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Article(id=1320881289977250764, tenantId=1146029695717560320, journalId=1260987677001138203, issueId=1320881182762447607, articleNumber=null, orderNo=null, doi=10.13386/j.issn1002-0306.2025070259, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1753027200000, receivedDateStr=2025-07-21, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1792852240318, onlineDateStr=2026-10-24, pubDate=1786723200000, pubDateStr=2026-08-15, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1792852240318, onlineIssueDateStr=2026-10-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1792852240318, creator=13701087609, updateTime=1792852240318, updator=13701087609, issue=Issue{id=1320881182762447607, tenantId=1146029695717560320, journalId=1260987677001138203, year='2026', volume='47', issue='16', pageStart='1', pageEnd='537', issueExtLink='null', onlineDate='null', pubDate='1786723200000', pubDateStr='2026-08-15', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1792852214756, creator='13701087609', updateTime=1792852214756, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext=null, issueFiles=null, downloadFileDto=null}, startPage=293, endPage=301, ext={EN=ArticleExt(id=1320881290216326093, articleId=1320881289977250764, tenantId=1146029695717560320, journalId=1260987677001138203, language=EN, title=Preparation of Phosphorylated Raffinose and Its in Vitro Antioxidant Properties, columnId=1261343843090313538, journalTitle=Science and Technology of Food Industry, columnName=Processing Technology, runingTitle=null, highlight=null, articleAbstract=

To enhance the in vitro antioxidant performance of raffinose, this study investigated the effects of temperature, time, pH, and the ratio of modifiers on the phosphate content in raffinose as single factors. The preparation process of raffinose was optimized by response surface methodology. The structures of raffinose before and after phosphorylation modification were characterized by Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR), and their in vitro antioxidant activities were studied. The results showed that the optimal preparation process of phosphorylated raffinose (P-raffinose) was as follows: pH of the reaction system was 9, the ratio of sodium tripolyphosphate to sodium trimetaphosphate was 4:3, the reaction temperature was 77 ℃, and the reaction time was 5.3 h. Under these conditions, the phosphate content in P-raffinose was 32.14%. Characterization results indicated that raffinose was successfully phosphorylated. Activity tests demonstrated that phosphorylation modification significantly improved the hydroxyl radical scavenging capacity and total antioxidant capacity of raffinose, increasing by 27.06% and 31.40% respectively compared to raffinose. This study provides theoretical basis and technical support for the application of P-raffinose in the development of new functional foods and antioxidants.

, authors=Xuzhen LIU, Kaikai LU, Wanying ZHAO, Chaoyun ZHANG, Yanqin CHEN*, authorsList=Xuzhen LIU, Kaikai LU, Wanying ZHAO, Chaoyun ZHANG, Yanqin CHEN, authorCompany=null, correspAuthors=Yanqin CHEN, 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=1320881293013926874, articleId=1320881289977250764, tenantId=1146029695717560320, journalId=1260987677001138203, language=CN, title=磷酸化棉子糖制备及其体外抗氧化性能, columnId=1261343845481066826, journalTitle=食品工业科技, columnName=工艺技术, runingTitle=null, highlight=null, articleAbstract=

为提升棉子糖体外抗氧化性能，本研究以温度、时间、pH、改性剂比例为单因素考察其对棉子糖中磷酸根含量的影响，采用响应面试验优化了棉子糖的制备工艺。通过傅里叶红外光谱法（Fourier Transform Infrared Spectroscopy，FT-IR）和核磁共振波谱（Nuclear Magnetic Resonance Spectroscopy，NMR）对磷酸化修饰前后的棉子糖进行结构表征，并对其体外抗氧化活性进行研究。结果显示，磷酸化棉子糖（phosphorylated-棉子糖，P-棉子糖）的最佳制备工艺为：反应体系pH为9、三偏磷酸钠与三聚磷酸钠比例4:3、反应温度77 ℃、反应时间5.3 h，在该条件下P-棉子糖中磷酸根含量为32.14%；表征结果显示，棉子糖被成功磷酸化；活性测试表明，磷酸化修饰对棉子糖的羟自由基清除能力及总抗氧化能力提高显著，相对棉子糖分别提高27.06%、31.40%。本研究为P-棉子糖在新型功能性食品及抗氧化剂开发领域提供了理论依据及技术支持。

, authors=刘旭珍, 卢凯凯, 赵婉英, 张朝云, 陈燕勤*, authorsList=刘旭珍, 卢凯凯, 赵婉英, 张朝云, 陈燕勤, authorCompany=null, correspAuthors=陈燕勤, authorNote=

刘旭珍（1998−），女，硕士研究生，研究方向：生物与医药，E-mail：

, correspAuthorsNote=
陈燕勤（1975−），女，博士，教授，研究方向：天然产物结构优化与农业废弃物处理，E-mail：。
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刘旭珍（1998−），女，硕士研究生，研究方向：生物与医药，E-mail：

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刘旭珍（1998−），女，硕士研究生，研究方向：生物与医药，E-mail：

