Pub Date : 2024-10-09DOI: 10.1016/j.fitote.2024.106245
Haizhen Liang , Fan Yang , Jie Zhang, Pengxin Lu, Guang Yang, Xiaojuan Chen, Qing Sun, Juan Song, Shuchen Liu, Baiping Ma
The husks of Xanthoceras sorbifolia Bunge have gradually attracted widespread attention in recent years due to the abundant resources and ideal pharmacological activities, with barrigenol-like triterpenoid saponins being its biological constituents. In this study, a feature-based molecular networking (FBMN) was utilized to perform the targeted isolation of triterpenoids. As a result, six undescribed barrigenol-type saponins (1–6) along with fourteen known analogues (7–22) were isolated from the extract of X. sorbifolia husk. Their structures were determined through a comprehensive analysis of NMR and HRMS spectroscopic data. Among them, compounds 1–3 are a specific type of saponin featuring a fucose moiety attached at C-21. The antitumor activities of isolated compounds were evaluated and compounds 7, 9 and 10 showed significant inhibitory activities against A549 and HepG2 cell lines in a dose-dependent manner.
{"title":"Targeted isolation of barrigenol-like triterpenoids from the husks of Xanthoceras sorbifolia Bunge based on feature-based molecular networking and their antitumor activities","authors":"Haizhen Liang , Fan Yang , Jie Zhang, Pengxin Lu, Guang Yang, Xiaojuan Chen, Qing Sun, Juan Song, Shuchen Liu, Baiping Ma","doi":"10.1016/j.fitote.2024.106245","DOIUrl":"10.1016/j.fitote.2024.106245","url":null,"abstract":"<div><div>The husks of <em>Xanthoceras sorbifolia</em> Bunge have gradually attracted widespread attention in recent years due to the abundant resources and ideal pharmacological activities, with barrigenol-like triterpenoid saponins being its biological constituents. In this study, a feature-based molecular networking (FBMN) was utilized to perform the targeted isolation of triterpenoids. As a result, six undescribed barrigenol-type saponins (<strong>1–6</strong>) along with fourteen known analogues (<strong>7–22</strong>) were isolated from the extract of <em>X. sorbifolia</em> husk. Their structures were determined through a comprehensive analysis of NMR and HRMS spectroscopic data. Among them, compounds <strong>1–3</strong> are a specific type of saponin featuring a fucose moiety attached at C-21. The antitumor activities of isolated compounds were evaluated and compounds <strong>7</strong>, <strong>9</strong> and <strong>10</strong> showed significant inhibitory activities against A549 and HepG2 cell lines in a dose-dependent manner.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106245"},"PeriodicalIF":2.5,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142406300","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-05DOI: 10.1016/j.fitote.2024.106242
Rong Huang, Xiujuan He, Xuan Wang, Xiaoxin Li, Yonggang Liu, Peng Tan
Polygonati Rhizoma, a Chinese medicine often used in the clinic, can irritate the tongue and throat, so it must be processed before use. Polygonati Rhizoma contains a variety of chemical components, with saponins being one of the main active ingredients. Saponins can be highly irritating to human mocous membranes and have toxicity. In this study, total saponins were extracted from raw and processed Polygonati Rhizoma and detected by UPLC-Q-TOF-MS to identify their constituents. A total of 46 saponins were detected in TSRPR(total saponins of raw Polygonati Rhizoma), TSSPR(total saponins of steamed Polygonati Rhizoma) and TSWPR(total saponins of Polygonati Rhizoma steamed in wine). Of these, 9 compounds that were present in TSRPR were not detected in TSSPR and TSWPR. C.elegans was used as a model animal to study the neurotoxic effect and its mechanisms. TSRPR was found to have neurotoxic effects on C.elegans, but TSSPR and TSWPR had no adverse effects on the nematodes. The disappearance of the irritant effect of raw Polygonati Rhizoma after processing might be related to the changes in the composition of saponins, and the main reason might be the structural transformation of saponins. In particular, the sugar chains of some highly irritating saponins may have been removed or highly irritating saponins isomerized into weakly irritating saponins. The mechanisms of neurotoxic effects on C.elegans may include upregulation of ced-3 and egl-1 expression to promote apoptosis, damage to GABAergic and cholinergic neurons, downregulation of the GABA transmitter receptor genes ggr-1 and gab-1, and a decrease in glutamate levels that impairs nerve signal transmission.
