Pub Date : 2026-01-13DOI: 10.1016/j.phytochem.2026.114780
An Jin , Zhuocan Huang , Hui Li , Jinling Chang , Hanli Ruan , Wenming Wu
A detailed phytochemical analysis of the dried, ripe fruits of Kadsura coccinea led to the isolation and structural characterization of eleven undescribed lignans, designated kadcolignan K–U (1–11), together with thirteen previously documented compounds (12–24). Notably, kadcolignan U (11) is particularly distinctive, representing a rare dearomatized lignan with a dienone moiety and an uncommon 7, 2′–oxygen bridge. Mechanistic evaluation of the most potent isolates, kadcolignan O (5) and kadcolignan Q (7), revealed their capacity to trigger apoptosis in activated mice B lymphocytes through mitochondrial-dependent pathways, as evidenced by dose-dependent elevation of pro-apoptotic Bax, suppression of anti-apoptotic Bcl-2/Bcl-xL, and release of cleaved caspase-3 and caspase-9. Additionally, both metabolites were found to disrupt the PI3K/AKT/mTOR signaling axis by inhibiting the phosphorylation of PI3K, AKT, and mTOR in a dose-dependent manner. Our findings highlight K. coccinea as a source of B cell-targeted immunosuppressants, with 5 and 7 emerging as promising candidates for further development in autoimmune disease therapy.
{"title":"Dibenzocyclooctadiene lignans from Kadsura coccinea and their immunosuppressive activities","authors":"An Jin , Zhuocan Huang , Hui Li , Jinling Chang , Hanli Ruan , Wenming Wu","doi":"10.1016/j.phytochem.2026.114780","DOIUrl":"10.1016/j.phytochem.2026.114780","url":null,"abstract":"<div><div>A detailed phytochemical analysis of the dried, ripe fruits of <em>Kadsura coccinea</em> led to the isolation and structural characterization of eleven undescribed lignans, designated kadcolignan K–U (<strong>1</strong>–<strong>11</strong>), together with thirteen previously documented compounds (<strong>12</strong>–<strong>24</strong>). Notably, kadcolignan U (<strong>11</strong>) is particularly distinctive, representing a rare dearomatized lignan with a dienone moiety and an uncommon 7, 2′–oxygen bridge. Mechanistic evaluation of the most potent isolates, kadcolignan O (<strong>5</strong>) and kadcolignan Q (<strong>7</strong>), revealed their capacity to trigger apoptosis in activated mice B lymphocytes through mitochondrial-dependent pathways, as evidenced by dose-dependent elevation of pro-apoptotic Bax, suppression of anti-apoptotic Bcl-2/Bcl-xL, and release of cleaved caspase-3 and caspase-9. Additionally, both metabolites were found to disrupt the PI3K/AKT/mTOR signaling axis by inhibiting the phosphorylation of PI3K, AKT, and mTOR in a dose-dependent manner. Our findings highlight <em>K. coccinea</em> as a source of B cell-targeted immunosuppressants, with <strong>5</strong> and <strong>7</strong> emerging as promising candidates for further development in autoimmune disease therapy.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114780"},"PeriodicalIF":3.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145979583","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}
Thirteen undescribed guaianolide lactones chryguaialactones A−M (1−13), together with ten known analogues (14−23), were isolated from the flowers of Chrysanthemum indicum L. The previously unreported structures including their absolute configurations were determined through spectroscopic techniques, combined with DP4+ NMR analysis, X-ray crystallography and calculated ECD methods. All compounds were screened on their IL-1β inhibitory activity in THP-1 cells, and most of them (1, 3−5, 7−8, 10, 12−17, and 19−23) displayed inhibitory effects with IC50 values in the range 0.31–15.95 μM. Besides, compound 13 showed the most potential activity with IC50 value of 0.31 ± 0.15 μM. Mechanismly, 13 inhibited the NLRP3 assembly and the activation of its downstream proteins. Furthermore, 13 could interact with NLRP3 protein illustrated by CETSA, DARTS and IP assays. Molecular docking revealed the covalent binding between the α, β unsaturated ketone in 13 and the NACHT domain of NLRP3. The suppression of 13 on NLRP3 inflammasome pathway was further proved in HFLS-RA cells. Hence, these findings uncovered an unrecognized role of 13 exerting anti rheumatoid arthritis activity in the regulation of NLRP3 inflammasome pathway.
