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PHYTOCHEMISTRY · 2018 · IF 3.186

Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit

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 · 药理学
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RSC Advances · 2016 ·Vol. 6 ·期 93 ·90646-90653 · IF 3.289

Phenolic profiles and chemical- or cell-based antioxidant activities of four star fruit (Averrhoa carambola) cultivars

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 · 植物化学 · 营养学
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MOLECULES · 2019 ·Vol. 24 ·期 2 ·256 · IF 3.06

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

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

CAS / MDL: 50-99-7 921-60-8
研究领域: 植物化学 · 风味化学 · 食品科学
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FITOTERAPIA · 2019 · IF 2.431

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

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 · 药理学 · 食品科学
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Journal of Materials Chemistry B · 2021 ·Vol. 9 ·期 35 ·7271-7277 · IF 6.331

Carambola-like Bi2Te3 superstructures with enhanced photoabsorption for highly efficient photothermal therapy in the second near-infrared biowindow

Ying Zhao,Yang Liu,Qishun Wang,Jianhua Liu,Songtao Zhang,Tianqi Zhang,Daguang Wang,Yinghui Wang,Longhai Jin,Hongjie Zhang

Photothermal therapy (PTT) stimulated by light in the second near-infrared (NIR-II) biowindow shows great superiorities in the penetration ability of tissue and maximum permissible exposure (MPE). Exploring new photothermal agents with good optical absorbance in the NIR-II region is highly desirable for efficient cancer therapy. Herein, we successfully prepare carambola-like bismuth telluride (Bi2Te3) superstructures modified with PEGylated phospholipid (Bi2Te3@PEG) for CT imaging-guided PTT in the NIR-II biowindow. Attributing to their superstructures, Bi2Te3@PEG exhibited enhanced photoabsorption with higher photothermal conversion efficiency (55.3% for 1064 nm) compared with that of Bi2Te3 nanoparticles. Furthermore, the good X-ray attenuation capacity of Bi endows Bi2Te3@PEG with an outstanding performance as computed tomography (CT) contrast agents. Bi2Te3@PEG superstructures have been confirmed to effectively eliminate tumor in vitro and in vivo with negligible long-term toxicities, offering them great potential to act as theranostic platforms for cancer diagnosis and treatment.

研究领域: 材料科学 · 纳米技术 · 生物医学工程 · 癌症研究 · 诊疗学
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