{"title":"The analysis of raw and processed Polygonatum kingianum saponins and stimulatory mechanism in Caenorhabditis elegans","authors":"Rong Huang, Xiujuan He, Xuan Wang, Xiaoxin Li, Yonggang Liu, Peng Tan","doi":"10.1016/j.fitote.2024.106242","DOIUrl":"10.1016/j.fitote.2024.106242","url":null,"abstract":"<div><div>Polygonati Rhizoma, a Chinese medicine often used in the clinic, can irritate the tongue and throat, so it must be processed before use. Polygonati Rhizoma contains a variety of chemical components, with saponins being one of the main active ingredients. Saponins can be highly irritating to human mocous membranes and have toxicity. In this study, total saponins were extracted from raw and processed Polygonati Rhizoma and detected by UPLC-Q-TOF-MS to identify their constituents. A total of 46 saponins were detected in TSRPR(total saponins of raw Polygonati Rhizoma), TSSPR(total saponins of steamed Polygonati Rhizoma) and TSWPR(total saponins of Polygonati Rhizoma steamed in wine). Of these, 9 compounds that were present in TSRPR were not detected in TSSPR and TSWPR. C.elegans was used as a model animal to study the neurotoxic effect and its mechanisms. TSRPR was found to have neurotoxic effects on C.elegans, but TSSPR and TSWPR had no adverse effects on the nematodes. The disappearance of the irritant effect of raw Polygonati Rhizoma after processing might be related to the changes in the composition of saponins, and the main reason might be the structural transformation of saponins. In particular, the sugar chains of some highly irritating saponins may have been removed or highly irritating saponins isomerized into weakly irritating saponins. The mechanisms of neurotoxic effects on C.elegans may include upregulation of ced-3 and egl-1 expression to promote apoptosis, damage to GABAergic and cholinergic neurons, downregulation of the GABA transmitter receptor genes ggr-1 and gab-1, and a decrease in glutamate levels that impairs nerve signal transmission.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106242"},"PeriodicalIF":2.5,"publicationDate":"2024-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142389193","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-01DOI: 10.1016/j.fitote.2024.106241
Chunping Tang , Yongzhe Zheng , Zhengguang Shao , Chang-Qiang Ke , Zheling Feng , Yang Ye
Artemisia plants are well-known for their abundant sesquiterpene compounds, which encompass various structural types and exhibit a range of biological activities. In this study, a systematic investigation of Artemisia atrovirens revealed the presence of germacrane-type sesquiterpenes for the first time. This included the discovery of 10 new compounds and three known analogues, among which were two rare dimeric germacrane-type compounds. Their structures were fully characterized through a comprehensive analysis involving MS, IR, 1D- and 2D-NMR spectroscopic data, single crystal X-ray diffraction, density functional theory (DFT) NMR calculations, and time-dependent DFT electronic circular dichroism (TDDFT ECD) calculations. Furthermore, all isolated compounds were evaluated for their anti-inflammatory activity in LPS-stimulated RAW 264.7 murine macrophages. Compound 10 demonstrated a potent inhibitory effect on NO production, with an IC50 value of 4.01 ± 0.09 μM. This study highlights the diverse chemical repertoire of Artemisia species and underscores their potential in drug discovery and development.
