Pub Date : 2025-01-21DOI: 10.1016/j.phytochem.2025.114414
Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu
Chemical investigation on the secondary metabolites of Aspergillus aculeatus led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (1–10). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo2(OAc)4-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds 1–4 belong to a rare class of 17-nor fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds 6, 7, and 10 exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC50 values ranging from 2.44 to 5.26 μM and LPS-induced B cell proliferation with IC50 values ranging from 4.18 to 5.78 μM, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.
{"title":"Aculeanoids A–D, the second 17-nor fusicoccane diterpenoids with immunosuppressive activity from Aspergillus aculeatus","authors":"Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu","doi":"10.1016/j.phytochem.2025.114414","DOIUrl":"10.1016/j.phytochem.2025.114414","url":null,"abstract":"<div><div>Chemical investigation on the secondary metabolites of <em>Aspergillus aculeatus</em> led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (<strong>1</strong>–<strong>10</strong>). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo<sub>2</sub>(OAc)<sub>4</sub>-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds <strong>1</strong>–<strong>4</strong> belong to a rare class of 17-<em>nor</em> fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds <strong>6</strong>, <strong>7</strong>, and <strong>10</strong> exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC<sub>50</sub> values ranging from 2.44 to 5.26 <em>μ</em>M and LPS-induced B cell proliferation with IC<sub>50</sub> values ranging from 4.18 to 5.78 <em>μ</em>M, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114414"},"PeriodicalIF":3.2,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143029338","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 : 2025-01-20DOI: 10.1016/j.phytochem.2025.114413
Yu Liang , Xuanni Chen , Qin Li , Ziming Zhao , Hao Wang , Qingyi Tong , Weiguang Sun , Hucheng Zhu , Yongji Lai , Chunmei Chen , Yonghui Zhang
Nine undescribed prenylxanthone derivatives, aspergixanthones L−T (1−9), were isolated from the fungus Aspergillus stellatus. Compound 4 represents the first propionylated prenylxanthone, while compounds 7−9 are the first examples of prenylxanthones adorned with a 2,3-butanediol group. Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction, Mo2(OAc)4 induced ECD experiment, and Mosherʼs method. Compound 9 showed cytotoxic effects against several human cancer cell lines with the IC50 values ranging from 3.35 ± 0.58 to 8.62 ± 1.18 μM. Compounds 7 and 8 showed suppressive effects on NO production with IC50 values of 7.30 ± 0.69 and 5.16 ± 0.17 μM, respectively.
{"title":"Aspergixanthones L−T, nine undescribed prenylxanthone derivatives from Aspergillus stellatus","authors":"Yu Liang , Xuanni Chen , Qin Li , Ziming Zhao , Hao Wang , Qingyi Tong , Weiguang Sun , Hucheng Zhu , Yongji Lai , Chunmei Chen , Yonghui Zhang","doi":"10.1016/j.phytochem.2025.114413","DOIUrl":"10.1016/j.phytochem.2025.114413","url":null,"abstract":"<div><div>Nine undescribed prenylxanthone derivatives, aspergixanthones L−T (<strong>1</strong>−<strong>9</strong>), were isolated from the fungus <em>Aspergillus stellatus</em>. Compound <strong>4</strong> represents the first propionylated prenylxanthone, while compounds <strong>7</strong>−<strong>9</strong> are the first examples of prenylxanthones adorned with a 2,3-butanediol group. Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction, Mo<sub>2</sub>(OAc)<sub>4</sub> induced ECD experiment, and Mosherʼs method. Compound <strong>9</strong> showed cytotoxic effects against several human cancer cell lines with the IC<sub>50</sub> values ranging from 3.35 ± 0.58 to 8.62 ± 1.18 <em>μ</em>M. Compounds <strong>7</strong> and <strong>8</strong> showed suppressive effects on NO production with IC<sub>50</sub> values of 7.30 ± 0.69 and 5.16 ± 0.17 <em>μ</em>M, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114413"},"PeriodicalIF":3.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143023990","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 : 2025-01-20DOI: 10.1016/j.phytochem.2025.114412
Shuai-Shuai Zhang , Zong-Mei Wu , Ying Wu , Ya-Jun Zeng , Yuan-Yuan Zhang , Xin-Li Lin , Si Zhang , Kai-Xuan Zhan , Hou-Wen Lin , Shu-Ping Wang
Four previously undescribed cyclic peptides, reniochpeptins A–D (1–4), were isolated from the marine sponge Reniochalina sp. Their structures were elucidated through comprehensive spectroscopic analyses and a modified advanced Marfey's method. This method utilized ultra-high-performance liquid chromatography coupled with tandem multiple reaction monitoring mass spectrometry, employing a CORTECS T3 column to achieve simultaneous separation of derivatized L-Leu, L-Ile, L-allo-Ile, D-Leu, D-Ile, and D-allo-Ile within 25 min in a single analytical run. Reniochpeptin A displayed moderate inhibitory activity against NCI–H460 cells, with an IC50 value of 4.7 μM, by inducing cell cycle arrest at the G2/M phase and promoting apoptosis.
