Pub Date : 2024-06-20DOI: 10.1016/j.phytochem.2024.114193
Yiwei Wang , Shu Xu , Guodong Zhang , Pirui Li , Chenyang Liu , Jiarui Zhou , Xu Feng , Linwei Li , Yu Chen
Lathyrisone A (1), a diterpene with an undescribed tricyclic 6/6/6 fused carbon skeleton, along with spirolathyrisins B-D (3–5), three diterpenes with a rare [4.5.0] spirocyclic carbon skeleton, and one known compound (2) were isolated from the roots of Euphorbia lathyris. Their chemical structures were characterized by extensive spectroscopic analysis, X-ray crystallography, ECD and quantum chemistry calculation. A plausible biosynthetic pathway for compounds 1–5 was proposed, which suggested it is a competitive pathway for ingenol biosynthesis in the plant. The anti-fungal activities of these compounds were tested, especially, compound 2 showed stronger anti-fungal activities against Fusarium oxysporum and Alternaria alternata than the positive control fungicide thiophanate-methyl. The preliminary structure–activity relationship of compounds 1–5 was also discussed. These results not only expanded the chemical diversities of E. lathyris, but also provided a lead compound for the control of plant pathogens.
从 Euphorbia lathyris 的根中分离出了 Lathyrisone A (1)(一种具有未被描述的三环 6/6/6 融合碳骨架的二萜)、spirolathyrisins B-D (3-5)(三种具有罕见的 [4.5.0] 螺环碳骨架的二萜)和一种已知化合物 (2)。通过大量光谱分析、X 射线晶体学、ECD 和量子化学计算,确定了这些化合物的化学结构特征。提出了化合物 1-5 的合理生物合成途径,并认为这是植物萌发醇生物合成的竞争性途径。对这些化合物的抗真菌活性进行了测试,特别是化合物 2 与阳性对照杀菌剂甲基硫菌灵相比,对镰刀菌和交替孢霉具有更强的抗真菌活性。此外,还讨论了化合物 1-5 的初步结构-活性关系。这些结果不仅拓展了 E. lathyris 的化学多样性,而且为防治植物病原体提供了一种先导化合物。
{"title":"Targeted discovery of unusual diterpenoids with anti-fungal activity from the root of Euphorbia lathyris","authors":"Yiwei Wang , Shu Xu , Guodong Zhang , Pirui Li , Chenyang Liu , Jiarui Zhou , Xu Feng , Linwei Li , Yu Chen","doi":"10.1016/j.phytochem.2024.114193","DOIUrl":"10.1016/j.phytochem.2024.114193","url":null,"abstract":"<div><p>Lathyrisone A (<strong>1</strong>), a diterpene with an undescribed tricyclic 6/6/6 fused carbon skeleton, along with spirolathyrisins B-D (<strong>3</strong>–<strong>5</strong>), three diterpenes with a rare [4.5.0] spirocyclic carbon skeleton, and one known compound (<strong>2</strong>) were isolated from the roots of <em>Euphorbia lathyris</em>. Their chemical structures were characterized by extensive spectroscopic analysis, X-ray crystallography, ECD and quantum chemistry calculation. A plausible biosynthetic pathway for compounds <strong>1</strong>–<strong>5</strong> was proposed, which suggested it is a competitive pathway for ingenol biosynthesis in the plant. The anti-fungal activities of these compounds were tested, especially, compound <strong>2</strong> showed stronger anti-fungal activities against <em>Fusarium oxysporum</em> and <em>Alternaria alternata</em> than the positive control fungicide thiophanate-methyl. The preliminary structure–activity relationship of compounds <strong>1</strong>–<strong>5</strong> was also discussed. These results not only expanded the chemical diversities of <em>E. lathyris</em>, but also provided a lead compound for the control of plant pathogens.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141440790","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 : 2024-06-20DOI: 10.1016/j.phytochem.2024.114189
Wen-Chao Tu , Lin-Fen Ding , Liu-Dong Song , Yong-Jiao Li , Run-Cheng Yan , Yun Wu , Wei-Yang Feng , Xing-De Wu
Eight previously undescribed diterpenoids, caesamins A–H (1–8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (6) represents the first example of cleistanthane diterpenoid from the genus Caesalpinia. Caesamins B (2) and F (6) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 45.67 ± 0.92 and 42.99 ± 0.24 μM, comparable to positive control 43.69 ± 2.62 μM of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.
