Pub Date : 2024-12-16DOI: 10.1016/j.phytochem.2024.114362
Hongcun Liu , Fandong Kong , Zhenxin Zhu , Yue Lu , Jie Weng , Lifang Yang , Mingguo Jiang
Nine previously undescribed azulenoid-type sesquiterpenoids, including four common (1-4), four 5/6-cleaved (5–8), and one rearranged (9), were isolated from the edible-medicinal fungi Irpex lacteus. The structures of the compounds were established by combining spectroscopic methods, including integrated NMR, MS, and UV, as well as quantum 13C NMR and ECD calculations. All compounds exhibited a meaningful reduction in triglycerides activity. Notably, compounds 3, 5, and 6 displayed significant hypolipidemic activity, with EC50 values of 43.8, 37.9, and 39.7 μmol/L, respectively. These values are comparable to the positive control, lovastatin, which exhibited an EC50 of 37.6 μmol/L.
{"title":"Hypolipidemic sesquiterpenoids with diverse structural skeletons from the medicinal fungus Irpex lacteus","authors":"Hongcun Liu , Fandong Kong , Zhenxin Zhu , Yue Lu , Jie Weng , Lifang Yang , Mingguo Jiang","doi":"10.1016/j.phytochem.2024.114362","DOIUrl":"10.1016/j.phytochem.2024.114362","url":null,"abstract":"<div><div>Nine previously undescribed azulenoid-type sesquiterpenoids, including four common (<strong>1-4</strong>), four 5/6-cleaved (<strong>5–8</strong>), and one rearranged (<strong>9</strong>), were isolated from the edible-medicinal fungi <em>Irpex lacteus</em>. The structures of the compounds were established by combining spectroscopic methods, including integrated NMR, MS, and UV, as well as quantum <sup>13</sup>C NMR and ECD calculations. All compounds exhibited a meaningful reduction in triglycerides activity. Notably, compounds <strong>3</strong>, <strong>5</strong>, and <strong>6</strong> displayed significant hypolipidemic activity, with EC<sub>50</sub> values of 43.8, 37.9, and 39.7 μmol/L, respectively. These values are comparable to the positive control, lovastatin, which exhibited an EC<sub>50</sub> of 37.6 μmol/L.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114362"},"PeriodicalIF":3.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142854552","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 : 2024-12-16DOI: 10.1016/j.phytochem.2024.114353
Lijia Chen , Juan Zou , Bingying Jiang , Peiran Li , Yiming Li , Liang Zhao , Fujiang Guo
Fourteen undescribed sesquiterpenes, named curcumaones A-N (1–14), as well as forty-four (15–58) known ones, were isolated from the secondary rhizomes of Curcuma wenyujin. The structures and absolute configurations of 1–14 were elucidated based on NMR spectroscopic analyses, high resolution electrospray ionization mass spectroscopy (HRESIMS) data and electronic circular dichroism (ECD) spectral analysis. Among these, five sesquiterpenes with the peroxide linkage (1–5) were obtained and the change of chemical shift between the α-C connecting the peroxide linkage and the oxygen atom has been discussed. In addition, all the isolated compounds were evaluated for their agonistic effect on farnesoid X receptors (FXR) situated with human embryonic kidney (HEK) 293T cells and the results showed that compounds 12 and 14 exhibited a significant agonistic effect dose-dependently at 20, 50 and 100 μM, while 8, 32, 17 and 34 possessed moderate to weak agonistic effects.
