors, Intestinal
D065826 Averrhoa Tropical trees in the family Oxalidaceae Averrhoa bilimbi,Averrhoa carambola,Carambola Tree,Cucumber Tree,Starfruit Tree,Averrhoas,Carambola Trees,Cucumber Trees,Starfruit Trees,Tree, Carambola,Tree, Cucumber,Tree, Starfruit,Trees, Carambola,Trees, Cucumber,Trees, Starfruit

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