Next Article in Journal
Sonochemical Degradation of Benzothiophene (BT) in Deionized Water, Natural Water and Sea Water
Previous Article in Journal
Targeting a Designer TIMP-1 to the Cell Surface for Effective MT1-MMP Inhibition: A Potential Role for the Prion Protein in Renal Carcinoma Therapy
Article Menu

Export Article

Open AccessArticle
Molecules 2019, 24(2), 256; https://doi.org/10.3390/molecules24020256

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

1,2,†
,
2,3,†
,
2,4
and
2,*
1
Sericultural & Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences/Key Laboratory of Functional Foods, Ministry of Agriculture and Rural Affairs/Guangdong Key Laboratory of Agricultural Products Processing, Guangzhou 510610, China
2
South China Botanical Garden, Chinese Academy of Sciences/Guangdong Provincial Key Laboratory of Applied Botany/Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangzhou 510650, China
3
School of Public Health, Jining Medical University, Jining 272067, China
4
College of Life Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
These authors contributed equally to this study.
*
Author to whom correspondence should be addressed.
Received: 22 November 2018 / Revised: 8 January 2019 / Accepted: 8 January 2019 / Published: 11 January 2019
(This article belongs to the Section Bioorganic Chemistry)
Full-Text   |   PDF [2486 KB, uploaded 11 January 2019]   |  

Abstract

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 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. Compound 11 was 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 (37, 9, and 10) C13-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit. View Full-Text
Keywords: Averrhoa carambola; star fruit; flavor precursor; C13-norisoprenoid glucoside; C15 norisoprenoid Averrhoa carambola; star fruit; flavor precursor; C13-norisoprenoid glucoside; C15 norisoprenoid
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Jia, X.; Yang, D.; Yang, Y.; Xie, H. Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit. Molecules 2019, 24, 256.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top