{"title":"Curcumaones A-N, sesquiterpenes from the secondary rhizomes of Curcuma wenyujin","authors":"Lijia Chen , Juan Zou , Bingying Jiang , Peiran Li , Yiming Li , Liang Zhao , Fujiang Guo","doi":"10.1016/j.phytochem.2024.114353","DOIUrl":"10.1016/j.phytochem.2024.114353","url":null,"abstract":"<div><div>Fourteen undescribed sesquiterpenes, named curcumaones A-N (<strong>1</strong>–<strong>14</strong>), as well as forty-four (<strong>15</strong>–<strong>58</strong>) known ones, were isolated from the secondary rhizomes of <em>Curcuma wenyujin</em>. The structures and absolute configurations of <strong>1</strong>–<strong>14</strong> were elucidated based on NMR spectroscopic analyses, high resolution electrospray ionization mass spectroscopy (HRESIMS) data and electronic circular dichroism (ECD) spectral analysis. Among these, five sesquiterpenes with the peroxide linkage (<strong>1</strong>–<strong>5</strong>) were obtained and the change of chemical shift between the <em>α</em>-C connecting the peroxide linkage and the oxygen atom has been discussed. In addition, all the isolated compounds were evaluated for their agonistic effect on farnesoid X receptors (FXR) situated with human embryonic kidney (HEK) 293T cells and the results showed that compounds <strong>12</strong> and <strong>14</strong> exhibited a significant agonistic effect dose-dependently at 20, 50 and 100 μM, while <strong>8</strong>, <strong>32</strong>, <strong>17</strong> and <strong>34</strong> possessed moderate to weak agonistic effects.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114353"},"PeriodicalIF":3.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142822434","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 : 2024-12-16DOI: 10.1016/j.phytochem.2024.114366
Kouharu Otsuki , Chihiro Hosoya , Riko Takamiya , Mayu Kimura , Takashi Kikuchi , Li Huang , Chin-Ho Chen , Wei Li
The plants of the genus Daphne (Thymelaeaceae) are known to be sources of anti-HIV diterpenoids. Therefore, the present study focused on investigating the anti-HIV diterpenoids in Daphne pseudomezereum, for which the isolation of diterpenoids has not been previously reported. The results showed that three previously undescribed daphnane diterpenoids, onishibarins A–C (1–3), along with seven known compounds (4–10) were isolated from the fruits of Daphne pseudomezereum. Their structures were established by comprehensive analysis of physicochemical and spectroscopic data. Evaluation of the anti-HIV activity and cytotoxicity of the isolated compounds showed that compounds 1, 9, and 10 exhibited potent anti-HIV activity at EC50 = 1.26, 0.84, and 0.78 nM, respectively, with cytotoxicity at IC50 > 5 μM.
{"title":"Anti-HIV diterpenoids from Daphne pseudomezereum","authors":"Kouharu Otsuki , Chihiro Hosoya , Riko Takamiya , Mayu Kimura , Takashi Kikuchi , Li Huang , Chin-Ho Chen , Wei Li","doi":"10.1016/j.phytochem.2024.114366","DOIUrl":"10.1016/j.phytochem.2024.114366","url":null,"abstract":"<div><div>The plants of the genus <em>Daphne</em> (Thymelaeaceae) are known to be sources of anti-HIV diterpenoids. Therefore, the present study focused on investigating the anti-HIV diterpenoids in <em>Daphne pseudomezereum</em>, for which the isolation of diterpenoids has not been previously reported. The results showed that three previously undescribed daphnane diterpenoids, onishibarins A–C (<strong>1</strong>–<strong>3</strong>), along with seven known compounds (<strong>4</strong>–<strong>10</strong>) were isolated from the fruits of <em>Daphne pseudomezereum</em>. Their structures were established by comprehensive analysis of physicochemical and spectroscopic data. Evaluation of the anti-HIV activity and cytotoxicity of the isolated compounds showed that compounds <strong>1</strong>, <strong>9</strong>, and <strong>10</strong> exhibited potent anti-HIV activity at EC<sub>50</sub> = 1.26, 0.84, and 0.78 nM, respectively, with cytotoxicity at IC<sub>50</sub> > 5 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114366"},"PeriodicalIF":3.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142855105","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 : 2024-12-16DOI: 10.1016/j.phytochem.2024.114363
Zachary Allen , Sheri P. Kernodle , Rui Shi , Hai Liu , Michael P. Timko , Tyler Steede , Ralph E. Dewey , Ramsey S. Lewis
Plant species can accumulate secondary metabolites in optically pure form or, occasionally, as enantiomeric mixtures. Interestingly, enantiomers of the same molecule can confer different biological activities. In tobacco (Nicotiana tabacum L.), the pyridine alkaloids nicotine, nornicotine, anatabine, and anabasine naturally exist as scalemic mixtures of (R)- or (S)-enantiomers, with the (S)-isoforms predominating. The mechanisms by which tobacco alkaloid enantiomers accumulate remain largely unknown. Experiments were carried out involving tobacco genotypes possessing induced deleterious mutations in three genes coding for nicotine demethylase (NND) enzymes and three genes coding for Berberine Bridge Like (BBL) enzymes that act near the end of the nicotine, anatabine, and anabasine biosynthetic pathways. Data indicate that (R)-nicotine is naturally produced at appreciable levels but is observed in only small amounts due to preferential demethylation by NND enzymes. Data further suggest that BBL-a and BBL-b are preferentially involved in the biosynthesis of (S)-alkaloid enantiomers, while BBL-c is preferentially involved in the biosynthesis of (R)-enantiomers. Gene duplication followed by genetic divergence thus played a role in the evolution of scalemic alkaloid accumulation in tobacco. Through a combination of mutation breeding and transgene overexpression, tobacco genotypes were generated in which the predominant alkaloid enantiomers were reversed from the (S)- to the (R)-isoforms. These results shed light on the genetic control of alkaloid accumulation in N. tabacum and on mechanisms of scalemic mixture formation of secondary metabolites in plants.
