Article(id=1320889305627738921, tenantId=1146029695717560320, journalId=1260987677001138203, issueId=1320888908896907909, articleNumber=null, orderNo=null, doi=10.13386/j.issn1002-0306.2025020096, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1739721600000, receivedDateStr=2025-02-17, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1792854151398, onlineDateStr=2026-10-24, pubDate=1772294400000, pubDateStr=2026-03-01, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1792854151398, onlineIssueDateStr=2026-10-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1792854151398, creator=13701087609, updateTime=1792854151398, updator=13701087609, issue=Issue{id=1320888908896907909, tenantId=1146029695717560320, journalId=1260987677001138203, year='2026', volume='47', issue='5', pageStart='1', pageEnd='503', issueExtLink='null', onlineDate='null', pubDate='1772294400000', pubDateStr='2026-03-01', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1792854056809, creator='13701087609', updateTime=1792854056809, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext=null, issueFiles=null, downloadFileDto=null}, startPage=92, endPage=100, ext={EN=ArticleExt(id=1320889305866814250, articleId=1320889305627738921, tenantId=1146029695717560320, journalId=1260987677001138203, language=EN, title=Mechanism of Photoisomerization of Astaxanthin: Experimental and Quantum Chemistry Study, columnId=1261336277291548795, journalTitle=Science and Technology of Food Industry, columnName=Research and Investigation, runingTitle=null, highlight=null, articleAbstract=

To investigate the photoisomerization mechanism of astaxanthin (AST), the types and contents of Z-configuration in photocatalytic conversion of AST were analyzed by HPLC and Q value method. Additionally, the AST configuration was optimized and frequency analysis was performed using density functional theory (DFT). Thermodynamic, kinetic, and energetic parameters of all-E- and Z-AST isomers were further calculated. The results demonstrated that 9-Z- and 13-Z-isomers were predominantly generated under photocatalysis, with the 13-Z content (17.72%) being significantly higher than 9-Z (13.57%) (P<0.05). Upon illumination, neutral AST molecules generated diradicals, facilitating bond twisting. All-E AST exhibited the smallest frontier orbital energy gap, promoting its transition from the ground state to the excited state, and subsequent isomerization into other configurations. Gibbs free energy analysis revealed the following stability order of AST isomers: all-E>9-Z>13-Z>15-Z, basically consistent with experimental observations. Moreover, the activation energy for all-E→9-Z conversion was higher than for all-E→15-Z/13-Z, while single-Z→double-Z isomerization required significantly higher energy than all-E→mono-Z conversion. Notably, the 13-Z-isomer formation rate was about 4-fold and 100-fold higher than that of 15-Z> and 9-Z, respectively. The negligible tunneling effect during mutual transformation explained the scarcity of multi-Z-isomers in experiments and the predominance of 13-Z over 9-Z AST. Collectively, these findings elucidate the controlled generation mechanism of AST isomers and establish a theoretical framework for carotenoid isomerization.

, authors=Lesong ZHOU, Xiaojun ZOU, Jialing CHEN, Jie XIAO, Yong CAO, Xiaojuan LIU^*, authorsList=Lesong ZHOU, Xiaojun ZOU, Jialing CHEN, Jie XIAO, Yong CAO, Xiaojuan LIU, authorCompany=null, correspAuthors=Xiaojuan LIU, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright © 2026 Science and Technology of Food Industry. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, fund=null), CN=ArticleExt(id=1320889309025125181, articleId=1320889305627738921, tenantId=1146029695717560320, journalId=1260987677001138203, language=CN, title=虾青素光异构化机理：实验与量子化学相结合研究, columnId=1261336277849391232, journalTitle=食品工业科技, columnName=研究与探讨, runingTitle=null, highlight=null, articleAbstract=

