Phytochemistry最新文献

{"title":"Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXXVI. Tsugaforrestiacids A–O: Structurally diverse C-18 carboxylated diterpenoids from the twigs and needles of the ‘vulnerable’ conifer Tsuga forrestii and their inhibitory effects on ATP-citrate lyase","authors":"Peng-Jun Zhou ,&nbsp;Ze-Yu Zhao ,&nbsp;Jin-Xin Zhu ,&nbsp;Yi Zang ,&nbsp;Menny M. Benjamin ,&nbsp;Juan Xiong ,&nbsp;Jia Li ,&nbsp;Jin-Feng Hu","doi":"10.1016/j.phytochem.2024.114221","DOIUrl":"10.1016/j.phytochem.2024.114221","url":null,"abstract":"<div><p>An extensive phytochemical investigation on the EtOAc-soluble fraction of the 90% MeOH extract from the twigs and needles of the ‘vulnerable’ Chinese endemic conifer <em>Tsuga forrestii</em> (Forrest's hemlock) led to the isolation and characterization of 50 structurally diverse diterpenoids, including 15 unreported C-18 carboxylated ones (tsugaforrestiacids A−O, <strong>1</strong>−<strong>15</strong>, resp.). Among them, compounds <strong>1</strong>−<strong>7</strong> are abieten-18-oic acids, compound <strong>8</strong> is an abieten-18-succinate, and compounds <strong>10</strong>−<strong>12</strong> are podocarpen-18-oic acids, whereas compounds <strong>13</strong>−<strong>15</strong> are pimarane-type, isopimarane-type, and totarane-type diterpenoid acids, respectively. Their structures and absolute configurations were determined by a combination of spectroscopic methods, GIAO NMR calculations and DP4+ probability analyses, electronic circular dichroism (ECD) data, and single crystal X-ray diffraction analyses. All the isolates were evaluated for their inhibitory activities against the ATP-citrate lyase (ACL), a key enzyme in cellular metabolism. Tsugaforrestiacids E (<strong>5</strong>) and H (<strong>8</strong>) were found to have significant inhibitory effects against ACL, with IC₅₀ values of 5.3 and 6.2 <em>μ</em>M, respectively. The interactions of the bioactive molecules with the ACL enzyme were examined by molecular docking studies. The isolated diterpenoids also provide chemotaxonomic evidence to support the delimitation of <em>Tsuga</em> from its closest sister group (<em>Nothotsuga</em>). The above findings highlight the importance of protecting plant species with unique and diverse secondary metabolites, which may be potential sources of new therapeutic agents for the treating ACL-associated diseases.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141604046","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}

{"title":"Sesquiterpene lactones from Tithonia diversifolia with ferroptosis-inducing activities","authors":"Ao-Xue Ding ,&nbsp;Yi-Ming Shan ,&nbsp;Chen-Yue Li ,&nbsp;Guo-Qing Qin ,&nbsp;Tong Chen ,&nbsp;Qing Wang ,&nbsp;Xiang-Gang Hu ,&nbsp;Peng-Ju Guo ,&nbsp;Hai-Jun Yu ,&nbsp;Wen-Qiong Wang ,&nbsp;Li-Jiang Xuan","doi":"10.1016/j.phytochem.2024.114219","DOIUrl":"10.1016/j.phytochem.2024.114219","url":null,"abstract":"<div><p>Eight previously undescribed sesquiterpene lactones (<strong>1</strong>–<strong>8</strong>), together with six known ones (<strong>9</strong>–<strong>14</strong>) were isolated from the aerial parts of <em>Tithonia diversifolia</em> (Hemsl.) A. Gray. The absolute configurations of these compounds were elucidated using HRMS, NMR spectroscopy, optical rotation measurements, X-ray crystallography, and ECD. Among them, sesquiterpene lactones <strong>2</strong>–<strong>4</strong> share a unique carbon skeleton with a rare C-3/C-4 ring-opened structure. Compounds <strong>1</strong> and <strong>8</strong> showed moderate inhibitory effects toward CT26 murine colon carcinoma cells by promoting lipid ROS production, highlighting their potential as ferroptosis inducers.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141601242","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}