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Fine Chemicals, 2025, 42（10）: 2190−2197., articleTitle=null, refAbstract=null), Reference(id=1320881827682824712, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=30, rfOrder=40, authorNames=null, journalName=null, refType=null, unstructuredReference=王俊龙, 江升旗, 刘梦瑶, 等. 磷酸化修饰鬼臼果多糖的制备及生物活性[J]. 精细化工, 2025, 42(9): 1994−2004. [WANG J L, JIANG S Q, LIU M Y, et al. Preparation and biological activity of phosphorylated podophyllum fruit polysaccharides[J]. 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Storage and Process, 2022, 22(11): 61−68,75.], articleTitle=null, refAbstract=null), Reference(id=1320881829469598220, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=32, rfOrder=44, authorNames=null, journalName=null, refType=null, unstructuredReference=JIANG W M, ZHOU S Y. Study on preparation and antioxidant activity of aloe polysaccharides and their derivatives[J]. 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Preparation, characterization, structural analysis and antioxidant activities of phosphorylated polysaccharide from Sanchi (Panax notoginseng) flower[J]. Journal of Food Science and Technology, 2022, 59(12): 4603−4614., articleTitle=null, refAbstract=null), Reference(id=1320881829679313423, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=35, rfOrder=47, authorNames=null, journalName=null, refType=null, unstructuredReference=姜振浩. 结球菊苣多糖及寡糖磷酸化衍生物的制备[D]. 沈阳: 沈阳化工大学, 2023. [JIANG Z H. Preparation of phosphorylated derivatives of heading chicory polysaccharides and oligosaccharides[D]. Shenyang: Shenyang University of Chemical Technology, 2023.], articleTitle=null, refAbstract=null), Reference(id=1320881829738033680, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=35, rfOrder=48, authorNames=null, journalName=null, refType=null, unstructuredReference=JIANG Z H. Preparation of phosphorylated derivatives of heading chicory polysaccharides and oligosaccharides[D]. Shenyang: Shenyang University of Chemical Technology, 2023., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1320881818111422888, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, xref=null, ext=[AuthorCompanyExt(id=1320881818124005801, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, companyId=1320881818111422888, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, China), AuthorCompanyExt(id=1320881818132394410, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, companyId=1320881818111422888, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=新疆农业大学化学化工学院，新疆乌鲁木齐 830052)])], figs=[ArticleFig(id=1320881821462671822, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=EN, label=Fig.1, caption=Influence of different factors on the phosphate content in P-raffinose, figureFileSmall=doqgeUB7HE3BiVidFbG/2g==, figureFileBig=i7v2E+lVVLeGQmAheg4ixw==, tableContent=null), ArticleFig(id=1320881821542363599, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=CN, label=图1, caption=不同单因素对P-棉子糖中磷酸根含量的影响

注：a. 反应体系pH；b. 三偏磷酸钠与三聚磷酸钠比例；c. 反应温度；d. 反应时间。

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注：a为温度与pH的交互作用；b为温度与时间的交互作用；c为时间与pH的交互作用。

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注：（a）棉子糖的13C NMR；（b） P-棉子糖的13C NMR。

, figureFileSmall=nWzTz6yaBPIYp8XXke6hmg==, figureFileBig=qW1nGUEjtmDY8Ph/tiRttA==, tableContent=null), ArticleFig(id=1320881822330892760, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=EN, label=Fig.6, caption=In vitro antioxidant results of phosphorylated raffinose and raffinose, figureFileSmall=YnmMln0t9+1Nd2+h+KiORg==, figureFileBig=/8jyIm6jyq35us1hADLFhg==, tableContent=null), ArticleFig(id=1320881822389613017, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=CN, label=图6, caption=棉子糖与P-棉子糖的体外抗氧化结果

注：a. DPPH自由基的清除率；b. 羟自由基的清除率；c. 铁离子还原力；d. 总抗氧化能力。

, figureFileSmall=YnmMln0t9+1Nd2+h+KiORg==, figureFileBig=/8jyIm6jyq35us1hADLFhg==, tableContent=null), ArticleFig(id=1320881822481887706, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=EN, label=Table 1, caption=

Coding and range of response surface methodology for influencing factors of Raffinose finose phosphorylation modification

, figureFileSmall=null, figureFileBig=null, tableContent=
影响因素水平编码
−101
A：反应体系pH8910
B：反应时间（h）456
C：反应温度（℃）708090
), ArticleFig(id=1320881822561579483, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=CN, label=表1, caption=

棉子糖磷酸化改性影响因素的响应曲面法编码及其范围

, figureFileSmall=null, figureFileBig=null, tableContent=
影响因素水平编码
−101
A：反应体系pH8910
B：反应时间（h）456
C：反应温度（℃）708090
), ArticleFig(id=1320881822628688348, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=EN, label=Table 2, caption=

