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Article(id=1308842117192057219, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2026-0516, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1777996800000, receivedDateStr=2026-05-06, revisedDate=1779120000000, revisedDateStr=2026-05-19, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981877849, onlineDateStr=2026-09-21, pubDate=1783785600000, pubDateStr=2026-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981877849, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981877849, creator=13701087609, updateTime=1789981877849, updator=13701087609, issue=Issue{id=1308841897058198067, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='7', pageStart='2377', pageEnd='2820', issueExtLink='null', onlineDate='null', pubDate='1783785600000', pubDateStr='2026-07-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981825365, creator='13701087609', updateTime=1789984154811, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851667525792021, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851667525792022, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2810, endPage=2820, ext={EN=ArticleExt(id=1308842117401772420, articleId=1308842117192057219, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Functional characterization of C-28-O-glycosyltransferases from Phytolacca acinosa, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

The dried roots of Phytolacca acinosa Roxb. are widely utilized in traditional Chinese medicine for their potent diuretic, anti-edematous, and detoxifying properties. Esculentosides, the primary bioactive constituents of P. acinosa, exhibit various pharmacological activities, including anti-inflammatory, anti-tumor, and antifungal effects. However, their clinical potential is hampered by low natural abundance and the inherent challenges of chemical synthesis due to their complex structural scaffolds, while synthetic biology represents a promising strategy for the sustainable and green production of esculentoside. However, the biosynthetic pathways remain unclear, and their key functional enzymes have not been reported yet. Herein, through activity-guided enzyme mining and transcriptome analyses, three novel glycosyltransferases (PaUGT2, PaUGT15, and PaUGT25) were functionally characterized from P. acinosa callus. These enzymes were capable of catalyzing the regio-selective glycosylation of 28-COOH of phytolaccagenin. Notably, PaUGT2 could efficiently catalyze 28-O-glycosylation of esculentoside A and esculentoside B, and PaUGT15 and PaUGT25 also exhibited catalytic activities toward these substrates. These findings not only preliminarily clarified the crucial enzymes for 28-O-glycosylation and elucidated the molecular basis for the structural diversity of oleanane-type esculentosides in Phytolacca plants, but also paved the way for further deciphering the biosynthetic pathway and constructing an artificial pathway of these glycosides.

, authors=Yan-fang LIANG, Meng-yuan WANG, Da-wei CHEN*, Jun-gui DAI*, authorsList=Yan-fang LIANG, Meng-yuan WANG, Da-wei CHEN, Jun-gui DAI, authorCompany=null, correspAuthors=Da-wei CHEN, Jun-gui DAI, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2026 Acta Pharmaceutica Sinica. 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=1308842118974636435, articleId=1308842117192057219, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=商陆皂苷C-28位O-糖基转移酶的发现及功能鉴定, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

商陆(Phytolacca acinosa Roxb.) 为我国传统中药, 以干燥根入药, 具有消肿利尿、解毒散结等功效。商陆皂苷是商陆的主要活性成分, 具有抗炎、抗肿瘤及抗真菌等多种药理活性, 但在商陆药材中含量低且结构复杂、化学合成困难, 致使其药源匮乏, 基于生物合成的合成生物学有望为其高效绿色生产提供新策略。但目前该类化合物的生物合成途径未被揭示, 关键功能酶未见报道。本研究通过酶活性导向的新颖酶挖掘结合转录组分析策略, 发现商陆愈伤组织中3个新颖糖基转移酶PaUGT2、PaUGT15和PaUGT25, 它们能够位置选择性催化商陆皂苷元28-COOH进行糖酯化反应; 同时发现PaUGT2还能高效催化商陆皂苷甲(esculentoside A) 和商陆皂苷乙(esculentoside B) 的28-COOH进行O-糖基化修饰, 而PaUGT15和PaUGT25对上述底物也具有催化活性。本研究发现并功能鉴定了商陆皂苷生物合成途径中C-28位O-糖基转移酶, 初步阐明了齐墩果烷型商陆皂苷结构多样性的酶学基础, 为其完整生物合成途径解析与重构奠定基础。

, authors=梁严方, 王梦源, 陈大伟*, 戴均贵*, authorsList=梁严方, 王梦源, 陈大伟, 戴均贵, authorCompany=null, correspAuthors=陈大伟, 戴均贵, authorNote=

作者贡献:

梁严方负责商陆愈伤组织样品的收集、PaUGTs基因生物信息学分析、基因筛选与克隆、载体构建、酶活性分析及论文初稿撰写; 王梦源负责论文修改和审阅; 戴均贵、陈大伟负责论文思路设计、指导实验及论文撰写与修改。