{"title":"Guaianolide sesquiterpenoids from Chrysanthemum indicum L. alleviate rheumatoid arthritis by targeting of NLRP3 inflammasome pathway","authors":"Gui-Min Xue , Hao Feng , Dong-Rong Zhu , Xin-Xin Guo , Ding-Qiao Xu , Yan-Jun Sun , Yan-Le Zhi , Zhi-Qiang Zhang , Guo-Sheng Li , Wu-Fa Dong , Jin-Feng Xue","doi":"10.1016/j.phytochem.2026.114768","DOIUrl":"10.1016/j.phytochem.2026.114768","url":null,"abstract":"<div><div>Thirteen undescribed guaianolide lactones chryguaialactones A−M (<strong>1</strong>−<strong>13</strong>), together with ten known analogues (<strong>14</strong>−<strong>23</strong>), were isolated from the flowers of <em>Chrysanthemum indicum</em> L. The previously unreported structures including their absolute configurations were determined through spectroscopic techniques, combined with DP4+ NMR analysis, X-ray crystallography and calculated ECD methods. All compounds were screened on their IL-1<em>β</em> inhibitory activity in THP-1 cells, and most of them (<strong>1</strong>, <strong>3</strong>−<strong>5</strong>, <strong>7</strong>−<strong>8</strong>, <strong>10</strong>, <strong>12</strong>−<strong>17</strong>, and <strong>19</strong>−<strong>23</strong>) displayed inhibitory effects with IC<sub>50</sub> values in the range 0.31–15.95 μM. Besides, compound <strong>13</strong> showed the most potential activity with IC<sub>50</sub> value of 0.31 ± 0.15 μM. Mechanismly, <strong>13</strong> inhibited the NLRP3 assembly and the activation of its downstream proteins. Furthermore, <strong>13</strong> could interact with NLRP3 protein illustrated by CETSA, DARTS and IP assays. Molecular docking revealed the covalent binding between the <em>α</em>, <em>β</em> unsaturated ketone in <strong>13</strong> and the NACHT domain of NLRP3. The suppression of <strong>13</strong> on NLRP3 inflammasome pathway was further proved in HFLS-RA cells. Hence, these findings uncovered an unrecognized role of <strong>13</strong> exerting anti rheumatoid arthritis activity in the regulation of NLRP3 inflammasome pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114768"},"PeriodicalIF":3.4,"publicationDate":"2026-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145906412","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}
Pub Date : 2026-01-02DOI: 10.1016/j.phytochem.2025.114766
Kai-Dong Liu , Jiao-Jiao Zhou , Jiang Fu , Teng-Teng Meng , Jing Qu
Five previously undescribed iridal-type triterpenoids (belamcaniridals A-C and polycycloiridals U–V), three undescribed stilbenes (belamcanenes C, D, F), and thirteen known compounds were isolated from the rhizomes of Iris domestica. The chemical structures of the unknown compounds were established by interpreting extensive spectroscopic data, including HR-ESIMS, NMR and ECD. The previously undescribed iridal-type triterpenoids isolated had a certain degree of novelty in structure. Stilbenes (mixture 6, 8) exhibited anti-inflammatory activities with inhibition rates of 65.31 ± 0.16 % and 64.53 ± 0.09 %, respectively, against the NF-κB signaling pathway at a concentration of 10 μM. Compounds 18 and 20 exhibited antiproliferative activities against the K562 human leukemia cell line with IC50 values of 15.54 ± 1.52 μM (18) and 4.20 ± 0.70 μM (20), respectively.
