Article(id=1320166304925987251, tenantId=1146029695717560320, journalId=1260987677001138203, issueId=1320166220377215955, articleNumber=null, orderNo=null, doi=10.13386/j.issn1002-0306.2025060157, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1750003200000, receivedDateStr=2025-06-16, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1792681774597, onlineDateStr=2026-10-22, pubDate=1780243200000, pubDateStr=2026-06-01, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1792681774597, onlineIssueDateStr=2026-10-22, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1792681774597, creator=13701087609, updateTime=1792681774597, updator=13701087609, issue=Issue{id=1320166220377215955, tenantId=1146029695717560320, journalId=1260987677001138203, year='2026', volume='47', issue='11', pageStart='1', pageEnd='514', issueExtLink='null', onlineDate='null', pubDate='1780243200000', pubDateStr='2026-06-01', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1792681754440, creator='13701087609', updateTime=1792681754440, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext=null, issueFiles=null, downloadFileDto=null}, startPage=205, endPage=212, ext={EN=ArticleExt(id=1320166305131508148, articleId=1320166304925987251, tenantId=1146029695717560320, journalId=1260987677001138203, language=EN, title=Evaluation of the Antioxidant Capacity and Gut Microbiota Modulation Effects of 6-Methoxy-Benzoxazolin-2-One and Benzoxazolin-2-One, columnId=1261336275769016441, journalTitle=Science and Technology of Food Industry, columnName=Bioengineering, runingTitle=null, highlight=null, articleAbstract=

To investigate the roles of 6-methoxy-benzoxazolin-2-one (MBOA) and benzoxazolin-2-one (BOA) in the health-promoting effects of whole-grain foods, this study evaluated their in vitro antioxidant capacity and modulatory effects on gut microbiota. The results demonstrated that while MBOA and BOA exhibited dose-dependent antioxidant activity, their efficacy was inferior to that of ferulic acid. Compared to equivalent doses of ferulic acid, MBOA, BOA, and the mixture significantly enhanced microbial diversity in a dose-dependent manner, with the mixture showing optimal efficacy. At the phylum level, these compounds significantly reduced the relative abundances of Proteobacteria and Bacteroidetes while increasing those of Firmicutes and Actinobacteria. At the genus level, they markedly elevated the relative abundances of Bifidobacterium and reduced Escherichia, Prevotella, and Bacteroides. This study indicates that MBOA and BOA in whole grains possess substantial prebiotic potential.

, authors=Ruoyan YANG, Luyao LI, Tianxi WANG, Lingxiao GONG*, Jing WANG*, authorsList=Ruoyan YANG, Luyao LI, Tianxi WANG, Lingxiao GONG, Jing WANG, authorCompany=null, correspAuthors=Lingxiao GONG, Jing WANG, 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=1320166307757142467, articleId=1320166304925987251, tenantId=1146029695717560320, journalId=1260987677001138203, language=CN, title=6-甲氧基-2-苯唑啉酮和2-苯并噁唑啉酮的抗氧化能力及肠道菌群调节作用评价, columnId=1261336277547401341, journalTitle=食品工业科技, columnName=生物工程, runingTitle=null, highlight=null, articleAbstract=

为了探究6-甲氧基-2-苯唑啉酮(6-Methoxy-benzoxazolin-2-one,MBOA)、2-苯并噁唑啉酮(Benzoxazolin-2-one,BOA)在全谷物食品保健功效中的作用,本研究评价了MBOA和BOA的体外抗氧化能力及肠道菌群调节作用。结果表明MBOA和BOA的抗氧化能力具有剂量依赖性,但抗氧化能力弱于阿魏酸。与同剂量阿魏酸相比,MBOA、BOA以及混合物均能显著提高菌群多样性,呈现剂量依赖性,其中混合物的效果最佳。在门水平上,显著降低变形菌门(Proteobacteria)和拟杆菌门(Bacteroidetes)的相对丰度,显著增加厚壁菌门(Firmicutes)和放线菌门(Actinobacteria)的相对丰度,在属水平上,显著增加了双歧杆菌属(Bifidobacterium)等的相对丰度,并显著降低了埃希杆菌属(Escherichia)、普雷沃氏菌属(Prevotella)和拟杆菌属( Bacteroides)等的相对丰度。本研究提示全谷物中的MBOA和BOA具有良好的益生潜力。

, authors=杨若言, 李璐瑶, 王田曦, 龚凌霄*, 王静*, authorsList=杨若言, 李璐瑶, 王田曦, 龚凌霄, 王静, authorCompany=null, correspAuthors=龚凌霄, 王静, authorNote=

杨若言(2000−),女,博士研究生,研究方向:天然产物与功能性食品,E-mail:

李璐瑶(2000−),女,硕士,研究方向:天然产物与功能性食品,E-mail:

, correspAuthorsNote=
龚凌霄(1981−),女,博士,教授,研究方向:天然产物与功能性食品,E-mail:。
王静(1976−),女,博士,教授,研究方向:食品功能因子与品质改良,E-mail:。
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Immune Network, 2024, 24(6): e41., articleTitle=null, refAbstract=null), Reference(id=1320166783273783855, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=37, rfOrder=40, authorNames=null, journalName=null, refType=null, unstructuredReference=YOO S, JUNG S C, KWAK K, et al. The role of prebiotics in modulating gut microbiota: Implications for human health[J]. International Journal of Molecular Sciences, 2024, 25(9): 4834., articleTitle=null, refAbstract=null), Reference(id=1320166783336698416, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=38, rfOrder=41, authorNames=null, journalName=null, refType=null, unstructuredReference=de BRUYN F, JAMES K, COTTENET G, et al. Combining Bifidobacterium longum subsp. infantis and human milk oligosaccharides synergistically increases short chain fatty acid production ex vivo[J]. Communications Biology, 2024, 7(1): 943., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1320166763124347342, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, xref=null, ext=[AuthorCompanyExt(id=1320166763132735951, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, companyId=1320166763124347342, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=School of Food and Health, Beijing Technology and Business University, China-Canada Joint Lab of Food Nutrition and Health (Beijing), Beijing Engineering and Technology Research Center of Food Additives, Beijing 100048, China), AuthorCompanyExt(id=1320166763141124560, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, companyId=1320166763124347342, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=北京工商大学食品与健康学院,中加食品营养与健康联合实验室(北京),食品添加剂与配料北京高校工程研究中心,北京 100048)])], figs=[ArticleFig(id=1320166766798557682, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.1, caption=DPPH radical scavenging capacity of MBOA, BOA and FA, figureFileSmall=+PlJGDHSt1MA5Ma7Pqy8Jw==, figureFileBig=VFNceVpOopb4++ZfQfbkpw==, tableContent=null), ArticleFig(id=1320166766874055155, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图1, caption=MBOA、BOA和FA的DPPH自由基清除能力

注:不同小写字母表示相同物质在不同浓度下的显著性水平(P<0.05),不同大写字母表示FA、BOA和MBOA在相同浓度下的显著性水平(P<0.05),图2、图3同。

, figureFileSmall=+PlJGDHSt1MA5Ma7Pqy8Jw==, figureFileBig=VFNceVpOopb4++ZfQfbkpw==, tableContent=null), ArticleFig(id=1320166766983107060, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.2, caption=ABTS+ radical scavenging capacity of MBOA, BOA and FA, figureFileSmall=OB8oyMM9Dieu/WqqWpqNiA==, figureFileBig=tycFh+sFnBXmjll3iBVBgA==, tableContent=null), ArticleFig(id=1320166767066993141, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图2, caption=MBOA、BOA和FA的ABTS+自由基清除能力, figureFileSmall=OB8oyMM9Dieu/WqqWpqNiA==, figureFileBig=tycFh+sFnBXmjll3iBVBgA==, tableContent=null), ArticleFig(id=1320166767142490614, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.3, caption=Ferrous ion reducing power of MBOA, BOA and FA, figureFileSmall=2xeFoyNpPcbdh95vqVDICg==, figureFileBig=/1zoE0LF2FNTSpon2zkOVg==, tableContent=null), ArticleFig(id=1320166767222182391, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图3, caption=MBOA、BOA和FA的亚铁离子还原能力, figureFileSmall=2xeFoyNpPcbdh95vqVDICg==, figureFileBig=/1zoE0LF2FNTSpon2zkOVg==, tableContent=null), ArticleFig(id=1320166767297679864, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.4, caption=Results of the Venn diagram, figureFileSmall=RACseUJvYXXutFoXClBYKg==, figureFileBig=qdR+Fp+qcxpWFAu5rf5AyQ==, tableContent=null), ArticleFig(id=1320166767368983033, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图4, caption=Venn图结果, figureFileSmall=RACseUJvYXXutFoXClBYKg==, figureFileBig=qdR+Fp+qcxpWFAu5rf5AyQ==, tableContent=null), ArticleFig(id=1320166767465452026, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.5, caption=Principal component analysis, figureFileSmall=pXdBr+inypmSVnsKpjf2Kw==, figureFileBig=Pqeaz0Sl92s8g1LgRpCKow==, tableContent=null), ArticleFig(id=1320166767545143803, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图5, caption=主成分分析, figureFileSmall=pXdBr+inypmSVnsKpjf2Kw==, figureFileBig=Pqeaz0Sl92s8g1LgRpCKow==, tableContent=null), ArticleFig(id=1320166767612252668, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Fig.6, caption=Species composition of gut microbiota, figureFileSmall=vX4mGqQ20kkmnfTkRuPKBQ==, figureFileBig=SuBHUNPCJVWyL3aZWxvhgw==, tableContent=null), ArticleFig(id=1320166767683555837, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=图6, caption=肠道菌群物种组成

注:(A)门水平;(B)属水平;(C)种水平。

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Experimental groups

, figureFileSmall=null, figureFileBig=null, tableContent=
实验分组添加量缩略语
KBN/AKB
MBOA3 mgMBOA-L
30 mgMBOA-M
90 mgMBOA-H
BOA3 mgBOA-L
30 mgBOA-M
90 mgBOA-H
FA3 mgFA-L
30 mgFA-M
90 mgFA-H
Mix1.5 mg MBOA+1.5 mg BOAMix-L
15 mg MBOA+15 mg BOAMix-M
45 mg MBOA+45 mg BOAMix-H
), ArticleFig(id=1320166769604547074, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=表1, caption=

实验分组

, figureFileSmall=null, figureFileBig=null, tableContent=
实验分组添加量缩略语
KBN/AKB
MBOA3 mgMBOA-L
30 mgMBOA-M
90 mgMBOA-H
BOA3 mgBOA-L
30 mgBOA-M
90 mgBOA-H
FA3 mgFA-L
30 mgFA-M
90 mgFA-H
Mix1.5 mg MBOA+1.5 mg BOAMix-L
15 mg MBOA+15 mg BOAMix-M
45 mg MBOA+45 mg BOAMix-H
), ArticleFig(id=1320166769680044547, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=EN, label=Table 2, caption=