, correspAuthorsNote=
陈大伟, E-mail:
戴均贵, E-mail:
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Bioactive triterpene saponins from the roots of Phytolacca americana [J]. J Nat Prod, 2008, 71: 35-40., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1308842119381483924, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, xref=null, ext=[AuthorCompanyExt(id=1308842119385678229, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, companyId=1308842119381483924, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=State Key Laboratory of Bioactive Substance and Function of Natural Medicines, NHC Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China), AuthorCompanyExt(id=1308842119394066838, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, companyId=1308842119381483924, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=中国医学科学院 北京协和医学院, 药物研究所, 天然药物及核药基础与新药创制全国重点实验室, 国家卫生健康委员会天然药物生物合成重点实验室, 北京 100050)])], figs=[ArticleFig(id=1308842121281503671, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=4WzDnbkI3O4VlHDBmmcYXA==, figureFileBig=PkszBe5rn6aLdwljNjZzrQ==, tableContent=null), ArticleFig(id=1308842121357001144, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.1, caption= Proposed biosynthetic pathway of partial triterpenoid saponins from Phytolacca acinosa. β-AS: β-Amyrin synthase; UGT: UDP-glycosyltransferase; MT: Methyltransferase, figureFileSmall=4WzDnbkI3O4VlHDBmmcYXA==, figureFileBig=PkszBe5rn6aLdwljNjZzrQ==, tableContent=null), ArticleFig(id=1308842121554133433, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=GcCXUv7KuBXmPbxglqm/BA==, figureFileBig=hVqOB/CDYpAPT4OrD8V6Ew==, tableContent=null), ArticleFig(id=1308842121705128378, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.2, caption= In vitro enzymatic reaction of crude enzyme extracted from P. acinosa callus cultures. A: HPLC analysis of the enzymatic reactions. The reaction mixtures contained crude protein extracts, phytolaccagenin (1) as the glycosyl acceptor, and UDP‑Glc or UDP‑Xyl as the donor. Boiled crude protein extracts with 1 served as the control. Peaks 1a and 1b represent the products formed with UDP‑Glc and UDP‑Xyl, respectively; B: Ultraviolet (UV) spectra of substrate 1, enzymatic products 1a and 1b. C: Typical negative ion mass spectrum (MS) of substrate 1, enzymatic products 1a and 1b; UDP-Glc: Uridine diphosphate glucose; UDP-Xyl: Uridine diphosphate xylose, figureFileSmall=GcCXUv7KuBXmPbxglqm/BA==, figureFileBig=hVqOB/CDYpAPT4OrD8V6Ew==, tableContent=null), ArticleFig(id=1308842121789014459, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=Oy7aw5bxyPrFM2g0MqYXzg==, figureFileBig=ZSLlBAzmtoud3wp1J2oreg==, tableContent=null), ArticleFig(id=1308842121856123324, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.3, caption= Phylogenetic analysis of UGT candidates from the transcriptome of P. acinosa callus cultures and known UGTs. The evolutionary history was inferred based on the neighbor-joining method using the software MEGA 11. The bootstrap values are 1 000 replicates, and the scale bar represents 0.2 amino acid substitutions per site. The GenBank accession numbers of UGTs used for analysis are as follows: UGT73C11 (AFN26667, B. vulgaris)[11]; UGT73C12 (AFN26668, B. vulgaris)[11]; UGT73AH1 (AUR26623, C. asiatica)[12]; UGT73AD1 (ALD84259, C. asiatica)[13]; UGT74M1 (ABK76266, S. vaccaria)[14]; UGT74AC1 (K7NBW3, Siraitia grosvenorii)[17]; UGT74AG5 (MK994508, Ilex asprella)[18]; PgUGT74AE2 (QEA68969, Panax ginseng)[19]; UGT73F3 (ACT34898, Medicago truncatula)[20]; UGT73C22 (AVW82178, B. vulgaris)[21]; UGT73C25 (AVW82181, B. vulgaris)[21]; Pq3-O-UGT1 (ALE15279, Panax quinquefolius)[22]; UGTPg45 (AKA44586, P. ginseng)[23]; AmUGT14 (OM913795, Astragalus membranaceus)[24]; AmUGT15 (OM913794, A. membranaceus)[24], figureFileSmall=Oy7aw5bxyPrFM2g0MqYXzg==, figureFileBig=ZSLlBAzmtoud3wp1J2oreg==, tableContent=null), ArticleFig(id=1308842121940009405, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=9n2xyR29EgxhaiF9x1x8IQ==, figureFileBig=XY9xnrmjG7lRjiL+86IKvQ==, tableContent=null), ArticleFig(id=1308842122107781566, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.4, caption= Enzymatic glycosylation of 1 catalyzed by recombinant PaUGTs. A: PaUGTs catalyzed the formation of glycosylated product of 1; B: HPLC analysis of enzymatic products of the PaUGT2, PaUGT15 and PaUGT25; C: UV and typical negative ion MS spectra of enzymatic product 1a, figureFileSmall=9n2xyR29EgxhaiF9x1x8IQ==, figureFileBig=XY9xnrmjG7lRjiL+86IKvQ==, tableContent=null), ArticleFig(id=1308842122233610687, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=tglqu/b0CIK+ScrAQgFElw==, figureFileBig=pyK90y56F7WoF7ikauYuVg==, tableContent=null), ArticleFig(id=1308842122300719552, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.5, caption= Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) of purified recombinant PaUGT proteins. Lane M: Protein marker; Lane 1: Recombinant PaUGT2 with trigger factor (predicted molecular weight, 104.6 kDa); Lane 2: Recombinant PaUGT15 with His tag (predicted molecular weight, 53.9 kDa); Lane 3: Recombinant PaUGT25 with His tag (predicted molecular weight, 57.2 kDa), figureFileSmall=tglqu/b0CIK+ScrAQgFElw==, figureFileBig=pyK90y56F7WoF7ikauYuVg==, tableContent=null), ArticleFig(id=1308842122510434753, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=kDLZlVONRDVPJyVzEjWN0g==, figureFileBig=SvHggAqnpr0kvOR6FtzO2w==, tableContent=null), ArticleFig(id=1308842122594320834, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.6, caption= Effects of pH (A), temperature (B), and divalent metal ions (C) on the activity of PaUGT2. Nonlinear regression (D, E) of the Michaelis-Menten equation for PaUGT2. 1 was used as the glycosyl acceptor, and UDP-Glc was used as the glycosyl donor. CK: Control check, figureFileSmall=kDLZlVONRDVPJyVzEjWN0g==, figureFileBig=SvHggAqnpr0kvOR6FtzO2w==, tableContent=null), ArticleFig(id=1308842122669818307, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=EN, label=null, caption=null, figureFileSmall=/KmtBYFLb6z/wv1MEr5OEg==, figureFileBig=xUqEv3k0RzWbh1z38Dr1Ig==, tableContent=null), ArticleFig(id=1308842122745315780, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842117192057219, language=CN, label=Fig.7, caption= Enzymatic glycosylation of the substrate catalyzed by recombinant PaUGT2. 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商陆皂苷C-28位O-糖基转移酶的发现及功能鉴定
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梁严方 , 王梦源 , 陈大伟 * , 戴均贵 *
药学学报 | 研究论文 2026,61(7): 2810-2820
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药学学报 |研究论文 2026 , 61 (7) : 2810 -2820
商陆皂苷C-28位O-糖基转移酶的发现及功能鉴定
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梁严方, 王梦源, 陈大伟* , 戴均贵*
作者信息
  • 中国医学科学院 北京协和医学院, 药物研究所, 天然药物及核药基础与新药创制全国重点实验室, 国家卫生健康委员会天然药物生物合成重点实验室, 北京 100050
通讯作者:
陈大伟, E-mail:
戴均贵, E-mail:
作者简介:

作者贡献:

梁严方负责商陆愈伤组织样品的收集、PaUGTs基因生物信息学分析、基因筛选与克隆、载体构建、酶活性分析及论文初稿撰写; 王梦源负责论文修改和审阅; 戴均贵、陈大伟负责论文思路设计、指导实验及论文撰写与修改。

