Composition of Anthocyanins and Proanthocyanidins in Three Tropical Vaccinium Species from Costa Rica

Abstract

Total polyphenol content (TPC), total flavonoid content (TFC), total anthocyanin content (TAC), and proanthocyanidin (PAC) content were determined in fruit from three tropical Vaccinium species (Vaccinium consanguineum, Vaccinium floribundum, and Vaccinium poasanum) from Costa Rica sampled at three stages of fruit development. Results show that TAC increased as the fruit developed, while TPC, TFC, and PAC content decreased. Anthocyanin profiles were evaluated using electrospray ionization tandem mass spectrometry. Cyanidin and delphinidin glycosides were the predominant anthocyanins for the three tropical Vaccinium species. Proanthocyanidins were characterized using attenuated total reflection Fourier transform infrared spectroscopy, nuclear magnetic resonance, and matrix-assisted laser desorption/ionization time-offlight mass spectrometry. The presence of procyanidin structures with B-type interflavan bonds were observed, but deconvolution of mass spectrometry isotope patterns indicated that PACs with one or more A-type interflavan bonds accounted for more than 74% of the oligomers at each degree of polymerization. KEYWORDS: proanthocyanidins, anthocyanin, A-type interflavan bonds, MALDI−TOF MS of the National Fruit Growing Program by the Costa Rican Department of Agriculture. 1,4,8 Polyphenols found in Vaccinium species, such as cranberry, contain hydroxycinnamic acids, flavonols, anthocyanins, and proanthocyanidins, among others. 9,10 Anthocyanins are watersoluble pigments that vary by the number of methyl, methoxy, or hydroxyl group, the nature and number of sugars attached to the molecule, and the nature and number of aliphatic or aromatic acids attached to sugars in the molecule. 11,12 Proanthocyanidins (PACs) are oligomers of flavan-3-ols. PAC structures vary by the nature of the monomer unit, interflavan linkage, and degree of polymerization (DP). 13 PACs are classified by the type of flavan-3-ol monomers, such as properlagonidins, which are oligomers of (epi)afzelechin, procyanidins, which are oligomers of (epi)catechin, and prodelphinidins, which are oligomers of (epi)gallocatechin. 14 However, many types of PACs contain more than one type of monomeric flavan-3-ols, such as PACs in grape seeds. PACs can have B-and A-type bonds. B-type bonds are defined by the presence of C 4 −C 8 or C 4 −C 6 interflavan bonds, whereas Atype bonds have C 4 −C 8 bonds but also have an additional interflavan bond between C 2 −O−C 7 or C 2 −O−C 5 . 9,13,15

Proanthocyanidins and Where to Find Them: A Meta-Analytic Approach to Investigate Their Chemistry, Biosynthesis, Distribution, and Effect on Human Health

“… Cluster distribution of proanthocyanidins based on the total proanthocyanidin content within plant families and according to previously published data [ 96 , 97 , 99 , 100 , 101 , 102 , 104 , 105 , 116 , 117 , 118 , 119 , 120 , 121 , 122 , 123 , 124 , 125 , 126 , 127 , 128 , 129 , 130 , 131 , 132 , 133 , 134 , 135 , 136 , 137 , 138 , 139 , 140 , 141 , 142 , 143 , 144 , 145 , 146 , 147 , 148 ]. Euclidean distances were calculated with the average linkage method.…”

Andean Blueberry of the Genus Disterigma: A High-Resolution Mass Spectrometric Approach for the Comprehensive Characterization of Phenolic Compounds

“…Malvidin and petunidin derivatives, which are major constituents of blueberries, were not found. It is worth mentioning that malvidin derivatives have not been identified in V. floribundum, an Andean blueberry that grows in the same regions as D. alaternoides [19,20]. In a previous paper by Ma et al [9], phenolic markers for discriminate North American and Neotropical blueberries were studied, comprising another member of the genus Disterigma (D. rimbachii).…”

Blueberry as an Attractive Functional Fruit to Prevent (Pre)Diabetes Progression

“…It belongs to the genus Vaccinium of Ericaceae family which includes approximately 450 species all over the world [ 60 ]. Some examples are the well-known Vaccinium corymbosum , Vaccinium ahei , Vaccinium poasanum, Vaccinium angustifolium and Vaccinium myrtillus , the later commonly denominated as bilberries across Europe [ 61 , 62 ]. BB are characterized by their enriched nutritive composition, containing high contents of a wide diversity of biologically active components.…”