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Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIX. Terpenoids and phenylpropanoid-substituted flavan-3-ols from the leaves of Camellia petelotii (golden-flower tea) and their bioactivities 中国特有珍稀濒危植物的植物化学生物学研究。XLIX一部分。金花茶叶中萜类和苯丙取代黄烷-3-醇及其生物活性研究。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-05 DOI: 10.1016/j.phytochem.2026.114808
Ze-Yu Zhao , Can Wang , Zhe-Lu Jiang , Jiang Wan , Juan Xiong , Yi Zang , Yeun-Mun Choo , Jia Li , Jin-Feng Hu
{"title":"Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIX. Terpenoids and phenylpropanoid-substituted flavan-3-ols from the leaves of Camellia petelotii (golden-flower tea) and their bioactivities","authors":"Ze-Yu Zhao ,&nbsp;Can Wang ,&nbsp;Zhe-Lu Jiang ,&nbsp;Jiang Wan ,&nbsp;Juan Xiong ,&nbsp;Yi Zang ,&nbsp;Yeun-Mun Choo ,&nbsp;Jia Li ,&nbsp;Jin-Feng Hu","doi":"10.1016/j.phytochem.2026.114808","DOIUrl":"10.1016/j.phytochem.2026.114808","url":null,"abstract":"<div><div><em>Camellia petelotii</em> (Merr.) Sealy, commonly known as golden-flower tea, is an endangered yellow-flowering species of the genus <em>Camellia</em> (Theaceae). As a medicine and food homology (MFH) plant, it possesses significant medicinal and edible value. However, because the chemical constituents of <em>C. petelotii</em> have rarely been investigated, its potential medicinal and nutritional benefits remain poorly understood, hindering its further utilization. In this study, a comprehensive phytochemical investigation was conducted on the EtOAc-soluble fraction of a 90% MeOH extract derived from the leaves of <em>C. petelotii</em>, resulting in the isolation and characterization of five previously undescribed (<strong>1</strong>−<strong>5</strong>) and 19 known (<strong>6</strong>−<strong>24</strong>) compounds. Among these compounds, campetelolides A (<strong>1</strong>) and B (<strong>2</strong>) are identified as guaianolides bearing a 2-methyl-2-butenoxyl moiety. Campetelols A (<strong>3</strong>), B (<strong>4</strong>), and C (<strong>5</strong>) are classified as phenylpropanoid-substituted flavan-3-ols. The chemical structures and absolute configurations of these metabolites were elucidated through spectroscopic techniques, supported by calculated NMR data, combined with DP4+ analysis, as well as by comparison of calculated and experimental electronic circular dichroism (ECD) spectra. Compounds <strong>1</strong>, <strong>2</strong>, and eupachinilide I (<strong>6</strong>) exhibited anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 cells by suppressing nitric oxide (NO) production, with IC<sub>50</sub> values of 5.8, 4.8, and 4.8 μM, respectively. In addition, compound <strong>2</strong> and 3<em>β</em>,11<em>α</em>,12,21<em>β</em>-tetrahydroxy-22-oxours-12-en-24-oic acid methyl ester (<strong>7</strong>) inhibited ATP-citrate lyase (ACL), exhibiting IC<sub>50</sub> values of 11.2 and 9.3 μM, respectively. The findings highlight the therapeutic potential of the endangered plant <em>C. petelotii</em>, offering prospects for the discovery of novel bioactive agents while simultaneously emphasizing the importance of its conservation and sustainable utilization.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114808"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146133153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Pyridinium alkaloids – a unique class of naturally occurring salt-form secondary metabolites: a comprehensive review of 68 years (1958–mid-2025) 吡啶生物碱——一类独特的天然盐状次生代谢物:68年(1958- 2025年中期)的综合回顾。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-09 DOI: 10.1016/j.phytochem.2026.114806