Functional characterization of C-28-O-glycosyltransferases from Phytolacca acinosa
Yan-fang LIANG, Meng-yuan WANG, Da-wei CHEN* , Jun-gui DAI*
Affiliations
  • State Key Laboratory of Bioactive Substance and Function of Natural Medicines, NHC Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
出版时间: 2026-07-12 doi: 10.16438/j.0513-4870.2026-0516
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摘要
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商陆(Phytolacca acinosa Roxb.) 为我国传统中药, 以干燥根入药, 具有消肿利尿、解毒散结等功效。商陆皂苷是商陆的主要活性成分, 具有抗炎、抗肿瘤及抗真菌等多种药理活性, 但在商陆药材中含量低且结构复杂、化学合成困难, 致使其药源匮乏, 基于生物合成的合成生物学有望为其高效绿色生产提供新策略。但目前该类化合物的生物合成途径未被揭示, 关键功能酶未见报道。本研究通过酶活性导向的新颖酶挖掘结合转录组分析策略, 发现商陆愈伤组织中3个新颖糖基转移酶PaUGT2、PaUGT15和PaUGT25, 它们能够位置选择性催化商陆皂苷元28-COOH进行糖酯化反应; 同时发现PaUGT2还能高效催化商陆皂苷甲(esculentoside A) 和商陆皂苷乙(esculentoside B) 的28-COOH进行O-糖基化修饰, 而PaUGT15和PaUGT25对上述底物也具有催化活性。本研究发现并功能鉴定了商陆皂苷生物合成途径中C-28位O-糖基转移酶, 初步阐明了齐墩果烷型商陆皂苷结构多样性的酶学基础, 为其完整生物合成途径解析与重构奠定基础。

商陆  /  商陆皂苷  /  O-糖基转移酶  /  O-糖基化  /  生物合成

The dried roots of Phytolacca acinosa Roxb. are widely utilized in traditional Chinese medicine for their potent diuretic, anti-edematous, and detoxifying properties. Esculentosides, the primary bioactive constituents of P. acinosa, exhibit various pharmacological activities, including anti-inflammatory, anti-tumor, and antifungal effects. However, their clinical potential is hampered by low natural abundance and the inherent challenges of chemical synthesis due to their complex structural scaffolds, while synthetic biology represents a promising strategy for the sustainable and green production of esculentoside. However, the biosynthetic pathways remain unclear, and their key functional enzymes have not been reported yet. Herein, through activity-guided enzyme mining and transcriptome analyses, three novel glycosyltransferases (PaUGT2, PaUGT15, and PaUGT25) were functionally characterized from P. acinosa callus. These enzymes were capable of catalyzing the regio-selective glycosylation of 28-COOH of phytolaccagenin. Notably, PaUGT2 could efficiently catalyze 28-O-glycosylation of esculentoside A and esculentoside B, and PaUGT15 and PaUGT25 also exhibited catalytic activities toward these substrates. These findings not only preliminarily clarified the crucial enzymes for 28-O-glycosylation and elucidated the molecular basis for the structural diversity of oleanane-type esculentosides in Phytolacca plants, but also paved the way for further deciphering the biosynthetic pathway and constructing an artificial pathway of these glycosides.