{"title":"Anti-inflammatory and cytotoxicity nitrogenous merosesquiterpenoids from the sponge Pseudoceratina purpurea","authors":"","doi":"10.1016/j.phytochem.2024.114220","DOIUrl":"10.1016/j.phytochem.2024.114220","url":null,"abstract":"<div><p>Fourteen undescribed nitrogenous merosesquiterpenoids, purpurols A−D (<strong>1</strong>–<strong>4</strong>) and puraminones A−J (<strong>5</strong>–<strong>14</strong>), along with three known related compounds (<strong>15</strong>–<strong>17</strong>) were isolated from the sponge <em>Pseudoceratina purpurea</em> collected in the South China Sea. Their structures and absolute configurations were unambiguously elucidated by a combination of spectroscopic data, X-ray diffraction analysis, electronic circular dichroism calculations, and chemical derivatization. Purpurols A−D (<strong>1</strong>–<strong>4</strong>) incorporated nitrogenous heterocycles, compounds <strong>1</strong> and <strong>2</strong> feature an unusual benzothiazole ring, while <strong>3</strong> and <strong>4</strong> feature benzoxazole ring. Puraminones A−J (<strong>5</strong>–<strong>14</strong>) represent sesquiterpenoid aminoquinones with different amine and amino acid side chains at C-20. Additionally, twenty unreported sesquiterpenoid aminoquinone analogues were obtained through chemical derivatization. It is worth noting that all compounds are featured with unusual rearranged 4,9-friedodrimane subunit. In the bioassays, purpurols A and B showed weak anti-inflammation in zebrafish, as well as some compounds showed activities against tumor cells, therefore, preliminary structure–cytotoxicity relationships are also discussed.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141601262","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}

{"title":"Vitifolignans, 3,4-dibenzyltetrahydrofuran lignans from Anemone vitifolia Buch.-Ham","authors":"Ya Lu ,&nbsp;Xueyan Huang ,&nbsp;Donovon A. Adpressa ,&nbsp;Linyun Mou ,&nbsp;Peter R. Taylor ,&nbsp;Benjamin R. Clark","doi":"10.1016/j.phytochem.2024.114217","DOIUrl":"10.1016/j.phytochem.2024.114217","url":null,"abstract":"<div><p><em>Anemone vitifolia</em> is a small herb found in Asia that is used to treat a range of diseases in Chinese traditional medicine. GNPS-based molecular networking of an <em>Anemone vitifolia</em> specimen revealed the presence of a network containing numerous ions indicating the presence of lignans, several of which suggested that there might be previously undescribed compounds in the extract. Fractionation of the organic extract yielded five undescribed lignans, the vitifolignans, together with one known. The structures were identified based on extensive spectroscopic data analysis (NMR, HR-ESI-MS, and UV), coupling constant calculation and comparison with reported data. Their absolute configurations were determined by comparison of experimental ECD spectra with calculated spectra. Compounds <strong>4/5</strong> showed weak inhibition of LPS-induced NO production in mouse mononuclear macrophages.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555353","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}

{"title":"Benzoate glycosides from Gentiana scabra Bge. and their lipid-lowering activity","authors":"","doi":"10.1016/j.phytochem.2024.114209","DOIUrl":"10.1016/j.phytochem.2024.114209","url":null,"abstract":"<div><p>Seven undescribed benzoate glycosides (<strong>1−7</strong>) and five known ones (<strong>8−12</strong>) were isolated from the rhizomes of <em>Gentiana scabra</em> Bge. Their structures were characterized by comprehensive NMR and MS spectroscopic data analysis. The lipid-lowering effects of these compounds were evaluated by measuring the triglyceride (TG) contents and intracellular lipid droplets (LDs) in oleic acid (OA)-treated HepG2 cells. The results showed that compounds <strong>1</strong>, <strong>5</strong>, <strong>7</strong>, and <strong>11</strong> significantly reduced the TG content at 20 μM, and the Bodipy staining displayed that OA enhanced the levels of LDs in the cell, while these compounds reversed the lipid accumulation caused by OA. These findings provide a basis for further development and utilization of <em>G</em>. <em>scabra</em> as a natural source of potential lipid-lowering agents.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555348","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}