{"title":"BBL enzymes exhibit enantiospecific preferences in the biosynthesis of pyridine alkaloids in Nicotiana tabacum L.","authors":"Zachary Allen , Sheri P. Kernodle , Rui Shi , Hai Liu , Michael P. Timko , Tyler Steede , Ralph E. Dewey , Ramsey S. Lewis","doi":"10.1016/j.phytochem.2024.114363","DOIUrl":"10.1016/j.phytochem.2024.114363","url":null,"abstract":"<div><div>Plant species can accumulate secondary metabolites in optically pure form or, occasionally, as enantiomeric mixtures. Interestingly, enantiomers of the same molecule can confer different biological activities. In tobacco (<em>Nicotiana tabacum</em> L.), the pyridine alkaloids nicotine, nornicotine, anatabine, and anabasine naturally exist as scalemic mixtures of (<em>R</em>)- or (<em>S</em>)-enantiomers, with the (<em>S</em>)-isoforms predominating. The mechanisms by which tobacco alkaloid enantiomers accumulate remain largely unknown. Experiments were carried out involving tobacco genotypes possessing induced deleterious mutations in three genes coding for nicotine demethylase (NND) enzymes and three genes coding for Berberine Bridge Like (BBL) enzymes that act near the end of the nicotine, anatabine, and anabasine biosynthetic pathways. Data indicate that (<em>R</em>)-nicotine is naturally produced at appreciable levels but is observed in only small amounts due to preferential demethylation by NND enzymes. Data further suggest that BBL-a and BBL-b are preferentially involved in the biosynthesis of (<em>S</em>)-alkaloid enantiomers, while BBL-c is preferentially involved in the biosynthesis of (<em>R</em>)-enantiomers. Gene duplication followed by genetic divergence thus played a role in the evolution of scalemic alkaloid accumulation in tobacco. Through a combination of mutation breeding and transgene overexpression, tobacco genotypes were generated in which the predominant alkaloid enantiomers were reversed from the (<em>S</em>)- to the (<em>R</em>)-isoforms. These results shed light on the genetic control of alkaloid accumulation in <em>N. tabacum</em> and on mechanisms of scalemic mixture formation of secondary metabolites in plants.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114363"},"PeriodicalIF":3.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142854382","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 : 2024-12-16DOI: 10.1016/j.phytochem.2024.114368
Le Wang, Shuhui Wang, Qiqi Wang, Yuqi Wang, Hong Liang, Qingying Zhang, Pengfei Tu
Twenty-one anthraquinones were discovered from the petroleum ether soluble fraction of the crude ethanol extract of Arnebia euchroma (Royle) I. M. Johnst. for the first time. 15 previously undescribed 1,4-dihydroxy-9,10-anthraquinone derivatives (1a-14), as well as 6 known anthraquinones (15a-18) were obtained from A. euchroma. Their structures and absolute configurations were determined by comprehensive analysis of HRESIMS, NMR spectra, and ECD spectra. All isolated compounds were tested for their cytotoxic activities against MCF-7, HepG2, and A549 cell lines. Compounds 2 and 16a showed moderate cytotoxic activities against MCF-7 and HepG2 cells with IC50 values of 10.00 and 13.12 μM, of 10.84 and 12.85 μM, respectively.