Experimental design and results of response surface methodology

, figureFileSmall=null, figureFileBig=null, tableContent=
实验号因素磷酸根含量（%）
A pHB反应时间C反应温度试验值预测值
100032.20±0.3232.46
201127.11±0.9226.46
300032.31±0.6832.46
40−1125.14±0.5524.68
51−1023.71±0.3127.43
600033.45±0.2432.46
700031.90±0.2932.46
8−1−1025.41±0.3628.58
90−1−125.82±0.3626.3
1000032.49±0.1032.46
11−10−127.11±0.9229.18
1201−129.53±0.3628.00
13−11026.10±0.4129.35
14−10125.02±0.5027.51
1510−126.22±0.1029.1
1611026.19±0.0929.90
1710126.50±0.1225.86
), ArticleFig(id=1320881822716768733, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=CN, label=表2, caption=

响应面试验设计及结果

, figureFileSmall=null, figureFileBig=null, tableContent=
实验号因素磷酸根含量（%）
A pHB反应时间C反应温度试验值预测值
100032.20±0.3232.46
201127.11±0.9226.46
300032.31±0.6832.46
40−1125.14±0.5524.68
51−1023.71±0.3127.43
600033.45±0.2432.46
700031.90±0.2932.46
8−1−1025.41±0.3628.58
90−1−125.82±0.3626.3
1000032.49±0.1032.46
11−10−127.11±0.9229.18
1201−129.53±0.3628.00
13−11026.10±0.4129.35
14−10125.02±0.5027.51
1510−126.22±0.1029.1
1611026.19±0.0929.90
1710126.50±0.1225.86
), ArticleFig(id=1320881822783877598, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=EN, label=Table 3, caption=

Analysis of variance for the regression model

, figureFileSmall=null, figureFileBig=null, tableContent=
方差来源平方和自由度均方FP显著性
模型167.44918.644<0.0001****
A-pH0.1310.130.30.6035
B-反应时间5.6115.6113.270.0083**
C-反应温度5.2815.2812.490.0095**
AB0.8110.811.920.2088
AC1.4411.443.410.1075
BC2.7212.726.440.0388*
A255.1155.1130.33<0.0001****
B251.36151.36121.48<0.0001****
C229.4129.469.54<0.0001****
残差2.9670.42
失拟项1.6730.561.720.3001不显著
纯误差1.2940.32
总相关170.416
R20.9826
R2Adj0.9603
预测系数R20.8316
C.V.%2.33
信噪比17.09
), ArticleFig(id=1320881822867763679, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320881289977250764, language=CN, label=表3, caption=

回归模型的方差分析

, figureFileSmall=null, figureFileBig=null, tableContent=
方差来源平方和自由度均方FP显著性
模型167.44918.644<0.0001****
A-pH0.1310.130.30.6035
B-反应时间5.6115.6113.270.0083**
C-反应温度5.2815.2812.490.0095**
AB0.8110.811.920.2088
AC1.4411.443.410.1075
BC2.7212.726.440.0388*
A255.1155.1130.33<0.0001****
B251.36151.36121.48<0.0001****
C229.4129.469.54<0.0001****
残差2.9670.42
失拟项1.6730.561.720.3001不显著
纯误差1.2940.32
总相关170.416
R20.9826
R2Adj0.9603
预测系数R20.8316
C.V.%2.33
信噪比17.09
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磷酸化棉子糖制备及其体外抗氧化性能
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刘旭珍 , 卢凯凯 , 赵婉英 , 张朝云 , 陈燕勤 *
食品工业科技 | 工艺技术 2026,47(16): 293-301
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食品工业科技 |工艺技术 2026 , 47 (16) : 293 -301
磷酸化棉子糖制备及其体外抗氧化性能
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刘旭珍 , 卢凯凯, 赵婉英, 张朝云, 陈燕勤*
作者信息
  • 新疆农业大学化学化工学院，新疆乌鲁木齐 830052
通讯作者:
陈燕勤（1975−），女，博士，教授，研究方向：天然产物结构优化与农业废弃物处理，E-mail：。
作者简介:

刘旭珍（1998−），女，硕士研究生，研究方向：生物与医药，E-mail：

Preparation of Phosphorylated Raffinose and Its in Vitro Antioxidant Properties
Xuzhen LIU , Kaikai LU, Wanying ZHAO, Chaoyun ZHANG, Yanqin CHEN*
Affiliations
  • College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, China
出版时间: 2026-08-15 doi: 10.13386/j.issn1002-0306.2025070259
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为提升棉子糖体外抗氧化性能，本研究以温度、时间、pH、改性剂比例为单因素考察其对棉子糖中磷酸根含量的影响，采用响应面试验优化了棉子糖的制备工艺。通过傅里叶红外光谱法（Fourier Transform Infrared Spectroscopy，FT-IR）和核磁共振波谱（Nuclear Magnetic Resonance Spectroscopy，NMR）对磷酸化修饰前后的棉子糖进行结构表征，并对其体外抗氧化活性进行研究。结果显示，磷酸化棉子糖（phosphorylated-棉子糖，P-棉子糖）的最佳制备工艺为：反应体系pH为9、三偏磷酸钠与三聚磷酸钠比例4:3、反应温度77 ℃、反应时间5.3 h，在该条件下P-棉子糖中磷酸根含量为32.14%；表征结果显示，棉子糖被成功磷酸化；活性测试表明，磷酸化修饰对棉子糖的羟自由基清除能力及总抗氧化能力提高显著，相对棉子糖分别提高27.06%、31.40%。本研究为P-棉子糖在新型功能性食品及抗氧化剂开发领域提供了理论依据及技术支持。