从 Caesalpinia minax Hance 的种子中分离并鉴定出八种以前未曾描述过的二萜类化合物,即 Caesamins A-H(1-8)。通过大量光谱数据和 X 射线晶体分析,确定了它们的结构特征。从结构上看,草铵膦 A(1)是第一个具有 C23 碳骨架的决明子类二萜化合物,其中含有一个不寻常的异丙基。草铵膦 F(6)是草铵膦属植物中第一个肉桂烷类二萜化合物。Caesamins B (2) 和 F (6) 对 RAW 264.7 巨噬细胞中 LPS 诱导的一氧化氮产生具有抑制活性,IC50 值分别为 45.67 ± 0.92 和 42.99 ± 0.24 μM,与阳性对照 NG-Monomethyl-L-arginine 的 43.69 ± 2.62 μM 相当。此外,还讨论了分离物的化学分类学意义。
{"title":"Structurally diverse diterpenoids from the seeds of Caesalpinia minax Hance and their bioactivities","authors":"Wen-Chao Tu , Lin-Fen Ding , Liu-Dong Song , Yong-Jiao Li , Run-Cheng Yan , Yun Wu , Wei-Yang Feng , Xing-De Wu","doi":"10.1016/j.phytochem.2024.114189","DOIUrl":"https://doi.org/10.1016/j.phytochem.2024.114189","url":null,"abstract":"<div><p>Eight previously undescribed diterpenoids, caesamins A–H (<strong>1</strong>–<strong>8</strong>), were separated and identified from the seeds of <em>Caesalpinia minax</em> Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (<strong>1</strong>) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (<strong>6</strong>) represents the first example of cleistanthane diterpenoid from the genus <em>Caesalpinia</em>. Caesamins B (<strong>2</strong>) and F (<strong>6</strong>) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC<sub>50</sub> values of 45.67 ± 0.92 and 42.99 ± 0.24 <em>μ</em>M, comparable to positive control 43.69 ± 2.62 <em>μ</em>M of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141435193","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 : 2024-06-19DOI: 10.1016/j.phytochem.2024.114192
Li-Li Shao , Kai-Qin Lin , Han-Fei Liu , Zhi-Yao Li , Ni Zhang , Chao Chen , Wei-Dong Pan , Hua-Yong Lou , Jin-Yu Li
Meliasanines A–L, twelve previously unreported tirucallane-type triterpenoids, together with fifteen known ones, have been isolated from the stem bark of Melia toosendan. Their structures and absolute configurations were determined based on HRESIMS, and NMR, combined with calculated ECD and single-crystal X-ray diffraction analyses. Subsequently, all compounds except 10 were evaluated for their inhibitory effect on the production of nitric oxide induced by lipopolysaccharide in RAW264.7 macrophage cells. The results indicated that seven compounds (1, 13, 14, 16, 20, 22, and 23) exhibited significant NO inhibitory effects, with IC50 values ranging from 1.35 to 5.93 μM, which were more effective than the positive control indomethacin (IC50 = 13.18 μM). Moreover, the corresponding results of Western blot analysis revealed that meliasanine A (1) can significantly suppress the protein expression of inducible nitric oxide synthase and cyclooxygenase 2 in a concentration-dependent manner. The mechanism study suggested that meliasanine A exerts an anti-inflammatory effect via the nuclear factor-κB signaling pathway by suppressing phosphorylation of P65 and IκBα.