{"title":"Anthraquinones from the root of Arnebia euchroma (Royle) I. M. Johnst. and their cytotoxic activities","authors":"Le Wang, Shuhui Wang, Qiqi Wang, Yuqi Wang, Hong Liang, Qingying Zhang, Pengfei Tu","doi":"10.1016/j.phytochem.2024.114368","DOIUrl":"10.1016/j.phytochem.2024.114368","url":null,"abstract":"<div><div>Twenty-one anthraquinones were discovered from the petroleum ether soluble fraction of the crude ethanol extract of <em>Arnebia euchroma</em> (Royle) I. M. Johnst. for the first time. 15 previously undescribed 1,4-dihydroxy-9,10-anthraquinone derivatives (<strong>1a</strong>-<strong>14</strong>), as well as 6 known anthraquinones (<strong>15a</strong>-<strong>18</strong>) were obtained from <em>A. euchroma</em>. Their structures and absolute configurations were determined by comprehensive analysis of HRESIMS, NMR spectra, and ECD spectra. All isolated compounds were tested for their cytotoxic activities against MCF-7, HepG2, and A549 cell lines. Compounds <strong>2</strong> and <strong>16a</strong> showed moderate cytotoxic activities against MCF-7 and HepG2 cells with IC<sub>50</sub> values of 10.00 and 13.12 μM, of 10.84 and 12.85 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114368"},"PeriodicalIF":3.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142855104","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 : 2024-12-13DOI: 10.1016/j.phytochem.2024.114356
Hua Wang , Qiang Wang , Yong-Hong Chen , Xi Chen , Dong-Kun Zheng , Zhen Xie , Du-Min Feng , Lin Liu , Jing Li , Yang Liu
Thirteen abietane-type diterpenoids, including seven previously undescribed compounds and six known analogs, were isolated from the root and aerial parts of Phlegmariurus carinatus. Their structures were elucidated by comprehensive spectroscopic data analysis (UV, IR, NMR, and HRESIMS) and quantum chemical calculations (calculated ECD or 13C NMR). Notably, these compounds exhibited high structural diversity. Compounds 1–8 possessed six distinct fused ring systems. Phlecarinatones I (2) and J (3) were identified as rare 6,7-seco-abietane diterpenoids featuring a five-membered lactone ring B. Compounds (1–12) were evaluated for their anti-proliferative activities in the U251 cell line. In particular, phlecarinatone I (2) exhibited potential inhibitory effects on U251 cell proliferation, with an IC50 value of 13.88 ± 1.82 μM. To elucidate the underlying molecular mechanism, p53 signal pathway was enriched from our RNA-seq data. Further investigations using western blot and immunofluorescence assays confirmed that p53 expression was up-regulated in a concentration-independent manner. Additionally, molecular docking studies suggested 2 likely binds to the MDM2-p53 binding region. Finally, an shRNA-mediated MDM2 knockdown experiment provided definitive evidence that 2 acts as a potent inhibitor of glioma proliferation, operating via the modulation of the MDM2-p53 pathway. These findings suggest that 2 might be a valuable of lead compound with anti-proliferative activity.
{"title":"Phlecarinatones H–N: Abietane-type diterpenoids from Phlegmariurus carinatus with proliferative inhibitory effect on U251 glioblastoma cells","authors":"Hua Wang , Qiang Wang , Yong-Hong Chen , Xi Chen , Dong-Kun Zheng , Zhen Xie , Du-Min Feng , Lin Liu , Jing Li , Yang Liu","doi":"10.1016/j.phytochem.2024.114356","DOIUrl":"10.1016/j.phytochem.2024.114356","url":null,"abstract":"<div><div>Thirteen abietane-type diterpenoids, including seven previously undescribed compounds and six known analogs, were isolated from the root and aerial parts of <em>Phlegmariurus carinatus</em>. Their structures were elucidated by comprehensive spectroscopic data analysis (UV, IR, NMR, and HRESIMS) and quantum chemical calculations (calculated ECD or <sup>13</sup>C NMR). Notably, these compounds exhibited high structural diversity. Compounds <strong>1</strong>–<strong>8</strong> possessed six distinct fused ring systems. Phlecarinatones I (<strong>2</strong>) and J (<strong>3</strong>) were identified as rare 6,7-<em>seco</em>-abietane diterpenoids featuring a five-membered lactone ring B. Compounds (<strong>1</strong>–<strong>12</strong>) were evaluated for their anti-proliferative activities in the U251 cell line. In particular, phlecarinatone I (<strong>2</strong>) exhibited potential inhibitory effects on U251 cell proliferation, with an IC<sub>50</sub> value of 13.88 ± 1.82 μM. To elucidate the underlying molecular mechanism, p53 signal pathway was enriched from our RNA-seq data. Further investigations using western blot and immunofluorescence assays confirmed that p53 expression was up-regulated in a concentration-independent manner. Additionally, molecular docking studies suggested <strong>2</strong> likely binds to the MDM2-p53 binding region. Finally, an shRNA-mediated MDM2 knockdown experiment provided definitive evidence that <strong>2</strong> acts as a potent inhibitor of glioma proliferation, operating via the modulation of the MDM2-p53 pathway. These findings suggest that <strong>2</strong> might be a valuable of lead compound with anti-proliferative activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114356"},"PeriodicalIF":3.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142829801","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 : 2024-12-12DOI: 10.1016/j.phytochem.2024.114360