Huu Canh Vo , Duc Trung Le , Minh Canh Nguyen , Le Viet Ha Tran , To Hoang Long , Vinh Han La , Quoc Tuan Le , Quang Ton That , Linh Tran , Khac-Minh Thai , Van-Kieu Nguyen , Huong Thi Thu Le , Huynh Nguyen Khanh Tran
{"title":"Pyridinium alkaloids – a unique class of naturally occurring salt-form secondary metabolites: a comprehensive review of 68 years (1958–mid-2025)","authors":"Huu Canh Vo ,&nbsp;Duc Trung Le ,&nbsp;Minh Canh Nguyen ,&nbsp;Le Viet Ha Tran ,&nbsp;To Hoang Long ,&nbsp;Vinh Han La ,&nbsp;Quoc Tuan Le ,&nbsp;Quang Ton That ,&nbsp;Linh Tran ,&nbsp;Khac-Minh Thai ,&nbsp;Van-Kieu Nguyen ,&nbsp;Huong Thi Thu Le ,&nbsp;Huynh Nguyen Khanh Tran","doi":"10.1016/j.phytochem.2026.114806","DOIUrl":"10.1016/j.phytochem.2026.114806","url":null,"abstract":"<div><div>Pyridinium alkaloids represent a structurally unique class of nitrogen-containing natural products, primarily obtained from marine sponges. These compounds range from simple mono-substituted derivatives to complex poly-alkylated and a series of unusual oligomeric structures. Additionally, they have also exhibited a wide range of documented biological activities, including cytotoxic, antimicrobial, antifungal, and neuroactive effects. Notably, several compounds, such as coscinoderines and cyclostellettamines, have been explored for their ability to exhibit selective cytotoxicity against nutrient-deprived cancer cells. Polyalkylpyridiniums also represent a promising avenue for drug development due to their potent and diverse biological activities. This is especially the case for halitoxin, a polymeric complex from sponges, which shows high cytotoxicity and strong antibacterial activity, as well as the ability to prevent the onslaught of marine organisms. This review aims to provide a comprehensive overview of 127 pyridinium alkaloid derivatives published in a ranging of 68 years from 1958 to mid-2025, highlighting their sources, structural classes, bioactivities, biosynthetic origins, and synthetic insights. Subsequent assessments and discussions will provide a foundation for further research and development on potential compounds of this class.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114806"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146166324","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Xylaricins A–I: Dearomatic xanthone derivatives from endolichenic fungus Xylaria sp. LCSS1a Xylaricins A-I:从内生真菌Xylaria sp. LCSS1a中提取的去芳香口山酮衍生物。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-01-31 DOI: 10.1016/j.phytochem.2026.114803
Wenge Zhang , Lihua Zhu , Kunkun Zhang , Ke Xu , Xiaoyi Luan , Jiabo Sun , Hehe Li , Wenzhuo Tan , Jiaozhen Zhang , Xiuyun Li , Hongxiang Lou
{"title":"Xylaricins A–I: Dearomatic xanthone derivatives from endolichenic fungus Xylaria sp. LCSS1a","authors":"Wenge Zhang ,&nbsp;Lihua Zhu ,&nbsp;Kunkun Zhang ,&nbsp;Ke Xu ,&nbsp;Xiaoyi Luan ,&nbsp;Jiabo Sun ,&nbsp;Hehe Li ,&nbsp;Wenzhuo Tan ,&nbsp;Jiaozhen Zhang ,&nbsp;Xiuyun Li ,&nbsp;Hongxiang Lou","doi":"10.1016/j.phytochem.2026.114803","DOIUrl":"10.1016/j.phytochem.2026.114803","url":null,"abstract":"<div><div>Chemical investigation of the ethyl acetate extract of the endolichenic fungus <em>Xylaria</em> sp. LCSS1a resulted in the isolation and identification of 24 natural metabolites. Among them, 15 were known compounds and 9 of them were characterized as previously unreported dearomatized xanthone derivatives with highly oxygenated substituents, which were designated as xylaricins A–I (<strong>1</strong>–<strong>9</strong>). The structures and absolute configurations of the previously unreported compounds were elucidated through extensive spectroscopic analysis, quantum chemical calculations (<sup>13</sup>C NMR DP4+ analysis, and TDDFT-ECD) and <em>X</em>-ray crystallography. The screening for cytotoxic and antibacterial assays revealed that compound <strong>9</strong> exhibited moderate inhibitory activity against A549 lung cancer cells, with an IC<sub>50</sub> value of 7.5 μM, while to <em>Staphylococcus aureus</em>, the MIC value was 16 μg/mL. Structure-activity relationships highlighted the importance of a conjugated π-system and free phenolic groups for bioactivity observed in this series.