{"title":"Phytochemicals from the flowers of Anthoshorea roxburghii (G.Don) P.S.Ashton & J.Heck. and their chemotaxonomic significance","authors":"Siriporn Yaisaeng , Mongkol Nontakitticharoen , Jarupong Prasopsuk , Oue-artorn Limtragool , Kitisak Poopasit , Surapon Saensouk , Chantana Boonyarat , Siripit Pitchuanchom","doi":"10.1016/j.bse.2025.105180","DOIUrl":null,"url":null,"abstract":"<div><div>The phytochemical ne resveratrol oligomer, pauciflorol B (<strong>1</strong>); two flavonols, kaempferol (<strong>2</strong>) and quercetin (<strong>3</strong>); three flavonol glycosides, kaempferol-3- <em>O</em>-glucoside (<strong>4</strong>), quercetin-3-<em>O</em>-glucoside (<strong>5</strong>), and quercetin-3-<em>O</em>-rhamnoside (<strong>6</strong>); one steroid glycoside, <em>β</em>-sitosterol-3-<em>O</em>-<em>β</em>-<span><em>d</em></span>-glucopyranoside (<strong>7</strong>) and one phenolic glycoside, arbutin (<strong>8</strong>). Their structures were elucidated by spectroscopic techniques (IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and 2D NMR) and mass spectrometry. Compound <strong>1</strong> exhibited stronger <em>α</em>-glucosidase inhibitory activity (IC<sub>50</sub> = 213.09 ± 6.67 μM) than the reference drug acarbose (IC<sub>50</sub> = 341.14 ± 6.34 μM). Compounds <strong>4</strong> and <strong>8</strong> were isolated from the Dipterocarpaceae family for the first time. Additionally, compounds <strong>1</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>8</strong> have not been reported in plants of the genus <em>Shorea</em> and <em>Anthoshorea</em>. Furthermore, the significance of these isolates from a chemotaxonomic approach was also presented.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"125 ","pages":"Article 105180"},"PeriodicalIF":2.2000,"publicationDate":"2026-04-01","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/S0305197825002297","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/11/21 0:00:00","PubModel":"Epub","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
The phytochemical ne resveratrol oligomer, pauciflorol B (1); two flavonols, kaempferol (2) and quercetin (3); three flavonol glycosides, kaempferol-3- O-glucoside (4), quercetin-3-O-glucoside (5), and quercetin-3-O-rhamnoside (6); one steroid glycoside, β-sitosterol-3-O-β-d-glucopyranoside (7) and one phenolic glycoside, arbutin (8). Their structures were elucidated by spectroscopic techniques (IR, 1H NMR, 13C NMR, and 2D NMR) and mass spectrometry. Compound 1 exhibited stronger α-glucosidase inhibitory activity (IC50 = 213.09 ± 6.67 μM) than the reference drug acarbose (IC50 = 341.14 ± 6.34 μM). Compounds 4 and 8 were isolated from the Dipterocarpaceae family for the first time. Additionally, compounds 1, 4, 6, and 8 have not been reported in plants of the genus Shorea and Anthoshorea. Furthermore, the significance of these isolates from a chemotaxonomic approach was also presented.
植物化学新白藜芦醇低聚物pauciflorol B (1);两种黄酮醇,山奈酚(2)和槲皮素(3);三种黄酮醇苷,山奈酚-3- o -葡萄糖苷(4)、槲皮素-3- o -葡萄糖苷(5)和槲皮素-3- o -鼠李糖苷(6);一种类固醇糖苷,β-谷甾醇-3- o -β-d-葡萄糖吡喃苷(7)和一种酚类糖苷,熊果苷(8)。通过IR、1H NMR、13C NMR和2D NMR等光谱技术和质谱技术对其结构进行了鉴定。化合物1的α-葡萄糖苷酶抑制活性(IC50 = 213.09±6.67 μM)高于对照药物阿卡波糖(IC50 = 341.14±6.34 μM)。化合物4和8为首次从龙掌科植物中分离得到。此外,化合物1、4、6和8未在石斛属植物和石斛属植物中发现。此外,从化学分类的角度也提出了这些分离物的意义。
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.