α-Diversity analysis

, figureFileSmall=null, figureFileBig=null, tableContent=
样品SobsShannonSimpsonAceChao
KB-0297.50±2.1AB3.39±0.07AB0.07±0.01AB348.01±0.19AB351.33±1.84A
KB-24248.50±3.54b3.37±0.04b0.06±0.00ab311.87±3.31ab331.89±17.60a
FA-L-0287.00±0.00AB3.34±0.05B0.07±0.01AB355.36±11.66AB351.13±26.46A
FA-L-24229.50±13.44b3.41±0.00b0.06±0.00ab294.48±18.98b310.79±7.42a
FA-M-0288.50±4.95AB3.42±0.02AB0.06±0.00AB347.63±177.13AB375.05±72.29A
FA-M-24286.50±14.85a3.50±0.17ab0.06±0.01ab367.55±9.39a368.53±4.91a
FA-H-0304.00±5.66AB3.39±0.15AB0.076±0.01AB362.95±26.45AB368.01±30.56A
FA-H-24244.50±0.71b3.41±0.05b0.06±0.00ab335.93±32.99ab332.32±6.11a
BOA-L-0296.50±7.78AB3.30±0.17B0.08±0.02A362.93±7.25AB386.15±35.31A
BOA-L-24242.50±2.12b3.55±0.03ab0.05±0.00b284.46±0.61b293.64±10.80a
BOA-M-0275.00±18.38B3.36±0.07AB0.07±0.01AB325.61±38.37B337.84±57.41A
BOA-M-24246.50±17.68b3.55±0.02ab0.05±0.00b301.98±28.98ab352.92±112.3a
BOA-H-0307.00±31.11AB3.39±0.15AB0.07±0.01AB416.58±93.93A409.23±57.20A
BOA-H-24249.50±30.41b3.49±0.02ab0.06±0.00ab311.08±61.02ab317.31±62.66a
MBOA-L-0299.00±5.66AB3.52±0.01AB0.06±0.00B346.41±12.20AB348.41±14.21A
MBOA-L-24252.00±8.49b3.38±0.01b0.07±0.00a316.74±18.03ab330.68±33.17a
MBOA-M-0300.00±4.24AB3.45±0.06AB0.06±0.00AB360.34±1.43AB385.75±25.10A
MBOA-M-24246.00±8.49b3.57±0.18ab0.05±0.02b296.42±1.13b291.24±2.68a
MBOA-H-0315.50±3.54A3.58±0.08A0.06±0.00B381.31±3.32AB387.61±5.06A
MBOA-H-24246.00±8.49b3.43±0.00ab0.06±0.00ab305.78±3.50ab311.58±8.80a
Mix-L-0309.00±25.46AB3.35±0.10B0.08±0.01AB388.98±53.43AB409.52±47.35A
Mix-L-24259.00±9.90b3.63±0.06a0.05±0.01b317.52±26.88ab316.34±12.85a
Mix-M-0303.50±20.51AB3.40±0.02AB0.07±0.01AB363.82±18.16AB361.76±1.47A
Mix-M-24249.00±8.49b3.41±0.11b0.06±0.00ab340.46±53.58ab307.78±34.30a
Mix-H-0292.50±0.71AB3.29±0.14B0.08±0.02A353.05±5.06AB372.47±6.41A
Mix-H-24255.50±3.54b3.55±0.09ab0.06±0.00ab319.56±12.41ab328.67±16.73a
), ArticleFig(id=1320166769914925573, tenantId=1146029695717560320, journalId=1260987677001138203, articleId=1320166304925987251, language=CN, label=表2, caption=

α-多样性分析

, figureFileSmall=null, figureFileBig=null, tableContent=
样品SobsShannonSimpsonAceChao
KB-0297.50±2.1AB3.39±0.07AB0.07±0.01AB348.01±0.19AB351.33±1.84A
KB-24248.50±3.54b3.37±0.04b0.06±0.00ab311.87±3.31ab331.89±17.60a
FA-L-0287.00±0.00AB3.34±0.05B0.07±0.01AB355.36±11.66AB351.13±26.46A
FA-L-24229.50±13.44b3.41±0.00b0.06±0.00ab294.48±18.98b310.79±7.42a
FA-M-0288.50±4.95AB3.42±0.02AB0.06±0.00AB347.63±177.13AB375.05±72.29A
FA-M-24286.50±14.85a3.50±0.17ab0.06±0.01ab367.55±9.39a368.53±4.91a
FA-H-0304.00±5.66AB3.39±0.15AB0.076±0.01AB362.95±26.45AB368.01±30.56A
FA-H-24244.50±0.71b3.41±0.05b0.06±0.00ab335.93±32.99ab332.32±6.11a
BOA-L-0296.50±7.78AB3.30±0.17B0.08±0.02A362.93±7.25AB386.15±35.31A
BOA-L-24242.50±2.12b3.55±0.03ab0.05±0.00b284.46±0.61b293.64±10.80a
BOA-M-0275.00±18.38B3.36±0.07AB0.07±0.01AB325.61±38.37B337.84±57.41A
BOA-M-24246.50±17.68b3.55±0.02ab0.05±0.00b301.98±28.98ab352.92±112.3a
BOA-H-0307.00±31.11AB3.39±0.15AB0.07±0.01AB416.58±93.93A409.23±57.20A
BOA-H-24249.50±30.41b3.49±0.02ab0.06±0.00ab311.08±61.02ab317.31±62.66a
MBOA-L-0299.00±5.66AB3.52±0.01AB0.06±0.00B346.41±12.20AB348.41±14.21A
MBOA-L-24252.00±8.49b3.38±0.01b0.07±0.00a316.74±18.03ab330.68±33.17a
MBOA-M-0300.00±4.24AB3.45±0.06AB0.06±0.00AB360.34±1.43AB385.75±25.10A
MBOA-M-24246.00±8.49b3.57±0.18ab0.05±0.02b296.42±1.13b291.24±2.68a
MBOA-H-0315.50±3.54A3.58±0.08A0.06±0.00B381.31±3.32AB387.61±5.06A
MBOA-H-24246.00±8.49b3.43±0.00ab0.06±0.00ab305.78±3.50ab311.58±8.80a
Mix-L-0309.00±25.46AB3.35±0.10B0.08±0.01AB388.98±53.43AB409.52±47.35A
Mix-L-24259.00±9.90b3.63±0.06a0.05±0.01b317.52±26.88ab316.34±12.85a
Mix-M-0303.50±20.51AB3.40±0.02AB0.07±0.01AB363.82±18.16AB361.76±1.47A
Mix-M-24249.00±8.49b3.41±0.11b0.06±0.00ab340.46±53.58ab307.78±34.30a
Mix-H-0292.50±0.71AB3.29±0.14B0.08±0.02A353.05±5.06AB372.47±6.41A
Mix-H-24255.50±3.54b3.55±0.09ab0.06±0.00ab319.56±12.41ab328.67±16.73a
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杨若言 , 李璐瑶 , 王田曦 , 龚凌霄 * , 王静 *
食品工业科技 | 生物工程 2026,47(11): 205-212
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食品工业科技 |生物工程 2026 , 47 (11) : 205 -212
6-甲氧基-2-苯唑啉酮和2-苯并噁唑啉酮的抗氧化能力及肠道菌群调节作用评价
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杨若言 , 李璐瑶 , 王田曦, 龚凌霄* , 王静*
作者信息
  • 北京工商大学食品与健康学院,中加食品营养与健康联合实验室(北京),食品添加剂与配料北京高校工程研究中心,北京 100048
通讯作者:
龚凌霄(1981−),女,博士,教授,研究方向:天然产物与功能性食品,E-mail:。
王静(1976−),女,博士,教授,研究方向:食品功能因子与品质改良,E-mail:。
作者简介:

杨若言(2000−),女,博士研究生,研究方向:天然产物与功能性食品,E-mail:

李璐瑶(2000−),女,硕士,研究方向:天然产物与功能性食品,E-mail:

Evaluation of the Antioxidant Capacity and Gut Microbiota Modulation Effects of 6-Methoxy-Benzoxazolin-2-One and Benzoxazolin-2-One
Ruoyan YANG , Luyao LI , Tianxi WANG, Lingxiao GONG* , Jing WANG*
Affiliations
  • School of Food and Health, Beijing Technology and Business University, China-Canada Joint Lab of Food Nutrition and Health (Beijing), Beijing Engineering and Technology Research Center of Food Additives, Beijing 100048, China
出版时间: 2026-06-01 doi: 10.13386/j.issn1002-0306.2025060157
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为了探究6-甲氧基-2-苯唑啉酮(6-Methoxy-benzoxazolin-2-one,MBOA)、2-苯并噁唑啉酮(Benzoxazolin-2-one,BOA)在全谷物食品保健功效中的作用,本研究评价了MBOA和BOA的体外抗氧化能力及肠道菌群调节作用。结果表明MBOA和BOA的抗氧化能力具有剂量依赖性,但抗氧化能力弱于阿魏酸。与同剂量阿魏酸相比,MBOA、BOA以及混合物均能显著提高菌群多样性,呈现剂量依赖性,其中混合物的效果最佳。在门水平上,显著降低变形菌门(Proteobacteria)和拟杆菌门(Bacteroidetes)的相对丰度,显著增加厚壁菌门(Firmicutes)和放线菌门(Actinobacteria)的相对丰度,在属水平上,显著增加了双歧杆菌属(Bifidobacterium)等的相对丰度,并显著降低了埃希杆菌属(Escherichia)、普雷沃氏菌属(Prevotella)和拟杆菌属( Bacteroides)等的相对丰度。本研究提示全谷物中的MBOA和BOA具有良好的益生潜力。

MBOA  /  BOA  /  肠道菌群  /  抗氧化

To investigate the roles of 6-methoxy-benzoxazolin-2-one (MBOA) and benzoxazolin-2-one (BOA) in the health-promoting effects of whole-grain foods, this study evaluated their in vitro antioxidant capacity and modulatory effects on gut microbiota. The results demonstrated that while MBOA and BOA exhibited dose-dependent antioxidant activity, their efficacy was inferior to that of ferulic acid. Compared to equivalent doses of ferulic acid, MBOA, BOA, and the mixture significantly enhanced microbial diversity in a dose-dependent manner, with the mixture showing optimal efficacy. At the phylum level, these compounds significantly reduced the relative abundances of Proteobacteria and Bacteroidetes while increasing those of Firmicutes and Actinobacteria. At the genus level, they markedly elevated the relative abundances of Bifidobacterium and reduced Escherichia, Prevotella, and Bacteroides. This study indicates that MBOA and BOA in whole grains possess substantial prebiotic potential.