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114803"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146106831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Triquinane sesquiterpene octanoates from Antrodiella zonata with their cytotoxicity and antimalarial activities 带状拟安蝇三奎宁倍半萜辛酸酯及其细胞毒性和抗疟活性
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-11 DOI: 10.1016/j.phytochem.2026.114825
Jie-Lin Yin , Qing-Shu Chen , Fang-Lu Wei , Wen-Tao Luo , Zheng-Hong Pan , Juan He
{"title":"Triquinane sesquiterpene octanoates from Antrodiella zonata with their cytotoxicity and antimalarial activities","authors":"Jie-Lin Yin ,&nbsp;Qing-Shu Chen ,&nbsp;Fang-Lu Wei ,&nbsp;Wen-Tao Luo ,&nbsp;Zheng-Hong Pan ,&nbsp;Juan He","doi":"10.1016/j.phytochem.2026.114825","DOIUrl":"10.1016/j.phytochem.2026.114825","url":null,"abstract":"<div><div>By modifying fermentation conditions, ten octanoate-containing triquinane sesquiterpenoids, including six previously undescribed ones, namely antrodizonatins M‒R, were isolated from the fungus <em>Antrodiella zonata</em>. Their structures and absolute configurations have been established by extensive spectroscopic methods, single crystal X-ray diffraction, ECD and <sup>13</sup>C NMR calculations. Notably, antrodizonatin Q features of an unusual adenine substituent. Antrodizonatins M‒O, and R demonstrated cytotoxic activity against the human tumor cell line MCF-7, with IC<sub>50</sub> values ranging from 2.2 to 17.6 μM. Antrodizonatins N–P, Antrodizonatin R, dihydrocoriolin C, and chloriolin C exhibited <em>in vitro</em> antimalarial activity against <em>Plasmodium falciparum</em>, with IC<sub>50</sub> values ranging from 21.4 to 33.7 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114825"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146191922","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Six previously undescribed bisabolane-type sesquiterpenes from marine derived fungus Aspergillus sp. WHUF04-170 and their antimicrobial activity 从海洋真菌曲霉(Aspergillus sp. WHUF04-170)中分离的6种新发现的双abolane型倍半萜及其抑菌活性。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-04 DOI: 10.1016/j.phytochem.2026.114799
Wen-Juan Ding , Hong-Ming Huang , Yu-Ning Liu , Dan-Mei Tian , Ya-Qi Yuan , Ya-Xin Xue , Kui Hong , Hong-Kai Bi , Jin-Shan Tang
{"title":"Six previously undescribed bisabolane-type sesquiterpenes from marine derived fungus Aspergillus sp. WHUF04-170 and their antimicrobial activity","authors":"Wen-Juan Ding ,&nbsp;Hong-Ming Huang ,&nbsp;Yu-Ning Liu ,&nbsp;Dan-Mei Tian ,&nbsp;Ya-Qi Yuan ,&nbsp;Ya-Xin Xue ,&nbsp;Kui Hong ,&nbsp;Hong-Kai Bi ,&nbsp;Jin-Shan Tang","doi":"10.1016/j.phytochem.2026.114799","DOIUrl":"10.1016/j.phytochem.2026.114799","url":null,"abstract":"<div><div>Marine-derived fungi have emerged as valuable sources of pharmacologically active lead compounds with potent antimicrobial properties. In this study, six previously undescribed bisabolane-type sesquiterpenes (<strong>1</strong>–<strong>6</strong>), including a rare 5,6-dihydrobenzoic acid derivative of the bisabolene skeleton (<strong>1</strong>), along with 18 known compounds (<strong>7</strong>–<strong>24</strong>), were isolated from the ethyl acetate extract of the marine fungus <em>Aspergillus</em> sp. WHUF04-170. The