{"title":"Lappanolides A−N, fourteen undescribed sesquiterpenoids from Saussurea costus (Syn. Saussurea lappa) and their anti HBV activity","authors":"Hong-Bo Li ,&nbsp;Shi-Qun Bai ,&nbsp;Teng-Yun Shu,&nbsp;Qiong Wang,&nbsp;Hao Chen,&nbsp;Li-Hua Su,&nbsp;Min Xu","doi":"10.1016/j.phytochem.2024.114207","DOIUrl":"10.1016/j.phytochem.2024.114207","url":null,"abstract":"<div><p>Lappanolides A−N (<strong>1</strong>–<strong>14</strong>), 14 undescribed sesquiterpenoids, along with 23 known ones (<strong>15</strong>–<strong>37</strong>), were isolated from the roots of <em>Saussurea costus</em>, which were primarily categorized into eudesmane, guaiane, and germacrane types. Lappanolide A (<strong>1</strong>) possessed an unprecedented pseudo-disesquiterpenoids. Their structures and absolute configurations were established using physical data analyses (HRESIMS, IR, 1D and 2D NMR) and ECD calculations. All isolated compounds were tested for anti-hepatitis B virus (anti-HBV) activity. Ten compounds (<strong>1</strong>, <strong>9</strong>, <strong>11</strong>, <strong>12</strong>, <strong>19</strong>, <strong>22</strong>, <strong>28</strong>, <strong>29</strong>, <strong>31</strong>, and <strong>36</strong>) exhibited activities against HBsAg secretions as determined by ELISA assay, with IC₅₀ values ranging from 5.2 to 45.7 μM. In particular, compounds <strong>28</strong> and <strong>29</strong> showed inhibition of HBsAg secretion with IC₅₀ values of 5.28 and 5.30 μM, and CC₅₀ values of 9.85 and 6.37 μM, respectively, though they all exhibited low selectivity. Several compounds displayed cytotoxicity in the MTT assay. Among them, compound <strong>28</strong> was the most notable and was chosen for further study using flow cytometry. The result showed that it significantly induced HepG2 cell arrest in the S phase and induced apoptosis.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555350","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}

{"title":"Unusual cadinane-involved sesquiterpenoid dimers from Artemisia annua and their antihepatoma effect","authors":"Xiao-Feng He ,&nbsp;Tian-Ze Li ,&nbsp;Yun-Bao Ma ,&nbsp;Meng-Fei Wang ,&nbsp;Ji-Jun Chen","doi":"10.1016/j.phytochem.2024.114216","DOIUrl":"10.1016/j.phytochem.2024.114216","url":null,"abstract":"<div><p><em>Artemisia annua</em> L. (“Qinghao” in Chinese) is a famous traditional Chinese medicinal herb and has been used to treat malaria and various tumors. Our preliminary screening indicated that the EtOAc extract of <em>A. annua</em> manifested activity against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 53.2%, 52.1%, and 59.6% at 200 μg/mL, respectively. Bioassay-guided isolation of <em>A. annua</em> afforded 14 unusual cadinane-involved sesquiterpenoid dimers, artemannuins A‒N (<strong>1</strong>–<strong>14</strong>), of which the structures were elucidated by extensive spectral analyses, ECD calculations, and single-crystal X-ray diffraction. Structurally, these compounds were classified into five different types based on the coupled modes of two monomeric sesquiterpenoids. Among them, compounds <strong>1</strong>–<strong>9</strong> represented the first examples of sesquiterpenoid dimers formed <em>via</em> the C-3‒C-3′ single bond of two 5(4 → 3)-<em>abeo</em>-cadinane sesquiterpenoid monomers, while compounds <strong>13</strong> and <strong>14</strong> were dimers fused by cadinane and humulane sesquiterpenoids <em>via</em> an ester bond. Methylated derivatives of <strong>1</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>8</strong> showed antihepatoma activity against HepG2, Huh7, and SK-Hep-1 cell lines with IC₅₀ values ranging from 30.5 to 57.2 μM.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555352","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}