蒿属植物以其丰富的倍半萜化合物而闻名，这些化合物具有多种结构类型，并表现出一系列生物活性。在这项研究中，对青蒿的系统研究首次发现了胚芽蒿类倍半萜化合物。研究发现了 10 种新化合物和 3 种已知类似物，其中包括两种罕见的二聚胚芽萜类化合物。通过涉及质谱、红外光谱、一维和二维核磁共振光谱数据、单晶 X 射线衍射、密度泛函理论（DFT）核磁共振计算和时间相关 DFT 电子圆二色性（TDDFT ECD）计算的综合分析，对这些化合物的结构进行了全面鉴定。此外，还评估了所有分离化合物在 LPS 刺激的 RAW 264.7 鼠巨噬细胞中的抗炎活性。化合物 10 对 NO 的产生具有强效抑制作用，其 IC50 值为 4.01 ± 0.09 μM。这项研究凸显了青蒿物种多样的化学成分，并强调了它们在药物发现和开发方面的潜力。
{"title":"Germacrane-type sesquiterpenes from Artemisia atrovirens and their anti-inflammatory activity","authors":"Chunping Tang , Yongzhe Zheng , Zhengguang Shao , Chang-Qiang Ke , Zheling Feng , Yang Ye","doi":"10.1016/j.fitote.2024.106241","DOIUrl":"10.1016/j.fitote.2024.106241","url":null,"abstract":"<div><div><em>Artemisia</em> plants are well-known for their abundant sesquiterpene compounds, which encompass various structural types and exhibit a range of biological activities. In this study, a systematic investigation of <em>Artemisia atrovirens</em> revealed the presence of germacrane-type sesquiterpenes for the first time. This included the discovery of 10 new compounds and three known analogues, among which were two rare dimeric germacrane-type compounds. Their structures were fully characterized through a comprehensive analysis involving MS, IR, 1D- and 2D-NMR spectroscopic data, single crystal X-ray diffraction, density functional theory (DFT) NMR calculations, and time-dependent DFT electronic circular dichroism (TDDFT ECD) calculations. Furthermore, all isolated compounds were evaluated for their anti-inflammatory activity in LPS-stimulated RAW 264.7 murine macrophages. Compound <strong>10</strong> demonstrated a potent inhibitory effect on NO production, with an IC<sub>50</sub> value of 4.01 ± 0.09 μM. This study highlights the diverse chemical repertoire of <em>Artemisia</em> species and underscores their potential in drug discovery and development.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106241"},"PeriodicalIF":2.5,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142371389","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-30DOI: 10.1016/j.fitote.2024.106221
Wen-Hui Xu , Yi-Ran Jiang , Tian-Tian Bei , Ying-Xiao Xiao , Yuan Gao , Hao Xu , Xue-Feng Wu , Hyun-Sun Lee , Long Cui
Six new sesquineolignans (1–6), have been isolated and elucidated from the stems of Akebia quinate together with five known analogues (7–11). Their structures were elucidated on the basis of comprehensive analysis of UV, IR, NMR, HRESIMS and CD spectroscopy experiments. All the isolates were evaluated for in vitro inhibitory activity against DGAT1 and DGAT2. Among them, compounds 1–11 were found to exhibit selective inhibitory activity on DGAT1 with IC50 values ranging from 60.4 ± 1.3 to 84.6 ± 1.3 μM. Besides, the potential binding sites of 1 were predicted by molecular docking.
{"title":"Six new sesquineolignans from the stems of Akebia quinate and their diacylglycerol acyltransferase activity","authors":"Wen-Hui Xu , Yi-Ran Jiang , Tian-Tian Bei , Ying-Xiao Xiao , Yuan Gao , Hao Xu , Xue-Feng Wu , Hyun-Sun Lee , Long Cui","doi":"10.1016/j.fitote.2024.106221","DOIUrl":"10.1016/j.fitote.2024.106221","url":null,"abstract":"<div><div>Six new sesquineolignans (<strong>1–6</strong>), have been isolated and elucidated from the stems of <em>Akebia quinate</em> together with five known analogues (<strong>7–11</strong>). Their structures were elucidated on the basis of comprehensive analysis of UV, IR, NMR, HRESIMS and CD spectroscopy experiments. All the isolates were evaluated for <em>in vitro</em> inhibitory activity against DGAT1 and DGAT2. Among them, compounds <strong>1–11</strong> were found to exhibit selective inhibitory activity on DGAT1 with IC<sub>50</sub> values ranging from 60.4 ± 1.3 to 84.6 ± 1.3 μM. Besides, the potential binding sites of <strong>1</strong> were predicted by molecular docking.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106221"},"PeriodicalIF":2.5,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142364946","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The use of phytomedicine in cancer therapy is a growing field of research that takes use of the medicinal properties of plant-derived compounds. Under the domain of cancer therapy and management, alkaloids, a prominent group of natural compounds, have showed significant potential. Alkaloids often affect a wide range of essential cellular mechanisms involved in cancer progression. These multi-targeting capabilities, can give significant advantages to alkaloids in overcoming resistance mechanisms. For example, berberine, an alkaloid found in Berberis species, is widely reported to induce apoptosis by activating caspases and regulating apoptotic pathways. Notably, alkaloids like as quinine have showed promise in inhibiting the formation of new blood vessels required for tumor growth. In addition, alkaloids have shown anti-proliferative and anticancer properties mostly via modulating key signaling pathways involved in metastasis, including those regulating epithelial-mesenchymal transition. This work provides a comprehensive overview of naturally occurring alkaloids that exhibit anticancer properties, with a specific emphasis on their underlying molecular mechanisms of action. Furthermore, many methods to modify previously reported difficult physicochemical properties using nanocarriers in order to enhance its systemic bioavailability have been discussed as well. This study also includes information on newly discovered alkaloids that are now being studied in clinical trials for their potential use in cancer treatment. Further, we have also briefly mentioned on the application of high-throughput screening and molecular dynamics simulation for acceleration on the identification of potent alkaloids based compounds to target and treat cancer.