chemical structures of these metabolites were elucidated through comprehensive spectroscopic analysis, including UV, IR, HRESIMS, and 1D/2D NMR spectroscopy. The antimicrobial potential of the isolated compounds was subsequently evaluated <em>in vitro</em>. Compounds <strong>9</strong>, <strong>10</strong>, <strong>15</strong>, <strong>16</strong>, and <strong>19</strong> exhibited moderate antibacterial activity against both the standard <em>Helicobacter pylori</em> strain G27 and the multidrug-resistant strain HP159, with minimal inhibitory concentration values ranging from 16 to 32 μg/mL. Notably, synergistic antimicrobial assays revealed that compounds <strong>1</strong> and <strong>15</strong> enhanced the activity of amphotericin B against <em>Candida albicans</em> strains, including both standard reference strains (SC5314 and ATCC 10231) and drug-resistant clinical isolates (C5 and C3). Collectively, these findings expand the structural diversity of bisabolane-type sesquiterpenes and highlight their dual antimicrobial potential, offering promising leads for the development of combination therapies against resistant pathogens.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114799"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146131044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Heterologous combinatorial biosynthesis of daurichromenic acid derivatives from a common metabolite in Rhododendron species and evaluation of their SARS-CoV-2 inhibitory activities 杜鹃花一种常见代谢物的异源组合生物合成达乌尔红素酸衍生物及其抑制SARS-CoV-2活性评价
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-03 DOI: 10.1016/j.phytochem.2026.114804
Chao Peng , Meng-Yun Guo , Lu Gao , Xu-Ping Zhang , Wei-Guang Wang
{"title":"Heterologous combinatorial biosynthesis of daurichromenic acid derivatives from a common metabolite in Rhododendron species and evaluation of their SARS-CoV-2 inhibitory activities","authors":"Chao Peng ,&nbsp;Meng-Yun Guo ,&nbsp;Lu Gao ,&nbsp;Xu-Ping Zhang ,&nbsp;Wei-Guang Wang","doi":"10.1016/j.phytochem.2026.114804","DOIUrl":"10.1016/j.phytochem.2026.114804","url":null,"abstract":"<div><div><em>Rhododendron</em> species, a globally recognized group of medicinal and edible plants, are known to produce a wide array of meroterpenoid natural products. Among these, daurichromenic acid (<strong>7</strong>) and its derivatives are widely distributed and exhibit diverse biological activities. However, their low natural abundance in plants and the incomplete elucidation of their biosynthetic pathways have hindered further development and application. Capitachromenic acid D (<strong>6</strong>), a representative chromene compound formed via successive oxidative transformations of <strong>7</strong>, was initially isolated from <em>R</em>. <em>capitatum</em> Maxim. and also shows promising biological potential for pharmaceutical applications. In this study, the heterologous combinatorial biosynthesis of compound <strong>6</strong> was achieved in <em>Aspergillus oryzae</em> through the introduction of genes responsible for the biosynthesis of the precursor griffolic acid (<strong>2</strong>) from <em>Fusarium graminearum</em> 1962, <em>A. oryzae</em>, and <em>Stachybotrys</em> sp. g12, along with a cyclase gene from <em>R</em>. <em>dauricum</em> L. In bioactivity assays, compounds <strong>5</strong> and <strong>6</strong> exhibited notable inhibitory activity against the main protease (M<sup>pro</sup>) of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), with IC<sub>50</sub> values of 16.5 ± 1.3 μM and 10.7 ± 1.6 μM, respectively, highlighting their potential as promising lead compounds for SARS-CoV-2 M<sup>pro</sup> inhibitor development.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114804"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146126095","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Glycosidic phenylpropanoid dimers and trimers from Castanopsis choboensis and their anti-inflammatory activities 甜槠中糖苷类苯丙二聚体和三聚体及其抗炎活性
