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Molecules 2013, 18(11), 14172-14185; doi:10.3390/molecules181114172
Article

Secondary Metabolites in Durian Seeds: Oligomeric Proanthocyanidins

1,†
,
2,†,* , 3
,
2
,
2
 and
3,4
1 Hubei Key Laboratory of TCM Based Functional Food Quality and Safety, Jing Brand Company, Daye 435100, China 2 College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan 430074, China 3 National University of Singapore (Suzhou) Research Institute, Suzhou Industrial Park, Suzhou 215123, China 4 Food Science and Technology Program, Department of Chemistry, National University of Singapore, 3 Science Dr. 3, Singapore 117543, Singapore These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 29 September 2013 / Revised: 6 November 2013 / Accepted: 7 November 2013 / Published: 15 November 2013
(This article belongs to the Section Metabolites)
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Abstract

Ethanolic extract of durian seeds was fractionated by reverse phase flash column chromatography and the fractions characterized by electrospray ionization mass spectroscopy. Among a few unknown compounds collected, oligomeric proanthocyanidins (OPCs) were found to be one of the main compounds. Based on this result, the OPCs were purified the first time from the durian seeds using standard procedures and gave a yield of 1.8 mg/g dry matter after fractionation by Sephadex LH-20 column. Structural analysis by 13C{1H} NMR and ESI-MS spectra showed the presence of primarily B-type procyanidins with mainly epicatechin as the extension units, which was further verified by matrix assisted laser desorption/ionization–time of flight mass spectra (MALDI-TOF MS), which shows a distribution of dimers to decamers. In addition, hydroxylated peaks with molecular weight 16 units more than the poly-epicatechins represented significant peaks. We suggest this might be due to hydroxylation occurring under the MALDI-TOF MS conditions. Consistently, depolymerization with α-toluenethiol resulted in epicatechin thioether as the major product, but undetectable amount of gallocatechin or its α-toluenethiol derivatives. The oligomershave a mean degree of polymerization of 7.30.
Keywords: durian seeds; oligomeric proanthocyanidins; thiolysis; polyphenolic compounds; MALDI-TOF MS durian seeds; oligomeric proanthocyanidins; thiolysis; polyphenolic compounds; MALDI-TOF MS
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.

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Liu, Y.; Feng, S.; Song, L.; He, G.; Chen, M.; Huang, D. Secondary Metabolites in Durian Seeds: Oligomeric Proanthocyanidins. Molecules 2013, 18, 14172-14185.

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