{"title":"Iridal-type triterpenoids and stilbenes with anti-inflammatory activities from the rhizomes of Iris domestica","authors":"Kai-Dong Liu , Jiao-Jiao Zhou , Jiang Fu , Teng-Teng Meng , Jing Qu","doi":"10.1016/j.phytochem.2025.114766","DOIUrl":"10.1016/j.phytochem.2025.114766","url":null,"abstract":"<div><div>Five previously undescribed iridal-type triterpenoids (belamcaniridals A-C and polycycloiridals U–V), three undescribed stilbenes (belamcanenes C, D, F), and thirteen known compounds were isolated from the rhizomes of <em>Iris domestica.</em> The chemical structures of the unknown compounds were established by interpreting extensive spectroscopic data, including HR-ESIMS, NMR and ECD. The previously undescribed iridal-type triterpenoids isolated had a certain degree of novelty in structure. Stilbenes (mixture <strong>6</strong>, <strong>8</strong>) exhibited anti-inflammatory activities with inhibition rates of 65.31 ± 0.16 % and 64.53 ± 0.09 %, respectively, against the NF-κB signaling pathway at a concentration of 10 μM. Compounds <strong>18</strong> and <strong>20</strong> exhibited antiproliferative activities against the K562 human leukemia cell line with IC<sub>50</sub> values of 15.54 ± 1.52 μM (<strong>18</strong>) and 4.20 ± 0.70 μM (<strong>20</strong>), respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114766"},"PeriodicalIF":3.4,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145900984","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}
Pub Date : 2025-12-29DOI: 10.1016/j.phytochem.2025.114764
Yewen Jia , Wen Dang , Xueni Zhang , Yu Sun , Juan Zhang , Degang Qing , Congzhao Fan , Huiming Hua , Yingjie Wang , Ning Li
Eleven undescribed terpenylated acetophenones (1, 2a/2b, 3a/3b, 4–6, 7a/7b, 8) and twelve known analogues (9a/9b, 10–12, 13a/13b, 14a/14b, 15, 16a/16b) were isolated from the roots of Ferula ferulaeoides (Steud.) Korov. (Apiaceae) by the guidance of bioactivity-guided approach. The structures and relative configurations of the new compounds were established by extensive analysis of UV, HR-ESI-MS, and NMR data, supported by 13C NMR calculations with custom DP4+ probability analysis. Through electronic circular dichroism, the absolute configurations of all compounds were determined for the first time. Cytotoxic activities of all compounds were evaluated against HCT-116, HT-29, and HCoEpiC cell lines, and most of them (1, 4, 7–15) showed significant or moderate selective cytotoxic activity toward colon cancer cells. Among them, compound 10 showed the most potent cytotoxic effects against HCT-116 cells (IC50, 8.23 ± 2.3 μM) and HT-29 cells (IC50, 12.43 ± 2.2 μM), while showing significantly lower cytotoxicity toward normal colonic epithelial cells (IC50, 52.26 ± 2.9 μM for HCoEpiC).
{"title":"Terpenylated acetophenones from the root of Ferula ferulaeoides (Steud.) Korov. with selective cytotoxic activity","authors":"Yewen Jia , Wen Dang , Xueni Zhang , Yu Sun , Juan Zhang , Degang Qing , Congzhao Fan , Huiming Hua , Yingjie Wang , Ning Li","doi":"10.1016/j.phytochem.2025.114764","DOIUrl":"10.1016/j.phytochem.2025.114764","url":null,"abstract":"<div><div>Eleven undescribed terpenylated acetophenones (<strong>1</strong>, <strong>2a</strong>/<strong>2b</strong>, <strong>3a</strong>/<strong>3b, 4</strong>–<strong>6</strong>, <strong>7a</strong>/<strong>7b</strong>, <strong>8</strong>) and twelve known analogues (<strong>9a</strong>/<strong>9b</strong>, <strong>10–12</strong>, <strong>13a/13b</strong>, <strong>14a</strong>/<strong>14b</strong>, <strong>15</strong>, <strong>16a</strong>/<strong>16b</strong>) were isolated from the roots of <em>Ferula ferulaeoides</em> (Steud.) Korov. (Apiaceae) by the guidance of bioactivity-guided approach. The structures and relative configurations of the new compounds were established by extensive analysis of UV, HR-ESI-MS, and NMR data, supported by <sup>13</sup>C NMR calculations with custom DP4+ probability analysis. Through electronic circular dichroism, the absolute configurations of all compounds were determined for the first time. Cytotoxic activities of all compounds were evaluated against HCT-116, HT-29, and HCoEpiC cell lines, and most of them (<strong>1</strong>, <strong>4</strong>, <strong>7</strong>–<strong>15</strong>) showed significant or moderate selective cytotoxic activity toward colon cancer cells. Among them, compound <strong>10</strong> showed the most potent cytotoxic effects against HCT-116 cells (IC<sub>50</sub>, 8.23 ± 2.3 μM) and HT-29 cells (IC<sub>50</sub>, 12.43 ± 2.2 μM), while showing significantly lower cytotoxicity toward normal colonic epithelial cells (IC<sub>50</sub>, 52.26 ± 2.9 μM for HCoEpiC).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114764"},"PeriodicalIF":3.4,"publicationDate":"2025-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145878864","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}
