Phytochemistry最新文献_第2页

Bioactive specialized metabolites of Trochila sp., an endophytic fungus of Lilium carniolicum 百合内生真菌Trochila sp.的生物活性特化代谢产物。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-24 DOI: 10.1016/j.phytochem.2025.114684

Mostafa Alilou , Yun Liu , Magdalena Steixner , Isidor Happacher , Sigrid Beate Abt , Ursula Fürnkranz , Fabio Gsaller , Ursula Peintner , Hubertus Haas

{"title":"Bioactive specialized metabolites of Trochila sp., an endophytic fungus of Lilium carniolicum","authors":"Mostafa Alilou , Yun Liu , Magdalena Steixner , Isidor Happacher , Sigrid Beate Abt , Ursula Fürnkranz , Fabio Gsaller , Ursula Peintner , Hubertus Haas","doi":"10.1016/j.phytochem.2025.114684","DOIUrl":"10.1016/j.phytochem.2025.114684","url":null,"abstract":"<div><div>Bioprospecting of a rice culture of Trochila sp. BGP15P7IS3, an undescribed endophytic fungus from Lilium carniolicum, resulted in isolation and identification of eleven specialized metabolites, of which four pyridone alkaloid derivatives (1, 2, 4, and 5) and a biphenyl derivative (8) were identified as previously undescribed natural products. Moreover, two dibenzofuran derivatives, isousnic acid and usnic acid (9 and 10) with S absolute configuration were reported for the first time from an endophytic fungus. Additionally, the absolute stereochemistry of the previously described compound 7 was determined. The structure of the compounds isolated was established by means of HR-ESI-MS, 1- and 2D NMR, and ECD calculations, as well as utilizing previously published data. All isolates available in sufficient quantities were evaluated for their antimicrobial activity against a plant pathogen, Botrytis cinerea, and four human pathogens, Aspergillus fumigatus, Aspergillus flavus, Candida albicans, and Cryptococcus neoformans, as well as a human sextually transmitted parasite, Trichomonas vaginalis. Compound 3 displayed antifungal activity only against C. neoformans with an MIC value of 12.5 μg/mL, and compound 6 exhibited promising antifungal activity with MIC values of 0.39–3.25 μg/mL against all the aforementioned fungal pathogens, and a concentration-dependent growth inhibitory property against T. vaginalis. Based on the identification of derivatives, a revised biosynthetic pathway for pyridone-type alkaloids was proposed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114684"},"PeriodicalIF":3.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145177481","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

Highly oxidized germacrane-type sesquiterpenoid dimers from Elephantopus tomentosus L.: Structural characterization, DFT calculation and anti-hepatoma potential 毛毛象高氧化型倍半萜类二聚体：结构表征、DFT计算和抗肝癌潜能

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-24 DOI: 10.1016/j.phytochem.2025.114686

Zi-Hao Ge , Si-Hui Mi , Wen-Long Kou , Guo-Dong Yao , Bin Lin , Jian Wang , Ming Bai , Xiao-Xiao Huang , Shao-Jiang Song

{"title":"Highly oxidized germacrane-type sesquiterpenoid dimers from Elephantopus tomentosus L.: Structural characterization, DFT calculation and anti-hepatoma potential","authors":"Zi-Hao Ge , Si-Hui Mi , Wen-Long Kou , Guo-Dong Yao , Bin Lin , Jian Wang , Ming Bai , Xiao-Xiao Huang , Shao-Jiang Song","doi":"10.1016/j.phytochem.2025.114686","DOIUrl":"10.1016/j.phytochem.2025.114686","url":null,"abstract":"<div><div>Four previously undescribed highly oxidized germacrane-type sesquiterpenoid dimers were isolated from Elephantopus tomentosus. Their planar structures and absolute configurations were unequivocally elucidated through comprehensive spectroscopic analysis, combined with experimental electronic circular dichroism (ECD) and time-dependent density functional theory (TDDFT) calculations. These dimers, characterized by an O-ether linkage, represent the first reported examples of such derivatives from the genus Elephantopus. The structural validity was verified by performing Hartree-Fock energy calculations within the quantum mechanical (QM) framework. All isolated sesquiterpenoid dimers exhibited moderate inhibitory activity against human hepatocellular carcinoma cell lines (HepG2 and Hep3B). Notably, compound 4 demonstrated the most significant cytotoxicity, with IC50 values of 1.64 μM (HepG2) and 4.85 μM (Hep3B). Furthermore, compound 4 markedly reduced mitochondrial membrane potential (MMP), indicating its role in inducing apoptosis via mitochondrial dysfunction. Network pharmacology and molecular docking further indicated that compound 4 could interact with HSP90AA1 by binding to key amino acid residues, potentially explaining its pharmacological activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114686"},"PeriodicalIF":3.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145158445","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