{"title":"Alkaloids in Cancer therapy: Targeting the tumor microenvironment and metastasis signaling pathways","authors":"Raoufeh Koochaki , Elaheh Amini , Sara Zarehossini , Danial Zareh , Saeed Mohammadian Haftcheshmeh , Saurav Kumar Jha , Prashant Kesharwani , Abolfazl Shakeri , Amirhossein Sahebkar","doi":"10.1016/j.fitote.2024.106222","DOIUrl":"10.1016/j.fitote.2024.106222","url":null,"abstract":"<div><div>The use of phytomedicine in cancer therapy is a growing field of research that takes use of the medicinal properties of plant-derived compounds. Under the domain of cancer therapy and management, alkaloids, a prominent group of natural compounds, have showed significant potential. Alkaloids often affect a wide range of essential cellular mechanisms involved in cancer progression. These multi-targeting capabilities, can give significant advantages to alkaloids in overcoming resistance mechanisms. For example, berberine, an alkaloid found in Berberis species, is widely reported to induce apoptosis by activating caspases and regulating apoptotic pathways. Notably, alkaloids like as quinine have showed promise in inhibiting the formation of new blood vessels required for tumor growth. In addition, alkaloids have shown anti-proliferative and anticancer properties mostly <em>via</em> modulating key signaling pathways involved in metastasis, including those regulating epithelial-mesenchymal transition. This work provides a comprehensive overview of naturally occurring alkaloids that exhibit anticancer properties, with a specific emphasis on their underlying molecular mechanisms of action. Furthermore, many methods to modify previously reported difficult physicochemical properties using nanocarriers in order to enhance its systemic bioavailability have been discussed as well. This study also includes information on newly discovered alkaloids that are now being studied in clinical trials for their potential use in cancer treatment. Further, we have also briefly mentioned on the application of high-throughput screening and molecular dynamics simulation for acceleration on the identification of potent alkaloids based compounds to target and treat cancer.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106222"},"PeriodicalIF":2.5,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344325","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The biological activities of plant products are extremely correlated to the constituents present in each derivate. The present research aims to obtain by gas chromatography, the chemical profile of Prunus armeniaca L. kernel volatile fractions. The evaluation of the in vitro antifungal activities of the sterilized powder and volatile fractions of the plant P. armeniaca L. kernels was performed. Diffusion in a solid medium and broth microdilution methods were applied on fungi with medical importance (dermatophytes, yeasts and Aspergillus spp.). P. armeniaca L. powder based antidermatphyte cream has been formulated. Hydro-distillation generated two volatile fractions (VF1 and VF2) and chromatographic analysis showed the presence of three compounds for VF1 (98.7 % benzaldehyde, 1.0 % benzyl alcohol and 0.3 % 1,8-cineole) and two compounds for VF2 (90.3 % benzaldehyde and 9.3 % benzyl alcohol). The 2.5 % to 5 % concentrations in powder showed antifungal activities against dermatophytic strains. 1.25 to 2 mg/mL concentrations in volatile fractions were efficient against yeast strains, with a better efficiency for the VF1. The creams formulated were stable, cosmetically attractive with satisfactory pH, viscosity and spread ability. Prunus armeniaca L. kernel powders and the cream derived from them exhibit potent antifungal activities. This work presents a simple, ecological and economical means of formulating antifungal active substances and valorizing natural products.