Kaempferia species have long been used in traditional medicine; however, their diterpenoid constituents remain underexplored, particularly in relation to anti-inflammatory potential. In this work, the chemical constituents and anti-inflammatory properties of Kaempferia aurora were investigated. Seven polyoxygenated cyclohex(a/e)ne diterpene esters, auroranes A–G (3–9), together with their biosynthetic precursors, antiacanthoic acid (1), and antiacanthol (2), were isolated from the rhizomes of K. aurora. Their structures and relative configurations were determined by extensive spectroscopic analyses. The absolute configurations of compounds 6–8 were assigned using NMR-based DP4+ probability calculations in combination with TDDFT-calculated ECD spectra. These compounds represent a structurally rare subclass of diterpenoids within the Zingiberaceae, contributing to the phytochemical diversity of this plant group. All compounds, except for compounds 2 and 3, were evaluated for their inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. Compounds 1, 4–6, 8, and 9 exhibited notable NO inhibitory activity, with IC50 values ranging from 4.82 to 9.00 μM. To explore potential molecular interactions, molecular docking and molecular dynamics simulations were performed, suggesting favorable binding of the active compounds to inducible nitric oxide synthase (iNOS). A preliminary structure–activity relationship (SAR) analysis indicated that the presence of an epoxide ring or a double bond within the cyclohexane ring moiety may contribute to the observed activity. These findings provide a basis for further investigation into the bioactive constituents of K. aurora and may support its value as a potential source of anti-inflammatory agents.
{"title":"Auroranes A–G: Polyoxygenated cyclohex(a/e)ne diterpenes from Kaempferia aurora and their anti-inflammatory activity via inhibition of nitric oxide production","authors":"Pornpuk Booranaseensuntorn , Jutatip Boonsombat , Sanit Thongnest , Jitnapa Sirirak , Patcharin Kongwaen , Orawan Jongsomjainuk , Tawit Suriyo , Napat Sitthimonchai , Saroj Ruchisansakun , Sitthivut Charoensutthivarakul , Prasat Kittakoop , Jutamaad Satayavivad , Chulabhorn Mahidol , Somsak Ruchirawat","doi":"10.1016/j.phytochem.2025.114767","DOIUrl":"10.1016/j.phytochem.2025.114767","url":null,"abstract":"<div><div>Kaempferia species have long been used in traditional medicine; however, their diterpenoid constituents remain underexplored, particularly in relation to anti-inflammatory potential. In this work, the chemical constituents and anti-inflammatory properties of <em>Kaempferia aurora</em> were investigated. Seven polyoxygenated cyclohex(a/e)ne diterpene esters, auroranes A–G (3–9), together with their biosynthetic precursors, antiacanthoic acid (1), and antiacanthol (2), were isolated from the rhizomes of K. aurora. Their structures and relative configurations were determined by extensive spectroscopic analyses. The absolute configurations of compounds 6–8 were assigned using NMR-based DP4+ probability calculations in combination with TDDFT-calculated ECD spectra. These compounds represent a structurally rare subclass of diterpenoids within the Zingiberaceae, contributing to the phytochemical diversity of this plant group. All compounds, except for compounds 2 and 3, were evaluated for their inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. Compounds 1, 4–6, 8, and 9 exhibited notable NO inhibitory activity, with IC50 values ranging from 4.82 to 9.00 μM. To explore potential molecular interactions, molecular docking and molecular dynamics simulations were performed, suggesting favorable binding of the active compounds to inducible nitric oxide synthase (iNOS). A preliminary structure–activity relationship (SAR) analysis indicated that the presence of an epoxide ring or a double bond within the cyclohexane ring moiety may contribute to the observed activity. These findings provide a basis for further investigation into the bioactive constituents of K. aurora and may support its value as a potential source of anti-inflammatory agents.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114767"},"PeriodicalIF":3.4,"publicationDate":"2025-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145878815","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}
Pub Date : 2025-12-28DOI: 10.1016/j.phytochem.2025.114765
Guang-Qiong Li , Hui Liu , Zheng-Hui Li , Ji-Kai Liu
Ten previously undescribed grifolin derivatives (1, 2, and 4–11), including three pairs of enantiomers, and five known analogs (3 and 12–15), were isolated from the ethanol extract of Albatrellus dispansus. Their chemical structures were determined based on spectroscopic analysis, electronic circular dichroism calculations, and acid hydrolysis. In addition, all 15 isolated compounds were evaluated for cytotoxicity and antibacterial activities. Compound 15 showed mild antibacterial activity against MRSA with MIC values of 6.2 μM. Compound 13 showed moderate cytotoxicity against the human cancer MCF-7 cell line with IC50 values of 4.06 μM.