Phytolacca acinosa  /  esculentoside  /  O-glycosyltransferase  /  O-glycosylation  /  biosynthesis
梁严方, 王梦源, 陈大伟, 戴均贵. 商陆皂苷C-28位O-糖基转移酶的发现及功能鉴定. 药学学报, 2026 , 61 (7) : 2810 -2820 . DOI: 10.16438/j.0513-4870.2026-0516
Yan-fang LIANG, Meng-yuan WANG, Da-wei CHEN, Jun-gui DAI. Functional characterization of C-28-O-glycosyltransferases from Phytolacca acinosa[J]. Acta Pharmaceutica Sinica, 2026 , 61 (7) : 2810 -2820 . DOI: 10.16438/j.0513-4870.2026-0516
正文
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商陆(Phytolacca acinosa Roxb.) 及其同属植物垂序商陆(Phytolacca americana L.) 的干燥根为我国传统中药[1], 在《神农本草经》及历代本草文献中均有记载, 具有消肿利尿、解毒散结等功效[2-5]。商陆中含有三萜皂苷、黄酮、酚酸、甾醇以及多糖等多种化学成分[6], 齐墩果烷型三萜皂苷是商陆的主要活性成分, 包括商陆皂苷甲(esculentoside A)、商陆皂苷乙(esculentoside B) 及商陆皂苷辛(esculentoside H) 等[7], 这些商陆皂苷类化合物通常含有C-3、C-28位糖链结构单元。现代药理学研究表明, 商陆皂苷类化合物不仅在体外实验中具有显著的抗炎、抗肿瘤及抗真菌等多种药理活性[8], 而且在小鼠体内也表现出显著的利尿和免疫调节活性, 具有极大的临床开发价值。目前, 商陆皂苷主要从商陆药材中提取分离获得, 因此严重依赖商陆原材料的产量及质量。同时, 该类化合物在商陆中含量低, 且含有约40种结构高度相似的同系物, 分离纯化困难[7]。再者, 商陆皂苷由具手性中心的多环骈合而成, 且涉及位置与立体选择性的羟基化、羧基化、糖基化反应, 化学合成困难[9]。由此可见, 活性商陆皂苷类化合物药源匮乏, 获取困难, 制约了其进一步新药研发。相较而言, 生物合成具有反应选择性强(位置和立体选择性)、效率高、反应条件温和、不受季节限制、环境友好等优势, 能克服上述难题[10]。因此, 解析商陆皂苷的生物合成途径, 功能鉴定其骨架形成、羟基化、糖基化等关键酶, 基于合成生物学进行绿色、高效生产, 可为商陆皂苷的可持续获取与开发提供新模式。
商陆皂苷的生物合成过程包括齐墩果烷五环三萜骨架形成及不同位点氧化、甲基化与糖基化后修饰。首先2, 3-氧化角鲨烯(2, 3-oxidosqualene) 经β-香树脂醇合酶(β-amyrin synthase, β-AS) 催化生成β-香树脂醇, 在C-28氧化酶(oxidase) 催化下形成齐墩果酸(oleanolic acid), 进一步经过C-2、C-23、C-30多位点氧化及C-30位O-甲基化反应形成商陆皂苷元(phytolaccagenin, 1); 商陆皂苷元在多个糖基转移酶作用下, 3-OH、28-COOH、4′-OH发生糖基化(葡萄糖基化、木糖基化等) 修饰生成结构多样的商陆皂苷类化合物(图1)。但目前商陆皂苷生物合成途径中五环三萜骨架形成、羟基化、糖基化等关键反应尚未阐明[9]。
目前五环三萜类糖基转移酶的催化位点主要集中在3-OH、28-COOH及23-OH, 其中C-3位和C-28位O-糖基转移酶研究最为深入, 且大多数属于UGT73、UGT74亚家族。例如, 十字花科植物欧洲山芥(Barbarea vulgaris) 中的4个糖基转移酶BvUGT73C10、BvUGT73C11、BvUGT73C12、BvUGT73C13均能催化常春藤皂苷元和齐墩果酸的3-OH进行单葡萄糖基化或连续两步葡萄糖基化[11]; 积雪草(Centella asiatica) 中糖基转移酶CaUGT73AD1和UGT73AH1能够催化积雪草酸或羟基积雪草酸的28-COOH进行糖基化修饰[12, 13]; 而来自王不留行(Saponaria vaccaria) 的SvUGT74M1可对丝石竹酸的28-COOH进行糖基化形成糖酯[14]。此外, 对23-OH及30-COOH进行糖基化修饰的关键酶也相继被发现, 例如来源于甘草(Glycyrrhiza uralensis) 的GuUGT73F17是首个发现的对齐墩果烷型三萜30-COOH进行糖基化的糖基转移酶, 其对C-30位羧基具有严格的底物特异性[15]。但商陆皂苷生物合成相关的C-3位、C-28位O-糖基转移酶及糖链延伸的4′-O-糖基转移酶均未被报道。
本研究通过酶活性导向的新颖酶挖掘结合转录组分析策略, 发现商陆愈伤组织中3个新颖糖基转移酶PaUGT2、PaUGT15和PaUGT25, 它们能够位置选择性催化商陆皂苷元28-COOH进行糖酯化反应。同时发现它们还能对商陆皂苷甲和商陆皂苷乙的28-COOH进行位置选择性O-糖基化。本研究揭示了商陆皂苷生物合成途径中C-28位O-糖基化关键反应, 为其完整生物合成途径解析与重构奠定基础。
材料和方法
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植物材料    实验材料为本实验室培养的商陆愈伤组织, 继代培养采用附加萘乙酸(NAA, 0.5 mg·L-1)、6-苄氨基嘌呤(6-BA, 0.5 mg·L-1)、2, 4-二氯苯氧乙酸(2, 4-D, 0.2 mg·L-1)、蔗糖(30 g·L-1)、琼脂(7 g·L-1) 的MS固体培养基, 灭菌前调pH为5.8, 于(25 ± 2) ℃黑暗培养。
菌株与质粒    大肠杆菌(Escherichia coli) DH5α感受态细胞、BL21 (DE3) 感受态细胞购自北京全式金生物技术有限公司; 原核表达载体pCold-TF、pET-28a (+) 由本实验室保存并提供。
实验试剂    商陆皂苷元及商陆皂苷甲购自成都埃法生物科技有限公司; 商陆皂苷乙由商陆皂苷甲经蜗牛酶水解制备[16]; UDP-D-葡萄糖(UDP-Glc; 北京熠得生物技术有限公司); UDP-D-木糖(UDP-Xyl; 铭合绿源生物技术有限公司); FastPure® Universal Plant Total RNA Isolation Kit (南京诺唯赞生物科技股份有限公司); SMARTerTM RACE cDNA Amplification Kit (Takara Bio公司, Japan); KOD OneTM PCR Master Mix (Toyobo公司, Japan); EasyPure®Quick Gel Extraction Kit和pEASY-Basic Seamless Cloning and Assembly Kit (TransGen Biotech公司); 限制性内切酶NdeⅠ、SalⅠ、EcoRⅠ、SacⅠ (New England Biolabs公司, USA); PageRulerTM Prestained Protein Ladders (杭州联科生物技术有限公司); 质粒提取试剂盒(北京擎科生物科技股份有限公司); 其他试剂均为国产分析纯。