Wine-red lignin revisited, dirigent proteins, and native lignin macromolecular configuration 酒红木质素重访，直接蛋白，和天然木质素大分子结构。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-20 DOI: 10.1016/j.phytochem.2025.114683

Dhrubojyoti D. Laskar , Michaël Jourdes , Gregory L. Helms , Qingyan Meng , Nancy A. Somerville , John R. Cort , Laurence B. Davin , Norman G. Lewis

{"title":"Wine-red lignin revisited, dirigent proteins, and native lignin macromolecular configuration","authors":"Dhrubojyoti D. Laskar , Michaël Jourdes , Gregory L. Helms , Qingyan Meng , Nancy A. Somerville , John R. Cort , Laurence B. Davin , Norman G. Lewis","doi":"10.1016/j.phytochem.2025.114683","DOIUrl":"10.1016/j.phytochem.2025.114683","url":null,"abstract":"<div><div>The wine-red coloration of xylem in antisense cinnamyl alcohol dehydrogenase (CAD) down-regulated tobacco (Nicotiana tabacum) has long been reported as due to wine-red colored lignin. To investigate validity of the wine-red lignin report, both wild type (WT) and anti-sense CAD down-regulated tobacco stem xylem tissues were examined, with the red pigment found to be facilely removed by treatment with an 0.5 % HCl in MeOH solution at 4 °C. The red pigment in the xylem tissues was rapidly reconstituted in both pre-treated antisense CAD and WT xylem tissues by incubation with sinapyl aldehyde in MeOH solution, and then facilely removed by subsequent 0.5 % HCl in MeOH treatment. Only sinapyl aldehyde was demonstrated as contributing to the red pigmentation, this being consistent with its anionic quinone methide canonical form. No evidence was obtained for a wine-red lignin. Additionally, lignin-derived isolates from both antisense CAD and WT lines essentially differed only in presence of small amounts (ca. 1.41 %) of 8–O–4′ linked sinapyl aldehyde end groups and a slightly smaller molecular weight distribution (MWD) of the lignin from the antisense CAD line. No evidence was obtained that poly-hydroxycinnamyl aldehydes contributed to bulk lignification; the slightly lower MWD may result from hydroxycinnamyl aldehydes functioning as terminators of polymerization during lignification. More importantly, these findings are placed in context of what is now known about 1) lignin macromolecular assembly proper in planta, 2) dirigent protein functions, 3D structures, and active sites as entry points to distinct plant phenol metabolic classes, including lignins, 3) AlphaFold2 modeling of Dir-e subfamily proteins involved in lignification, and 4) what urgently remains to be done in the study of lignification.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"242 ","pages":"Article 114683"},"PeriodicalIF":3.4,"publicationDate":"2025-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145113907","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

Clavatol derivatives from the endophytic fungus Penicillium commune XL-0473 Clavatol源自内生真菌青霉菌公社XL-0473。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-16 DOI: 10.1016/j.phytochem.2025.114679

Liangxiu Liao , Tao Zhu , Shan Ran , Yizhou Bian , Ming Yao , Qingpei Liu , Wenjing Wang , Xiaolong Yang

{"title":"Clavatol derivatives from the endophytic fungus Penicillium commune XL-0473","authors":"Liangxiu Liao , Tao Zhu , Shan Ran , Yizhou Bian , Ming Yao , Qingpei Liu , Wenjing Wang , Xiaolong Yang","doi":"10.1016/j.phytochem.2025.114679","DOIUrl":"10.1016/j.phytochem.2025.114679","url":null,"abstract":"<div><div>Thirteen previously undescribed clavatol derivatives (1, 2, 3a, 3b, and 4−12), along with thirteen known compounds were isolated from the endophytic fungus Penicillium commune XL-0473. Their structures were established through comprehensive spectroscopic analyses, quantum chemical electronic circular dichroism calculations, single-crystal X-ray diffraction, and chemical synthesis experiment. Notably, compounds 1 and 2 represent the first reported clavatol dimers conjugated with amino acids. Compounds 8–11 are unprecedented derivatives containing a 1,6-dioxaspiro[4.4]nonane framework. Compound 16 demonstrated potent antibacterial activity against multidrug-resistant pathogens, with MIC values ranging from 3.13 to 6.25 μg/mL. A plausible nonenzymatic self-assembly mechanism involving ortho-quinone methide intermediates was proposed to explain their biosynthesis pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114679"},"PeriodicalIF":3.4,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145086781","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

