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Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C(13)- and C(15)-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were...

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Autores principales: Jia, Xuchao, Yang, Dan, Yang, Yue, Xie, Haihui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6359364/
https://www.ncbi.nlm.nih.gov/pubmed/30641936
http://dx.doi.org/10.3390/molecules24020256
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author Jia, Xuchao
Yang, Dan
Yang, Yue
Xie, Haihui
author_facet Jia, Xuchao
Yang, Dan
Yang, Yue
Xie, Haihui
author_sort Jia, Xuchao
collection PubMed
description The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C(13)- and C(15)-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 C(13)-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C(15)-norisoprenoid, (6S,7E,10S)-Δ(9,15)-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. Compound 11 was a rare C(15)-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, and 10) C(13)-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.
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spelling pubmed-63593642019-02-06 Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit Jia, Xuchao Yang, Dan Yang, Yue Xie, Haihui Molecules Article The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C(13)- and C(15)-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 C(13)-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C(15)-norisoprenoid, (6S,7E,10S)-Δ(9,15)-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. Compound 11 was a rare C(15)-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, and 10) C(13)-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit. MDPI 2019-01-11 /pmc/articles/PMC6359364/ /pubmed/30641936 http://dx.doi.org/10.3390/molecules24020256 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Jia, Xuchao
Yang, Dan
Yang, Yue
Xie, Haihui
Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title_full Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title_fullStr Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title_full_unstemmed Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title_short Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit
title_sort carotenoid-derived flavor precursors from averrhoa carambola fresh fruit
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6359364/
https://www.ncbi.nlm.nih.gov/pubmed/30641936
http://dx.doi.org/10.3390/molecules24020256
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