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-01-31 DOI: 10.1016/j.phytochem.2026.114798
Nao Pang , Yafeng Wang , Shuyao Li , Guiqin Li , Li Ge , Zhangbin Liu , Ruijie He , Kedi Yang , Yonglin Huang
{"title":"Glycosidic phenylpropanoid dimers and trimers from Castanopsis choboensis and their anti-inflammatory activities","authors":"Nao Pang ,&nbsp;Yafeng Wang ,&nbsp;Shuyao Li ,&nbsp;Guiqin Li ,&nbsp;Li Ge ,&nbsp;Zhangbin Liu ,&nbsp;Ruijie He ,&nbsp;Kedi Yang ,&nbsp;Yonglin Huang","doi":"10.1016/j.phytochem.2026.114798","DOIUrl":"10.1016/j.phytochem.2026.114798","url":null,"abstract":"<div><div>The first phytochemical study of <em>Castanopsis choboensis</em> Hickel &amp; A. Camus (Paul Robert Hickel &amp; Aimée Camus) leaves resulted in the isolation and structural characterization of nine previously undescribed glycosidic phenylpropanoid dimers and trimers, designated Choboensins A–I (<strong>1</strong>–<strong>9</strong>), along with nine known analogues (<strong>10</strong>–<strong>18</strong>). Comprehensive spectroscopic analysis, including HRESIMS and NMR spectroscopy, enabled full structural elucidation of these compounds. Absolute configurations were unambiguously assigned through comparison of experimental and calculated ECD spectra. Of particular structural significance, compound <strong>8</strong> represented the first reported glycosidic phenylpropanoid trimer featuring an unprecedented scaffold formed through the fusion of an aryltetralin-type lignan and a dihydrobenzofuran-type neolignan. Eyerin E exhibited moderate anti-inflammatory activity by inhibiting NO production (IC<sub>50</sub> = 15.1 μM) in LPS-stimulated macrophages, highlighting its pharmacological potential.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114798"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098689","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Specialized metabolites from the Chinese liverwort Heteroscyphus coalitus (Hook.) Schiffn and their anti-inflammatory activity 中国苔类植物Heteroscyphus coalitus (Hook.)的特殊代谢物希夫及其抗炎活性。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-06-01 Epub Date: 2026-02-09 DOI: 10.1016/j.phytochem.2026.114818
Shuangzhi Yuan , Jiaozhen Zhang , Chunyang Zhang , Yanan Qiao , Hong-Xiang Lou
{"title":"Specialized metabolites from the Chinese liverwort Heteroscyphus coalitus (Hook.) Schiffn and their anti-inflammatory activity","authors":"Shuangzhi Yuan ,&nbsp;Jiaozhen Zhang ,&nbsp;Chunyang Zhang ,&nbsp;Yanan Qiao ,&nbsp;Hong-Xiang Lou","doi":"10.1016/j.phytochem.2026.114818","DOIUrl":"10.1016/j.phytochem.2026.114818","url":null,"abstract":"<div><div>Four previously undescribed diterpenoids, <em>ent</em>-clerodanoids, coalitins A-C (<strong>1</strong>–<strong>3</strong>), an <em>ent</em>-abietanoid, coalisin A (<strong>5</strong>), and one 2-nor<em>-ent-</em>aromadendrane-type sesquiterpenoid, coalisin B (<strong>15</strong>), along with sixteen known compounds were isolated from the liverwort <em>Heteroscyphus coalitus</em> (Hook.) Schiffn. Interestingly, coalisin B (<strong>15</strong>), a norsesquiterpenoid featuring an unprecedented 2-nor-<em>ent</em>-aromadendrane skeleton different from the common natural series, was identified. Their structures were determined by NMR spectroscopic data analysis, high resolution electrospray ionization mass spectroscopy data and experimental electronic circular dichroism measurements. Subsequently, bioactivity assessments revealed that compounds <strong>12</strong>, <strong>17</strong>, and <strong>20</strong> exhibited potent NO inhibition in RAW 264.7 cells, with IC<sub>50</sub> values of 21.35, 27.36 and 13.98 μM, respectively. Further mechanistic studies manifested that the potent anti-inflammatory activity of <strong>12</strong>, <strong>17</strong>, and <strong>20</strong> were precisely evidenced by their ability to downregulate the relative phosphorylation levels of NF-κB p65 and concurrently suppress the production of cytokines TNF-α, IL-6, and IL-1β.