Ivanildo A. Brito , Erica V. Castro Levatti , Luis O. Regasini , Edgard A. Ferreira , Flavia B. Lopes , João Paulo S. Fernandes , João M. Batista Jr. , Andre G. Tempone , João Henrique G. Lago
As part of our continuous study on the Annonaceae species Porcelia macrocarpa, in the present work, eight chemically related 2-alkyl-3-hydroxy-4-methyl-γ-lactones (1–8) were isolated. Their structures were characterised by NMR, MS, and VCD. Their antitrypanosomal activity was evaluated in vitro against intracellular amastigotes with EC50 values ranged from 13.9 to 1.1 μM for compounds 1–3 and 6–8, while compounds 4 and 5 were inactive (EC50 > 100 μM). Compounds 1–8 did not exert toxicity against NCTC cells at the highest tested concentration (CC50 > 200 μM). Compared with the standard drug benznidazole (EC50 = 3.6 μM and SI > 54.6), compound 8 proved to be the most potent γ-lactone with an EC50 of 1.1 μM and an SI of >181.8. Finally, the structure–activity relationship analysis suggested that flexibility and length of side chain of the related γ-lactones 1–8 play an important role in the activity against amastigotes. The results contribute to the discovery of new molecular prototypes that can be used as scaffolds for developing drugs to treat Chagas disease.
{"title":"Homologous acetylenic acetogenins from Porcelia macrocarpa R.E. (Fries) displayed potent activity against amastigotes from Trypanosoma cruzi","authors":"Ivanildo A. Brito , Erica V. Castro Levatti , Luis O. Regasini , Edgard A. Ferreira , Flavia B. Lopes , João Paulo S. Fernandes , João M. Batista Jr. , Andre G. Tempone , João Henrique G. Lago","doi":"10.1016/j.phytochem.2024.114360","DOIUrl":"10.1016/j.phytochem.2024.114360","url":null,"abstract":"<div><div>As part of our continuous study on the Annonaceae species <em>Porcelia macrocarpa</em>, in the present work, eight chemically related 2-alkyl-3-hydroxy-4-methyl-γ-lactones (<strong>1</strong>–<strong>8</strong>) were isolated. Their structures were characterised by NMR, MS, and VCD. Their antitrypanosomal activity was evaluated <em>in vitro</em> against intracellular amastigotes with EC<sub>50</sub> values ranged from 13.9 to 1.1 μM for compounds <strong>1</strong>–<strong>3</strong> and <strong>6</strong>–<strong>8</strong>, while compounds <strong>4</strong> and <strong>5</strong> were inactive (EC<sub>50</sub> > 100 μM). Compounds <strong>1</strong>–<strong>8</strong> did not exert toxicity against NCTC cells at the highest tested concentration (CC<sub>50</sub> > 200 μM). Compared with the standard drug benznidazole (EC<sub>50</sub> = 3.6 μM and SI > 54.6), compound <strong>8</strong> proved to be the most potent γ-lactone with an EC<sub>50</sub> of 1.1 μM and an SI of >181.8. Finally, the structure–activity relationship analysis suggested that flexibility and length of side chain of the related γ-lactones <strong>1</strong>–<strong>8</strong> play an important role in the activity against amastigotes. The results contribute to the discovery of new molecular prototypes that can be used as scaffolds for developing drugs to treat Chagas disease.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114360"},"PeriodicalIF":3.2,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142822492","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}
Voagafries A–E, five undescribed monoterpenoid indole alkaloids (MIAs), were isolated from the stem bark of Voacanga africana. Voagafrie A (1) has a unique 6/5/5/6/6 spiral ring skeleton with an indolone-fused 9-oxo-3-aza-tricyclo[6,3,1,03,7]-12-alkane-10-carbonyllactone. Voagafrie B (2) is a rare 5,6-seco diazine scaffold, whereas voagafrie C (3) possesses an octahydropyrrolo[2,3-b] pyrrole-fused 2,8-diazabicyclo[3.3.1] nonane. In addition, voagafrie D (4) represents an additional 3C ibogamine-type MIA. Their structures were elucidated using extensive spectroscopic and computational analyses and a plausible biosynthetic pathway originating from conopharyngine was proposed. Furthermore, voagafries B (2) and E (5) exhibited significant cytotoxicity against SH-SY5Y at 10 μmol/L with cell viabilities of 72.7 ± 3.8 and 79.5 ± 2.1, respectively, which were comparable to that of the positive drug paclitaxel (64.1 ± 0.9). Based on the research on several cell death-related factors, these compounds may be involved in apoptosis; therefore, it is necessary to advance our understanding of them through future studies.