为探究虾青素（astaxanthin，AST）的光异构化机理，采用HPLC技术和Q值法分析光催化转化AST的顺式构型种类和含量，通过密度泛函理论对AST构型进行优化与频率分析，计算得到全反式（all-E）和顺式（Z）AST相互转化的热力学、动力学和能量参数。结果表明，全反式AST在光催化下主要形成9顺式（9-Z）和13顺式（13-Z），13-Z含量（17.72％）显著高于9-Z（13.57％）（P<0.05）。光照后，中性AST分子形成双自由基，双键容易发生扭转。全反式AST的前线轨道能隙差最小，更容易从基态转变为激发态，从而异构为其它构型；根据吉布斯自由能，AST异构体的相对稳定性顺序为：全反式>9-Z>13-Z>15-Z，与实验结果趋势基本相符；全反式AST形成9-Z的活化能高于15-Z和13-Z，单顺式AST转化为多顺式的活化能远高于全反式AST转化为单顺式异构体；13-Z构型生成速率分别约为15-Z和9-Z的4倍和100倍，且相互转化的隧穿效应可以忽略不计，与实验中多顺式异构体难以观察到相吻合，同时阐明实验中出现的13-Z AST比例显著高于9-Z的原因。研究结果揭示了AST可控实现异构体的生成机制，同时为其它类胡萝卜素异构化研究提供理论基础。

, authors=周乐松, 邹晓君, 陈佳玲, 肖杰, 曹庸, 刘晓娟^*, authorsList=周乐松, 邹晓君, 陈佳玲, 肖杰, 曹庸, 刘晓娟, authorCompany=null, correspAuthors=刘晓娟, authorNote=, correspAuthorsNote=, copyrightStatement=版权所有 © 2026《食品工业科技》编辑部, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=+30IAN2Ko5atu/1Aui90gg==, magXml=wV1Cqnd+KbDenIW2Xiz4EQ==, pdfUrl=null, pdf=kPsv8duhQsKN7w0ad4OItA==, pdfFileSize=3673635, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=bBrOsZKKMnFBWe/EC8wLbQ==, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=kjv9n/Dmr7be4c5hiok3CQ==, mapNumber=null, fund=null)}, authors=[Author(id=1320889309322920770, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, orderNo=0, firstName=null, middleName=null, lastName=null, nameCn=null, orcid=null, stid=null, country=null, authorPic=null, dead=0, email=lesongzhou@163.com, emailSecond=null, emailThird=null, correspondingAuthor=0, authorType=1, ext={EN=AuthorExt(id=1320889309415195460, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, authorId=1320889309322920770, language=EN, stringName=Lesong ZHOU, firstName=Lesong, middleName=null, lastName=ZHOU, prefix=null, suffix=null, authorComment=null, nameInitials=null, affiliation=null, department=null, xref=null, address=College of Food Science, South China Agricultural University, Guangdong Provincial Key Laboratory of Nutraceuticals and Functional Foods, Guangzhou 510642, China, bio=null, bioImg=null, bioContent=null, aboutCorrespAuthor=null), CN=AuthorExt(id=1320889309473915717, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, authorId=1320889309322920770, language=CN, stringName=周乐松, firstName=null, middleName=null, lastName=null, prefix=null, suffix=null, authorComment=null, nameInitials=null, affiliation=null, department=null, xref=null, address=华南农业大学食品学院，广东省功能食品活性物重点实验室，广东广州 510642, bio={"content":"

周乐松（1998−），男，硕士研究生，研究方向：功能食品学，食品生物化学及营养学，E-mail：lesongzhou@163.com

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周乐松（1998−），男，硕士研究生，研究方向：功能食品学，食品生物化学及营养学，E-mail：lesongzhou@163.com

