Characterization of Carotenoid Fatty Acid Esters from the Peels of the Persimmon <i>Diospyros kaki</i>

Abstract

Separation and structural determination of the chloroform-soluble components obtained from the peels of the persimmon (Diospyros kaki Thunb.) were performed. β-Carotene, lycopene, β-cryptoxanthin monomyristic acid ester, zeaxanthin di-myristic acid ester, the latter two of which were accompanied by a small amount of palmitoleic acid in the fatty acid moiety, and oleanolic acid were identified. Among these components, the mono-fatty acid ester of β-cryptoxanthin and the di-fatty acid ester of zeaxanthin were characterized for the first time.Key words persimmon peel; carotenoid; β-cryptoxanthin mono-fatty acid ester; zeaxanthin di-fatty acid ester; myristic acid; palmitoleic acidThe persimmon Diospyros kaki Thunb. is a fruit that is indigenous to Japan, and China, Korea, and Japan produce most of the fruits used for commercial consumption. Persimmons (Kaki) are also used traditionally for medicinal purposes, because of their preventive action against infection, diabetes, and arteriosclerosis, and because of their diuretic effect.1) The persimmon contains many compounds such as different sugars, starch, organic acids, ascorbic acid, tannins, flavonoids, carotenoids, triterpenoids, and fatty acids.2-7) With regard to its pharmacological activities, many studies have reported pharmacological effects including antioxidant activity and tyrosinase inhibitory activity. 3,[8][9][10] The peels of fresh astringent persimmons are usually removed and dried, which yields sweet dried persimmon peels. The peel was found to contain more polyphenols 11) and carotenoids 12) than the fruit body. The persimmon flesh contained large amounts of carotenoids, which are responsible for the color of the fruits.4,5) Unlike vitamin C and vitamin E, β-carotene and other carotenoids can scavenge singlet oxygen.13) Also, carotenoids are known to exist as free compounds or as fatty acid esters in plants. Because the peels of persimmons are usually discarded, we believe that it might be possible to recover the peels for industrial utilization or for use as a food supplement.Breithaupt and Bamedi 14) suggested, on the basis of HPLC results, the occurrence of carotenoid esters as β-cryptoxanthin ester and zeaxanthin ester in persimmons. Weller and Breithaupt 15) also suggested, on the basis of LC/MS results, the presence of zeaxanthin esters as diesters of dipalmitate and of palmitate and stearate in persimmons. However, they did not isolate these compounds as pure single entities. Differences in the chemical structure of each carotenoid and its ester would lead to different pharmacological effects and physicochemical characteristics. For example, synthetic lutein myristate ester was more stable than free lutein after heat or UV treatment. 16)Sugawara et al. 17) found that Caco-2 cells easily took up more hydrophobic carotenoids than less hydrophobic carotenoids. One can easily envision that different carotenoids with or without ester moieties would have different polar characteristics and that differences in structure would lead to different bioch...

Characterization of Carotenoid and Carotenoid Esters of Astringent Persimmon Tissues (<em>Diospyros kaki </em>Thunb. var.<em> Rojo Brillante</em>). Effects of Thermal and High Pressure Non-Thermal Processing

“…Mercadante et al (2017) [37] reported that reliable identification of carotenoid esters based only in the elution order or retention time is not possible and can lead wrong assignments due to co-elution or poor baseline separation. In the present study, no problems were found to assign hydrocarbon carotenoids as showed Previous studies about the carotenoid and carotenoid esters composition of persimmon peel [15] reported the presence of β-carotene, lycopene, β-cryptoxanthin mono-myristic acid ester, zeaxanthin di-myristic acid ester, using silica gel chromatography followed by structural characterization by 1 H-NRM and 13 C-NMR.…”

“…Persimmon carotenoid profile had been reported by several authors [13,14,9], but in all of these studies only saponified extracts were characterized and in all cases a C18 column was used by HPLC carotenoid separation, being trans-β-cryptoxanthin, trans-zeaxanthin, trans-lutein, trans-βand α-carotene and lycopene the major carotenoids found in these saponified extracts. Only, Hitaka et al (2013) [15] reported the characterization of carotenoid fatty acid esters from persimmon peels using the isolation of the main carotenoids and their esters by purification via silica gel column chromatography and the characterization of their structures buy using HR-FAB-MS, 1 H-and 13 C-NMR. β-carotene, lycopene, β-cryptoxanthin mono myristic acid ester, zeaxanthin di-myristic acid ester, and small amounts of xanthophyll esters of palmitoleic and oleanolic acid were found.…”

FTIR‐based comparative analysis of glucomannan contents in some tuberous orchids, and effects of pre‐processing on glucomannan measurement

“…Additionally, the mode at 2929 cm −1 represents C‐H stretching and arises from methyl units . Ester carbonyl groups (C=O), mainly sourced from acetyl group of glucomannan and hemicellulose appear at 1732 cm −1 while the C=O stretch vibration from GM with the contribution of protein amide groups may be found at 1635 cm −1 . In addition, the C‐O‐C fragment was observed at 1154 cm −1 .…”

From Diospyros kaki L. (Persimmon) Phytochemical Profile and Health Impact to New Product Perspectives and Waste Valorization

“…Esters of carotenoid fatty acids ( Diospyros kaki THUNB. ), lycopene, β-carotene, ester of zeaxanthin di-myristic acid, and mono-myristic acid ester of β-cryptoxanthin have all been characterized in the persimmon peel, while a small quantity of palmitoleic acid in the fatty acid and oleanolic acid fraction was found [ 52 , 53 ].…”

“…In persimmon extracts, organic acids (malic, oxoglutamic, citric, succinic, and aspartic), amino acids (gamma-aminobutyric acid (GABA), alanine, arginine, valine, leucine, and isoleucine), fatty acids (palmitoleic acid methyl ester, myristic acid, and linoleic acid) [ 40 , 52 ], vitamins (trigonelline and ascorbic acid), α-tocopherol, oleanolic acid, betulinic acid, β-sitosterol, and uridine have also been identified [ 40 ].…”