Eleven previously undescribed sesquiterpenoids with anti-inflammatory activity isolated from the cultures of basidiomycete Marasmiellus candidus 11个先前描述的具有抗炎活性的倍半萜类化合物从担子菌中分离出来。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-16 DOI: 10.1016/j.phytochem.2025.114678

Lan Yao , Shiyu Li , Jinxiu Zhang , Zhuang Li , Jianhua Lv

引用次数: 0

Nor-halimane and spiro-labdane diterpenoids with anti-inflammatory activity from Leucas ciliata Benth 毛缕木中具有抗炎活性的非halimane和spirolabdane二萜。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-16 DOI: 10.1016/j.phytochem.2025.114681

Jia-Cai Kuang , Fu-Ling Cen , Xuan Zhang , Xu-Hua Nong , Xue-Ming Zhou , Xiao-Bao Li , Zhang-Xin Yu , Guang-Ying Chen

{"title":"Nor-halimane and spiro-labdane diterpenoids with anti-inflammatory activity from Leucas ciliata Benth","authors":"Jia-Cai Kuang , Fu-Ling Cen , Xuan Zhang , Xu-Hua Nong , Xue-Ming Zhou , Xiao-Bao Li , Zhang-Xin Yu , Guang-Ying Chen","doi":"10.1016/j.phytochem.2025.114681","DOIUrl":"10.1016/j.phytochem.2025.114681","url":null,"abstract":"<div><div>Eleven previously undescribed diterpenoids, cilileucapenoids A–K (1–10 and 12), comprising two halimane diterpenoids (1 and 12) and nine spiro-labdane diterpenoids (2–10), along with one known analogue (11), were isolated from the whole plant of Leucas ciliata. The structures and absolute configurations were determined through the analysis of their HR-ESI-MS, 1D/2D NMR, electronic circular dichroism (ECD) calculations, Mosher's esterification, and single-crystal X-ray diffraction. Notably, 1 represents the first reported aromatic halimane diterpenoid, while 2 features as a rare dispiro-tetrahydrofuran-labdane skeleton. Compounds 3–10 uniformly incorporate a spiro-tetrahydrofuran moiety. In bioactivity assessments, compounds 1, 3, 4, and 7 demonstrated significant anti-inflammatory effects by inhibiting nitric oxide (NO) production in LPS-stimulated RAW264.7 macrophages, with IC50 values ranging from 9.13 to 25.94 μM. Structure-activity relationship (SAR) analysis further established that the Z-configuration of these diterpenoids confers markedly enhanced anti-inflammatory efficacy relative to the E-configuration.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114681"},"PeriodicalIF":3.4,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145086840","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

Nigraenes A-E: Racemic stilbene dimers from Morus nigra exhibiting stereospecific suppression of diabetic kidney disease 黑檀烯A-E：黑檀的外消旋二苯乙烯二聚体对糖尿病肾病具有立体特异性抑制作用。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-16 DOI: 10.1016/j.phytochem.2025.114682

Liping Shen, Chunyue Huang, Tianhong Chen, Yugang Wu, Xudong Mao, Xiao Hu

引用次数: 0

Peniterretonins A-D, terretonin-type meroterpenoids from the marine-derived fungus Penicillium simplicissimum 戊萜素A-D，从海洋真菌单纯青霉中提取的戊萜素型戊萜类。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-16 DOI: 10.1016/j.phytochem.2025.114680

Yanan Yang , Xiao Han , Peiling Cai , Congcong Zhao , Anran Fu , Kun Liu , Xuli Tang , Guoqiang Li

引用次数: 0

Acroeremophilanes A–I, eremophilane-type sesquiterpenoids from the Sinomenium acutum-derived symbiotic fungus Acrocalymma cycadis 从青藤衍生的共生真菌Acrocalymma cycadis中提取的嗜酸根烷A-I，嗜酸根烷型倍半萜类化合物。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-15 DOI: 10.1016/j.phytochem.2025.114677