{"title":"Meliasanines A–L, tirucallane-type triterpenoids from Melia toosendan with anti-inflammatory properties via NF-κB signaling pathway","authors":"Li-Li Shao , Kai-Qin Lin , Han-Fei Liu , Zhi-Yao Li , Ni Zhang , Chao Chen , Wei-Dong Pan , Hua-Yong Lou , Jin-Yu Li","doi":"10.1016/j.phytochem.2024.114192","DOIUrl":"10.1016/j.phytochem.2024.114192","url":null,"abstract":"<div><p>Meliasanines A–L, twelve previously unreported tirucallane-type triterpenoids, together with fifteen known ones, have been isolated from the stem bark of <em>Melia toosendan</em>. Their structures and absolute configurations were determined based on HRESIMS, and NMR, combined with calculated ECD and single-crystal X-ray diffraction analyses. Subsequently, all compounds except <strong>10</strong> were evaluated for their inhibitory effect on the production of nitric oxide induced by lipopolysaccharide in RAW264.7 macrophage cells. The results indicated that seven compounds (1, 13, 14, 16, 20, 22, and 23) exhibited significant NO inhibitory effects, with IC<sub>50</sub> values ranging from 1.35 to 5.93 μM, which were more effective than the positive control indomethacin (IC<sub>50</sub> = 13.18 μM). Moreover, the corresponding results of Western blot analysis revealed that meliasanine A (<strong>1</strong>) can significantly suppress the protein expression of inducible nitric oxide synthase and cyclooxygenase 2 in a concentration-dependent manner. The mechanism study suggested that meliasanine A exerts an anti-inflammatory effect via the nuclear factor-κB signaling pathway by suppressing phosphorylation of P65 and IκBα.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141432488","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 : 2024-06-18DOI: 10.1016/j.phytochem.2024.114191
Zhiqiao Tan , Cong Chen , Lu Chen , Jia Zeng , Wenxin Zhang , Jingwen Xu , Xiangjiu He , Yihai Wang
Herein, 17 previously undescribed polyacetylenes and 9 known ones were isolated from Tridax procumbens L. Their structures were identified using spectroscopic techniques (NMR, UV, IR, MS and optical rotation), the modified Mosher method, electronic circular dichroism (ECD) data and ECD calculation. The cytotoxicity of polyacetylenes on six human tumour cell lines (K562, K562/ADR, AGS, MGC-803, SPC-A-1 and MDA-MB-231) was evaluated. (3S,10R)-tridaxin B (2a), (3S,10S)-tridaxin B (2b) and tridaxin F (8) demonstrated substantial cytotoxic effects against the K562 cell line, with half-maximal inhibitory concentration (IC50) values of 2.62, 14.43 and 17.91 μM, respectively. Cell and nucleus morphology assessments and Western blot analysis confirmed that the cytotoxicity of the three polyacetylenes on K562 cells was mediated through a dose-dependent apoptosis pathway. Furthermore, (3S,10R)-tridaxin A (1a) and tridaxin G (9) exhibited considerable inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages, with IC50 values of 15.92 and 20.35 μM, respectively. Further investigations revealed that 9 exerted anti-inflammatory activities by impeding the nuclear translocation of NF-κB and down-regulating the expression of pro-inflammatory factors, including those of iNOS, COX-2, IL-1β and IL-6, in a concentration-dependent manner. The study provides evidence that polyacetylenes from T. procumbens may serve as a potential source of anti-tumour or anti-inflammatory agents for treating related diseases.
利用光谱技术(核磁共振、紫外、红外、质谱和旋光)、改良莫舍法、电子圆二色性(ECD)数据和 ECD 计算确定了它们的结构。评估了聚乙炔类化合物对六种人类肿瘤细胞系(K562、K562/ADR、AGS、MGC-803、SPC-A-1 和 MDA-MB-231)的细胞毒性。(3S,10R)-tridaxin B (2a)、(3S,10S)-tridaxin B (2b) 和 tridaxin F (8) 对 K562 细胞株具有显著的细胞毒性作用,其半最大抑制浓度 (IC50) 值分别为 2.62、14.43 和 17.91 μM。细胞和细胞核形态评估以及 Western 印迹分析证实,这三种多乙酰烯类化合物对 K562 细胞的细胞毒性是通过剂量依赖性凋亡途径介导的。此外,(3S,10R)-三萜类化合物 A(1a)和三萜类化合物 G(9)对脂多糖刺激 RAW 264.7 巨噬细胞产生一氧化氮具有相当大的抑制作用,IC50 值分别为 15.92 和 20.35 μM。进一步研究发现,9 通过阻碍 NF-κB 的核转位和下调促炎因子(包括 iNOS、COX-2、IL-1β 和 IL-6 的表达)的表达,以浓度依赖性的方式发挥抗炎活性。该研究提供的证据表明,普鲁卡因中的多乙酰烯类可能是治疗相关疾病的抗肿瘤或抗炎药物的潜在来源。