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Journal of Agricultural and Food Chemistry, 2017, 65(4): 818−826., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1320889309226451774, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, xref=null, ext=[AuthorCompanyExt(id=1320889309234840383, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, companyId=1320889309226451774, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=College of Food Science, South China Agricultural University, Guangdong Provincial Key Laboratory of Nutraceuticals and Functional Foods, Guangzhou 510642, China), AuthorCompanyExt(id=1320889309239034688, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, companyId=1320889309226451774, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=华南农业大学食品学院，广东省功能食品活性物重点实验室，广东广州 510642)])], figs=[ArticleFig(id=1320889311596233577, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.1, caption=HPLC chromatograms of AST after photoisomerization (A), all-E (B), 9-Z (C) and 13-Z (D) astaxanthin and corresponding electronic absorption spectra (E~G), figureFileSmall=Omm/PBga+oNkMq11FH7xDQ==, figureFileBig=bBrOsZKKMnFBWe/EC8wLbQ==, tableContent=null), ArticleFig(id=1320889311675925354, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图1, caption=光异构化AST（A）、全反式（B）、9顺式（C）、13顺式（D）AST的HPLC色谱图以及对应的电子吸收光谱（E~G）, figureFileSmall=Omm/PBga+oNkMq11FH7xDQ==, figureFileBig=bBrOsZKKMnFBWe/EC8wLbQ==, tableContent=null), ArticleFig(id=1320889311881446251, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.2, caption=Structure of neutral and di-radical forms of all-E (A), 9-Z (B), 13-Z (C) and 15-Z (D) astaxanthin, figureFileSmall=Jo/EKV8ktu5+aN9iEyVeRg==, figureFileBig=Gx+TuDOkWFdONNgyh9Ivdw==, tableContent=null), ArticleFig(id=1320889311948555116, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图2, caption=全反式（A）、9顺式（B）、13顺式（C）和15顺式（D）AST中性和双自由基形式的结构, figureFileSmall=Jo/EKV8ktu5+aN9iEyVeRg==, figureFileBig=Gx+TuDOkWFdONNgyh9Ivdw==, tableContent=null), ArticleFig(id=1320889312015663981, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.3, caption=Molecular structure of all-E (A), 9-Z (B), 13-Z (C) and 15-Z (D) astaxanthin, figureFileSmall=porVXuMkTS+50/S6QFr5AQ==, figureFileBig=uROLzIWJM/3oNGAhblwqbw==, tableContent=null), ArticleFig(id=1320889312086967150, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图3, caption=全反式（A）、9顺式（B）、13顺式（C）和15顺式（D）AST的分子结构, figureFileSmall=porVXuMkTS+50/S6QFr5AQ==, figureFileBig=uROLzIWJM/3oNGAhblwqbw==, tableContent=null), ArticleFig(id=1320889312149881711, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.4, caption=Specific bond length parameters of neutral and diatomic radicals of all-E (A), 9-Z (B), 13-Z (C) and 15-Z (D) astaxanthin, figureFileSmall=ks8JTJbh4r5rChkZyN9qFw==, figureFileBig=cH/S10qebYt20piYFs85tw==, tableContent=null), ArticleFig(id=1320889312225379184, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图4, caption=全反式（A）、9顺式（B）、13顺式（C）和15顺式（D）AST的中性和双自由基两种形态特定键长参数

注：a：中性；b：双自由基；键长以Å表示和二面角参数ζ（单位为°）。

, figureFileSmall=ks8JTJbh4r5rChkZyN9qFw==, figureFileBig=cH/S10qebYt20piYFs85tw==, tableContent=null), ArticleFig(id=1320889312313459569, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.5, caption=Frontline molecular orbital energy diagrams of all-E (A), 9-Z (B), 13-Z (C) and 15-Z (D) astaxanthin, figureFileSmall=BbDE1c0YoZx0sNu9uzWzRg==, figureFileBig=xSOIoLrInLgIYbEE/F5Yzw==, tableContent=null), ArticleFig(id=1320889312384762738, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图5, caption=全反式（A）、9顺式（B）、13顺式（C）和15顺式（D）AST的前线分子轨道能级图