棉子糖  /  磷酸化  /  响应面法  /  结构表征  /  抗氧化活性

To enhance the in vitro antioxidant performance of raffinose, this study investigated the effects of temperature, time, pH, and the ratio of modifiers on the phosphate content in raffinose as single factors. The preparation process of raffinose was optimized by response surface methodology. The structures of raffinose before and after phosphorylation modification were characterized by Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR), and their in vitro antioxidant activities were studied. The results showed that the optimal preparation process of phosphorylated raffinose (P-raffinose) was as follows: pH of the reaction system was 9, the ratio of sodium tripolyphosphate to sodium trimetaphosphate was 4:3, the reaction temperature was 77 ℃, and the reaction time was 5.3 h. Under these conditions, the phosphate content in P-raffinose was 32.14%. Characterization results indicated that raffinose was successfully phosphorylated. Activity tests demonstrated that phosphorylation modification significantly improved the hydroxyl radical scavenging capacity and total antioxidant capacity of raffinose, increasing by 27.06% and 31.40% respectively compared to raffinose. This study provides theoretical basis and technical support for the application of P-raffinose in the development of new functional foods and antioxidants.

raffinose  /  phosphorylation  /  response surface methodology  /  structural characterization  /  antioxidant activity
刘旭珍, 卢凯凯, 赵婉英, 张朝云, 陈燕勤. 磷酸化棉子糖制备及其体外抗氧化性能. 食品工业科技, 2026 , 47 (16) : 293 -301 . DOI: 10.13386/j.issn1002-0306.2025070259
Xuzhen LIU, Kaikai LU, Wanying ZHAO, Chaoyun ZHANG, Yanqin CHEN. Preparation of Phosphorylated Raffinose and Its in Vitro Antioxidant Properties[J]. Science and Technology of Food Industry, 2026 , 47 (16) : 293 -301 . DOI: 10.13386/j.issn1002-0306.2025070259
正文
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棉子糖是由一分子半乳糖、一分子葡萄糖和一分子果糖组成的低聚糖，普遍存在于棉籽、大豆、甜菜、卷心菜和一些油料植物的籽仁中，其中棉籽仁中棉子糖的含量达4%~5%[1]，但天然棉子糖生物活性较弱[2]，对有益菌增殖效果有限[3]，过量摄入还易引发腹泻[4]，使其在食品领域的应用受到限制。