{"title":"Grifolin derivatives from the fruiting bodies of Albatrellus dispansus","authors":"Guang-Qiong Li , Hui Liu , Zheng-Hui Li , Ji-Kai Liu","doi":"10.1016/j.phytochem.2025.114765","DOIUrl":"10.1016/j.phytochem.2025.114765","url":null,"abstract":"<div><div>Ten previously undescribed grifolin derivatives (<strong>1</strong>, <strong>2</strong>, and <strong>4</strong>–<strong>11</strong>), including three pairs of enantiomers, and five known analogs (<strong>3</strong> and <strong>12</strong>–<strong>15</strong>), were isolated from the ethanol extract of <em>Albatrellus dispansus</em>. Their chemical structures were determined based on spectroscopic analysis, electronic circular dichroism calculations, and acid hydrolysis. In addition, all 15 isolated compounds were evaluated for cytotoxicity and antibacterial activities. Compound <strong>15</strong> showed mild antibacterial activity against MRSA with MIC values of 6.2 μM. Compound <strong>13</strong> showed moderate cytotoxicity against the human cancer MCF-7 cell line with IC<sub>50</sub> values of 4.06 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"245 ","pages":"Article 114765"},"PeriodicalIF":3.4,"publicationDate":"2025-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145864610","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}
Pub Date : 2025-12-27DOI: 10.1016/j.phytochem.2025.114763
Xinyu Zhao , Xiaochen Hu , Ruixue Wang , Gang Zhang , Yuanyuan Han , Feng Yan , Mengmeng Liu
Rheum officinale Baill. (Chinese rhubarb) is a traditional medicinal plant known for its diverse therapeutic effects, including anti-inflammatory, antifungal, and antitumor activities, which are largely attributed to its anthraquinone glycosides. However, the UDP-glycosyltransferases (UGTs) responsible for the biosynthesis of these bioactive compounds remain poorly characterized. In this study, we identified and functionally characterized six UGTs (RoUGT1,2,4,5,6,8) from R. officinale that catalyze the glucosylation of emodin to form emodin-6-O-glucopyranoside, a key anthraquinone glycoside. Biochemical assays revealed distinct substrate specificities and kinetic parameters among the RoUGTs, with RoUGT1 exhibiting the highest catalytic efficiency. Molecular docking analysis, combined with site-directed mutagenesis, identified key amino acid residues involved in substrate recognition and catalysis. These findings provide new insights into the biosynthetic pathway of anthraquinone glycosides in R. officinale and lay the groundwork for metabolic engineering and synthetic biology strategies aimed at enhancing the production of pharmacologically active glycosides.