{"title":"Chemical composition and antifungal efficacy of Tunisian Prunus armeniaca L. kernels with formulation of an antidermatophyte cream based on kernel powder","authors":"Soukaina Hrichi , Raja Chaâbane-Banaoues , Haikel Hrichi , Sameh Belgacem , Oussama Babba , Guido Flamini , Hamouda Babba","doi":"10.1016/j.fitote.2024.106223","DOIUrl":"10.1016/j.fitote.2024.106223","url":null,"abstract":"<div><div>The biological activities of plant products are extremely correlated to the constituents present in each derivate. The present research aims to obtain by gas chromatography, the chemical profile of <em>Prunus armeniaca</em> L. kernel volatile fractions. The evaluation of the in vitro antifungal activities of the sterilized powder and volatile fractions of the plant <em>P. armeniaca</em> L. kernels was performed. Diffusion in a solid medium and broth microdilution methods were applied on fungi with medical importance (dermatophytes, yeasts and <em>Aspergillus</em> spp.). <em>P. armeniaca</em> L. powder based antidermatphyte cream has been formulated. Hydro-distillation generated two volatile fractions (VF1 and VF2) and chromatographic analysis showed the presence of three compounds for VF1 (98.7 % benzaldehyde, 1.0 % benzyl alcohol and 0.3 % 1,8-cineole) and two compounds for VF2 (90.3 % benzaldehyde and 9.3 % benzyl alcohol). The 2.5 % to 5 % concentrations in powder showed antifungal activities against dermatophytic strains. 1.25 to 2 mg/mL concentrations in volatile fractions were efficient against yeast strains, with a better efficiency for the VF1. The creams formulated were stable, cosmetically attractive with satisfactory pH, viscosity and spread ability. <em>Prunus armeniaca</em> L. kernel powders and the cream derived from them exhibit potent antifungal activities. This work presents a simple, ecological and economical means of formulating antifungal active substances and valorizing natural products.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106223"},"PeriodicalIF":2.5,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344327","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-26DOI: 10.1016/j.fitote.2024.106234
Ping Hai , Haiyan Jia , Zhiqiang Luo , Huixia Fan , Yunqing He , Xianyan Li , Peng Lin , Qin Zhang , Yuan Gao , Jian Yang
Two new meroterpenoids, arneuchrols A and B (1 and 2), together with twelve known analogs (3–14) were isolated from the root of Arnebia euchroma. The structures of 1 and 2 including their absolute configurations were elucidated by NMR, HRESIMS, and DFT calculation of their NMR and ECD data. The structure of pseudoshikonin I, firstly isolated from Lithospermi radix was revised as shikonofuran E (4). Anti-triple negative breast cancer (anti-TNBC) and antimicrobial activities of the isolated compounds were tested. Compounds 3, 4, 6, 7, 9, 10, and 13 exhibited potent inhibitory activity against TNBC (MDA-MB-231 cells) with IC50 values in the range of 0.18–4.58 μM. Compound 10 displayed antifungal activity against five plant pathogenic fungi with MIC values in the range of 6.25–25 μg/mL. Compound 9 exhibited antibacterial activity against Micrococcus lysodeikticus with MIC value of 12.5 μg/mL.
{"title":"Meroterpenoids with anti-triple negative breast cancer and antimicrobial activities from Arnebia euchroma","authors":"Ping Hai , Haiyan Jia , Zhiqiang Luo , Huixia Fan , Yunqing He , Xianyan Li , Peng Lin , Qin Zhang , Yuan Gao , Jian Yang","doi":"10.1016/j.fitote.2024.106234","DOIUrl":"10.1016/j.fitote.2024.106234","url":null,"abstract":"<div><div>Two new meroterpenoids, arneuchrols A and B (<strong>1</strong> and <strong>2</strong>), together with twelve known analogs (<strong>3</strong>–<strong>14</strong>) were isolated from the root of <em>Arnebia euchroma</em>. The structures of <strong>1</strong> and <strong>2</strong> including their absolute configurations were elucidated by NMR, HRESIMS, and DFT calculation of their NMR and ECD data. The structure of pseudoshikonin I, firstly isolated from <em>Lithospermi radix</em> was revised as shikonofuran E (<strong>4</strong>). Anti-triple negative breast cancer (anti-TNBC) and antimicrobial activities of the isolated compounds were tested. Compounds <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, <strong>7</strong>, <strong>9</strong>, <strong>10</strong>, and <strong>13</strong> exhibited potent inhibitory activity against TNBC (MDA-MB-231 cells) with IC<sub>50</sub> values in the range of 0.18–4.58 μM. Compound <strong>10</strong> displayed antifungal activity against five plant pathogenic fungi with MIC values in the range of 6.25–25 μg/mL. Compound <strong>9</strong> exhibited antibacterial activity against <em>Micrococcus lysodeikticus</em> with MIC value of 12.5 μg/mL.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106234"},"PeriodicalIF":2.5,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344335","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-25DOI: 10.1016/j.fitote.2024.106240