粗酶提取与体外活性检测    取10 g培养7 d的商陆愈伤组织于液氮中研磨成细粉, 加入40 mL磷酸钾缓冲液[100 mmol·L-1, pH 6.5, 2 mmol·L-1苯甲磺酰氟(PMSF), 5 mmol·L-1二硫苏糖醇(DTT), 1 g交联聚乙烯吡咯烷酮(PVPP)], 涡旋混匀后置冰上孵育20 min。随后于4 ℃、6 000 ×g离心10 min, 转移上清于超速离心管中以9 300 ×g离心55 min, 并经0.45 μm滤膜过滤。滤液经10 kDa超滤管于3 850 ×g离心浓缩60 min至约5 mL, 再通过PD-10柱进行缓冲液置换。以50 mmol·L-1 Tris-HCl缓冲液洗脱, 洗脱体积为3.5 mL, 收集洗脱液作为最终粗酶液。
粗酶活性检测采用两批独立提取的愈伤组织粗酶提取物作为平行样品。反应体系包括40 mmol·L-1商陆皂苷元1 μL, 40 mmol·L-1 UDP-Glc (或UDP-Xyl) 2 μL和97 μL粗酶液, 30 ℃条件下反应12 h; 随后加入等体积预冷甲醇终止反应, 振荡混匀, 15 000 ×g离心30 min, 上清液用Agilent 1260高效液相色谱仪(美国Agilent公司) 对反应进行HPLC-UV-MS分析。HPLC检测条件: AcclaimTM 120 C18液相色谱柱(250 mm × 4.6 mm, 5 μm, Thermo Fisher Scientific, USA); 流动相为乙腈(B)-0.1%甲酸水溶液(A), 梯度洗脱程序(0~20 min, 35%~55% B; 20~21 min, 55%~100% B; 21~25 min, 100% B); 柱温30 ℃; 检测波长203 nm。质谱分析条件: 电喷雾离子源(ESI), 扫描模式为正、负离子同时扫描并自动触发多级质谱, 参数为: 鞘气流速, 20 (arbitrary units); 辅助气流速, 5 (arbitrary units); 喷雾电压, 5 000 V; 毛细管温度, 350 ℃; 碰撞诱导解离(CID) 电压, 35 V。
转录组测序与系统进化树分析    分别取生长7和30 d的商陆愈伤组织, 利用Illumina高通量测序技术构建转录组文库。在获取基因全长序列后, 结合已明确功能的三萜糖基转移酶信息, 使用ClustalW进行氨基酸多序列比对。比对结果导入MEGA11软件, 采用邻接法(neighbor-joining) 构建系统进化树, 获得候选糖基转移酶。
总RNA提取及cDNA合成    以新鲜商陆愈伤组织为原料, 利用FastPure® Universal Plant Total RNA Isolation Kit进行商陆愈伤组织中总RNA提取, 用1%非变性琼脂糖凝胶电泳检测总RNA的完整性。使用SMARTerTM RACE cDNA Amplification Kit逆转录试剂盒进行反转录, 将其合成第一链cDNA模板, -20 ℃保存。
重组表达载体的构建    以商陆cDNA为模板, 使用KOD OneTM PCR Master Mix进行候选基因扩增, PCR体系为: 2×KOD OneTM PCR Master Mix 25 μL、正向和反向引物(10 μmol·L-1) 各2 μL、cDNA 1 μL, 双蒸水补足至50 μL。反应条件为: 94 ℃预变性2 min; 98 ℃、10 s, 56 ℃、5 s, 68 ℃、30 s进行35个循环, 程序循环结束后68 ℃延伸反应10 min。1%琼脂糖凝胶电泳检测PCR产物, 切胶回收。使用pEASY-Basic Seamless Cloning and Assembly Kit, 通过无缝克隆技术将回收后的PCR产物分别构建至pET-28a (+) 和pCold-TF表达载体中。随后, 挑选生长良好的单克隆菌落, 进行菌落PCR初步鉴定, 并将阳性克隆送测序公司进行测序, 以验证插入目的基因的正确性。
重组蛋白异源表达与纯化    将成功构建的重组表达载体进行质粒提取, 并转入大肠杆菌表达感受态BL21 (DE3) 中。分别利用含50 μg·mL-1卡那霉素(以pET-28a (+) 为表达载体) 或50 μg·mL-1氨苄霉素(以pCold-TF为表达载体) 的LB液体培养基, 37 ℃、200 r·min-1振荡培养12 h。将种子液按1∶100比例加入含卡那霉素或氨苄霉素的新鲜LB液体培养基中, 37 ℃、200 r·min-1培养至菌液A600为0.6, 加入异丙基-β-D-硫代半乳糖苷(isopropyl-β-D-thiogalactopyranoside, IPTG) 至终浓度为0.2 mmol·L-1, 于16 ℃、200 r·min-1条件下诱导20 h。
诱导结束后, 于4 ℃、6  000 ×g离心6 min收集菌体, 用去离子水洗涤。将菌体重悬于结合缓冲液[20 mmol·L-1磷酸缓冲液(PBS, pH 7.4)、20 mmol·L-1咪唑、500 mmol·L-1 NaCl] 中, 冰浴条件下超声破碎细胞, 破碎功率40%, 工作5 s, 间隔5 s, 共破碎20 min。细胞破碎液于6  000 ×g离心50 min, 上清液经0.45 μm滤膜过滤后, 上样至预先平衡好的Ni2+螯合树脂亲和色谱柱。先用结合缓冲液洗脱除去杂蛋白, 后依次以含50、100、500 mmol·L-1咪唑的洗脱缓冲液[20 mmol·L-1 PBS (pH 7.4)、500 mmol·L-1 NaCl] 进行梯度洗脱, 收集目的蛋白。目的蛋白经超滤管(30 kDa) 离心浓缩脱盐后, 置于脱盐缓冲液(50 mmol·L-1 Tris-HCl、50 mmol·L-1 NaCl、1 mmol·L-1二硫苏糖醇、1%甘油, pH 7.4) 中, 于-80 ℃保存备用。
糖基转移酶的功能鉴定    为验证重组蛋白的催化活性, 本研究以商陆皂苷元为糖基受体, UDP-Glc (或UDP-Xyl) 为糖基供体进行体外酶促反应。反应体系为: 40 mmol·L-1商陆皂苷元1 μL, 40 mmol·L-1 UDP-Glc (或UDP-Xyl) 2 μL, 重组蛋白500 μg, Tris-HCl buffer (pH 7.4, 50 mmol·L-1) 补足至100 μL。30 ℃孵育12 h后, 加入100 μL预冷甲醇终止反应, 振荡混匀并在15 000 ×g离心30 min, 取上清液进行HPLC-UV-MS分析, 检测条件同上。对需要结构确证的糖基化产物, 将反应体系等比例放大至50 mL进行分离纯化。