注：红色表示正值部分，绿色表示负值部分，代表相位和相互之间的作用。HOMO最高占据轨道，LUMO最低未占轨道。

, figureFileSmall=BbDE1c0YoZx0sNu9uzWzRg==, figureFileBig=xSOIoLrInLgIYbEE/F5Yzw==, tableContent=null), ArticleFig(id=1320889312456065907, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.6, caption=Potential energy distribution diagram of Z-isomerization of all-E astaxanthin in the form of double free radicals, figureFileSmall=4ps/IjsPLyqkU82MEp4skQ==, figureFileBig=Hu8bZfM3irhGFPM7aBugZg==, tableContent=null), ArticleFig(id=1320889312514786164, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图6, caption=双自由基形式全反式 AST顺式异构化的势能分布图, figureFileSmall=4ps/IjsPLyqkU82MEp4skQ==, figureFileBig=Hu8bZfM3irhGFPM7aBugZg==, tableContent=null), ArticleFig(id=1320889312590283637, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.7, caption=Transition state structure and virtual frequency of astaxanthin in double radical form, figureFileSmall=/pGctUx2f+Hfp7uRsNrlYw==, figureFileBig=TeeJKVNmp2ieZdMfBWB2KA==, tableContent=null), ArticleFig(id=1320889312653198198, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图7, caption=双自由基形式AST过渡态结构及其虚频率, figureFileSmall=/pGctUx2f+Hfp7uRsNrlYw==, figureFileBig=TeeJKVNmp2ieZdMfBWB2KA==, tableContent=null), ArticleFig(id=1320889312711918455, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.8, caption=Transition state structure and virtual frequency of bis-Z astaxanthin in the form of bis-free radicals, figureFileSmall=0+npHz0HaneMVE8ZgkgyBA==, figureFileBig=9Pt6L9LuCmydu6rzYDehUQ==, tableContent=null), ArticleFig(id=1320889312787415928, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图8, caption=双自由基形式双顺式AST的过渡态结构及其虚频率, figureFileSmall=0+npHz0HaneMVE8ZgkgyBA==, figureFileBig=9Pt6L9LuCmydu6rzYDehUQ==, tableContent=null), ArticleFig(id=1320889312867107705, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Fig.9, caption=Schematic diagram of Z-isomerization of astaxanthin and its mechanism, figureFileSmall=9hAH9BJdaKEpUEHzDHNmVw==, figureFileBig=o8TjUHpgO6tfdEbUmsF0QA==, tableContent=null), ArticleFig(id=1320889312934216570, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=图9, caption=虾青素光顺式异构化及其机制示意图, figureFileSmall=9hAH9BJdaKEpUEHzDHNmVw==, figureFileBig=o8TjUHpgO6tfdEbUmsF0QA==, tableContent=null), ArticleFig(id=1320889313001325435, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Table 1, caption=

Retention time, absorption wavelength and Q value of astaxanthin isomers

, figureFileSmall=null, figureFileBig=null, tableContent=

峰	AST 异构体	保留 时间（min）	顺式峰 波长（nm）	主峰波长 （nm）	Q值
					测定值	报道值[8,20]
峰1	全反式	8.31	373	469	0.11	0.09	−
峰2	9顺式	11.34	381	477	0.15	0.11	0.20
峰3	13顺式	12.27	371	467	0.55	0.55	0.52

), ArticleFig(id=1320889313076822908, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=表1, caption=

虾青素异构体保留时间、吸收波长及其Q值

, figureFileSmall=null, figureFileBig=null, tableContent=

峰	AST 异构体	保留 时间（min）	顺式峰 波长（nm）	主峰波长 （nm）	Q值
					测定值	报道值[8,20]
峰1	全反式	8.31	373	469	0.11	0.09	−
峰2	9顺式	11.34	381	477	0.15	0.11	0.20
峰3	13顺式	12.27	371	467	0.55	0.55	0.52

), ArticleFig(id=1320889313164903293, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Table 2, caption=

Gibbs free energy difference obtained by single point energy correction of astaxanthin

