Phytochemistry最新文献

Linaggrenoids A−I, structurally diverse lindenane sesquiterpenoids with anti-hepatic fibrosis effects from Lindera aggregata

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-11 DOI: 10.1016/j.phytochem.2025.114477

Wen-Xian Li , Lu Gan , Yi-Ling Liao , Yu-Wei Wu , Bai-Hui Zhang , De-an Guo , Wei Li

引用次数: 0

Clerochinoids A‒H, aromatic abietane diterpenoids with cytotoxic activity from the roots and stems of Clerodendrum chinense

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-10 DOI: 10.1016/j.phytochem.2025.114474

Jieting Chen , Zhilong Liu , Yuepei Huang , Yushi Huang , Lihua Peng , Weilin Qiao , Wei Li , De-an Guo

{"title":"Clerochinoids A‒H, aromatic abietane diterpenoids with cytotoxic activity from the roots and stems of Clerodendrum chinense","authors":"Jieting Chen , Zhilong Liu , Yuepei Huang , Yushi Huang , Lihua Peng , Weilin Qiao , Wei Li , De-an Guo","doi":"10.1016/j.phytochem.2025.114474","DOIUrl":"10.1016/j.phytochem.2025.114474","url":null,"abstract":"<div><div>Eight previously undescribed aromatic abietane diterpenoids, clerochinoids A−H (1–8), including seven 17(15 → 16)-abeo-abietanes (1–7) and one 17(15 → 16),18(4 → 3)-diabeo-abietane (8), along with 12 known analogues (9–20) were isolated from the roots and stems of Clerodendrum chinense. Their structures were elucidated by extensive spectroscopic data analysis, X-ray crystallography, and ECD calculations. All the compounds were screened for their cytotoxic activity against two human non-small cell lung cancer cell lines, H1975 and HCC827. Compounds 3, 9, 10, 12−14, 16, 17, 18, and 20 exhibited enhanced activity compared to the positive control, gefitinib. The succinct structure−activity relationship of these abietane diterpenoids was also discussed.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114474"},"PeriodicalIF":3.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143610517","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

Hyperhelianthemones A-D: Polycyclic polyprenylated benzoylphloroglucinols from Hypericum helianthemoides.

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-10 DOI: 10.1016/j.phytochem.2025.114473

Salar Hafez-Ghoran, Ioannis P Gerothanassis, Michael G Siskos, Seyed Abdulmajid Ayatollahi, Sammer Yousuf, Moslem Naderian, M Iqbal Choudhary, Anake Kijjoa

{"title":"Hyperhelianthemones A-D: Polycyclic polyprenylated benzoylphloroglucinols from Hypericum helianthemoides.","authors":"Salar Hafez-Ghoran, Ioannis P Gerothanassis, Michael G Siskos, Seyed Abdulmajid Ayatollahi, Sammer Yousuf, Moslem Naderian, M Iqbal Choudhary, Anake Kijjoa","doi":"10.1016/j.phytochem.2025.114473","DOIUrl":"https://doi.org/10.1016/j.phytochem.2025.114473","url":null,"abstract":"Phytochemical investigation of the n-hexane-soluble fraction of the aqueous ethanol extract of the aerial parts of Hypericum helianthemoides (Spach) Boiss. (Hypericaceae), furnished four undescribed polycylic polyprenylated benzoylphloroglucinols (PPBPs) 1-4, together with phytyl formate (5) and thirteen previously reported prenylated phloroglucinol derivatives, including yezo'otogirin C (6), hyperibrins A (7) and F (8), hyperibones G (9), J (10), La (11a)/Lb (11b), 7-epi-clusianone a (12a)/7-epi-clusianone b (12b), and hypermongones A (13), C (14), E (15), G (16), H (17), and sampsonione L (18). The structures of 1-4 were established by extensive 1D and 2D NMR spectral analysis as well as HREI-MS. The absolute configurations of the stereogenic carbons in 1 were established by X-ray crystallographic analysis, while the stereochemistry of 2 was assigned by quantum chemical calculation of its 1H and 13C NMR chemical shift values using DP4+ probability analysis. The isolated compounds were assayed for antileishmanial activity on Leishmania tropica and L. major parasites. Compounds 9 and 16 displayed activities against L. tropica, with IC50 values of 17.7 and 31.5 μM, respectively. Moreover, 9 was only active against L. major, with IC50 value of 34.2 μM.","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":" ","pages":"114473"},"PeriodicalIF":3.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143616755","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