PaUGT2酶学性质研究    以UDP-Glc为糖基供体, 商陆皂苷元为糖基受体, 考察不同pH缓冲液、温度、二价金属离子条件对PaUGT2催化糖基化反应活性的影响。反应体系同上。考察不同pH缓冲液对PaUGT2催化糖基化反应的影响时, 将反应体系中的Tris-HCl缓冲液分别置换为以下四种缓冲液体系(浓度均为50 mmol·L-1): 柠檬酸-柠檬酸钠缓冲液(pH 5.0、5.5、6.0)、磷酸氢二钠-磷酸二氢钠缓冲液(pH 6.0、6.5、7.0、7.5、8.0)、三羟甲基氨基甲烷-盐酸(Tris-HCl) 缓冲液(pH 8.0、8.5、9.0、9.5、10.0)、碳酸钠-碳酸氢钠缓冲液(pH 10.0、10.5), 各体系的各pH设置三组平行, 30 ℃反应4 h。考察不同温度对酶催化糖基化反应活性的影响时, 分别设置反应温度为15、20、25、30、35、40、45、50 ℃, 每个温度设置三组平行。反应在50 mmol·L-1 Tris-HCl缓冲液(pH 8.0) 中进行, 反应时间为4 h。考察不同金属离子对酶催化反应活性影响时, 分别向反应体系中加入终浓度为5 mmol·L-1的CaCl2、ZnCl2、MgCl2、CuCl2、MnCl2、BaCl2、CoCl2、NiSO4、SrCl2和EDTA (金属离子螯合剂), 以不添加金属离子的空白组作为对照(control check, CK), 于40 ℃的Tris-HCl buffer (pH 8.0) 中反应4 h, 每个反应设置三组平行。反应结束后, 加入100 μL冷甲醇终止反应, 混匀后于15 000 ×g离心30 min, 取上清进行HPLC-UV检测, 反应转化率通过HPLC谱图中峰面积的比值来估算。
测定PaUGT2对糖基受体的酶促反应动力学时, 固定反应体系中UDP-Glc的浓度800 μmol·L-1, 设置商陆皂苷元不同浓度梯度(100~1 200 μmol·L-1); 测定PaUGT2对糖基供体的酶促反应动力学时, 固定商陆皂苷元的浓度400 μmol·L-1, 设置UDP-Glc不同浓度梯度(20~1 400 μmol·L-1)。反应体系中金属离子Mn2+终浓度为5 mmol·L-1, 重组PaUGT2蛋白400 μg, 并用pH 8.0的50 mmol·L-1 Tris-HCl缓冲液补足至100 μL, 于40 ℃水浴中反应20 min。反应后处理及分析条件同上。分别以商陆皂苷元的浓度或UDP-Glc的浓度为横坐标, 反应速率为纵坐标, 采用非线性回归分析软件GraphPad Prism 10.4进行拟合得到米氏常数Km。
PaUGT2对其他商陆皂苷底物的催化活性研究    分别以商陆皂苷乙(2) 与商陆皂苷甲(3) 作为底物, 反应体系为: 40 mmol·L-1底物1 μL、40 mmol·L-1 UDP-Glc 2 μL、500 mmol·L-1 MnCl2 1 μL、纯化蛋白500 μg、Tris-HCl缓冲液(pH 8.0, 50 mmol·L-1) 补足至100 μL。40 ℃下水浴反应12 h, 反应后处理同上。HPLC检测流动相为乙腈(B)-0.1%甲酸水溶液(A), 梯度洗脱程序(0~20 min, 25%~60% B; 20~21 min, 60%~100% B; 21~25 min, 100% B); 柱温30 ℃; 检测波长203 nm。并以50 mL酶促反应体系制备糖基化产物, 反应体系为0.4 mmol·L-1底物, 0.8 mmol·L-1 UDP-Glc, 5 mmol·L-1 MnCl2, 5 mg·mL-1纯化蛋白PaUGT2和50 mmol·L-1 Tris-HCl缓冲液(pH 8.0), 40 ℃反应12 h, 经液相检测底物不再转化时终止反应, 反应转化率通过HPLC谱图中峰面积的比值来计算。反应液用水饱和正丁醇萃取, 有机相减压蒸干, 甲醇复溶, 经0.45 µm滤膜过滤后用Dionex UltiMate3000高效液相色谱仪(Thermo Fisher Scientific, USA) 对反应产物进行反相半制备HPLC分离、纯化。并通过质谱(ESI-MS) 和核磁共振波谱(NMR) 分析确定产物的结构。
结果
收起
1　粗酶提取与体外活性检测
以培养7天的10 g新鲜愈伤组织为材料进行粗酶提取, 获得3.5 mL粗酶提取物。分别以商陆皂苷元和UDP-Glc或UDP-Xyl为底物, 加入粗酶中进行酶促反应, 并通过HPLC-UV-MS检测。HPLC-UV分析发现, 与对照组相比, UDP-Glc作为糖供体的实验组在7.98 min处出现新化合物1a色谱峰, UDP-Xyl作为糖供体的实验组在11.80 min处出现新化合物1b色谱峰(图2A), 二者紫外吸收光谱与底物1一致(图2B)。MS分析表明, 1a的分子量(m/z 738.93 [M+HCOO]-) 较底物1的分子量 (m/z 576.82 [M+HCOO]-) 增加了162 Da (图2C), 1b的分子量(m/z 708.89 [M+HCOO]-) 较底物1的分子量增加了132 Da (图2C), 推测1a和1b分别为底物1的单葡萄糖基化和单木糖基化产物。上述实验结果表明, 商陆愈伤组织粗酶中存在相关糖基转移酶, 能催化商陆皂苷元发生葡萄糖基化以及木糖基化反应, 这为后续糖基转移酶基因挖掘提供依据。
2　愈伤组织转录组分析
测序共获得125 337条unigenes, 其中40 811条(32.56%) 序列在NR、Swiss-Prot、eggnog、CAZy等公共数据库中获得功能注释。利用KEGG (Kyoto Encyclopedia of Genes and Genomes) 数据库对unigene进行代谢通路分析, 即通过比对参考生物的完整基因组中的蛋白序列, 进行直系同源分类, 预测基因可能参与的代谢通路。分析结果显示, 共有16 555个Unigenes富集于相关次生代谢物生物合成通路, 涉及多种酶催化反应, 包括氧化、糖基化、甲基化等修饰过程。
以“glucosyltransferase”和“glycosyltransferase”为检索词对转录组数据进行筛选, 初步获得196条候选基因。通过生物信息学分析, 剔除片段长度不足1 000 bp的序列及涉及初级代谢序列, 共获得68条糖基转移酶候选基因。利用MEGA软件将上述基因编码的蛋白序列与已报道的15条植物源[人参(Panax ginseng)、积雪草(C. asiatica) 等] 三萜C-3位、C-28位O-糖基转移酶[11-14, 17-24]蛋白序列构建系统发育进化树。如图3所示, 已知具有三萜皂苷C-3位、C-28位糖基化活性的糖基转移酶主要聚集于UGT73和UGT74两个分支, 商陆来源的36条糖基转移酶亦聚类于上述亚家族, 并与已知功能酶形成相同或相邻的分支, 说明其亲缘关系较近。综合候选基因与已知功能酶的聚类关系, 最终从UGT73和UGT74分支中筛选出36条候选基因, 编号为PaUGT1~PaUGT36, 进行后续酶学功能验证。
3　糖基转移酶体外功能验证
对36条候选基因进行扩增, 其中34条基因被成功扩增为全长并测序正确, 分别构建pET-28a (+) 和pCold-TF重组质粒并进行异源表达, 该34个候选蛋白均实现了可溶性表达。收集菌体裂解上清液进行蛋白纯化与浓缩, 以商陆皂苷元为糖基受体、UDP-Glc或UDP-Xyl为供体对纯化后的候选蛋白进行功能鉴定, HPLC-UV-MS对反应产物进行检测。如图4所示, 以UDP-Glc为供体时, 添加重组蛋白PaUGT2、PaUGT15和PaUGT25的实验组均在7.98 min检测到同一产物峰, 其保留时间、紫外吸收光谱及质谱特征均与粗酶反应所得产物1a一致, 可确定为同一单糖基化产物。重组蛋白PaUGT2催化糖基化的转化率为32.6%, 活性优于PaUGT15 (转化率为17.1%) 和PaUGT25 (转化率为10.6%)。而以UDP-Xyl为供体时, 所有候选蛋白实验组均未检测到木糖基化产物。SDS-PAGE图表明, 纯化后的重组蛋白pCold-TF-PaUGT2、pET-28a-PaUGT15及pET-28a-PaUGT25在预期分子量位置均呈现清晰的特异性条带(图5)。
4　糖基化产物制备及结构鉴定
