MOLECULES
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2019
·Vol. 24
·期 2
·256
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IF 3.06
Xuchao Jia,Dan Yang,Yue Yang,Haihui Xie
The fruit ofAverrhoa carambolaL. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C13- and C15-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were tentatively identified by GC-MS analysis after enzymatic hydrolysis. To gain accurate information about glycosidically bound flavor precursors in star fruit, a phytochemical study was conducted, which led to the isolation of 16 carotenoid derivatives—One new C13-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C15-norisoprenoid, (6S,7E,10S)-Δ9,15-10-hydroxyabscisic alcohol (11); and 14 known ones, of which 12 were in glucoside form. The structures of the two new compounds were elucidated on the basis of extensive spectroscopic data analysis and chemical reaction. Compound11was a rare C15-norisoprenoid with a double bond between C-9 and C-15, and its possible biogenetic pathway was proposed. The known compounds were identified by comparison of their mass and nuclear magnetic resonance (NMR) data with those reported in the literature. The structure identification of one new (1) and seven known (3–7,9, and10) C13-norisoprenoid glucosides from the genusAverrhoafor the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.Keywords:Averrhoa carambola;star fruit;flavor precursor;C13-norisoprenoid glucoside;C15norisoprenoid
研究领域:
植物化学
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风味化学
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食品科学
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DOI
PubMed
高影响因子
Journal of Functional Foods
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2017
·
IF 3.144
Xuchao Jia,Dan Yang,Haihui Xie,Yueming Jiang,Xiaoyi Wei
The fruit of Averrhoa carambola L. (Oxalidaceae) is a commercially important fruit. Our study on the chemical constituents present in the fresh sweet fruit led to the isolation of eleven non-flavonoid phenolic compounds. Their structures were identified by analyses of spectroscopic data. They were two new alkyl phenol diglucosides, carambolasides K ( 1 ) and L ( 2 ), four phenylpropanoids, (+)-isolariciresinol 9- O -β- d -glucoside ( 3 ), (+)-lyoniresinol 9- O -β- d -glucoside ( 4 ), (−)-lyoniresinol 9- O -β- d -glucoside ( 5 ), and 1- O -feruloyl-β- d -glucose ( 6 ), three benzoic acids, protocatechuic acid ( 7 ), 1- O -vanilloyl-β- d -glucose ( 8 ), and tecomin ( 9 ), a simple phenol, koaburaside ( 10 ), and a naphthoquinone, (+)-cryptosporin ( 11 ). All of them were reported from A. carambola fruit for the first time. Compounds 1 – 8 and 10 showed 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity comparable to l -ascorbic acid, while compounds 3 , 5 , and 7 exhibited potent ferric reducing antioxidant power (FRAP). In addition, compounds 6 and 11 demonstrated weak porcine pancreatic lipase inhibitory activity.
研究领域:
植物化学
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药理学
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食品科学
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高影响因子
FITOTERAPIA
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2019
·
IF 2.431
Yue Yang,Haihui Xie,Yueming Jiang,Xiaoyi Wei
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(3 H )-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(3 H )-pyranone ( 2 ), epicatechin-(7,8-bc)-4β-( p -hydroxyphenyl)-dihydro-2(3 H )-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.
研究领域:
植物化学
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药理学
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食品科学
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DOI
PubMed
高影响因子
PHYTOCHEMISTRY
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2018
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IF 3.186
Xuchao Jia,Haihui Xie,Yueming Jiang,Xiaoyi Wei
Thirteen flavonoids were isolated from the fresh sweet fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit, and their structures were determined by spectroscopic and chemical methods. 8-Carboxymethyl-(+)-epicatechin methyl ester , pinobanksin 3- O -β- d -glucoside, and carambolasides M–Q were undescribed structures. (+)-Epicatechin, aromadendrin 3- O -β- d -glucoside, helicioside A, taxifolin 3′- O -β- d -glucoside, galangin 3- O -rutinoside, and isorhamnetin 3- O -rutinoside were reported from this species for the first time. Pinobanksin 3- O -β- d -glucoside and carambolasides M–Q showed more potent 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity (IC 50 = 5.3–2.3 μM) than l -ascorbic acid (10.5 μM). Further, (+)-epicatechin, pinobanksin 3- O -β- d -glucoside, isorhamnetin 3- O -rutinoside, and carambolasides O–Q exhibited weak porcine pancreatic lipase inhibitory activity.
研究领域:
植物化学
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药理学
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DOI
PubMed
高影响因子
RSC Advances
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2016
·Vol. 6
·期 93
·90646-90653
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IF 3.289
Daorui Pang,Lijun You,Tong Li,Lin Zhou,Dongxiao Sun-Waterhouse,Rui Hai Liu
The objectives of this study were to investigate the phytochemical profiles and antioxidant activities of four cultivars of star fruit (Averrhoa carambola). The free, bound and total phenolic contents of the four cultivars were 162.5–286.8, 6.4–19.7, and 174.5–293.1 mg gallic acid equivalents per 100 g fresh weight (FW), respectively. The free, bound and total flavonoid contents were 100.7–234.0, 1.1–7.8, and 104.4–235.1 mg catechin equivalents per 100 g FW, respectively. The cellular antioxidant activity (CAA) values with or without a phosphate buffered saline wash protocol ranged from 25.80 to 63.29 and from 32.41 to 68.96 μmol quercetin equivalents per 100 g FW, respectively. The Taiguo cultivar had the highest phytochemical content and antioxidant activity among the four cultivars tested. High performance liquid chromatography analysis revealed the presence of gallic acid, syringic acid, p-coumaric acid, epicatechin, isoquercetin and procyanidin B2 in Averrhoa carambola. The type of cultivars influenced the phytochemical profile and extractability, antioxidant activity, and ultimately health-promoting potential of star fruit.
研究领域:
食品科学
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植物化学
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营养学
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DOI
高影响因子
Food & Function
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2017
·Vol. 8
·期 12
·4496-4507
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IF 3.247
Daorui Pang,Lijun You,Lin Zhou,Tong Li,Bisheng Zheng,Rui Hai Liu
The objective of the present study is to investigate the hepatic steatosis relieving effect of Averrhoa carambola free phenolic extract (ACF) on leptin receptor-deficient (db/db) mice and elucidate the modulation hepatic lipogenesis mechanisms. The serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) assays, accompanying hematoxylin and eosin (H&E) staining, were applied to identify the alleviation of liver histopathological changes. Serum and hepatic lipid assays, combined with oil red O staining, were used to investigate the amelioration of lipid accumulation. Further assessments by quantitative real-time PCR and western blot assays were used to elucidate the suppression of the fatty acid and triglyceride (TG) synthesis mechanisms underlying ACF protection. These results indicated that ACF treatment significantly reduced the liver TG of db/db mice (p < 0.05). The mechanisms are partly through phosphorylation of AMPK α and down-regulation of SREBP-1c expression, and further down-regulation of FAS and SCD1 (p < 0.05). In addition, the expression levels of mircoRNA-34a and mircoRNA-33, which modulate this signaling pathway, were significantly down-regulated by ACF treatment (p < 0.05). Collectively, these results revealed that ACF exhibited a potent hepatic steatosis relieving effect partly by inhibiting the signal transduction of hepatic lipogenesis.
研究领域:
药理学
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分子生物学
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肝病学
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DOI
PubMed
高影响因子
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