{"title":"Discovery and configurations assignment of Ile/Leu-containing cyclic peptides with cytotoxic activity, Reniochpeptins A–D, from the marine sponge Reniochalina sp.","authors":"Shuai-Shuai Zhang , Zong-Mei Wu , Ying Wu , Ya-Jun Zeng , Yuan-Yuan Zhang , Xin-Li Lin , Si Zhang , Kai-Xuan Zhan , Hou-Wen Lin , Shu-Ping Wang","doi":"10.1016/j.phytochem.2025.114412","DOIUrl":"10.1016/j.phytochem.2025.114412","url":null,"abstract":"<div><div>Four previously undescribed cyclic peptides, reniochpeptins A–D (<strong>1</strong>–<strong>4</strong>), were isolated from the marine sponge <em>Reniochalina</em> sp. Their structures were elucidated through comprehensive spectroscopic analyses and a modified advanced Marfey's method. This method utilized ultra-high-performance liquid chromatography coupled with tandem multiple reaction monitoring mass spectrometry, employing a CORTECS T<sub>3</sub> column to achieve simultaneous separation of derivatized <sub>L</sub>-Leu, <sub>L</sub>-Ile, <sub>L</sub>-<em>allo</em>-Ile, <sub>D</sub>-Leu, <sub>D</sub>-Ile, and <sub>D</sub>-<em>allo</em>-Ile within 25 min in a single analytical run. Reniochpeptin A displayed moderate inhibitory activity against NCI–H460 cells, with an IC<sub>50</sub> value of 4.7 μM, by inducing cell cycle arrest at the G2/M phase and promoting apoptosis.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114412"},"PeriodicalIF":3.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143023992","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 : 2025-01-18DOI: 10.1016/j.phytochem.2025.114408
Yan Liu , Junnan Li , Yan Sun , Juan Pan , Yumeng Luo , Wei Guan , Qingshan Chen , Lili Zhang , Anam Naseem , Haixue Kuang , Bingyou Yang
Nine previously undescribed chromones, named sadivamones O–W (1–9), and five known analogues (10–14), were isolated from the roots of Saposhnikovia divaricata (Turcz.) Schischk. The detailed structural analysis of each compound was finalized by a variety of methods including NMR (1D and 2D), mass spectrometry (HR-ESI-MS) spectroscopic data, and sugar hydrolysis. The absolute configurations of compounds (4–5) were determined by CD. Moreover, compounds 1–14 were evaluated for their inhibition of IL-1β-induced proliferative activity in SW982 cells. The results demonstrated that compounds 2–4 and 11–12 exhibited notable inhibitory effects on IL-1β-induced proliferation in a concentration-dependent manner, with the most pronounced inhibition observed at a concentration of 20 μM.