研究发现，天然棉子糖分子结构中缺乏如VC结构中的烯二醇、邻二酚羟基等强抗氧化基团，从而使棉子糖无法像VC一样通过分子内电子转移或共轭效应稳定自由基中间体。在糖类化合物功能化修饰技术体系中，磷酸化修饰通过引入极性磷酸基团，将低聚糖分子中羟基上的氢原子置换为磷酸基团，引起低聚糖分子空间构象改变，提升低聚糖分子的抗氧化活性[5−7]，因此，对棉子糖进行磷酸化修饰成为提高棉子糖抗氧化能力的关键突破路径。当前对糖类磷酸化修饰的主要方法包括磷酸盐法[8]、酸法[9]与磷酰氯法[10]三大类，其中因磷酸盐法在安全性、经济成本以及工艺等方面更具优势使其成为低聚糖磷酸化修饰的主要途径[11−12]。例如，王晓凤等[13]研究发现与红菊苣寡糖相比，磷酸化红菊苣寡糖对羟自由基清除率提高了15.87%；张亚坤[14]研究发现磷酸化修饰甘露寡糖可以通过抑制肠道有害菌提高大鼠免疫力；张元等[15]研究发现磷酸化壳寡糖具有通过促进小鼠脾淋巴细胞增殖增强小鼠免疫力的益生元效能。
值得注意的是，当前针对低聚糖改性的相关研究较少，尤其是在棉子糖磷酸化改性方面，而研究发现通过磷酸化改性提升低聚糖抗氧化活性的过程，其性能往往受自身特性及磷酸化浓度等关键参数调控[16−18]。对此，本文聚焦磷酸盐法，通过引入亲水性磷酸基团改善棉子糖水溶性并激活生物活性位点，通过对反应温度、时间、溶液反应体系pH及磷酸盐比例等关键参数精准调控，构建高效、可控、绿色的棉子糖磷酸化修饰体系，以期为棉子糖磷酸化修饰工艺及产物开发应用提供理论支撑，并为同类低聚糖功能修饰研究与产业化转化提供案例、奠定基础，进而推动其在功能型食品、食品添加剂等领域的应用转化，并助力低聚糖产业的高质量发展。
1　材料与方法
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1.1　材料与仪器
棉子糖（≥98%）　陕西晨明生物科技有限公司；100 Da透析袋　湖南翊博生物科技有限公司；无水硫酸钠、三聚磷酸钠、三偏磷酸钠、氢氧化钠、硫酸亚铁、磷酸氢二钠　国药集团化学试剂有限公司；溴化钾、浓硫酸、浓盐酸、水杨酸、三氯乙酸（TCA）　天津市致远化学试剂有限公司；铁氰化钾　天津市福晨化学试剂厂；钼酸铵　天津市光复科技发展有限公司；抗坏血酸（VC）、无水乙醇、三氯化铁　天津市鑫铂特化工有限公司；1,1-二苯基-2-三硝基苯肼（DPPH）　上海麦克林生化科技股份有限公司；所有试剂均为国产分析纯。
AL204-IC电子天平　梅特勒-托利多仪器有限公司；DHG-9140A电热恒温鼓风干燥箱　上海齐欣科学仪器有限公司；SY18-1智能磁力搅拌加热锅　上海司乐仪器有限公司；SHA-C水浴恒温振荡器　金坛市医疗仪器厂；C1609041可见分光光度计　上海菁华科技仪器有限公司；JM-16D-40液晶单频超声波清洗仪器　深圳市洁盟清洗设备有限公司；LGJ-12-80真空冷冻干燥机　河南兄弟仪器设备有限公司；THY-15压片机　天津天光光学仪器有限公司。
1.2　实验方法
1.2.1　P-棉子糖的制备与条件优化
1.2.1.1　P-棉子糖的制备
参照Yang等[19]的方法，进行P-棉子糖的制备。将0.25 g的棉子糖、1.25 g的无水硫酸钠、磷酸化试剂（三偏磷酸钠与三聚磷酸钠）用25 mL去离子水充分溶解，用0.5 mol/L的HCl、NaOH调节反应体系pH为8，去离子水透析48 h，冷冻干燥得到P-棉子糖。
1.2.1.2　P-棉子糖取代度的测定
参照Estela等[20]方法，采用钼蓝比色法测定P-棉子糖中磷酸根含量。将磷酸二氢钾配制成10 μg/mL的磷标准溶液，分别取磷标准溶液0、0.5、1.0、1.5、2.0、2.5、3.0、3.5、4.0、4.5和5 mL置于25 mL试管中，依次加入去离子水至5 mL，3 mL的定磷试剂（1 mL 3 mol/L硫酸、1 mL 3%钼酸铵和1 mL 20%抗坏血酸的混合溶液），充分混匀，45 ℃水浴加热30 min，静置冷却至室温，在660 nm处测定其吸光值，以吸光度值为纵轴，磷酸根质量浓度为横轴，绘制磷酸根质量浓度的标准曲线，线性回归方程为：Y=0.0413X−0.0049，R2=0.9990，在0~10 μg/mL范围内，磷酸根质量浓度与吸光度值线性关系良好。
取2 mg P-棉子糖样品，加入3 mL定磷试剂，用去离子水定容至50 mL，45 ℃水浴加热30 min，在660 nm处测定其吸光值并计算样品中磷酸根含量。P-棉子糖中磷酸根含量按公式（1）计算。
$ 磷酸根含量(\text{%})=\frac{50\times 10^{-3}(\text{Y}+0.0049)}{0.0413\text{m}}\times 100 $
式中：m为样品质量（mg），Y为吸光度，50×10−3为体积换算系数，0.0049、0.0413为标准曲线拟合得到的定量系数。
1.2.1.3　单因素实验
将0.25 g棉子糖、1.25 g无水硫酸钠用25 mL去离子水充分溶解，选择反应体系pH、改性剂比例（三偏磷酸钠与三聚磷酸钠）、温度、时间为单因素进行实验，每次实验只改变一个因素条件，选取最佳的单因素条件进行后续实验。其中，反应体系pH选取7、8、9、10、11，改性剂比例选取1:6、2:5、3:4、4:3、5:2、6:1，反应温度选取50、60、70、80、90 ℃，反应时间选取3、4、5、6、7 h，通过计算P-棉子糖的磷酸根含量百分比，确定棉子糖磷酸化改性的最佳工艺条件。