{"title":"Structurally diverse diterpenoids from the leaves of Croton mangelong and their anti-diabetic activity","authors":"Zhi-Yong Jiang ,&nbsp;Qi Niu ,&nbsp;Hao-Xin Wang ,&nbsp;Hao-Nan Xu ,&nbsp;Hong-Xi Xie ,&nbsp;Lin Chen ,&nbsp;Rong Chen ,&nbsp;Hong-Lei Zhang ,&nbsp;Lu Gao ,&nbsp;Ai-Xue Zuo ,&nbsp;Hong-Ping He","doi":"10.1016/j.phytochem.2024.114206","DOIUrl":"10.1016/j.phytochem.2024.114206","url":null,"abstract":"<div><p>Eighteen compounds including eleven previously undescribed diterpenes were isolated from the leaves of <em>Croton mangelong</em>. The structures were determined by HRESIMS, IR, NMR, X-ray diffraction and ECD spectroscopic analysis. All isolates were assayed for their anti-hyperglycemic activities in insulin resistance (IR) 3T3-L1 adipocytes, and compound <strong>4</strong> was tested for its anti-diabetic activity <em>in vivo</em>. Results suggested compound <strong>4</strong> could effectively reduce blood glucose level in diabetic SD rats in a dose of 30 mg/kg.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555351","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}

{"title":"Identification of lignans as selective cyclooxygenase-2 inhibitors from the extract of Acanthopanacis cortex","authors":"Hao-Dong Yang ,&nbsp;Yuan-Gui Yang ,&nbsp;Zhi-Shu Tang ,&nbsp;Kang Ma ,&nbsp;Hong-Bo Xu","doi":"10.1016/j.phytochem.2024.114208","DOIUrl":"10.1016/j.phytochem.2024.114208","url":null,"abstract":"<div><p><em>Acanthopanacis</em> cortex (the dried root bark of <em>Acanthopanax gracilistylus</em> W. W. Smith) has been used for the treatment of rheumatic diseases in China for over 2000 years. Four previously undescribed lignans (<strong>1</strong>–<strong>4</strong>) and 12 known lignans (<strong>5</strong>–<strong>16</strong>) were isolated from <em>Acanthopanacis</em> cortex. In this study, the inhibitory activities of compounds <strong>1</strong>–<strong>16</strong> against neutrophil elastase (NE), cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) are reported. The results show that compounds <strong>1</strong>–<strong>16</strong> exhibit weak inhibitory activities against NE and COX-1. However, compounds <strong>2</strong>, <strong>6</strong>–<strong>8</strong> and <strong>13</strong>–<strong>16</strong> demonstrate better COX-2 inhibitory effects with IC₅₀ values from 0.75 to 8.17 <em>μ</em>Μ. These findings provide useful information for the search for natural selective COX-2 inhibitors.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141555349","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}

{"title":"Chemical constituents from the roots of Cynanchum wilfordii with PCSK9 secretion inhibitory activities","authors":"Son Min-Gyung ,&nbsp;Pisey Pel ,&nbsp;Chae-Yeong An ,&nbsp;Chan-Woong Park ,&nbsp;Sae Hyun Lee ,&nbsp;Tae-Jin Yang ,&nbsp;Young-Won Chin","doi":"10.1016/j.phytochem.2024.114205","DOIUrl":"10.1016/j.phytochem.2024.114205","url":null,"abstract":"<div><p>From the <em>Cynanchum wilfordii</em> roots, 32 compounds, including 5 previously undescribed (<strong>1</strong>, <strong>4-6</strong>, <strong>12</strong>) and 27 known (<strong>2</strong>, <strong>3</strong>, <strong>7-11</strong>, <strong>13-32</strong>) compounds, were isolated, and their structures were elucidated using NMR spectroscopic data and MS data aided by ECD calculations or the modified Mosher’s reaction. All isolates were tested for their inhibitory effects on proprotein convertase subtilisin/kexin type 9 (PCSK9) secretion. Among the isolates, compound <strong>4</strong>, a methyl cholesterol analog, exhibited the most potent effect in reducing PCSK9 secretion, along with PCSK9 downregulation at the mRNA and protein levels via FOXO1/3 upregulation. Moreover, compound <strong>4</strong> attenuated statin-induced PCSK9 expression and enhanced the uptake of DiI-LDL low-density lipoprotein. Thus, compound <strong>4</strong> is suggested to be a potential candidate for controlling cholesterol levels.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141545161","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}