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"246 ","pages":"Article 114818"},"PeriodicalIF":3.4,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146166332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Single-site amino acid residue mutation reshapes the characteristics of double bond positions for protostadienol-type triterpenols. 单位点氨基酸残基突变重塑了原二烯醇型三萜醇双键位置的特征。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-05-07 DOI: 10.1016/j.phytochem.2026.114950
Pengyang Lin, Yunpeng Wang, Bing Li, Xuebingting Zhang, Baolian Fan, Ruoshi Huang, Zhongju Ji, Fan Zhang, Jingcai Liang, Lixin Duan
{"title":"Single-site amino acid residue mutation reshapes the characteristics of double bond positions for protostadienol-type triterpenols.","authors":"Pengyang Lin, Yunpeng Wang, Bing Li, Xuebingting Zhang, Baolian Fan, Ruoshi Huang, Zhongju Ji, Fan Zhang, Jingcai Liang, Lixin Duan","doi":"10.1016/j.phytochem.2026.114950","DOIUrl":"https://doi.org/10.1016/j.phytochem.2026.114950","url":null,"abstract":"<p><p>Protostadienol-type tetracyclic triterpenes, characterized by a rare chair-boat-chair (C-B-C) cyclized sterol-type backbone, serve as high-value pharmaceutical precursors due to their positionally isomeric double bonds. Plant derived-protostane triterpenoids have different skeletons at the double bond positions from fungal protostane triterpenoids. The characteristic mechanisms of double bond positions for the two types of protostane-type triterpenols remain unknown. Our previous research has shown that T726 in AoPDS is the key residue for plant protostadienol synthase, and mutating at this site can reshape the function of the other four-ring C-B-C type OSC enzymes, producing plant protostadienol. In this study, we constructed an F726 saturation mutagenesis library based on AoCAS. Strikingly, the F726N mutant simultaneously produced both Δ<sup>13(17)</sup> and Δ<sup>17(20)</sup>-protostadienols. Mechanistic studies identified N726 as a general base deprotonating the protosteryl cation to yield divergent products. Homologous mutations X in other types of C-B-C OSCs revealed consistent functional reshaping results for the hybrid product of two double bond positions. This work achieves the first reprogramming of a plant OSC to produce fungal-specific Δ<sup>17(20)</sup>-protostadienol, overcoming natural biosynthetic constraints. Our findings establish a basis for precise triterpenoid biosynthesis and efficient pharmaceutical precursor preparation.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114950"},"PeriodicalIF":3.4,"publicationDate":"2026-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147863972","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Functional characterization of a plant germacrene D-4-ol synthase enabling the production of bioactive α-cadinol and τ-muurolol under changed catalysis conditions. 在改变催化条件下产生具有生物活性的α-二醇和τ-穆罗尔的植物烯d -4-醇合成酶的功能表征。
IF 3.4 2区 生物学
Phytochemistry Pub Date : 2026-05-07 DOI: 10.1016/j.phytochem.2026.114945
Shao-Jun Cheng, Shi-Jie Liu, Wan-Jun Liang, Qin-Qin Shen, Zhong-Zhu Yuan, Zong-Hua Xiao, Yan Liu, Sheng-Hong Li
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