1.2.1.4　响应面工艺优化
在单因素实验的基础上，以磷酸根含量百分比为响应值，使用Design-Expert 10软件（Stat-Easelnc，美国）进行实验设计和统计分析。基于响应面法（Response Surface Methodology，RSM）中Box-Behnken Design（BBD）模型的设计原理[21]及单因素实验结果，选取反应体系pH（A）、反应时间（B）、反应温度（C）为自变量，在3个水平上进行RSM试验，使用Box-Behnken软件对棉子糖磷酸化修饰条件实验进行优化设计，RSM试验因素与水平如表1所示。
1.2.2　结构表征
1.2.2.1　FT-IR分析
将棉子糖与制备的P-棉子糖分别与KBr以1:100的质量比混合，研磨至粉末状并压成薄片置于红外光谱仪中，并在4000~500 cm−1范围内进行光谱分析。
1.2.2.2　NMR分析
用99.8% D2O分别溶解棉子糖和P-棉子糖样品，采用400 MHz核磁共振谱仪（AVANCEII，Bruker）进行分析，并记录棉子糖、P-棉子糖的13C核磁共振波谱。
1.2.3　P-棉子糖的抗氧化实验
1.2.3.1　DPPH自由基清除率的测定
参照Li等[22]方法，进行DPPH自由基清除实验。配制0.8、4、10、20、40、60 mg/mL的棉子糖和P-棉子糖溶液，取1.0 mL样品溶液，加入1.0 mL 5%的DPPH-乙醇溶液充分混匀，室温下避光反应30 min，在517 nm波长处测定吸光度值。A0组用等量去离子水代替DPPH-乙醇溶液，AC组用等量去离子水代替样品，阳性对照组用等量VC代替样品。DPPH自由基清除活性按式（2）计算：
$ \text{DPPH自由基清除率}(\text{%})=\left(1-\frac{{\text{A}}_{\text{S}}-{\text{A}}_{0}}{{\text{A}}_{\text{C}}}\right)\times 100 $
式中：AS为样品组吸光度，A0为空白组吸光度，AC为对照组吸光度。
1.2.3.2　羟自由基清除率的测定
参照Chen等[23]方法，进行羟自由基清除实验。配制0.8、4、10、20、40、60 mg/mL的棉子糖和P-棉子糖样品溶液，取1.0 mL样品溶液，加入1.0 mL 9 mol/L的Fe2SO4溶液和9 mol/L水杨酸-乙醇溶液，最后加入1.0 mL 8.8 mmol/L H2O2溶液，混匀，37 ℃水浴30 min，冷却至室温，在510 nm波长处测定吸光值。A0组用等量去离子水代替水杨酸-乙醇溶液，AC组用等量去离子水代替样品，阳性对照组用等量VC代替样品。羟自由基清除率按式（3）计算：
$ \text{羟自由基清除率}(\text{%})=\left(1-\frac{{\text{A}}_{\text{S}}-{\text{A}}_{0}}{{\text{A}}_{\text{C}}}\right)\times 100 $
式中：AS为样品吸光度，A0为空白吸光度，AC为对照组吸光度。
1.2.3.3　铁离子还原能力的测定
参照Chen等[24]方法，进行铁离子还原力实验。制0.8、4、10、20、40、60 mg/mL的棉子糖和P-棉子糖样品溶液，取1.0 mL样品溶液，加入1.25 mL 0.2 mol/L（pH6.6）磷酸盐缓冲溶液和1% K3[Fe（CN）6]溶液，50 ℃水浴30 min，冷却至室温，加入1.25 mL 10%的TCA溶液，50 r/s离心10 min，取1.25 mL上清液，加入1.25 mL去离子水和0.25 mL 0.1% FeCl3溶液，静置10 min，在700 nm波长处测定吸光度。F0组用等量去离子水代替样品，阳性对照组用等量VC代替样品。铁离子还原力按式（4）计算：
$ \text{总还原能力}={\text{F}}_{1}-{\text{F}}_{0} $
式中：F1为样品吸光度，F0为空白吸光度。
1.2.3.4　总抗氧化能力的测定
参照李兰等[25]方法，进行总抗氧化能力实验。配制0.8、4、10、20、40、60 mg/mL的棉子糖和P-棉子糖溶液，将0.6 mol/L H2SO4，28 mol/L Na3PO4和4 mol/L钼酸铵溶液三种溶液按照1:1:1比例混匀得到工作液，取1.0 mL样品溶液，加入3.0 mL工作液，95 ℃加热1.5 h，冷却至室温，在695 nm波长处测定吸光度。F0组用等量去离子水代替样品，阳性对照组用等量VC代替样品。计算方法同1.2.3.3。
1.3　数据处理
本研究所有实验组及对照组均设置三次平行实验。使用Microsoft Excel 2010（Microsoft Corporation，USA）和Origin 2021软件进行数据分析和作图。采用Design Expert 10软件和方差分析（ANOVA）评价实验数据和分析。采用Tukey's检验评价显著性差异，P<0.05定义为显著性差异，P<0.01定义为极显著性差异，P>0.05定义为无显著性差异。
2　结果与分析
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2.1　单因素实验