{"title":"Cytotoxic and anti-inflammatory polyacetylenes from Tridax procumbens L","authors":"Zhiqiao Tan , Cong Chen , Lu Chen , Jia Zeng , Wenxin Zhang , Jingwen Xu , Xiangjiu He , Yihai Wang","doi":"10.1016/j.phytochem.2024.114191","DOIUrl":"10.1016/j.phytochem.2024.114191","url":null,"abstract":"<div><p>Herein, 17 previously undescribed polyacetylenes and 9 known ones were isolated from <em>Tridax procumbens</em> L. Their structures were identified using spectroscopic techniques (NMR, UV, IR, MS and optical rotation), the modified Mosher method, electronic circular dichroism (ECD) data and ECD calculation. The cytotoxicity of polyacetylenes on six human tumour cell lines (K562, K562/ADR, AGS, MGC-803, SPC-A-1 and MDA-MB-231) was evaluated. (3<em>S</em>,10<em>R</em>)-tridaxin B (<strong>2a</strong>), (3<em>S</em>,10<em>S</em>)-tridaxin B (<strong>2b</strong>) and tridaxin F (<strong>8</strong>) demonstrated substantial cytotoxic effects against the K562 cell line, with half-maximal inhibitory concentration (IC<sub>50</sub>) values of 2.62, 14.43 and 17.91 μM, respectively. Cell and nucleus morphology assessments and Western blot analysis confirmed that the cytotoxicity of the three polyacetylenes on K562 cells was mediated through a dose-dependent apoptosis pathway. Furthermore, (3<em>S</em>,10<em>R</em>)-tridaxin A (<strong>1a</strong>) and tridaxin G (<strong>9</strong>) exhibited considerable inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages, with IC<sub>50</sub> values of 15.92 and 20.35 μM, respectively. Further investigations revealed that <strong>9</strong> exerted anti-inflammatory activities by impeding the nuclear translocation of NF-<em>κ</em>B and down-regulating the expression of pro-inflammatory factors, including those of iNOS, COX-2, IL-1<em>β</em> and IL-6, in a concentration-dependent manner. The study provides evidence that polyacetylenes from <em>T. procumbens</em> may serve as a potential source of anti-tumour or anti-inflammatory agents for treating related diseases.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141432487","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 : 2024-06-18DOI: 10.1016/j.phytochem.2024.114190
Dongxv Lu, Peng Jiang, Yanfu Wang, Yanying, Li, Anam Naseem, Adnan Mohammed Algradi, Juan Pan, Wei Guan, Jiatong Wu, Haixue Kuang, Bingyou Yang, Yan Liu
{"title":"Corrigendum to ‘Undescribed steroidal alkaloids from the bulbs of Fritillaria ussuriensis Maxim and their anti-inflammatory activities’ [Journal Title 225 (2024) 114172]","authors":"Dongxv Lu, Peng Jiang, Yanfu Wang, Yanying, Li, Anam Naseem, Adnan Mohammed Algradi, Juan Pan, Wei Guan, Jiatong Wu, Haixue Kuang, Bingyou Yang, Yan Liu","doi":"10.1016/j.phytochem.2024.114190","DOIUrl":"https://doi.org/10.1016/j.phytochem.2024.114190","url":null,"abstract":"","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0031942224002279/pdfft?md5=d44d75d9173ed98ed30950a1d4ab02fc&pid=1-s2.0-S0031942224002279-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141423332","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}
Ten undescribed diterpenoids (1–10) and three undescribed phenanthrene derivatives (11–13), together with seven known compounds, were isolated from the roots of Baliospermum solanifolium. Their structures were determined by a combination of spectroscopic data analysis, electronic circular dichroism calculations and single-crystal X-ray diffraction studies. Compounds 1–7 (baliosperoids A–G) represent the examples of 20-nor-ent-podocarpane class first discovered in nature. In particular, compound 7 possesses a unique 2,3-seco ring system incorporating γ-butanolide moiety. All isolates were assessed for their cytotoxic activities against HT-29, HCT-116, HCT-15, MCF-7, and A549 cell lines as well as their inhibitory effects on lipopolysaccharide-induced NO production in RAW264.7 cells. Compound 1, a 20-nor-ent-podocarpane-type diterpenoid possessing a Δ1,2 double bond, not only exhibited considerable proliferation inhibition against five human cancer cell lines, with IC50 values ranging from 4.13 to 23.45 μM, but also displayed the most potent inhibitory activity on NO production with IC50 value at the nanomolar level (0.63 ± 0.21 μM).