MBOA  /  BOA  /  gut microbiota  /  antioxidant activity
杨若言, 李璐瑶, 王田曦, 龚凌霄, 王静. 6-甲氧基-2-苯唑啉酮和2-苯并噁唑啉酮的抗氧化能力及肠道菌群调节作用评价. 食品工业科技, 2026 , 47 (11) : 205 -212 . DOI: 10.13386/j.issn1002-0306.2025060157
Ruoyan YANG, Luyao LI, Tianxi WANG, Lingxiao GONG, Jing WANG. Evaluation of the Antioxidant Capacity and Gut Microbiota Modulation Effects of 6-Methoxy-Benzoxazolin-2-One and Benzoxazolin-2-One[J]. Science and Technology of Food Industry, 2026 , 47 (11) : 205 -212 . DOI: 10.13386/j.issn1002-0306.2025060157
全谷物富含多种公认的功能因子,如膳食纤维、矿物质、维生素和植物化学物质(包括木脂素、烷基间苯二酚、甾醇和酚酸),被证实具有抗氧化、益生等健康效应[1]。近年来,苯并噁嗪类化合物(Benzoxazinoids,BZs)作为一类新兴的全谷物功能因子,被发现存在于成熟小麦[2]、黑麦[3]和玉米[4]等谷物籽粒中及其加工制品中[5]。BZs主要分为异羟肟酸类(Hydroxamic acid)、内酰胺类(Lactams)、苯并噁唑啉酮类(Benzoxazolinones,BXs)[6],在谷物加工(如研磨、热处理)和消化过程中,不稳定的异羟肟酸类BZs极易转化为结构更稳定、生物可利用度可能更高的苷元形式—6-甲氧基-2-苯唑啉酮(6-Methoxy-benzoxazolin-2-one,MBOA)和2-苯并噁唑啉酮(Benzoxazolin-2-one,BOA)[5,7]。因此,MBOA和BOA是全谷物及其制品中摄入的主要BXs代表物,对其功能活性的研究具有重要意义。
BXs现有的功能活性研究包括降血糖作用[8]、调控食欲[9]、抗菌及抗癌等[10−11]。目前针对MBOA和BOA的功能研究大多仍集中于抗化感、抗菌以及昆虫防御方面[12],以全谷物为来源或以全谷物摄入量和生物利用度为参考的功能活性研究证据较少。氧化应激是炎症、癌症等多种慢性病的共同病理基础[13−14],有研究表明BZs中2,4-二羟基-2H-1,4-苯并噁嗪-3(4H)-酮(2,4-Dihydroxy-1,4-benzoxazin-3(4H)-one,DIBOA)[15]、2-β-D-吡喃葡萄糖酰氧基-1,4-苯并噁嗪-3-酮(2-β-D-Glucopyranosyloxy-1,4-benzoxazin-3-one,HBOA-Glc)显示出体外抗氧化活性[16],但有关MBOA和BOA自身的体外或体内抗氧化能力目前缺乏直接证据报道,明确其抗氧化效力有助于理解其相关健康机制。此外,MBOA和BOA表现出显著的抗菌活性,能够有效抑制金黄色葡萄球菌、大肠杆菌和变形链球菌等致病细菌以及致病性尖孢镰刀菌等真菌。然而,目前对MBOA和BOA抗菌效果的研究主要集中在单一菌株或多菌株共培养,在复杂的人体肠道菌群条件下的作用尚不清楚。肠道菌群的组成与机体的免疫调节、营养物质代谢等功能密切相关[17],维持肠道菌群的稳定性和多样性对人类健康至关重要。因此,阐明MBOA和BOA对于复杂菌群的调控作用也具有重要意义。
在体外评估益生元对肠道菌群的影响时,益生元的生物利用度是至关重要的,这决定了益生元在体内到达结肠并发挥作用的浓度。Baranzelli等[2]在体外模拟消化过程中评估了小麦萌发前后BXs的生物利用度,经过上消化道消化,苯并噁嗪类化合物DIBOA的含量下降,而2,4-二羟基-7-甲氧基-1,4-苯并噁嗪-3-酮(2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one,DIMBOA)的含量保持不变。此外,一些研究[18]报道了BXs在人体中的代谢吸收,对志愿者食用的面包中12种苯并噁嗪类物质的定量分析显示,HBOA-Glc是在血浆和尿液中发现的主要化合物,而BOA被快速代谢,但在尿液中仍可检测到BOA水平,这提示肠道中BOA和MBOA可能来源于DIBOA和类似化合物的转化和分解[19]。Adhikari等[11]根据北欧地区黑麦的消费量估算了BXs的每日摄入量,发现从特定品牌的全谷物黑麦面包中BXs每日总摄入量超过5 mg/d。在中国,小麦、玉米等谷物是BXs的重要食物来源。现有研究发现,谷物中BXs含量范围在31~859 μg/g[20−21]。而加工方法的选择能够改变BXs的分布,将大部分羟肟酸转化为MBOA和BOA,例如DIBOA自发分解为MBOA和BOA[5]。并且,加工方法与谷物制品中MBOA和BOA的含量变化密切相关,例如水热和水冷加工方法,可以显著增加麦麸中MBOA和BOA的含量,MBOA含量最高可达3.64±0.01 μg/g,BOA含量最高达1.21±0.02 μg/g[8]。
因此,为了进一步探究全谷物中MBOA和BOA的潜在健康功效,以全谷物中具有明确抗氧化能力、肠道菌群调控能力的阿魏酸[22]作为阳性对照,依据中国居民推荐的全谷物每日摄入量范围[23],采用体外模型探究全谷物背景下MBOA和BOA的抗氧化特性及其对人体肠道菌群改善的潜在健康效应,为MBOA和BOA健康效应的分子机制探究提供参考,为全谷物健康作用的全面解析提供依据。