反应体系pH、三偏磷酸钠与三聚磷酸钠比例、反应温度及反应时间对P-棉子糖中磷酸根含量的影响结果见图1。图1结果显示，各因素对P-棉子糖中磷酸根含量影响均呈“Λ”变化趋势，都是通过影响底物结构或催化效率呈现出显著的阈值效应[26]。
如图1a所示，当反应体系pH为9时，P-棉子糖磷酸根含量达到20.13%，反应体系pH通过调控催化环境影响反应进程，过碱环境则因磷酸盐形态转化（如三聚磷酸钠水解）削弱协同催化能力，导致磷酸化程度下降[27]，因此，本试验适宜反应体系pH初步定为9。
如图1b所示，当三偏磷酸钠与三聚磷酸钠比例4:3时，P-棉子糖中磷酸根含量达到20.57%，此时三偏磷酸钠与三聚磷酸钠协同催化效应达到最大，超过该比例后，过量磷酸盐会引发空间位阻或竞争吸附，导致磷酸化程度下降[28]，因此，本试验适宜改性剂比例初步定为4:3。
如图1c所示，反应温度80 ℃时，P-棉子糖中磷酸根含量达到21.88%，继续升高反应温度棉子糖分子内糖苷键会断裂引起空间构象破坏，导致磷酸基团结合位点减少[29]，因此，本试验适宜反应温度初步定为80 ℃。
如图1d所示，当反应时间5 h时P-棉子糖中磷酸根含量达到24.2%，再延长反应时间，高温持续作用引发棉子糖异构化或降解，显著降低磷酸化效率[30]，因此，本试验适宜反应时间初步定为5 h。
2.2　RSM设计与分析
不同反应条件下获得的P-棉子糖中磷酸根含量的响应面试验值和预测值如表2所示。P-棉子糖的试验值在23.7%~33.4%之间，基于多元回归分析，通过Design Expert 10软件建立的响应值和三个变量的二次多项式模型如下：
Y=32.46−0.1250A+0.8375B−0.8125C+0.4500AB+0.6000AC−0.8250BC−3.62A2−3.49B2−2.64C2
其中，Y为P-棉子糖的磷酸根含量；A为反应体系pH；B为反应时间；C为反应温度。
模型评估结果见表3，R2为0.9826且R2Adj达到0.9603，表明该模型具备良好的拟合度。统计学检验进一步证实了模型的可靠性：F值=44且P<0.0001，失拟项P=0.3001>0.05，说明回归方程具有显著统计学意义且无显著失拟现象；C.V.%=2.33%<10%及信噪比17.09>4的结果，印证了实验系统的稳定性与方程预测的准确性。
模型的实验实际值与预测值、残差正态概率分布如图2所示，图2a显示，实际值（Actual）和预测值（Predicted）构成的点与参考线的偏离程度小、吻合度高，表明模型对P-棉子糖改性工艺条件的精准预测能力，图2b显示，实际测量值紧密围绕标准化残差曲线分布，证实了数据拟合的稳定性。此外，结合表3分析发现，模型显著性检验的P<0.05，表明模型整体显著；失拟项显著性检验的P>0.05，说明模型无显著失拟。因此，该二次多项式模型不仅拟合精度高，且统计显著性良好，可有效描述P-棉子糖中磷酸根含量的量化关系，具备实用价值。
反应体系pH、反应时间及温度对P-棉子糖中磷酸根含量影响的交互作用如图3所示。图3显示，反应体系pH、反应时间及温度两两交互作用图均为凸面且存在最大值，说明试验范围内P-棉子糖存在最优制备条件。其中，反应温度与反应时间的响应曲面陡峭且等高线呈椭圆形，说明二者交互作用显著；而反应时间与反应体系pH、反应温度与反应体系pH的响应曲面虽陡峭，但等高线介于椭圆与圆形之间，说明其交互作用不显著。响应面优化结果显示反应体系pH为8.718、温度77.32 ℃、时间5.278 h，预测P-棉子糖中磷酸根含量为32.46%。结合生产实际修正工艺条件为反应体系pH9、温度77 ℃、时间5.3 h，在此条件下开展三次平行实验，测量值32.14%与预测值32.46%相对偏差仅0.99%，验证了模型的准确性与可靠度。
2.3　结构表征
2.3.1　FT-IR分析
棉子糖和P-棉子糖的红外吸收光谱如图4所示。图4为典型的低聚糖吸收峰，P-棉子糖和棉子糖在3431 cm−1处均呈现出强吸收特征峰，该吸收峰属于糖分子内或糖分子间氢键作用下的O–H伸缩振动峰，在2800~3000 cm−1区域内两者均有弱吸收峰且高度重合，该吸收峰是由对应糖环及亚甲基的C–H对称或不对称伸缩振动引起，1000~1200 cm−1区间的糖苷键特征峰簇是由C–O–C伸缩与弯曲耦合振动引起，P-棉子糖的红外吸收光谱在此区域虽因磷酸取代发生局部峰形微调，但其振动模式与裂分规律没有发生改变，说明磷酸化修饰前后的棉子糖主要结构没有变化。P-棉子糖在1658、1276、887 cm−1处新增特征吸收，其中，1658 cm−1属于磷酸基团P=O伸缩的伴峰，由氢键或取代位阻导致位移引起，1276 cm−1对应P=O不对称伸缩振动是磷酸酯键典型特征峰，887 cm−1为P–O弯曲振动或P–OH振动引起是磷酸基团特征峰，1658、1276、887 cm−1处出现的特征峰表明磷酸化修饰成功[13]。
2.3.2　NMR分析