Li-Bin Lin , Xue Cao , Wei Shi , Dan Shen , Mei-Niu Wang , Jing-Yu Wang , Jia-Hao Ning , Jia-Yao Hu , Dong-Zhu Duan , Xiao-Ling Wang , Jian Xiao

{"title":"Acroeremophilanes A–I, eremophilane-type sesquiterpenoids from the Sinomenium acutum-derived symbiotic fungus Acrocalymma cycadis","authors":"Li-Bin Lin , Xue Cao , Wei Shi , Dan Shen , Mei-Niu Wang , Jing-Yu Wang , Jia-Hao Ning , Jia-Yao Hu , Dong-Zhu Duan , Xiao-Ling Wang , Jian Xiao","doi":"10.1016/j.phytochem.2025.114677","DOIUrl":"10.1016/j.phytochem.2025.114677","url":null,"abstract":"<div><div>This study separated nine previously undescribed highly oxygenated eremophilane sesquiterpenoids, designated as acroeremophilanes A–I (1–9), as well as three identified analogs (10–12), in the symbiotic fungus Acrocalymma cycadis derived from Sinomenium acutum. Structural elucidation of the metabolites was achieved using 1D and 2D NMR; HR-ESI-TOF-MS; single-crystal X-ray diffraction; and ECD spectra calculations. Notably, acroeremophilane A (1) was identified as an unusual chlorinated nor-eremophilane sesquiterpenoid incorporating an α,β-unsaturated ketone unit with an enol fragment. Acroeremophilanes F–H (6–8) were characterized as rare glycosylated eremophilane sesquiterpenoids derived from the symbiotic fungus. The in vitro cytotoxicities showed that C-1 substituted chlorinated eremophilane sesquiterpenoids displayed obvious cytotoxicity, in which acroeremophilane C (3) exhibited potent cytotoxicity to HeLa and A549 cells, and IC50 values were 2.89 and 4.55 μM, separately. The results of the apoptosis assays indicated that compound 3 primarily induces apoptotic cell death.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114677"},"PeriodicalIF":3.4,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145081354","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

Immunomodulatory activity of isolated phenanthrene and dihydrophenanthrene derivatives (coelotrinins A-L) from Coelogyne trinervis 从黄芩中分离的菲和二氢菲衍生物（黄芩苷A-L）的免疫调节活性。

IF 3.4 2区生物学

Phytochemistry Pub Date : 2025-09-14 DOI: 10.1016/j.phytochem.2025.114676

Chattarika Pengdee , Adeline Dehlinger , May Thazin Thant , Al Arofatus Naini , Sofa Fajriah , Yanyong Punpreuk , Wanwimon Mekboonsonglarp , Virunh Kongkatitham , Siriporn Jungsuttiwong , Chatchai Chaotham , Chotima Böttcher , Boonchoo Sritularak

{"title":"Immunomodulatory activity of isolated phenanthrene and dihydrophenanthrene derivatives (coelotrinins A-L) from Coelogyne trinervis","authors":"Chattarika Pengdee , Adeline Dehlinger , May Thazin Thant , Al Arofatus Naini , Sofa Fajriah , Yanyong Punpreuk , Wanwimon Mekboonsonglarp , Virunh Kongkatitham , Siriporn Jungsuttiwong , Chatchai Chaotham , Chotima Böttcher , Boonchoo Sritularak","doi":"10.1016/j.phytochem.2025.114676","DOIUrl":"10.1016/j.phytochem.2025.114676","url":null,"abstract":"<div><div>Twelve previously undescribed compounds, named coelotrinins A-L (1–12), comprising eight dihydrophenanthrene derivatives (1, 4–5, and 7–11), two phenanthrene derivatives (2–3), and two phenanthrene-dihydrophenanthrene derivatives (6 and 12), along with twenty-one known compounds (13–33), were isolated from the pseudobulbs of Coelogyne trinervis. The structures were elucidated via spectroscopic data analysis, and their configurations were determined by optical rotation values and by comparing experimental and calculated electronic circular dichroism curves. Among these compounds, four compounds (1, 16, 23, and 24) showed immunomodulatory effects by inhibiting LPS-induced TNF-α production in THP-1 monocytes. Only coelotrinin A (1) exhibited an immunomodulatory effect with suppression on human peripheral blood mononuclear cells isolated from patients with multiple sclerosis.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114676"},"PeriodicalIF":3.4,"publicationDate":"2025-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145075980","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