MBOA(纯度97%)、BOA(纯度98%) 美国Sigma公司;阿魏酸(纯度99.93%) 源叶生物科技有限公司;酵母提取物、碳酸钠(分析纯)、七水硫酸镁(分析纯)、L-半胱氨酸(分析纯)、氯化钾(分析纯)、磷酸二氢钾(分析纯)、盐酸(分析纯) 中国医药集团公司;氯化钠、六水氯化钙 分析纯,西陇化工公司;磷酸氢钾(分析纯)、Tween 80(分析纯)、氯化血红素(分析纯)、维生素K1(分析纯)、胆盐、亚甲蓝 北京化工厂;总抗氧化能力检测试剂盒(FRAP法)、总抗氧化能力检测试剂盒(ABTS法) 上海碧云天生物技术有限公司。
DG250厌氧培养箱 Don whitley scientic公司;1260 infinity三重四级杆质谱、Cary 100紫外分光光度计 安捷伦科技(中国)有限公司;YXQ-LS-50A高压灭菌锅 上海云泰仪器仪表有限公司;ME104电子天平 梅特勒-托利多仪器有限公司;BioTekSynergy H1MDG酶标仪 美国伯腾仪器有限公司。
本研究以阿魏酸(Ferulic acid,FA)为阳性对照,测定MBOA和BOA的体外亚铁离子还原能力、ABTS+自由基清除能力和DPPH自由基清除能力[24]。FA、MBOA和BOA标准溶液用甲醇溶解,配制浓度为5 mg/mL的储备液,在0.1、0.5、1、3、5 mg/mL浓度下分别测定MBOA、BOA和FA的抗氧化能力,每个样品浓度下设置三组平行。
参照Bolling等[25]的方法并稍作修改,DPPH溶液浓度为0.04 mg/mL,DPPH溶液和样品或空白溶剂以9:1(v/v)混合均匀,室温下避光静置30 min后,测定在517 nm下的吸光度,DPPH自由基清除率(%)计算公式为:
$\rm DPPH自由基清除率(\text{%})=\frac{A_0-(A_i-A_j)}{A_0}\times 100$
式中:A0为空白对照(不含样品的DPPH溶液)的吸光度,Ai为受试样品(含样品或阳性对照的DPPH溶液)的吸光度,Aj为不含DPPH的样品溶液的吸光度。
采用碧云天总抗氧化能力检测试剂盒(ABTS法)进行测定。10 mmol/L Trolox标准溶液稀释至0.15、0.3、0.6、0.9、1.2和1.5 mmol/L,绘制标准曲线,过氧化物酶溶液与样品或空白溶剂以2:1(v/v)混合,用ABTS溶液补足体系,室温孵育6 min后于414 nm处测定吸光度。根据Trolox标准曲线计算样品的ABTS+自由基清除能力,并用Trolox标准溶液的摩尔浓度表示[26]。
亚铁离子还原能力采用总抗氧化能力检测试剂盒(FRAP法)进行测定,以100 mmol/L的FeSO4·7H2O为标准物质,稀释至0.15、0.3、0.6、0.9、1.2和1.5 mmol/L,绘制标准曲线,样品与FRAP工作液于37 ℃孵育3~5 min,以甲醇溶液作为空白对照在593 nm处测定溶液的吸光度。根据标准曲线计算样品的亚铁离子还原能力,以FeSO4标准溶液浓度表示[27]。
参考Yang等[28]的实验方法并稍加改动,收集3名健康志愿者的粪便样品,其中,提供粪便样品的志愿者身体健康,实验前至少3个月未接受过抗生素治疗并且没有肠胃病史(审批号:P2022010)。将三位志愿者粪便样品混合并收集至厌氧盒中,冰盒运输并立即放置于37 ℃厌氧工作站中,工作站中气体为10%的氢气,10%二氧化碳和80%氮气,之后肠道菌群所有实验操作均需在粪便收集后2 h内进行。用灭菌过的PBS缓冲溶液(0.1 mol/L,pH6.8)将收集到的粪便样品以20%(w/v)的比例进行稀释,充分搅拌,经4层无菌纱布过滤得到粪便接种液。粪便微生物培养基配方为2 g酵母提取物,2 g蛋白胨,2 g碳酸钠,0.1 g氯化钠,0.01 g七水合硫酸镁,0.04 g磷酸氢钾,0.01 g六水合氯化钙,2 mL吐温80,10 μL维生素K1,0.5 g猪胆盐,0.5 g L-半胱氨酸,50 mg氯化血红素,1 mg刃天青,定容至1 L,混匀备用,并于121 ℃灭菌15 min。
分组包括不添加任何底物的空白对照组,以FA作为阳性对照,实验组分别为MBOA组、BOA组、混合组(MBOA:BOA=1:1,m/m)。其中,各组样品添加量和比例考虑到全谷物及其制品的加工方式对MBOA、BOA含量的影响,并参考每人每天全谷物摄入量(50~150 g)[22]分别设置低、中、高浓度,如表1所示。分别取不同质量底物与27 mL培养基、3 mL粪便接种液充分混合于厌氧密封管,在37 ℃厌氧工作站中进行发酵,分别在0 h和24 h取发酵液保存于−80 ℃直至分析,每个样品做3组平行。
取各组0 h和24 h发酵液作为样本,每组取6个平行样本,提取0 h和24 h发酵液中的微生物总基因组DNA,对目标片段的16S rDNA V3-V4区域进行PCR扩增,采用琼脂糖凝胶电泳法对DNA样本进行质控,检测合格的样本按照Yang等[28]的方法略作修改,采用双端测序策略对文库进行测序。测序和标准生物信息学数据处理在Illumina Miseq(Illumina,USA)上进行,对肠道菌群进行聚类分析、α多样性、β多样性分析以及物种组成分析。
测定结果以平均数±标准差(X±SD)表示,采用Microsoft Excel进行数据分析和绘图,采用SPSS软件进行单因素方差分析(ANOVA)。以P<0.05为阈值确定差异具有统计学意义。
如图1所示,MBOA和BOA都表现出一定的DPPH自由基清除活性,具有剂量依赖性。当浓度为5 mg/mL时,MBOA和BOA的DPPH自由基清除能力分别为43.2%和55.6%。BOA对DPPH自由基的清除能力显著高于MBOA,MBOA和BOA的DPPH自由基清除能力显著低于FA(P<0.05),这种活性差异可能归因于其化学结构的差异,与FA的酚羟基相比,MBOA苯环上连接的甲氧基和BOA的苯环上连接的氢还原性较弱[29]。MBOA和BOA是DIBOA自发分解的产物[5],DIBOA本身也表现出剂量依赖性的抗氧化活性,这可能与其在较高浓度下具有更大的羟基可利用性有关[15]。DIBOA及其衍生物的富集部分对DPPH自由基的清除活性同样显著弱于酚类化合物[16],与本研究结果一致。因此,MBOA和BOA的抗氧化活性显著弱于酚类物质,可能与其化学结构相似且不含有羟基等强还原性基团相关。