Higginsianin F, one skeletal rearrangement diterpenoid α-pyridone with phytotoxic activity isolated from Colletotrichum higginsianum

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-10 DOI: 10.1016/j.phytochem.2025.114475

Kang Chen , Kainan Song , Xiaoyang Hao , Chen Wang , Liwen Zhang , Qun Yue , Linan Xie , Yuquan Xu

{"title":"Higginsianin F, one skeletal rearrangement diterpenoid α-pyridone with phytotoxic activity isolated from Colletotrichum higginsianum","authors":"Kang Chen , Kainan Song , Xiaoyang Hao , Chen Wang , Liwen Zhang , Qun Yue , Linan Xie , Yuquan Xu","doi":"10.1016/j.phytochem.2025.114475","DOIUrl":"10.1016/j.phytochem.2025.114475","url":null,"abstract":"<div><div>Higginsianin F (1), a previously undescribed diterpenoid α-pyridone skeleton featuring a unique N-hydroxyethyl-3-(5-acetyl-4-hydroxy)-α-pyridone ring, along with three undescribed diterpenoid pyrones, higginsianins G–I (2–4), were isolated from the mycelium of the phytopathogenic fungus Colletotrichum higginsianum. Their structures were elucidated through comprehensive analysis using NMR, HRESIMS, and ECD experiments. The absolute configuration of compound 2 was determined to be opposite to the other three compounds based on ECD experiments and the measured optical rotation value. A biosynthetic pathway for the N-hydroxyethyl-3-(5-acetyl-4-hydroxy)-α-pyridone ring in 1 was proposed, involving a key Friedel-Crafts acylation reaction. Compound 1 exhibited potential phytotoxic activity, inducing the formation of necrotic spots on Chenopodium album L. leaves at a concentration of 2 μg/μL, and inhibiting the germination of Amaranthus retroflexus L. seeds by 94.8 % at a concentration of 1000 μg/mL.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114475"},"PeriodicalIF":3.2,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143600796","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

Arnebinfuranoids A–G, seven unique heterodimers of meroterpenoids from Arnebia euchroma

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-05 DOI: 10.1016/j.phytochem.2025.114461

Ling-Hao Zhao, Hai-Wei Yan, Jian-Shuang Jiang, Xu Zhang, Ya-Nan Yang, Xiang Yuan, Pei-Cheng Zhang

引用次数: 0

Antiviral prenylated C6–C3 derivatives containing a methylenedioxyl group from the roots of Illicium brevistylum 从Illicium brevistylum根中提取的含有亚甲基二氧基的抗病毒前烯化C6-C3衍生物。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-03-04 DOI: 10.1016/j.phytochem.2025.114462

Jing-Yu Zhang , Qian-Ru Wang , Hui-Lin Yang , Rong-Mei Gao , Mi Li , Jia Yang , Yu-Huan Li , Li Li , Shuang-Gang Ma

{"title":"Antiviral prenylated C6–C3 derivatives containing a methylenedioxyl group from the roots of Illicium brevistylum","authors":"Jing-Yu Zhang , Qian-Ru Wang , Hui-Lin Yang , Rong-Mei Gao , Mi Li , Jia Yang , Yu-Huan Li , Li Li , Shuang-Gang Ma","doi":"10.1016/j.phytochem.2025.114462","DOIUrl":"10.1016/j.phytochem.2025.114462","url":null,"abstract":"<div><div>Five previously undescribed prenylated C6–C3 compounds (1–3 and 5–6) and four known prenylated C6–C3 compounds (4 and 7–9) were isolated from the roots of Illicium brevistylum A. C. Smith. Their structures were elucidated using extensive spectroscopic analyses, including HRESIMS, NMR (1H and 13C NMR, 1H–1H COSY, HSQC, HMBC and NOESY), and CD spectra, ECD calculations, and NOE difference experiments. The absolute configurations of 1–3 were further determined using the modified Mosher's method. All the isolates were evaluated for their antiviral activity against Coxsackievirus B3 and influenza virus A/Hanfang/359/95, their anti-inflammatory potential for nitric oxide generation in lipopolysaccharide-stimulated RAW264.7 and BV2 cells, and their cytotoxicity against the HGC27, T98G, HepG2, A549 and MCF-7 cell lines. Compounds 1–2, 5, and 7–8 exhibited moderate activity against CVB3, whereas all the isolates displayed weak anti-inflammatory effects and no significant cytotoxicity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114462"},"PeriodicalIF":3.2,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143573587","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