{"title":"Voagafries A–E, undescribed indole alkaloids with anti-glioma activity from Voacanga africana","authors":"Cai-Feng Ding , Ma-Long Qin , Kun-Ying Zhao , Wen Gao , Shan-Ze Yin , Xian-Guang Hu , Gui-Guang Cheng , Rong-Ping Zhang , Wei-Yan Hu","doi":"10.1016/j.phytochem.2024.114361","DOIUrl":"10.1016/j.phytochem.2024.114361","url":null,"abstract":"<div><div>Voagafries A–E, five undescribed monoterpenoid indole alkaloids (MIAs), were isolated from the stem bark of <em>Voacanga africana</em>. Voagafrie A (<strong>1</strong>) has a unique 6/5/5/6/6 spiral ring skeleton with an indolone-fused 9-oxo-3-aza-tricyclo[6,3,1,0<sup>3,7</sup>]-12-alkane-10-carbonyllactone. Voagafrie B (<strong>2</strong>) is a rare 5,6-seco diazine scaffold, whereas voagafrie C (<strong>3</strong>) possesses an octahydropyrrolo[2,3-b] pyrrole-fused 2,8-diazabicyclo[3.3.1] nonane. In addition, voagafrie D (<strong>4</strong>) represents an additional 3C ibogamine-type MIA. Their structures were elucidated using extensive spectroscopic and computational analyses and a plausible biosynthetic pathway originating from conopharyngine was proposed. Furthermore, voagafries B (<strong>2</strong>) and E (<strong>5</strong>) exhibited significant cytotoxicity against SH-SY5Y at 10 μmol/L with cell viabilities of 72.7 ± 3.8 and 79.5 ± 2.1, respectively, which were comparable to that of the positive drug paclitaxel (64.1 ± 0.9). Based on the research on several cell death-related factors, these compounds may be involved in apoptosis; therefore, it is necessary to advance our understanding of them through future studies.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114361"},"PeriodicalIF":3.2,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142824337","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 : 2024-12-12DOI: 10.1016/j.phytochem.2024.114359
Shan-Shan Liu , Yun Li , Yun-He An , Jing-Jing Zhu , Mei Zhang , Wei Wang , Li-Hua Yan , Zhi-Min Wang
A pair of dinor-sesquiterpene enantiomers (1a/1b), eight pairs of guaiane-type sesquiterpenes enantiomers (2a/2b, 3a/3b, 4a/4b, 5a/5b, 6a/6b, 7a/7b, 8a/8b, 9a/9b) and two guaiane-type sesquiterpenes (10, 11), including eleven undescribed ones (1a, 1b, 2a, 2b, 3a, 3b, 4a, 5b, 6a, 10, and 11), were isolated from the aqueous extract of Alismatis Rhizoma. The structures were elucidated by combining 1D and 2D NMR and HRESIMS spectroscopic data. The absolute configurations were determined by experimental and calculated ECD spectra, [Mo2(OAc)4]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of similar analogs. Compound 5b (NO inhibition rate, 52.63%) and 8b (36.49%) showed comparable activity to indomethacin (46.36%) against LPS-induced NO production in RAW 264.7 murine macrophages at 100 μM with obvious stereoselectivity, whereas compounds 1–10 exerted no or extremely low cytotoxicities against MCF-7 and MDA-MB-231 cells (IC50 ＞ 100 μM).