如图2所示,MBOA和BOA均表现出具有剂量依赖性的ABTS+自由基清除活性。MBOA和BOA对ABTS+自由基的清除能力均显著弱于相同浓度的阳性对照FA(P<0.05),在相同浓度下,其ABTS+自由基清除能力约为FA的1/2~2/3。Gleńsk等[30]在体外对环异羟污酸的抗氧化活性进行了评价,DIMBOA的ABTS+自由基清除能力较强,DIMBOA(0.03404 mg/mL)对ABTS+自由基的清除率为3.54 μmol Trolox/mL,显著高于MBOA和BOA,同样可能与其化学结构的羟基可利用性有关[5,15−16,29]。
如图3所示,MBOA的亚铁离子还原能力是BOA的1~1.2倍,表现出浓度依赖性。MBOA和BOA的亚铁离子还原能力显著低于阳性对照FA(P<0.05),约为FA的1/3~1/2,同样弱于相同浓度DIMBOA的亚铁离子还原能力[30]。现有研究表明,并非所有的植物来源的天然化合物都具有很强的抗氧化活性。它们的抗氧化能力受化学结构、浓度和评估抗氧化活性的方法等因素的影响[31]。Baranzelli等[32]的研究同样证明苯并噁嗪类化合物的抗氧化活性弱于黄酮类物质。因此,MBOA和BOA作为BXs的代表性物质,在全谷物食品中不作为主要的抗氧化物质。
如表2所示,24 h各组的Sobs指数、Simpson指数普遍下降,Chao指数和Ace指数也呈下降趋势,Shannon指数普遍上升。这表明微生物总体丰度的下降可能与某些微生物种群的抑制或促进有关。发酵24 h后,4组添加不同底物的菌种丰度和多样性大多优于KB组。图4表明Mix组和BOA组的总物种组成显著优于其他组,分别有527个和520个物种,其中5组间共有菌包括374个物种,4组间共有菌包括64个物种,3组间共有菌包括62个物种,2组间共有菌包括52个物种,而每组的独有菌包括73个物种。
对0 h和24 h的发酵液进行主成分分析(Principal component analysis,PCA),PCA反映了不同发酵样品组中肠道微生物菌群结构的相似性。2个样品组在坐标轴上投影距离越近,表示微生物组成结构差异越小,反之,微生物组成结构差异越大。如图5所示,BOA-H-24组和Mix-H-24组的肠道微生物结构与其他组间具有显著差异,与KB组相比,发酵24 h后的MBOA低、中、高剂量组、混合组的低、中剂量组、BOA组的低、中剂量组和FA的低、中、高剂量组间的肠道微生物结构无显著差异。发酵液0 h所有样品组间的肠道微生物结构均无显著差异,均与发酵24 h后的样品组间具有显著差异。因此,发酵24 h后,肠道菌群结构改变,尤其是BOA-H-24组和Mix-H-24组。Dai等[33]研究了MBOA对布氏田鼠肠道微生物结构的影响,结果表明MBOA能够显著改变布氏田鼠盲肠微生物群落的α和β-多样性,与本研究结果一致。
在门水平上,注释了6个门(图6A),包括厚壁菌门(Firmicutes)、拟杆菌门(Bacteroidetes)、变形菌门(Proteobacteria)、放线菌门(Actinobacteria)、梭杆菌门(Fusobacteria)和疣微菌门(Verrucomicrobia)。不同底物发酵液在门水平上的微生物组成在0 h和24 h基本一致。0 h时,各组肠道菌群的优势菌门均为厚壁菌门(平均丰度为57%)和拟杆菌门(平均丰度为33%)。与KB-24组相比,不同底物的低剂量组放线菌门丰度无明显变化,而中剂量组和高剂量组放线菌门丰度增加了1%~5%,且丰度与底物浓度成正比。这说明中剂量组和高剂量组底物的添加促进了放线菌的生长。与KB组相比,BOA-H和Mix-H显著(P<0.05)降低了变形菌门的相对丰度(降低了20%~30%),增加了放线菌门的相对丰度(增加了5%~6%)。发酵24 h后,KB组厚壁菌门与拟杆菌门的比例为1。MBOA-M、MBOA-H组和Mix-L组降低了该比例(0.6%~0.9%)。而KB组与不同浓度FA、MBOA-H、BOA-L组的厚壁菌门和拟杆菌门比例差异均无统计学意义(P>0.05)。Dai等[33]在不同剂量的MBOA处理的布氏田鼠的盲肠微生物群中检测到相同的厚壁菌门相对丰度的趋势,短链脂肪酸测定结果表明,厚壁菌门的代谢产物乙酸盐和丙酸盐含量增加,但差异不显著。
属水平上,共注释到34个属(如图6B),包括拟杆菌属(Bacteroides)、瘤胃球菌属(Ruminococcus)、埃希氏杆菌属(Escherichia)、克雷白氏杆菌属(Pneumoniae)、嗜胆菌属(Bilophila)、副拟杆菌属(Parabacteroides)、梭杆菌属(Fusobacterium)、双歧杆菌属(Bifidobacterium)等。发酵24 h后,包括KB组在内的各组大肠埃希菌属(Escherichia)、肺炎杆菌属(Klebsiella)、嗜胆菌属(Bilophila)和副拟杆菌属(Parabacteroides)等有害菌均增加。但与KB组(8.62%)相比,BOA-H组、MBOA-H组和Mix-H组大肠埃希菌属的相对丰度显著降低(P<0.05),分别为<0.1%、1.62%和<0.1%。与KB组相比,低剂量组和中剂量组的大肠埃希菌属丰度无显著差异(P>0.05)。大肠埃希菌属是具有代表性的有害菌属。例如,产肠毒素的大肠杆菌可以引起腹泻和其他胃肠道疾病[34]。此外,研究表明,大肠埃希菌属和瘤胃球菌属等可能增加炎症的风险[35]。因此,MBOA和BOA对肠道病原菌的有效抑制对维持人体健康具有重要意义。