Exploring evolutionary use of single residue switches for alternative product outcome in class II diterpene cyclases 探索第二类二萜环化酶中单个残基开关对替代产物结果的进化作用

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-02-28 DOI: 10.1016/j.phytochem.2025.114459

Ahmed M.A.A. Raslan, Reuben J. Peters

{"title":"Exploring evolutionary use of single residue switches for alternative product outcome in class II diterpene cyclases","authors":"Ahmed M.A.A. Raslan, Reuben J. Peters","doi":"10.1016/j.phytochem.2025.114459","DOIUrl":"10.1016/j.phytochem.2025.114459","url":null,"abstract":"<div><div>Class II diterpene cyclases (DTCs) define the widespread labdane-related diterpenoids. These are particularly prevalent in plants due to the requisite production of gibberellin (GA) phytohormones, specifically from gene duplication and neofunctionalization of the relevant DTC. Alteration of product outcome can be predicted/engineered to some extent by changes in the ancestral histidine-asparagine catalytic base dyad found in the ent-copalyl pyrophosphate (ent-CPP) synthases (CPSs) involved in GA biosynthesis. It has been shown such changes can switch product outcome in CPSs, with substitution of alanine for either leading to incorporation of water – i.e., production of 8α-hydroxy-ent-labda-13-en-15-yl pyrophosphate (ent-LPP), while replacing the histidine with tyrosine leads to production of a rearranged product – i.e., ent-kolavenyl pyrophosphate (ent-KPP). Indeed, native ent-KPP synthases from dicots with such substitution have been found, and restoration of the ancestral residue results in production of ent-CPP. Observation of a similar ent-KPP synthase and, strikingly, an ent-LPP synthase with serine in place of the asparagine, along with another DTC with such substitution but still producing ent-CPP, was recently made in non-seed plants. Here the role of these substitutions was examined by ancestral residue restoration. Notably, while this led to the production of ent-CPP in the first two concordant cases, in the latter incongruent DTC this had little effect. This presumably reflects extended adaptation, consistent with its more distant phylogenetic relationship to those from GA biosynthesis. This demonstrates both the utility but also limitations of the ability of changes to the ancestral catalytic base dyad to affect product outcome.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114459"},"PeriodicalIF":3.2,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143529164","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

Crotoscheffleriolides, ent-clerodane diterpenoids from Kenyan Croton scheffleri

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-02-28 DOI: 10.1016/j.phytochem.2025.114460

Mona Diri , Moses K. Langat , Eduard Mas-Claret , Thomas A.K. Prescott , Cristina D. Cruz , Päivi Tammela , Sianne Schwikkard

{"title":"Crotoscheffleriolides, ent-clerodane diterpenoids from Kenyan Croton scheffleri","authors":"Mona Diri , Moses K. Langat , Eduard Mas-Claret , Thomas A.K. Prescott , Cristina D. Cruz , Päivi Tammela , Sianne Schwikkard","doi":"10.1016/j.phytochem.2025.114460","DOIUrl":"10.1016/j.phytochem.2025.114460","url":null,"abstract":"<div><div>Kenyan Croton scheffleri has yielded nineteen compounds. The stem bark gave six undescribed ent-clerodane diterpenoids (1–4, 6 and 7), three undescribed sesquiterpene lactones (9, 11 and 12) and four known compounds (5, 8, 10 and 13). From the leaves six known compounds were identified, ayanin (14), pheophytin a (15), ferulic acid (16), 1,3,4-trihydroxybenzene (17), sitosterol (18), and podosterol (19). The structures of the compounds were determined using spectroscopic and spectrometric methods, NMR, IR, UV, polarimetry, ECD, HRESIMS, and GC-MS. The undescribed compounds were assessed against HIV-1 Reverse Transcriptase and both gram-positive bacteria Staphylococcus aureus 29213 and Enterococcus faecalis 29212, as well as gram-negative bacteria Escherichia coli 25922 and Pseudomonas aeruginosa 27853. Compounds 1, 4, 5, 6, 7, 10, 12 and 19 increased the proliferation of serum starved dermal fibroblast cells at a concentration of 100 nM. All compounds inhibited human dermal fibroblast cell proliferation at 100 μM, while compounds 1, 4 and 19 inhibited fibroblast proliferation at 10 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114460"},"PeriodicalIF":3.2,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143537554","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Antitumor activity and mechanistic study of steroidal saponins from the rhizomes of Paris polyphylla var. yunnanensis