为制备足量糖基化产物用于结构确证, 将上述酶促反应体系等比例放大至50 mL, 其中商陆皂苷元和UDP-Glc的终浓度分别为0.4和0.8 mmol·L-1, 重组蛋白PaUGT2终浓度为5 mg·mL-1, 于Tris-HCl缓冲液(50 mmol·L-1, pH 7.4) 中30 ℃反应12 h, 经反相半制备HPLC纯化后获得化合物1a, 并经ESI-MS和NMR确证其结构。质谱分析显示, 1a的分子量较底物商陆皂苷元增加162 Da, 表明1a为底物1的单葡萄糖基化产物。进一步利用1H NMR、13C NMR和HMBC进行结构解析。化合物1a的13C NMR和1H NMR数据与底物商陆皂苷元相比, 多出一组葡萄糖基信号: δC 96.3 (C-1′), 74.6 (C-2′), 79.9 (C-3′), 71.4 (C-4′), 79.4 (C-5′), 62.3 (C-6′) 以及端基氢δH 6.34 (1H, d, J = 8.2 Hz, H-1′)。同时, 在13C NMR谱中, C-28的化学位移向高场移至176.6 ppm, 说明商陆皂苷元的C-28位可能发生了糖基化。在HMBC谱中, H-1′ (δH 6.34) 和C-28 (δC 176.6) 相关, 进一步证明了葡萄糖基连接在C-28位羧基上。葡萄糖基的端基质子具有较大的偶合常数J = 8.2 Hz, 说明其糖苷键为β构型。通过以上综合分析并与文献报道数据[25]比对, 确定该产物的结构为商陆皂苷元-28-O-β-D-葡萄糖苷。因此, PaUGT2、PaUGT15和PaUGT25均是C-28位O-糖基转移酶。进化树分析发现, PaUGT2与王不留行(S. vaccaria) 中28-O-糖基转移酶UGT74M1[14]的序列相似度最高, 为51.64%; PaUGT15和PaUGT25则与罗汉果(S. grosvenorii) 中3-O-糖基转移酶UGT74AC1[17]最为相近, 相似度分别为46.18%和34.71%。因PaUGT2催化效率较高, 选择PaUGT2进行后续的酶学性质及底物谱考察。
5　PaUGT2酶学性质及酶促反应动力学研究
以商陆皂苷元为糖基化受体底物对PaUGT2的酶学性质及酶动力学进行考察(图6)。PaUGT2在pH 5.0~10.5内均具有活性, pH 8.0时活性最强(图6A); PaUGT2在反应温度15~40 ℃时随温度的升高活性逐渐增强, 40 ℃时活性最强, 继续升温PaUGT2的酶活力显著降低(图6B); 添加金属离子螯合剂EDTA后PaUGT2仍保留较高水平的催化活性, 表明该酶的催化功能不依赖于金属离子。在二价金属离子中, Mn2+与Co2+可极大促进PaUGT2糖基化活性, 而其余所试金属离子影响微弱或呈现不同程度的抑制效应(图6C)。在最适条件下(添加MnCl2至终浓度为5 mmol·L-1, 并于Tris-HCl pH 8.0缓冲液中40 ℃) 反应4 h后, 反应体系中商陆皂苷元的转化率可达71.5%。酶动力学参数结果显示, PaUGT2对商陆皂苷元糖基化的Km和kcat/Km分别为679.9 μmol·L-1和7.95 L·mol-1·s-1 (图6D), 对UDP-Glc糖基化的Km和kcat/Km分别为395.5 μmol·L-1和15.56 L·mol-1·s-1 (图6E)。
6　PaUGT2对其他商陆皂苷底物的催化活性研究
为了探讨商陆皂苷生物合成中C-28位O-糖基化反应顺序, 本研究在最适条件下考察了PaUGT2对C-3位糖基化生物合成中间体—商陆皂苷乙与商陆皂苷甲的催化活性。HPLC-UV-MS分析显示(图7), 最适条件下反应12 h后, PaUGT2对商陆皂苷乙与商陆皂苷甲均具有较高的催化活性(转化率分别为87.9%、91.2%), 与商陆皂苷元活性相当(90.8%); 通过核磁数据分析发现, 商陆皂苷乙与商陆皂苷甲的糖基化位置均为28-COOH。上述实验结果表明, PaUGT2对C-28位羧基的区域选择性糖基化不受C-3位糖链延伸或空间位阻增加的影响, 能够稳定催化糖酯键的形成。因此, PaUGT2为商陆皂苷生物合成中C-28位特异性O-糖基转移酶, 其对C-3位不同糖基化程度的底物均具有催化活性, 提示C-28位糖基化修饰与C-3位糖基化反应可能呈现复杂的网络途径。此外, PaUGT15和PaUGT25也能催化底物2和3的28-COOH进行糖基化反应, 但其催化效率相对较低(< 15%)。本研究初步阐明了齐墩果烷型商陆皂苷结构多样性的酶学基础, 为活性商陆皂苷的生物合成途径解析奠定了基础。
7　糖基化产物波谱数据
28-O-β-D-Glucopyranosyl phytolaccagenin (1a): 白色固体, C37H58O12, ESI-MS m/z 739.07 [M+HCOO]-; 1H NMR (C5D5N, 600 MHz) δH 6.34 (1H, d, J = 8.2 Hz, H-1′, Glc), 5.62 (1H, d, J = 3.7 Hz, H-12), 4.55 (1H, d, J = 3.8 Hz, H-2), 3.72 (1H, d, J = 10.5 Hz, H-23), 3.61 (3H, s, H-31), 3.30~3.20 (1H, m, H-18), 1.64 (3H, s, H-25), 1.38 (3H, s, H-24), 1.24 (3H, s, H-27), 1.22 (3H, s, H-26), 1.19 (3H, s, H-29); 13C NMR (C5D5N, 150 MHz) δC 45.4 (C-1), 72.1 (C-2), 73.4 (C-3), 42.9 (C-4), 48.6 (C-5), 18.8 (C-6), 33.4 (C-7), 40.5 (C-8), 49.1 (C-9), 37.7 (C-10), 24.4 (C-11), 124.0 (C-12), 144.3 (C-13), 42.7 (C-14), 28.8 (C-15), 24.0 (C-16), 47.0 (C-17), 43.7 (C-18), 42.9 (C-19), 44.4 (C-20), 31.0 (C-21), 34.5 (C-22), 68.0 (C-23), 15.0 (C-24), 18.0 (C-25), 17.8 (C-26), 26.6 (C-27), 176.6 (C-28), 28.7 (C-29), 177.4 (C-30), 52.2 (C-31), 96.3 (C-1′, Glc), 74.6 (C-2′, Glc), 79.9 (C-3′, Glc), 71.4 (C-4′, Glc), 79.4 (C-5′, Glc), 62.3 (C-6′, Glc), 上述数据与文献报道的28-O-β-D-glucopyranosyl phytolaccagenin一致[25]。