Heping Hui , Hui Jin , Xiaoyan Yang , Xuejun Wang , Bo Qin
An O-acetyl mannoglucan (BHP-1) from Lanzhou lily bulbs was structurally elucidated using partial acid hydrolysis, GC–MS, and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) built on prior research, revealing a backbone of -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp- with the most potential side chains -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → 4)-Glcp-α-D-(1 → Glcp- and -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → Glcp-, attached to O-2 and O-3 of glucose and mannose residues, and featuring O-acetyl groups at O-2 or O-3 position of mannose. The terminal residue was α-D-(1 → Glcp. BHP-1 demonstrated anti-aging and hypoglycemic effects, as assessed by C. elegans model and glycolytic enzyme effect in vitro, respectively. The results showed that BHP-1 dose-dependently prolonged lifespan of C. elegans by 33 % at 4 mg/mL under normal conditions, with greater extensions under thermal and oxidative stress (50 % and 80 % increases, respectively, p < 0.05), which were attributed to enhanced antioxidant enzymes (SOD and CAT) and lowered MDA levels of C. elegans. Additionally, BHP-1 exhibited remarkable inhibition on α-glucosidase (93 %) and moderate inhibition on α-amylase (53 %) at 4 mg/mL, with competitive inhibition of α-glucosidase and mixed non-competitive inhibition of α-amylase, respectively. These potential effects might be linked to BHP-1's diverse sugar linkages, higher content of Glc, and certain O-acetyl contents.
{"title":"The structure elucidation, anti-aging and hypoglycemic effects of an O-acetyl mannoglucan from the bulbs of Lanzhou lily","authors":"Heping Hui , Hui Jin , Xiaoyan Yang , Xuejun Wang , Bo Qin","doi":"10.1016/j.fitote.2024.106240","DOIUrl":"10.1016/j.fitote.2024.106240","url":null,"abstract":"<div><div>An <em>O</em>-acetyl mannoglucan (BHP-1) from Lanzhou lily bulbs was structurally elucidated using partial acid hydrolysis, GC–MS, and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) built on prior research, revealing a backbone of -<em>α</em>-D-(1 → 4)-Glc<em>p</em>-<em>β</em>-D-(1 → 4)-Man<em>p</em>- with the most potential side chains -<em>α</em>-D-(1 → 4)-Glc<em>p-β</em>-D-(1 → 4)-Man<em>p-α</em>-D-(1 → 4)-Glc<em>p</em>-<em>α</em>-D-(1 → Glc<em>p</em>- and -<em>α</em>-D-(1 → 4)-Glc<em>p</em>-<em>β</em>-D-(1 → 4)-Man<em>p-α-</em>D-(1 → Glc<em>p</em>-, attached to <em>O</em>-2 and <em>O</em>-3 of glucose and mannose residues, and featuring <em>O</em>-acetyl groups at <em>O</em>-2 or <em>O</em>-3 position of mannose. The terminal residue was <em>α</em>-D-(1 → Glc<em>p</em>. BHP-1 demonstrated anti-aging and hypoglycemic effects, as assessed by <em>C. elegans</em> model and glycolytic enzyme effect in vitro, respectively. The results showed that BHP-1 dose-dependently prolonged lifespan of <em>C. elegans</em> by 33 % at 4 mg/mL under normal conditions, with greater extensions under thermal and oxidative stress (50 % and 80 % increases, respectively, <em>p</em> < 0.05), which were attributed to enhanced antioxidant enzymes (SOD and CAT) and lowered MDA levels of <em>C. elegans</em>. Additionally, BHP-1 exhibited remarkable inhibition on <em>α</em>-glucosidase (93 %) and moderate inhibition on <em>α</em>-amylase (53 %) at 4 mg/mL, with competitive inhibition of <em>α</em>-glucosidase and mixed non-competitive inhibition of <em>α</em>-amylase, respectively. These potential effects might be linked to BHP-1's diverse sugar linkages, higher content of Glc, and certain <em>O</em>-acetyl contents.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106240"},"PeriodicalIF":2.5,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-25DOI: 10.1016/j.fitote.2024.106228
Shun Liu , Xing Zheng , Zhongqin Luo , Caihong Tang , Yufei Hu , Qingying Peng , Pengbing Mi , Hongfei Chen , Xu Yao
Background
Apigenin, a naturally occurring compound with a flavone core structure, is known for its diverse bioactivities, including anti-inflammation, anti-toxicant, anti-cancer and so on. There has been significant interest in the medicinal chemistry community. To address these challenges, researchers have developed various derivatives of apigenin to address challenges such as poor water-solubility and low intestinal absorption, aiming to enhance the pharmacological activities and pharmacokinetic properties of this compound.