大黄。（中国大黄）是一种传统的药用植物，以其多种治疗作用而闻名，包括抗炎，抗真菌和抗肿瘤活性，这主要归功于其蒽醌苷。然而，负责这些生物活性化合物的生物合成的udp -糖基转移酶（UGTs）的特征仍然很差。在本研究中，我们从officinale中鉴定了6个ugt (RoUGT1,2,4,5,6,8)，并对其进行了功能表征，这些ugt催化大黄素的糖基化生成大黄素-6- o -glucopyranoside，这是一种关键的蒽醌苷。生化分析显示，RoUGT1具有不同的底物特异性和动力学参数，其中RoUGT1具有最高的催化效率。分子对接分析，结合定点诱变，确定了参与底物识别和催化的关键氨基酸残基。这些研究结果为深入了解铁皮石斛中蒽醌类苷的生物合成途径提供了新的思路，并为进一步开发具有药理活性的蒽醌类苷的代谢工程和合成生物学策略奠定了基础。
{"title":"Identification of a group of UDP-glycosyltransferases catalyze emodin glycosylation in Rheum officinale with substrates promiscuity","authors":"Xinyu Zhao , Xiaochen Hu , Ruixue Wang , Gang Zhang , Yuanyuan Han , Feng Yan , Mengmeng Liu","doi":"10.1016/j.phytochem.2025.114763","DOIUrl":"10.1016/j.phytochem.2025.114763","url":null,"abstract":"<div><div><em>Rheum officinale</em> Baill. (Chinese rhubarb) is a traditional medicinal plant known for its diverse therapeutic effects, including anti-inflammatory, antifungal, and antitumor activities, which are largely attributed to its anthraquinone glycosides. However, the UDP-glycosyltransferases (UGTs) responsible for the biosynthesis of these bioactive compounds remain poorly characterized. In this study, we identified and functionally characterized six UGTs (RoUGT1,2,4,5,6,8) from <em>R. officinale</em> that catalyze the glucosylation of emodin to form emodin-6-<em>O</em>-glucopyranoside, a key anthraquinone glycoside. Biochemical assays revealed distinct substrate specificities and kinetic parameters among the RoUGTs, with RoUGT1 exhibiting the highest catalytic efficiency. Molecular docking analysis, combined with site-directed mutagenesis, identified key amino acid residues involved in substrate recognition and catalysis. These findings provide new insights into the biosynthetic pathway of anthraquinone glycosides in <em>R. officinale</em> and lay the groundwork for metabolic engineering and synthetic biology strategies aimed at enhancing the production of pharmacologically active glycosides.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114763"},"PeriodicalIF":3.4,"publicationDate":"2025-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145857518","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}
Pub Date : 2025-12-26DOI: 10.1016/j.phytochem.2025.114762
Jiarui Wu, Siyang Fan, Man Yang, Huali Wu, Fujiang Guo, Kaixian Chen, Liuqiang Zhang, Yiming Li
Ginger (Zingiber officinale Roscoe), a widely used culinary and medicinal plant, has recently gained significant attention for its whitening properties. While gingerols are the primary components of ginger, the whitening effects of their numerous, structurally similar gingerols remain underexplored, particularly with insufficient structure-activity relationship (SAR) analyses. This study aimed to comprehensively investigate the anti-melanogenic effects and SAR of diverse gingerols and their derivatives. Thirty-five gingerols and their derivatives were isolated from ginger oleoresin, including two rare monoterpene-gingerol conjugates (1–2), two unreported isogingerols (3–4), and one shogaol derivative (5). Compounds 6–9 were isolated from a natural source for the first time. Structural elucidation via spectroscopic analysis, specific rotation, and electronic circular dichroism confirmed their structures and configurations, with zingerol A (1) featuring an unprecedented 1-phenyl-2-geranyl-decane scaffold. Twenty-five isolates (1–2, 4–17, 19–21, 23, 25–26, and 32–34) demonstrated dose-dependent inhibition of melanogenesis in B16F10 cells. Shogaols (19–21) exhibited equivalent anti-melanogenic activity to hydroquinone at ≤ 2.5 μM. SAR studies revealed that geranyl substitution at C-2 and aliphatic chain elongation enhanced the bioactivity, with the C-3 carbonyl group serving as a critical pharmacophore.