{"title":"Sesquiterpene enantiomers from Alismatis Rhizoma","authors":"Shan-Shan Liu , Yun Li , Yun-He An , Jing-Jing Zhu , Mei Zhang , Wei Wang , Li-Hua Yan , Zhi-Min Wang","doi":"10.1016/j.phytochem.2024.114359","DOIUrl":"10.1016/j.phytochem.2024.114359","url":null,"abstract":"<div><div>A pair of dinor-sesquiterpene enantiomers (<strong>1a/1b</strong>), eight pairs of guaiane-type sesquiterpenes enantiomers (<strong>2a/2b, 3a/3b, 4a/4b, 5a/5b, 6a/6b, 7a/7b, 8a/8b, 9a/9b</strong>) and two guaiane-type sesquiterpenes (<strong>10, 11</strong>), including eleven undescribed ones (<strong>1a, 1b, 2a, 2b, 3a, 3b, 4a, 5b, 6a, 10,</strong> and <strong>11</strong>), were isolated from the aqueous extract of Alismatis Rhizoma. The structures were elucidated by combining 1D and 2D NMR and HRESIMS spectroscopic data. The absolute configurations were determined by experimental and calculated ECD spectra, [Mo<sub>2</sub>(OAc)<sub>4</sub>]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of similar analogs. Compound <strong>5b</strong> (NO inhibition rate, 52.63%) and <strong>8b</strong> (36.49%) showed comparable activity to indomethacin (46.36%) against LPS-induced NO production in RAW 264.7 murine macrophages at 100 μM with obvious stereoselectivity, whereas compounds <strong>1</strong>–<strong>10</strong> exerted no or extremely low cytotoxicities against MCF-7 and MDA-MB-231 cells (IC<sub>50</sub> ＞ 100 μM).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"232 ","pages":"Article 114359"},"PeriodicalIF":3.2,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142824336","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 : 2024-12-09DOI: 10.1016/j.phytochem.2024.114354
Zhi Zeng , Hua-liang He , Lin Qiu , Qiao Gao , Hong-shuai Gao , Jin Xue , Xiao-nian Li , You-zhi Li , Wen-bing Ding
Two heterocyclic sesquiterpenoid oligomers (1, 2) and four previously undescribed seco-pseudoguaianolide derivatives (3−6) were isolated from the inflorescence of Ambrosia artemisiifolia. Ambrosiadimer A (1) is an unprecedented dimer featuring a hexahydropyrrolizine core scaffold and two pseudoguaianolide units. Ambrosiatrimer A (2) is a trimer formed from three pseudoguaianolide units via a pyrrolidine ring. The structures and absolute configurations of these compounds were determined through NMR, MS, and Cu Kα X-ray crystallographic analysis. A plausible cycloaddition reaction was proposed for 1 and 2. Moreover, compounds 2 and 7 exhibited moderate cytotoxicities in human cancer cell lines, with IC50 values ranging from 7.22 to 27.45 μM and 9.32–33.45 μM, respectively.
{"title":"Heterocyclic pseudoguaianolide oligomers and seco-pseudoguaianolide derivatives from the inflorescence of Ambrosia artemisiifolia","authors":"Zhi Zeng , Hua-liang He , Lin Qiu , Qiao Gao , Hong-shuai Gao , Jin Xue , Xiao-nian Li , You-zhi Li , Wen-bing Ding","doi":"10.1016/j.phytochem.2024.114354","DOIUrl":"10.1016/j.phytochem.2024.114354","url":null,"abstract":"<div><div>Two heterocyclic sesquiterpenoid oligomers (<strong>1, 2</strong>) and four previously undescribed <em>seco</em>-pseudoguaianolide derivatives (<strong>3</strong>−<strong>6</strong>) were isolated from the inflorescence of <em>Ambrosia artemisiifolia</em>. Ambrosiadimer A (<strong>1</strong>) is an unprecedented dimer featuring a hexahydropyrrolizine core scaffold and two pseudoguaianolide units. Ambrosiatrimer A (<strong>2</strong>) is a trimer formed from three pseudoguaianolide units <em>via</em> a pyrrolidine ring. The structures and absolute configurations of these compounds were determined through NMR, MS, and Cu Kα X-ray crystallographic analysis. A plausible cycloaddition reaction was proposed for <strong>1</strong> and <strong>2</strong>. Moreover, compounds <strong>2</strong> and <strong>7</strong> exhibited moderate cytotoxicities in human cancer cell lines, with IC<sub>50</sub> values ranging from 7.22 to 27.45 μM and 9.32–33.45 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114354"},"PeriodicalIF":3.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142814115","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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