{"title":"Chromones from Saposhnikovia divaricata and their inhibition of IL-1β-induced proliferative activity in SW982 cells","authors":"Yan Liu , Junnan Li , Yan Sun , Juan Pan , Yumeng Luo , Wei Guan , Qingshan Chen , Lili Zhang , Anam Naseem , Haixue Kuang , Bingyou Yang","doi":"10.1016/j.phytochem.2025.114408","DOIUrl":"10.1016/j.phytochem.2025.114408","url":null,"abstract":"<div><div>Nine previously undescribed chromones, named sadivamones O–W (<strong>1</strong>–<strong>9</strong>), and five known analogues (<strong>10</strong>–<strong>14</strong>), were isolated from the roots of <em>Saposhnikovia divaricata</em> (Turcz.) Schischk. The detailed structural analysis of each compound was finalized by a variety of methods including NMR (1D and 2D), mass spectrometry (HR-ESI-MS) spectroscopic data, and sugar hydrolysis. The absolute configurations of compounds (<strong>4</strong>–<strong>5</strong>) were determined by CD. Moreover, compounds <strong>1</strong>–<strong>14</strong> were evaluated for their inhibition of IL-1<em>β</em>-induced proliferative activity in SW982 cells. The results demonstrated that compounds <strong>2</strong>–<strong>4</strong> and <strong>11</strong>–<strong>12</strong> exhibited notable inhibitory effects on IL-1<em>β</em>-induced proliferation in a concentration-dependent manner, with the most pronounced inhibition observed at a concentration of 20 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114408"},"PeriodicalIF":3.2,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009584","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 : 2025-01-18DOI: 10.1016/j.phytochem.2025.114410
Yergazy Shybyray , Liu Liu , Haiqing Zhao , Jun Li , Haji Akber Aisa
Twelve flavonoid glycosides including five undescribed ones, lepisativutimines Q−U, were isolated and identified from Lepidium sativum seeds. Acid hydrolysis followed by acetic derivatization and GC analysis were conducted to determine the absolute configurations for sugars. Lepisativutimine U and beitingxinhuangtong A were uncommon kaempferol 8-S-glycosides, and complete NMR data of beitingxinhuangtong A were provided for the first time. Mass fragmentation pathways of isolated compounds were deduced based on their MS/MS data, and characteristic mass fragmentation patterns were summarized. Lepisativutimine U and kaempferol-7-O-α-l-rhamnopyranoside exhibited weak anti-diabetic activity against PTP1B with IC50 values of 60.58 ± 3.53 and 33.90 ± 2.89 μM, respectively, quercetin-7-O-α-l-rhamnopyranoside displayed significant anti-diabetic activity against α-glucosidase with an IC50 value of 25.96 ± 0.30 μM, and kaempferol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside and kaempferol-7-O-α-l-rhamnopyranoside showed weak inhibitory activity against NO release in LPS-induced RAW264.7 cells with IC50 values of 92.28 ± 4.19 and 40.77 ± 1.50 μM, respectively.
从Lepidium satium种子中分离鉴定了12种黄酮类苷，其中5种为未描述的lepisativatimine Q-U。通过酸水解、乙酸衍生化和气相色谱分析确定糖的绝对构型。麻草碱U和北京新黄通A是少见的山奈酚8- s苷类化合物，首次获得了北京新黄通A的完整NMR数据。根据分离化合物的质谱/质谱数据，推导了分离化合物的质谱裂解途径，总结了分离化合物的质谱裂解模式。槲皮素-7- o -α-l-鼠李糖苷对α-葡萄糖苷酶的IC50值为25.96±0.30 μM，槲皮素-7- o -α-l-鼠李糖苷对PTP1B的IC50值为60.58±3.53 μM，山奈酚-7- o -α-l-鼠李糖苷对α-葡萄糖苷酶的IC50值为33.90±2.89 μM。山奈酚3-O-β-d-葡萄糖吡喃糖基-(1→2)-β-d-半乳糖吡喃苷-7- o -α-l-鼠李糖苷和山奈酚7- o -α-l-鼠李糖苷对lps诱导的RAW264.7细胞NO释放的抑制作用较弱，IC50值分别为92.28±4.19 μM和40.77±1.50 μM。
{"title":"Flavonoid glycosides in Lepidium sativum seeds and their bioactivities","authors":"Yergazy Shybyray , Liu Liu , Haiqing Zhao , Jun Li , Haji Akber Aisa","doi":"10.1016/j.phytochem.2025.114410","DOIUrl":"10.1016/j.phytochem.2025.114410","url":null,"abstract":"<div><div>Twelve flavonoid glycosides including five undescribed ones, lepisativutimines Q−U, were isolated and identified from <em>Lepidium sativum</em> seeds. Acid hydrolysis followed by acetic derivatization and GC analysis were conducted to determine the absolute configurations for sugars. Lepisativutimine U and beitingxinhuangtong A were uncommon kaempferol 8-<em>S</em>-glycosides, and complete NMR data of beitingxinhuangtong A were provided for the first time. Mass fragmentation pathways of isolated compounds were deduced based on their MS/MS data, and characteristic mass fragmentation patterns were summarized. Lepisativutimine U and kaempferol-7-<em>O</em>-<em>α</em>-<span>l</span>-rhamnopyranoside