{"title":"Gingerols and their derivatives from ginger oleoresin and the anti-melanogenic effect in IBMX-stimulated B16F10 melanoma cells","authors":"Jiarui Wu, Siyang Fan, Man Yang, Huali Wu, Fujiang Guo, Kaixian Chen, Liuqiang Zhang, Yiming Li","doi":"10.1016/j.phytochem.2025.114762","DOIUrl":"10.1016/j.phytochem.2025.114762","url":null,"abstract":"<div><div>Ginger (<em>Zingiber officinale</em> Roscoe), a widely used culinary and medicinal plant, has recently gained significant attention for its whitening properties. While gingerols are the primary components of ginger, the whitening effects of their numerous, structurally similar gingerols remain underexplored, particularly with insufficient structure-activity relationship (SAR) analyses. This study aimed to comprehensively investigate the anti-melanogenic effects and SAR of diverse gingerols and their derivatives. Thirty-five gingerols and their derivatives were isolated from ginger oleoresin, including two rare monoterpene-gingerol conjugates (<strong>1</strong>–<strong>2</strong>), two unreported isogingerols (<strong>3</strong>–<strong>4</strong>), and one shogaol derivative (<strong>5</strong>). Compounds <strong>6</strong>–<strong>9</strong> were isolated from a natural source for the first time. Structural elucidation <em>via</em> spectroscopic analysis, specific rotation, and electronic circular dichroism confirmed their structures and configurations, with zingerol A (<strong>1</strong>) featuring an unprecedented 1-phenyl-2-geranyl-decane scaffold. Twenty-five isolates (<strong>1</strong>–<strong>2</strong>, <strong>4</strong>–<strong>17</strong>, <strong>19</strong>–<strong>21</strong>, <strong>23</strong>, <strong>25</strong>–<strong>26</strong>, and <strong>32</strong>–<strong>34</strong>) demonstrated dose-dependent inhibition of melanogenesis in B16F10 cells. Shogaols (<strong>19</strong>–<strong>21</strong>) exhibited equivalent anti-melanogenic activity to hydroquinone at ≤ 2.5 μM. SAR studies revealed that geranyl substitution at C-2 and aliphatic chain elongation enhanced the bioactivity, with the C-3 carbonyl group serving as a critical pharmacophore.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114762"},"PeriodicalIF":3.4,"publicationDate":"2025-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145850621","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}
Pub Date : 2025-12-24DOI: 10.1016/j.phytochem.2025.114760
Lo-Yun Chen , Bo-Rong Peng , Thanh Hao Huynh , You-Ying Chen , Yu-Cheng Chen , Ngoc-Thac Pham , Huong-Giang Le , Quoc-Vu Pham , Phuong Vu Luu , Ying-Mi Lai , Mohamed El-Shazly , Tsong-Long Hwang , Kuei-Hung Lai
In this study, by using untargeted LC-MS/MS-based multi-informative molecular networking, 12 briarane diterpenoids were isolated from a closed-system cultured soft coral Briareum stechei. Among them, six unreported compounds were identified and named briastechols A–F (1–6). Notably, briastechols A (1) and B (2) possess a rare 11,14-ether bridge, while briastechols C (3) and D (4) feature a tetrahydrofuran moiety with an ether linkage between C-5 and C-8. Additionally, the absolute configurations of briastechol F (6) and briarenol H (10) were determined for the first time via X-ray crystallographic analysis. Evaluation of bioactivity indicated that the crude extract exerted pronounced anti-inflammatory effects, as reflected in the inhibition of superoxide anion formation and elastase secretion in human neutrophils triggered by N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB). Among the isolated compounds, briastechol E (5) showed significant anti-inflammatory potential, with IC50 values of 7.89 ± 0.38 μM and 4.53 ± 0.68 μM against superoxide anion generation and elastase release, respectively. These findings underscore the structural novelty and chemical diversity of metabolites from cultured B. stechei using a closed system, highlighting its potential as a sustainable source of anti-inflammatory agents and further supporting the viability of closed aquaculture systems for marine natural product research.