{"title":"Structurally diverse diterpenoids and phenanthrene derivatives from the roots of Baliospermum solanifolium","authors":"Jiangbo Chen, Yue Li, Haoqiang Xu, Mingjing Lian, Hongying Wang, Dongrong Zhu","doi":"10.1016/j.phytochem.2024.114194","DOIUrl":"10.1016/j.phytochem.2024.114194","url":null,"abstract":"<div><p>Ten undescribed diterpenoids (<strong>1</strong>–<strong>10</strong>) and three undescribed phenanthrene derivatives (<strong>11</strong>–<strong>13</strong>), together with seven known compounds, were isolated from the roots of <em>Baliospermum solanifolium</em>. Their structures were determined by a combination of spectroscopic data analysis, electronic circular dichroism calculations and single-crystal X-ray diffraction studies. Compounds <strong>1</strong>–<strong>7</strong> (baliosperoids A–G) represent the examples of 20-nor-<em>ent</em>-podocarpane class first discovered in nature. In particular, compound <strong>7</strong> possesses a unique 2,3-seco ring system incorporating <em>γ</em>-butanolide moiety. All isolates were assessed for their cytotoxic activities against HT-29, HCT-116, HCT-15, MCF-7, and A549 cell lines as well as their inhibitory effects on lipopolysaccharide-induced NO production in RAW264.7 cells. Compound <strong>1</strong>, a 20-nor-<em>ent</em>-podocarpane-type diterpenoid possessing a Δ<sup>1,2</sup> double bond, not only exhibited considerable proliferation inhibition against five human cancer cell lines, with IC<sub>50</sub> values ranging from 4.13 to 23.45 μM, but also displayed the most potent inhibitory activity on NO production with IC<sub>50</sub> value at the nanomolar level (0.63 ± 0.21 μM).</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141427425","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 : 2024-06-16DOI: 10.1016/j.phytochem.2024.114187
Zhibo Hu , Haishan Cui , Qiang Wang , Cheng Li , Senhua Chen , Zhizeng Gao , Lan Liu , Bo Peng , Jing Li
Seven previously undescribed compounds, including four diketomorpholine alkaloids (1‒4), one indole diketopiperazine alkaloid (9), one chromone (10), and one benzoic acid derivative (13), and nine known compounds (5–8, 11, 12, and 14–16) were isolated from two different fungal sources. Nine of these metabolites (1–9) were obtained from a seagrass-derived Aspergillus alabamensis SYSU-6778, while the others were obtained from a mixed culture of A. alabamensis SYSU-6778 and a co-isolated fungus A. fumigatiaffinis SYSU-6786. The chemical structures of the compounds were deduced via spectroscopic techniques (including HRESIMS, 1D and 2D NMR), chemical reactions, and ECD calculations. It is worth noting that compound 10 was identified as a defensive secondary metabolite of strain SYSU-6786, produced through the induction of compound 8 under co-culture conditions. Compounds 3 and 4 possessed a naturally rare isotryptophan core. Moreover, compounds 1 and 2 exhibited potent inhibitory activities against fish pathogenic bacterium Edwardsiella ictalurid, with minimum inhibitory concentration values of 10.0 μg/mL for both compounds.
{"title":"Induced production of defensive secondary metabolites from Aspergillus fumigatiaffinis by co-culture with Aspergillus alabamensis","authors":"Zhibo Hu , Haishan Cui , Qiang Wang , Cheng Li , Senhua Chen , Zhizeng Gao , Lan Liu , Bo Peng , Jing Li","doi":"10.1016/j.phytochem.2024.114187","DOIUrl":"10.1016/j.phytochem.2024.114187","url":null,"abstract":"<div><p>Seven previously undescribed compounds, including four diketomorpholine alkaloids (<strong>1</strong>‒<strong>4</strong>), one indole diketopiperazine alkaloid (<strong>9</strong>), one chromone (<strong>10</strong>), and one benzoic acid derivative (<strong>13</strong>), and nine known compounds (<strong>5</strong>–<strong>8</strong>, <strong>11</strong>, <strong>12</strong>, and <strong>14</strong>–<strong>16</strong>) were isolated from two different fungal sources. Nine of these metabolites (<strong>1</strong>–<strong>9</strong>) were obtained from a seagrass-derived <em>Aspergillus alabamensis</em> SYSU-6778, while the others were obtained from a mixed culture of <em>A. alabamensis</em> SYSU-6778 and a co-isolated fungus <em>A</em>. <em>fumigatiaffinis</em> SYSU-6786. The chemical structures of the compounds were deduced via spectroscopic techniques (including HRESIMS, 1D and 2D NMR), chemical reactions, and ECD calculations. It is worth noting that compound <strong>10</strong> was identified as a defensive secondary metabolite of strain SYSU-6786, produced through the induction of compound <strong>8</strong> under co-culture conditions. Compounds <strong>3</strong> and <strong>4</strong> possessed a naturally rare isotryptophan core. Moreover, compounds <strong>1</strong> and <strong>2</strong> exhibited potent inhibitory activities against fish pathogenic bacterium <em>Edwardsiella ictalurid,</em> with minimum inhibitory concentration values of 10.0 μg/mL for both compounds.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141420381","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 : 2024-06-13DOI: 10.1016/j.phytochem.2024.114188
Shan-Shan Jiao , Rui-Feng Ding , Xin Yuan , Xiao-Ping He , Yan Liu , Kai Guo , Sheng-Hong Li
Phytochemical investigation on the fruits of Cydonia oblonga Mill., a traditional Uighur medicine, led to the isolation of seven undescribed and nine known megastigmane glycosides. Their structures including absolute configurations were characterized by an extensive analysis of spectroscopic data including HRESIMS and NMR, combined with ECD calculations. Additionally, compounds 1, 2, 4, and 6–16 exhibited anti-inflammatory activity by inhibiting the secretion of cytokines TNF-α and IL-6 in RAW264.7 cells induced by lipopolysaccharides (LPS) with inhibitory rates of 10.79%–44.58% at 20 μM.
{"title":"Megastigmane glycosides from the traditional Uighur medicine Cydonia oblonga Mill.","authors":"Shan-Shan Jiao , Rui-Feng Ding , Xin Yuan , Xiao-Ping He , Yan Liu , Kai Guo , Sheng-Hong Li","doi":"10.1016/j.phytochem.2024.114188","DOIUrl":"10.1016/j.phytochem.2024.114188","url":null,"abstract":"<div><p>Phytochemical investigation on the fruits of <em>Cydonia oblonga</em> Mill., a traditional Uighur medicine, led to the isolation of seven undescribed and nine known megastigmane glycosides. Their structures including absolute configurations were characterized by an extensive analysis of spectroscopic data including HRESIMS and NMR, combined with ECD calculations. Additionally, compounds <strong>1</strong>, <strong>2</strong>, <strong>4</strong>, and <strong>6</strong>–<strong>16</strong> exhibited anti-inflammatory activity by inhibiting the secretion of cytokines TNF-<em>α</em> and IL-6 in RAW264.7 cells induced by lipopolysaccharides (LPS) with inhibitory rates of 10.79%–44.58% at 20 μM.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141327779","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 : 2024-06-13DOI: 10.1016/j.phytochem.2024.114186
Shuai Huang , Jian-Zhu Wang , Yang-Li Pu , Yu-Yan Liu , Ying Chen , Lin Chen , Xian-Li Zhou
The ethanol extract of the whole plant of Delphinium trichophorum Franch was subjected to a phytochemical study, leading to the isolation of ten unprecedented diterpenoid alkaloids, including nine delnudine-type C20-diterpenoid alkaloids named trichophodines A–I and one kusnezoline-type C20-diterpenoid alkaloid named trichophozine A. Additionally, seven known compounds were also identified. Their structures were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, 1H–1H COSY, NOESY and X-ray crystallographic analysis. Most isolated compounds were screened for inhibitory activities against LPS-induced NO production in RAW 264.7 macrophage cells and acetylcholinesterase inhibitory effects. Guan-fu base V exhibited potent inhibitory activity against acetylcholinesterase, demonstrating an inhibitory rate of 53.81% at a concentration of 40 μM.