Esculentoside S (2a): 白色固体, C42H66O16, ESI-MS m/z 871.04 [M+HCOO]-; 1H NMR (C5D5N, 600 MHz) δH 6.33 (1H, d, J = 8.2 Hz, H-1″, Glc), 5.60 (1H, t, J = 3.8 Hz, H-12), 5.09 (1H, d, J = 7.6 Hz, H-1′, Xyl), 4.80 (1H, d, J = 3.7 Hz, H-2), 4.34 (1H, d, J = 3.8 Hz, H-3), 3.71 (1H, d, J = 10.6 Hz, H-23), 3.61 (3H, s, H-31), 3.24 (1H, dd, J = 13.9, 4.9 Hz, H-18), 1.62 (3H, s, H-25), 1.38 (3H, s, H-24), 1.25 (3H, s, H-27), 1.20 (6H, s, H-26, H-29); 13C NMR (C5D5N, 150 MHz) δC 44.4 (C-1), 71.4 (C-2), 83.3 (C-3), 42.6 (C-4), 49.1 (C-5), 18.5 (C-6), 33.4 (C-7), 40.5 (C-8), 48.2 (C-9), 37.5 (C-10), 24.4 (C-11), 124.0 (C-12), 144.2 (C-13), 43.3 (C-14), 28.8 (C-15), 24.0 (C-16), 47.0 (C-17), 43.7 (C-18), 42.8 (C-19), 44.8 (C-20), 31.0 (C-21), 34.5 (C-22), 65.7 (C-23), 15.5 (C-24), 18.0 (C-25), 17.8 (C-26), 26.6 (C-27), 176.5 (C-28), 28.7 (C-29), 177.4 (C-30), 52.2 (C-31), 107.3 (C-1′, Xyl), 75.9 (C-2′, Xyl), 79.0 (C-3′, Xyl), 71.6 (C-4′, Xyl), 67.7 (C-5′, Xyl), 96.3 (C-1″, Glc), 74.6 (C-2″, Glc), 79.9 (C-3″, Glc), 71.5 (C-4″, Glc), 79.4 (C-5″, Glc), 62.3 (C-6″, Glc), 上述数据与文献报道的esculentoside S一致[26]。
Esculentoside H (3a): 白色固体, C48H76O21, ESI-MS m/z 1 033.73 [M+HCOO]-; 1H NMR (C5D5N, 600 MHz) δH 6.33 (1H, d, J = 8.2 Hz, H-1‴, Glc), 5.60 (1H, t, J = 3.8 Hz, H-12), 5.07 (1H, d, J = 7.9 Hz, H-1″, Glc), 5.00 (1H, d, J = 7.5 Hz, H-1′, Xyl), 3.69 (1H, d, J = 10.5 Hz, H-23), 3.62 (3H, s, H-31), 3.24 (1H, dd, J = 13.4, 3.5 Hz, H-18), 1.61 (3H, s, H-25), 1.36 (3H, s, H-24), 1.25 (3H, s, H-27), 1.20 (6H, s, H-26, H-29); 13C NMR (C5D5N, 150 MHz) δC 44.7 (C-1), 71.4 (C-2), 83.3 (C-3), 42.8 (C-4), 49.0 (C-5), 18.4 (C-6), 33.4 (C-7), 40.5 (C-8), 48.2 (C-9), 37.4 (C-10), 24.4 (C-11), 123.8 (C-12), 144.2 (C-13), 43.3 (C-14), 28.7 (C-15), 24.0 (C-16), 47.0 (C-17), 43.7 (C-18), 42.6 (C-19), 44.4 (C-20), 31.0 (C-21), 34.5 (C-22), 65.7 (C-23), 15.4 (C-24), 17.8 (C-25), 18.0 (C-26), 26.6 (C-27), 176.5 (C-28), 28.8 (C-29), 177.4 (C-30), 52.2 (C-31), 106.9 (C-1′, Xyl), 75.5 (C-2′, Xyl), 76.9 (C-3′, Xyl), 78.6 (C-4′, Xyl), 65.2 (C-5′, Xyl), 104.0 (C-1″, Glc), 74.7 (C-2″, Glc), 79.4 (C-3″, Glc), 72.2 (C-4″, Glc), 79.3 (C-5″, Glc), 63.1 (C-6″, Glc), 96.3 (C-1‴, Glc), 74.6 (C-2‴, Glc), 79.8 (C-3‴, Glc), 71.4 (C-4‴, Glc), 77.9 (C-5‴, Glc), 62.3 (C-6‴, Glc), 上述数据与文献报道的esculentoside H一致[27]。
讨论
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本研究通过商陆愈伤组织粗酶液提取与体外活性检测, 发现商陆愈伤组织中存在能够催化商陆皂苷元发生糖基化修饰的功能酶。在此基础上, 结合转录组分析、异源表达及体外生化反应, 成功发现并鉴定了3个糖基转移酶PaUGT2、PaUGT15和PaUGT25, 它们均能催化商陆皂苷元28-COOH生成商陆皂苷元-28-O-β-D-葡萄糖苷。PaUGT2还能高效催化商陆皂苷乙和商陆皂苷甲的C-28位进行O-糖基化反应, 表明商陆皂苷生物合成中C-28位糖基化修饰与C-3位糖链延伸可能呈现复杂的网络途径。因此, PaUGT2为商陆皂苷生物合成途径中特异性28-O-糖基转移酶, 对商陆皂苷生物合成中间体均具有催化活性。此外, PaUGT15和PaUGT25也能对商陆皂苷乙和商陆皂苷甲的28-COOH进行糖基化修饰。本研究揭示了商陆皂苷生物合成途径中C-28位O-糖基化关键反应, 初步阐明了齐墩果烷型商陆皂苷结构多样性的酶学基础, 为其完整生物合成途径解析与重构奠定基础。

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2026年第61卷第7期
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doi: 10.16438/j.0513-4870.2026-0516
  • 接收时间：2026-05-06
  • 首发时间：2026-09-21
  • 出版时间：2026-07-12
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  • 收稿日期：2026-05-06
  • 修回日期：2026-05-19
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    中国医学科学院 北京协和医学院, 药物研究所, 天然药物及核药基础与新药创制全国重点实验室, 国家卫生健康委员会天然药物生物合成重点实验室, 北京 100050

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2种不同金属材料的力学参数
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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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