具有代表性的有益菌双歧杆菌属在发酵24 h后相对丰度显著提高(P<0.05),与KB组(0.58%)相比,FA-H组、BOA-H组和Mix-H组的相对丰度分别为2.79%、3.60%和4.06%。MBOA-H组相对丰度为0.95%,与KB组差异无统计学意义(P>0.05)。低剂量组和中剂量组与KB组比较差异无统计学意义(P>0.05)。双歧杆菌被广泛认为是一种有益的益生菌,具有抗炎、调节糖脂代谢和维持肠道屏障等作用[31]。因此,BOA-H和Mix-H组的添加显著降低了埃希菌等有害菌的相对丰度,显著提高了双歧杆菌等有益菌的丰度。此外,发酵24 h后,MBOA-H组和MBOA-M组的普雷沃氏菌属(Prevotella)相对丰度显著低于其他组(P<0.05),BOA-H组的普雷沃氏菌属(Prevotella)相对丰度也呈降低趋势,但无显著差异(P>0.05),与Dai等[33]的研究结果类似,可能与MBOA和BOA调节葡萄糖稳态的活性有关[8]。
种水平上,共注释到48个种(图6C),包括多形拟杆菌(Bacteroides thetaiotaomicron)、大肠杆菌-志贺菌(Escherichia shigella)、coprocola拟杆菌(Bacteroides coprocola)、狄氏拟杆菌(Parabacteroides distasonis)、粪副拟杆菌(Parabacteroides merdae)、长双歧杆菌(Bifidobacterium longum)、青春双岐杆菌(Bifidobacterium adloescentis)和沃氏嗜胆菌(Bilophila wadsworthia)等。在种水平上对24 h发酵后的体外发酵液的菌群进一步分析,可视化圈图(图7)反映了每组样本中的优势菌种以及各优势菌种在不同分组中的分布情况。与KB组的多形拟杆菌丰度10%相比,MBOA-M组(11%)、MBOA-H组(15%)、Mix-M(12%)、Mix-L(12%)的丰度都相应提高,尤其是MBOA-H组能够显著提高其丰度(P<0.05)。发酵24 h后,与KB组中大肠杆菌-志贺菌的相对丰度(15%)相比,MBOA-H组、BOA-H组、Mix-H组对大肠杆菌-志贺菌相对丰度抑制百分比分别达81.3%、99.54%、99.3%,均显示极显著的抑制效果(P<0.01),而高浓度阿魏酸组虽也能显著(P<0.05)降低其丰度,但相对其他高浓度实验组较低,抑制百分比为7.4%,其他低、中浓度组对大肠杆菌-志贺菌丰度也有较强的抑制作用,其抑制效果呈剂量依赖性。青春双歧杆菌和长双歧杆菌为双歧杆菌属的常见菌种,KB组中青春双歧杆菌和长双歧杆菌的相对丰度分别为3.2%和2.5%,添加Mix-H组(24%和22%)、BOA-H组(20%和24%)、FA-H组(16%和16%)和MBOA-H组(5.4%和4.9%)都可以显著(P<0.05)提高青春双歧杆菌和长双歧杆菌的相对丰度,尤其是Mix-H组和BOA-H组是KB组青春双歧杆菌丰度6倍以上,是KB组长双歧杆菌丰度8倍以上。长双歧杆菌是婴儿和成人中最常见的双歧杆菌,在维持肠道微环境和整体肠道健康方面起着至关重要的作用[36]。许多研究表明,益生元抑制病原菌生长、促进有益菌增殖的机制与短链脂肪酸的产生有关[37],双歧杆菌与乙酸、丙酸、异丁酸、丁酸、异戊酸、戊酸的浓度呈正相关,因此,MBOA和BOA对肠道菌群结构的调节作用可能与短链脂肪酸的产生有关[38]。本研究通过体外实验证明MBOA和BOA具有良好的益生元特性。然而,这些发现并不能完全反映肠道微生物群的变化。因此,需要进一步研究MBOA和BOA的体内益生元活性及其具体机制。
本研究对比了全谷物新兴功能因子MBOA和BOA的体外抗氧化活性以及对肠道菌群的调节作用。尽管其体外抗氧化活性显著弱于传统强效成分FA,并非全谷物抗氧化功能的主要贡献者,然而MBOA和BOA均表现出独特的肠道菌群调节特性,通过体外发酵模型证实,MBOA、BOA及其等剂量混合物可剂量依赖性地强效抑制沙门氏菌(Salmonella)和大肠埃希氏菌(Escherichia)等致病菌(抑制率>80%),同时显著促进双歧杆菌(Bifidobacterium)等有益菌增殖(是空白组的6~8倍),其中MBOA和BOA等剂量混合物的作用更为显著,表明MBOA和BOA在全谷物中的益生作用可能存在协同效应。该结果提示MBOA和BOA是全谷物中的潜在益生元,为构建以肠道微生态精准调控为特色的全谷物健康产品体系提供理论依据,但其发挥健康功效的具体机制仍需深入研究。

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doi: 10.13386/j.issn1002-0306.2025060157
  • 接收时间:2025-06-16
  • 首发时间:2026-10-22
  • 出版时间:2026-06-01
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  • 收稿日期:2025-06-16
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    北京工商大学食品与健康学院,中加食品营养与健康联合实验室(北京),食品添加剂与配料北京高校工程研究中心,北京 100048

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龚凌霄(1981−),女,博士,教授,研究方向:天然产物与功能性食品,E-mail:。
王静(1976−),女,博士,教授,研究方向:食品功能因子与品质改良,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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