P-棉子糖和棉子糖的13C NMR分析结果如图5所示。与棉子糖的13C NMR图5（a）相比，图5（b）P-棉子糖的13C NMR谱在67~77 ppm和90~110 ppm处出现显著变化：其中67~77 ppm峰属于磷酸化修饰的伯羟基碳（如Gal/Glc C-6、Fru C-5）信号，因C-O-P键吸电子效应导致化学位移向低场移动；90~110 ppm峰则是由于棉子糖中葡萄糖或半乳糖的端基碳信号峰（90~110 ppm）向低场移动，表明棉子糖中葡萄糖或半乳糖单元的端基碳（C-1）可能受磷酸化取代的空间位阻影响。P-棉子糖的13C NMR谱中70~85 ppm附近的共振信号明显减弱或偏移，说明棉子糖中葡萄糖和半乳糖单元的C-2、C-3或C-4位置以及果糖单元的C-3、C-4位置也可能被磷酸基团取代，P-棉子糖在-4~-26 ppm区间出现多个特征共振峰，而棉子糖13C NMR在此区间无特征共振峰出现，表明棉子糖中成功引入磷酸基团[31−32]。图4中P-棉子糖在1276 cm−1（P=O伸缩振动）和887 cm−1（C-O-P特征吸收）处呈现的磷酸酯键与磷酸基团特征峰，与图5（b）中P-棉子糖相较于棉子糖所出现的碳信号位移及分布变化相吻合。此变化符合磷酸化低聚糖因C-6位空间位阻较小而优先发生取代、致使C-6信号（约60 ppm附近）位移的规律，证明棉子糖已成功磷酸化修饰，且取代最可能发生于半乳糖或葡萄糖单元的C-6位以及果糖单元的C-5位[33−34]。
2.4　P-棉子糖体外抗氧化活性
P-棉子糖体外抗氧化活性测定结果如图6所示。以VC为阳性对照，结果显示改性前后棉子糖体外抗氧化活性与浓度（0.8~60 mg/mL）呈正相关，且P-棉子糖的体外抗氧化活性始终高于棉子糖。本研究得出的结论，与姜志炫等[5]、Yuan等[16]、姜振浩[35]针对磷酸化低聚糖开展的体外抗氧化研究结果一致，均呈现出浓度依赖性。
以VC为阳性对照，当浓度为60 mg/mL时，P-棉子糖的DPPH自由基清除率为87.94%，较接近20 mg/mL时VC的DPPH自由基清除率99.29%，较棉子糖的DPPH自由基清除率83.14%相对提高5.77%，表明磷酸化修饰可增强棉子糖对DPPH自由基的捕获能力；P-棉子糖的羟基自由基清除率为39.67%，低于20 mg/mL时VC的羟基自由基清除率99.27%，较棉子糖的羟基自由基清除率31.22%相对提高27.06%，表明磷酸化修饰可有效增强棉子糖对羟自由基的清除能力；P-棉子糖的铁离子还原力为0.74%，接近20 mg/mL时VC的铁离子还原力1.64%，较棉子糖的铁离子还原力0.73%相对提高1.37%，表明磷酸化修饰对Raf铁离子还原能力提升效果不显著；P-棉子糖总抗氧化能力为2.26%，接近20 mg/mL时VC的总抗氧化能力2.61%，较棉子糖的总抗氧化能力1.72%相对提高31.40%，表明磷酸化修饰可大幅提高Raf的总抗氧化能力，但目前P-棉子糖的抗氧化作用机理还不明确，仍需进一步探讨研究。
3　结论
收起
本研究在单因素实验的基础上通过响应面优化法得到最佳制备工艺，P-棉子糖中磷酸根含量为32.14%，与模型预期值32.46%偏差极小，证实了工艺模型的可靠度；FT-IR及NMR结果显示，棉子糖磷酸化修饰成功，且P-棉子糖中磷酸基团的取代位置最有可能在棉子糖中半乳糖或葡萄糖单元的C-6位置以及果糖单元的C-5位置；抗氧化实验结果表明，当浓度为60 mg/mL时，P-棉子糖的DPPH自由基的清除能力、羟自由基清除能力、铁离子还原能力、总抗氧化能力相对棉子糖分别提高了5.77%、27.06%、1.37%、31.40%，说明磷酸化修饰可有效提高棉子糖的体外抗氧化活性。本研究为P-棉子糖制备工艺及活性的进一步研究提供了理论依据，更为低聚糖作为抗氧化产品在食品和医药等领域的深入研究和拓展提供数据支撑，后续可进一步考察P-棉子糖在体内生物活性及其益生元功效，扩展P-棉子糖在食药领域的开发与利用。

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2026年第47卷第16期
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doi: 10.13386/j.issn1002-0306.2025070259
  • 接收时间：2025-07-21
  • 首发时间：2026-10-24
  • 出版时间：2026-08-15
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  • 收稿日期：2025-07-21
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    新疆农业大学化学化工学院，新疆乌鲁木齐 830052

通讯作者:

陈燕勤（1975−），女，博士，教授，研究方向：天然产物结构优化与农业废弃物处理，E-mail：。
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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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