{"title":"Briarane-type diterpenes from a closed-system cultured soft coral Briareum stechei","authors":"Lo-Yun Chen , Bo-Rong Peng , Thanh Hao Huynh , You-Ying Chen , Yu-Cheng Chen , Ngoc-Thac Pham , Huong-Giang Le , Quoc-Vu Pham , Phuong Vu Luu , Ying-Mi Lai , Mohamed El-Shazly , Tsong-Long Hwang , Kuei-Hung Lai","doi":"10.1016/j.phytochem.2025.114760","DOIUrl":"10.1016/j.phytochem.2025.114760","url":null,"abstract":"<div><div>In this study, by using untargeted LC-MS/MS-based multi-informative molecular networking, 12 briarane diterpenoids were isolated from a closed-system cultured soft coral <em>Briareum stechei</em>. Among them, six unreported compounds were identified and named briastechols A–F (<strong>1</strong>–<strong>6</strong>). Notably, briastechols A (<strong>1</strong>) and B (<strong>2</strong>) possess a rare 11,14-ether bridge, while briastechols C (<strong>3</strong>) and D (<strong>4</strong>) feature a tetrahydrofuran moiety with an ether linkage between C-5 and C-8. Additionally, the absolute configurations of briastechol F (<strong>6</strong>) and briarenol H (<strong>10</strong>) were determined for the first time via X-ray crystallographic analysis. Evaluation of bioactivity indicated that the crude extract exerted pronounced anti-inflammatory effects, as reflected in the inhibition of superoxide anion formation and elastase secretion in human neutrophils triggered by <em>N</em>-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB). Among the isolated compounds, briastechol E (<strong>5</strong>) showed significant anti-inflammatory potential, with IC<sub>50</sub> values of 7.89 ± 0.38 μM and 4.53 ± 0.68 μM against superoxide anion generation and elastase release, respectively. These findings underscore the structural novelty and chemical diversity of metabolites from cultured <em>B. stechei</em> using a closed system, highlighting its potential as a sustainable source of anti-inflammatory agents and further supporting the viability of closed aquaculture systems for marine natural product research.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114760"},"PeriodicalIF":3.4,"publicationDate":"2025-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145834464","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}
Pub Date : 2025-12-24DOI: 10.1016/j.phytochem.2025.114761
Yali Wang , Huadong Zhang , Yuxia Leng , Lingxiao Ren , Zhiqi Zhang , Lixia Chen , Hua Li
Twelve previously undescribed eudesmane-type sesquiterpenoids, named atractymacronoids A-L (1–12), together with eighteen known ones (13–30), were obtained from the rhizomes of Atractylodes macrocephala. Their structures and absolute configurations were determined by analysis of spectroscopic data, electronic circular dichroism (ECD), and X-ray diffraction analyses. Atractymacronoids A and B (1 and 2) were the first example of an unprecedented noreudesmane-type scaffold featuring a 6/5 fused-ring system. A pair of C-9 epimers, atractymacronoids J and K (10 and 11), were assigned via X-ray crystallographic analysis. Among the isolated compounds, 8α-methoxyepiasterolid (24) exhibited weak inhibition of LPS-induced NO production in RAW264.7 macrophage cells.
{"title":"Atractymacronoids A-L, sesquiterpenoids from the rhizomes of Atractylodes macrocephala and their anti-inflammatory activities","authors":"Yali Wang , Huadong Zhang , Yuxia Leng , Lingxiao Ren , Zhiqi Zhang , Lixia Chen , Hua Li","doi":"10.1016/j.phytochem.2025.114761","DOIUrl":"10.1016/j.phytochem.2025.114761","url":null,"abstract":"<div><div>Twelve previously undescribed eudesmane-type sesquiterpenoids, named atractymacronoids A-L (<strong>1</strong>–<strong>12</strong>), together with eighteen known ones (<strong>13</strong>–<strong>30</strong>), were obtained from the rhizomes of <em>Atractylodes macrocephala</em>. Their structures and absolute configurations were determined by analysis of spectroscopic data, electronic circular dichroism (ECD), and X-ray diffraction analyses. Atractymacronoids A and B (<strong>1</strong> and <strong>2</strong>) were the first example of an unprecedented noreudesmane-type scaffold featuring a 6/5 fused-ring system. A pair of C-9 epimers, atractymacronoids J and K (<strong>10</strong> and <strong>11</strong>), were assigned via X-ray crystallographic analysis. Among the isolated compounds, 8<em>α</em>-methoxyepiasterolid (<strong>24</strong>) exhibited weak inhibition of LPS-induced NO production in RAW264.7 macrophage cells.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"244 ","pages":"Article 114761"},"PeriodicalIF":3.4,"publicationDate":"2025-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842169","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}
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