, figureFileSmall=null, figureFileBig=null, tableContent=

AST构型/状态	中性分子（kcal/mol）	双自由基（kcal/mol）
全反式	0	0
9顺式	1.50	2.14
13顺式	1.72	−14.39
15顺式	2.66	−12.64

), ArticleFig(id=1320889313252983678, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=表2, caption=

虾青素单点能修正得到吉布斯自由能差

, figureFileSmall=null, figureFileBig=null, tableContent=

AST构型/状态	中性分子（kcal/mol）	双自由基（kcal/mol）
全反式	0	0
9顺式	1.50	2.14
13顺式	1.72	−14.39
15顺式	2.66	−12.64

), ArticleFig(id=1320889313324286847, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Table 3, caption=

HOMO and LUMO energies and energy gaps of all-E, 9-Z, 13-Z and 15-Z neutral astaxanthin

, figureFileSmall=null, figureFileBig=null, tableContent=

中性AST	HOMO（au）	LUMO（au）	HOMO−LUMO（au）
全反式	−0.10298	−0.17892	0.07594
9顺式	−0.10151	−0.17875	0.07724
13顺式	−0.10147	−0.17972	0.07825
15顺式	−0.10207	−0.1802	0.07819

), ArticleFig(id=1320889313403978625, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=表3, caption=

全反式、9顺式、13顺式、15顺式中性AST的HOMO和LUMO能量及能隙

, figureFileSmall=null, figureFileBig=null, tableContent=

中性AST	HOMO（au）	LUMO（au）	HOMO−LUMO（au）
全反式	−0.10298	−0.17892	0.07594
9顺式	−0.10151	−0.17875	0.07724
13顺式	−0.10147	−0.17972	0.07825
15顺式	−0.10207	−0.1802	0.07819

), ArticleFig(id=1320889313483670403, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Table 4, caption=

Calculation results of all-E astaxanthin, 9-Z, 13-Z and 15-Z-astaxanthin and transition states of three Z isomers by unrestricted open shell (S²)

, figureFileSmall=null, figureFileBig=null, tableContent=

AST构型	S2
全反式	2.0984
9顺式	2.0971
13顺式	2.0992
15顺式	2.0984
9顺式过渡态	2.1446
13顺式过渡态	2.1515
15顺式过渡态	2.1499

), ArticleFig(id=1320889313966015365, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=表4, caption=

全反式、9顺式、13顺式和15顺式和三种顺式AST过渡态的无限制开壳层计算结果（S²）

, figureFileSmall=null, figureFileBig=null, tableContent=

AST构型	S2
全反式	2.0984
9顺式	2.0971
13顺式	2.0992
15顺式	2.0984
9顺式过渡态	2.1446
13顺式过渡态	2.1515
15顺式过渡态	2.1499

), ArticleFig(id=1320889314041512838, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=EN, label=Table 5, caption=

Three kinds of tunneling correction between Wigner method a and Skodje-Truhlar method b

, figureFileSmall=null, figureFileBig=null, tableContent=

过程	隧道效应校正a	速率常数	隧道效应校正b	速率常数
全反式⇌9顺式	1.011	2.6031×103	1.011	2.6034×103
全反式⇌13顺式	1.006	2.7778×105	1.006	2.7779×105
全反式⇌15顺式	1.016	6.3759×104	1.016	6.3770×104

), ArticleFig(id=1320889314121204615, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320889305627738921, language=CN, label=表5, caption=

维格纳法a与Skodje-Truhlar法b的三种相互转换的隧道效应校正

, figureFileSmall=null, figureFileBig=null, tableContent=

过程	隧道效应校正a	速率常数	隧道效应校正b	速率常数
全反式⇌9顺式	1.011	2.6031×103	1.011	2.6034×103
全反式⇌13顺式	1.006	2.7778×105	1.006	2.7779×105
全反式⇌15顺式	1.016	6.3759×104	1.016	6.3770×104

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