Objective
In recent years, there has been a proliferation of apigenin derivatives with enhanced bioactivity. However, there is a lack of comprehensive reviews on the function-based modification of these derivatives. In this paper, we provide an overview of the apigenin derivatives with varying bioactivities and explored their structure activity relationships. And the functions of different groups of apigenin derivatives were also analyzed.
Conclusion
This review summarized the current achievements that could provide some clues for further study of apigenin-based drugs.
{"title":"The synthesis and bioactivity of apigenin derivatives","authors":"Shun Liu , Xing Zheng , Zhongqin Luo , Caihong Tang , Yufei Hu , Qingying Peng , Pengbing Mi , Hongfei Chen , Xu Yao","doi":"10.1016/j.fitote.2024.106228","DOIUrl":"10.1016/j.fitote.2024.106228","url":null,"abstract":"<div><h3>Background</h3><div>Apigenin, a naturally occurring compound with a flavone core structure, is known for its diverse bioactivities, including anti-inflammation, anti-toxicant, anti-cancer and so on. There has been significant interest in the medicinal chemistry community. To address these challenges, researchers have developed various derivatives of apigenin to address challenges such as poor water-solubility and low intestinal absorption, aiming to enhance the pharmacological activities and pharmacokinetic properties of this compound.</div></div><div><h3>Objective</h3><div>In recent years, there has been a proliferation of apigenin derivatives with enhanced bioactivity. However, there is a lack of comprehensive reviews on the function-based modification of these derivatives. In this paper, we provide an overview of the apigenin derivatives with varying bioactivities and explored their structure activity relationships. And the functions of different groups of apigenin derivatives were also analyzed.</div></div><div><h3>Conclusion</h3><div>This review summarized the current achievements that could provide some clues for further study of apigenin-based drugs.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106228"},"PeriodicalIF":2.5,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344333","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The biotransformation of natural compounds by fungal microorganisms is a complex biochemical process. Tandem whole-cell biotransformation offers a promising, alternative, and cost-effective method for modifying of bioactive novel compounds. This approach is particularly beneficial for structurally complex natural products that are difficult to be synthesized through traditional synthetic methods. Biotransformation also provides significant regio- and stereoselectivity, making it a valuable tool for the chemical modification of natural compounds. By utilizing microbial conversion reactions, the biological activity and structural diversity of natural products can be enhanced. In this review, we have summarized 282 novel metabolites resulting from microbial transformation by various microorganisms. We discussed the chemical structures and pharmacological properties of these novel biotransformation products. The review would assist scientists working in the fields of biotechnology, organic chemistry, medicinal chemistry, and pharmacology.
{"title":"Modification of natural compounds through biotransformation process by microorganisms and their pharmacological properties","authors":"Nigora Rustamova , Guozheng Huang , Maksud Isokov , Jakhongir Movlanov , Ruziev Farid , Islamov Buston , Hua Xiang , Kahramon Davranov , Abulimiti Yili","doi":"10.1016/j.fitote.2024.106227","DOIUrl":"10.1016/j.fitote.2024.106227","url":null,"abstract":"<div><div>The biotransformation of natural compounds by fungal microorganisms is a complex biochemical process. Tandem whole-cell biotransformation offers a promising, alternative, and cost-effective method for modifying of bioactive novel compounds. This approach is particularly beneficial for structurally complex natural products that are difficult to be synthesized through traditional synthetic methods. Biotransformation also provides significant regio- and stereoselectivity, making it a valuable tool for the chemical modification of natural compounds. By utilizing microbial conversion reactions, the biological activity and structural diversity of natural products can be enhanced. In this review, we have summarized 282 novel metabolites resulting from microbial transformation by various microorganisms. We discussed the chemical structures and pharmacological properties of these novel biotransformation products. The review would assist scientists working in the fields of biotechnology, organic chemistry, medicinal chemistry, and pharmacology.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106227"},"PeriodicalIF":2.5,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344330","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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