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-02-27 DOI: 10.1016/j.phytochem.2025.114455

Yu Zhang , Yu-Chen Fan , Yu-Chen Zhang , Qing Li , Yun-Yun Su , Chen-Sen Xu , Hao-Lin Yu , Chao Wang , Jing Zhang , Zhi-Xin Liao

{"title":"Antitumor activity and mechanistic study of steroidal saponins from the rhizomes of Paris polyphylla var. yunnanensis","authors":"Yu Zhang , Yu-Chen Fan , Yu-Chen Zhang , Qing Li , Yun-Yun Su , Chen-Sen Xu , Hao-Lin Yu , Chao Wang , Jing Zhang , Zhi-Xin Liao","doi":"10.1016/j.phytochem.2025.114455","DOIUrl":"10.1016/j.phytochem.2025.114455","url":null,"abstract":"<div><div>Through phytochemical analysis of the large roots of Paris polyphylla var. yunnanensis, three previously undescribed steroidal saponins (Polypharsis A-C, 1–3) and four known steroidal saponins (4–7) were isolated. The structures of 1–3 were elucidated by 1D/2D NMR, HR-ESI-MS, acid hydrolysis and ECD calculations. The cytotoxic activity tests of seven compounds against three tumor cell lines (HepG2, MCF-7, and A549) were conducted. Among them, compounds 6 and 7 belong to the protodioscin class of compounds. Compound 6 exhibits significant inhibition of HepG2 cell growth with an IC50 value of 7.53 ± 2.07 μM, comparable to that of Doxorubicin (6.82 ± 1.59 μM). Compound 7 shows a strong inhibitory effect on the growth of the MCF-7 cell line with an IC50 value of 0.69 ± 0.26 μM, which is more potent than Doxorubicin (5.56 ± 0.08 μM). Subsequently, the antitumor efficacy of compound 6 against HepG2 cells and compound 7 against MCF-7 cells was investigated through in vitro experiments, and their respective mechanisms of action were further predicted using network pharmacology and molecular docking.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114455"},"PeriodicalIF":3.2,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143531838","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

Structurally diverse abietane diterpenoids from the whole plants of Salvia przewalskii Maxim. With anti-inflammatory activity 从 Salvia przewalskii Maxim.具有抗炎活性

IF 3.2 2区生物学

Phytochemistry Pub Date : 2025-02-26 DOI: 10.1016/j.phytochem.2025.114456

Rui Guo , Cun-Lin Wang , Tong Zhang , Shuang Xu , Xin Qiao , Guo-Shun Zhang , Qiong Zhang

{"title":"Structurally diverse abietane diterpenoids from the whole plants of Salvia przewalskii Maxim. With anti-inflammatory activity","authors":"Rui Guo , Cun-Lin Wang , Tong Zhang , Shuang Xu , Xin Qiao , Guo-Shun Zhang , Qiong Zhang","doi":"10.1016/j.phytochem.2025.114456","DOIUrl":"10.1016/j.phytochem.2025.114456","url":null,"abstract":"<div><div>Using bioactivity guidance, eight previously undescribed abietane diterpenoids (1–8), were isolated from the whole plants of Salvia przewalskii Maxim. along with seven known analogues (9–15). Their structures were elucidated by extensive spectroscopic analyses, quantum chemical calculations, and single crystal X-ray diffraction. Among them, compound 1, an abietane diterpenoid bearing unique C-20 m-cymen-8-ol monoterpenoid moiety, was the first example of the adduct between a monocyclic monoterpenoid and an abietane diterpenoid connected by ester bond within the Salvia genus. The plausible biosynthetic pathways of 1–8 were proposed. All isolates were tested for their inhibitory activity towards the LPS-induced NO production in RAW 264.7 cells. Compounds 3, 5, 6 and 9 significantly inhibited nitric oxide (NO) production in RAW264.7 cells, which also could suppress the release of pro-inflammatory factors (TNF-α, IL-1β and IL-6). The key structure-activity relationships of these abietane-type diterpenes for anti-inflammatory effects have been summarized.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"235 ","pages":"Article 114456"},"PeriodicalIF":3.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143527323","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