Chemophenetically relevant iridoids and phenolics from Betonica and Stachys (Lamioideae, Lamiaceae)

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology Pub Date : 2025-08-26 DOI:10.1016/j.bse.2025.105113

Isabelle Herre , Thomas Stegemann , Christian Zidorn

{"title":"Chemophenetically relevant iridoids and phenolics from Betonica and Stachys (Lamioideae, Lamiaceae)","authors":"Isabelle Herre , Thomas Stegemann , Christian Zidorn","doi":"10.1016/j.bse.2025.105113","DOIUrl":null,"url":null,"abstract":"<div><div>Betonica L. and Stachys L. are closely related genera within the Lamiaceae family, yet comparative phytochemical data on their secondary metabolites remain limited. In this study, we investigated and compared the iridoid and phenolic profiles of selected species from both genera to better understand their secondary metabolite diversity. RP-UHPLC-DAD-HRMS analyses of the methanolic extracts of three Betonica species (B. alopecuros L., B. macrantha K.Koch, and B. officinalis L.) and three Stachys species [S. arvensis (L.) L., S. byzantina K.Koch, and S. sylvatica L.] revealed pronounced differences in their secondary metabolite profiles. Chlorogenic acid, harpagide, and martynoside were detected in all investigated species. The iridoid glycoside allobetonicoside was present exclusively in the examined Betonica species, while flavone glycosides showed genus-specific patterns: isoscutellarein and hypolaetin derivatives occurred only in Stachys, whereas tricin and tricetin glucuronides were restricted to Betonica. These differences highlight distinct secondary metabolite profiles between the two genera. Allobetonicoside, tricin 7-O-glucuronide, and tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide might therefore serve as chemophenetic markers for the genus Betonica, while the presence of hypolaetin 4′-methylether 7-O-[6‴-acetylallosyl (1→2) glucoside] and isoscutellarein 7-O-[6‴-acetylallosyl (1→2) glucoside] exclusively in Stachys supports their value as marker compounds for this genus.</div><div>Tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide, which had previously only been reported from Artemisia frigida Willd. (Asteraceae) as friginoside A, was isolated from B. officinalis. A detailed analysis of the methanolic extract of B. officinalis confirmed the presence of known compounds, including the phenylpropanoids verbascoside, forsythoside B, leucosceptoside B, martynoside, betonyoside F, and stachysoside B; the iridoids harpagide, 8-O-acetylharpagide, and allobetonicoside; and the flavonoid isoorientin. These findings might contribute to chemophentically characterize the genera Betonica and Stachys.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"123 ","pages":"Article 105113"},"PeriodicalIF":2.0000,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197825001620","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

Abstract

Betonica L. and Stachys L. are closely related genera within the Lamiaceae family, yet comparative phytochemical data on their secondary metabolites remain limited. In this study, we investigated and compared the iridoid and phenolic profiles of selected species from both genera to better understand their secondary metabolite diversity. RP-UHPLC-DAD-HRMS analyses of the methanolic extracts of three Betonica species (B. alopecuros L., B. macrantha K.Koch, and B. officinalis L.) and three Stachys species [S. arvensis (L.) L., S. byzantina K.Koch, and S. sylvatica L.] revealed pronounced differences in their secondary metabolite profiles. Chlorogenic acid, harpagide, and martynoside were detected in all investigated species. The iridoid glycoside allobetonicoside was present exclusively in the examined Betonica species, while flavone glycosides showed genus-specific patterns: isoscutellarein and hypolaetin derivatives occurred only in Stachys, whereas tricin and tricetin glucuronides were restricted to Betonica. These differences highlight distinct secondary metabolite profiles between the two genera. Allobetonicoside, tricin 7-O-glucuronide, and tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide might therefore serve as chemophenetic markers for the genus Betonica, while the presence of hypolaetin 4′-methylether 7-O-[6‴-acetylallosyl (1→2) glucoside] and isoscutellarein 7-O-[6‴-acetylallosyl (1→2) glucoside] exclusively in Stachys supports their value as marker compounds for this genus.

Tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide, which had previously only been reported from Artemisia frigida Willd. (Asteraceae) as friginoside A, was isolated from B. officinalis. A detailed analysis of the methanolic extract of B. officinalis confirmed the presence of known compounds, including the phenylpropanoids verbascoside, forsythoside B, leucosceptoside B, martynoside, betonyoside F, and stachysoside B; the iridoids harpagide, 8-O-acetylharpagide, and allobetonicoside; and the flavonoid isoorientin. These findings might contribute to chemophentically characterize the genera Betonica and Stachys.

Abstract Image

查看原文本刊更多论文

川芎科、川芎科中环烯醚萜和酚类化合物的化学表型研究

Betonica L.和Stachys L.在Lamiaceae家族中是密切相关的属，但它们的次生代谢产物的比较植物化学数据仍然有限。在本研究中，我们研究并比较了两属植物的环烯醚萜类和酚类化合物，以更好地了解它们的次生代谢物多样性。三种Betonica （B. alopecuros L.， B. macrantha k.k koch， B. officinalis L.）和三种Stachys的甲醇提取物的RP-UHPLC-DAD-HRMS分析[j]。薄荷(l)L.， S. byzantina K.Koch和S. sylvatica L.]揭示了它们次生代谢物谱的显著差异。在所有被调查的物种中均检测到绿原酸、哈弗苷和马丁苷。环烯醚萜苷只存在于甜菜属中，而黄酮类苷则具有属特异性：异花蓟苷和次花蓟苷衍生物仅存在于Stachys中，而tricin和tricetin glucuronides仅存在于甜菜属中。这些差异突出了两个属之间不同的次生代谢物谱。因此，同种异体甜菜糖苷、tricin 7-O-葡糖苷和tricin 3 ',4 ',5 ' -三甲基醚-7-O-葡糖苷可以作为Betonica属的化学标记物，而在Stachys中只存在hypaetin 4 ' -甲基醚7-O-[6′-乙酰氨基乙基（1→2）葡萄糖苷]和异花蓟苷7-O-[6′-乙酰氨基乙基（1→2）葡萄糖苷]支持它们作为该属标记物的价值。曲西汀3 ',4 ',5 ' -三甲基醚-7- o -葡糖苷，此前仅报道从冷蒿中分离得到。（Asteraceae）为friginoside A，从officinalis中分离得到。对牛头草的甲醇提取物进行了详细分析，证实了已知化合物的存在，包括苯丙素毛蕊花苷、连珠合苷B、白藜芦醇苷B、马丁花苷、皂荚苷F和水苏糖苷B；环烯醚萜类化合物哈巴苷、8- o -乙酰哈巴苷和异素甜菜甙；还有类黄酮异荭草苷。这些发现可能有助于Betonica属和Stachys属的化学化学特征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Biochemical Systematics and Ecology 生物-进化生物学

CiteScore

3.00

自引率

12.50%

发文量

147

审稿时长

43 days

期刊介绍： Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology). In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.