TY - JOUR
T1 - Improved carotenoid processing with sustainable solvents utilizing Z-isomerization-induced alteration in physicochemical properties
T2 - A review and future directions
AU - Honda, Masaki
AU - Kageyama, Hakuto
AU - Hibino, Takashi
AU - Zhang, Yelin
AU - Diono, Wahyu
AU - Kanda, Hideki
AU - Yamaguchi, Ryusei
AU - Takemura, Ryota
AU - Fukaya, Tetsuya
AU - Goto, Motonobu
N1 - Funding Information:
This work was partly supported by JSPS KAKENHI Grant Number 19K15779 (to M.H.) and the Tatematsu Foundation (to M.H.). The authors are grateful to Tsutomu Kumagai, Chitoshi Kitamura, Yoshinori Inoue, and Munenori Takehara (Department of Materials Science, The University of Shiga Prefecture), and Hiroyuki Ueda, Takuma Higashiura, and Kohei Ichihashi (Innovation Division, Kagome Co., Ltd.) for their kind help and constructive suggestions.
Publisher Copyright:
© 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/).
PY - 2019/6/7
Y1 - 2019/6/7
N2 - Carotenoids-natural fat-soluble pigments-have attracted considerable attention because of their potential to prevent of various diseases, such as cancer and arteriosclerosis, and their strong antioxidant capacity. They have many geometric isomers due to the presence of numerous conjugated double bonds in the molecule. However, in plants, most carotenoids are present in the all-E-configuration. (all-E)-Carotenoids are characterized by high crystallinity as well as low solubility in safe and sustainable solvents, such as ethanol and supercritical CO2 (SC-CO2). Thus, these properties result in the decreased efficiency of carotenoid processing, such as extraction and emulsification, using such sustainable solvents. On the other hand, Z-isomerization of carotenoids induces alteration in physicochemical properties, i.e., the solubility of carotenoids dramatically improves and they change from a “crystalline state” to an “oily (amorphous) state”. For example, the solubility in ethanol of lycopene Z-isomers is more than 4000 times higher than the all-E-isomer. Recently, improvement of carotenoid processing efficiency utilizing these changes has attracted attention. Namely, it is possible to markedly improve carotenoid processing using safe and sustainable solvents, which had previously been difficult to put into practical use due to the low efficiency. The objective of this paper is to review the effect of Z-isomerization on the physicochemical properties of carotenoids and its application to carotenoid processing, such as extraction, micronization, and emulsification, using sustainable solvents. Moreover, aspects of Z-isomerization methods for carotenoids and functional difference, such as bioavailability and antioxidant capacity, between isomers are also included in this review.
AB - Carotenoids-natural fat-soluble pigments-have attracted considerable attention because of their potential to prevent of various diseases, such as cancer and arteriosclerosis, and their strong antioxidant capacity. They have many geometric isomers due to the presence of numerous conjugated double bonds in the molecule. However, in plants, most carotenoids are present in the all-E-configuration. (all-E)-Carotenoids are characterized by high crystallinity as well as low solubility in safe and sustainable solvents, such as ethanol and supercritical CO2 (SC-CO2). Thus, these properties result in the decreased efficiency of carotenoid processing, such as extraction and emulsification, using such sustainable solvents. On the other hand, Z-isomerization of carotenoids induces alteration in physicochemical properties, i.e., the solubility of carotenoids dramatically improves and they change from a “crystalline state” to an “oily (amorphous) state”. For example, the solubility in ethanol of lycopene Z-isomers is more than 4000 times higher than the all-E-isomer. Recently, improvement of carotenoid processing efficiency utilizing these changes has attracted attention. Namely, it is possible to markedly improve carotenoid processing using safe and sustainable solvents, which had previously been difficult to put into practical use due to the low efficiency. The objective of this paper is to review the effect of Z-isomerization on the physicochemical properties of carotenoids and its application to carotenoid processing, such as extraction, micronization, and emulsification, using sustainable solvents. Moreover, aspects of Z-isomerization methods for carotenoids and functional difference, such as bioavailability and antioxidant capacity, between isomers are also included in this review.
KW - Astaxanthin
KW - Crystallinity
KW - E/Z-isomerization
KW - Emulsification
KW - Extraction
KW - Lycopene
KW - Micronization
KW - Solubility
KW - Supercritical CO
KW - β-carotene
UR - http://www.scopus.com/inward/record.url?scp=85067234851&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85067234851&partnerID=8YFLogxK
U2 - 10.3390/molecules24112149
DO - 10.3390/molecules24112149
M3 - Review article
C2 - 31181605
AN - SCOPUS:85067234851
SN - 1420-3049
VL - 24
JO - Molecules
JF - Molecules
IS - 11
M1 - 2149
ER -