通过对 Delphinium trichophorum Franch 全株的乙醇提取物进行植物化学研究,分离出了 10 种前所未有的二萜生物碱,其中包括 9 种名为 trichophodines A-I 的 delnudine 型 C20 二萜生物碱和 1 种名为 trichophozine A 的 kusnezoline 型 C20 二萜生物碱,此外还鉴定出了 7 种已知化合物。通过大量光谱分析,包括 HSQC、HMBC、1H-1H COSY、NOESY 和 X 射线晶体分析,阐明了这些化合物的结构。对大多数分离出的化合物进行了筛选,以检测其对 RAW 264.7 巨噬细胞中 LPS 诱导的 NO 生成的抑制活性以及对乙酰胆碱酯酶的抑制作用。Guan-fu base V 对乙酰胆碱酯酶有很强的抑制活性,在浓度为 40 μM 时抑制率为 53.81%。
{"title":"Diterpenoid alkaloids from Delphinium trichophorum","authors":"Shuai Huang , Jian-Zhu Wang , Yang-Li Pu , Yu-Yan Liu , Ying Chen , Lin Chen , Xian-Li Zhou","doi":"10.1016/j.phytochem.2024.114186","DOIUrl":"10.1016/j.phytochem.2024.114186","url":null,"abstract":"<div><p>The ethanol extract of the whole plant of <em>Delphinium trichophorum</em> Franch was subjected to a phytochemical study, leading to the isolation of ten unprecedented diterpenoid alkaloids, including nine delnudine-type C<sub>20</sub>-diterpenoid alkaloids named trichophodines A–I and one kusnezoline-type C<sub>20</sub>-diterpenoid alkaloid named trichophozine A. Additionally, seven known compounds were also identified. Their structures were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, <sup>1</sup>H–<sup>1</sup>H COSY, NOESY and X-ray crystallographic analysis. Most isolated compounds were screened for inhibitory activities against LPS-induced NO production in RAW 264.7 macrophage cells and acetylcholinesterase inhibitory effects. Guan-fu base V exhibited potent inhibitory activity against acetylcholinesterase, demonstrating an inhibitory rate of 53.81% at a concentration of 40 μM.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141327778","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 : 2024-06-12DOI: 10.1016/j.phytochem.2024.114185
Ting-Ting Zhou , Man-Wen Zhang , Yan-Chun Liu , Xiao-Nian Li , Yan Liu , Kai Guo , Sheng-Hong Li
Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A−E, two undescribed penta-nor-leucosesterterpane (C20) sesterterpenoids, nor-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of Leucosceptrum canum of Chinese origin. Leucosceptrines A−C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. Nor-leucosceptrines A and B possesses an unusual penta-nor-leucosesterterpane skeleton. Their structures were unambiguously elucidated through comprehensive spectroscopic analyses and single-crystal X-ray diffraction. A plausible biogenetic pathway for these sesterterpenoids was proposed. The immunosuppressive effects of these isolates on the secretion of the cytokine IFN-γ by T cells stimulated with anti-CD3/CD28 monoclonal antibodies were observed with different potencies.
研究人员从中国产的Leucosceptrum canum的气生部分获得了五种未曾描述过的单桉树酯类化合物(leucosceptrines A-E)、两种未曾描述过的五正桉树酯类化合物(C20)(nor-leucosceptrines A 和 B)以及三种已知的类似物。Leucosceptrines A-C 是首例具有非封闭二氢吡喃环和手性中心 C-4 和/或 C-12 反向构型的白果三萜类化合物。Nor-leucosceptrines A 和 B 具有不寻常的五-正亮氨酸酯烷骨架。通过全面的光谱分析和单晶 X 射线衍射,它们的结构得到了明确的阐释。提出了这些酯类化合物的合理生物遗传途径。观察到这些分离物对小鼠脾细胞在抗 CD3/CD28 单克隆抗体刺激下分泌细胞因子 IFN-γ 的免疫抑制作用具有不同的效力。
{"title":"Immunosuppressive leucosesterterpane and penta-nor-leucosesterterpane sesterterpenoids from Leucosceptrum canum","authors":"Ting-Ting Zhou , Man-Wen Zhang , Yan-Chun Liu , Xiao-Nian Li , Yan Liu , Kai Guo , Sheng-Hong Li","doi":"10.1016/j.phytochem.2024.114185","DOIUrl":"10.1016/j.phytochem.2024.114185","url":null,"abstract":"<div><p>Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A−E, two undescribed penta-<em>nor</em>-leucosesterterpane (C<sub>20</sub>) sesterterpenoids, <em>nor</em>-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of <em>Leucosceptrum canum</em> of Chinese origin. Leucosceptrines A−C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. <em>Nor</em>-leucosceptrines A and B possesses an unusual penta-<em>nor</em>-leucosesterterpane skeleton. Their structures were unambiguously elucidated through comprehensive spectroscopic analyses and single-crystal X-ray diffraction. A plausible biogenetic pathway for these sesterterpenoids was proposed. The immunosuppressive effects of these isolates on the secretion of the cytokine IFN-γ by T cells stimulated with anti-CD3/CD28 monoclonal antibodies were observed with different potencies.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141321346","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}