exhibited weak anti-diabetic activity against PTP1B with IC<sub>50</sub> values of 60.58 ± 3.53 and 33.90 ± 2.89 <em>μ</em>M, respectively, quercetin-7-<em>O</em>-<em>α</em>-<span>l</span>-rhamnopyranoside displayed significant anti-diabetic activity against <em>α</em>-glucosidase with an IC<sub>50</sub> value of 25.96 ± 0.30 <em>μ</em>M, and kaempferol 3-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranosyl-(1 → 2)-<em>β</em>-<span>d</span>-galactopyranoside-7-<em>O</em>-<em>α</em>-<span>l</span>-rhamnopyranoside and kaempferol-7-<em>O</em>-<em>α</em>-<span>l</span>-rhamnopyranoside showed weak inhibitory activity against NO release in LPS-induced RAW264.7 cells with IC<sub>50</sub> values of 92.28 ± 4.19 and 40.77 ± 1.50 <em>μ</em>M, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114410"},"PeriodicalIF":3.2,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009746","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 : 2025-01-18DOI: 10.1016/j.phytochem.2025.114403
Yueyue Lei , Dawei Xu , Yuexuan Wang , Shiwen Guo , Lujun Li , Mengyin Luo , Xu Li , Xinyi Liu , Chunyang Shi
Previously undescribed triterpenoid saponins (1–8), along with eight previously reported analogues (9–16), were isolated from an EtOAc extract obtained from the roots of Rubus setchuenensis. Structures were established based on HRESIMS, 1D and 2D NMR, as well as by literature comparisons. All compounds were isolated for the first time from the genus Rubus. Compounds 3–4, 6–8, and 12–15 displayed inhibitory activities against NO production in a RAW264.7 cell inflammation model induced by LPS. Moreover, 4, 6–8, and 12–13 exhibited inhibitory effects in a LPS-induced BV-2 cell neuroinflammation model.
{"title":"Triterpenoid saponins from Rubus setchuenensis roots and their anti-inflammatory activities in vitro","authors":"Yueyue Lei , Dawei Xu , Yuexuan Wang , Shiwen Guo , Lujun Li , Mengyin Luo , Xu Li , Xinyi Liu , Chunyang Shi","doi":"10.1016/j.phytochem.2025.114403","DOIUrl":"10.1016/j.phytochem.2025.114403","url":null,"abstract":"<div><div>Previously undescribed triterpenoid saponins (<strong>1–8</strong>), along with eight previously reported analogues (<strong>9–16</strong>), were isolated from an EtOAc extract obtained from the roots of <em>Rubus setchuenensis</em>. Structures were established based on HRESIMS, 1D and 2D NMR, as well as by literature comparisons. All compounds were isolated for the first time from the genus <em>Rubus</em>. Compounds <strong>3</strong>–<strong>4</strong>, <strong>6</strong>–<strong>8,</strong> and <strong>12</strong>–<strong>15</strong> displayed inhibitory activities against NO production in a RAW264.7 cell inflammation model induced by LPS. Moreover, <strong>4, 6</strong>–<strong>8,</strong> and <strong>12–13</strong> exhibited inhibitory effects in a LPS-induced BV-2 cell neuroinflammation model.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114403"},"PeriodicalIF":3.2,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009766","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 : 2025-01-16DOI: 10.1016/j.phytochem.2025.114409
Meng-Fei Wang , Tian-Ze Li , Yun-Bao Ma , Yong-Cui Wang , Qi-Hao Li , Feng-Jiao Li , Ji-Jun Chen
Artemyriantholidimers A-G (1–7), seven undescribed guaiane-type sesquiterpenoid dimers (GSDs), and 27 known compounds (8–34) were isolated from Artemisia myriantha (Asteraceae). Their structures and relative configurations were elucidated based on the comprehensive analyses of UV, IR, MS, NMR data, quantum chemical NMR calculations with DP4+ probability analyses, and the absolute configurations were elucidated by ECD calculations. The undescribed GSDs (1–7) were presumably formed via Diels-Alder reactions, and compounds 5–7 were rare GSDs with α-configuration of H-6'. Compounds 4–7 showed significant inhibition on HepG2, Huh7, and SK-Hep-1 cells with IC50 values ranging from 6.9 to 13.0 μM by antihepatoma assay. The best active compound 5 was deduced to be targeted on the protein AURKA of the p53 signaling pathway by network pharmacological analysis with a high bind affinity of AURKA (total score: −8.98) by molecular docking, and had a KD value of 62.4 μM by surface plasmon resonance assay.
{"title":"Artemyriantholidimers A-G, undescribed guaiane-type sesquiterpenoid dimers from Artemisia myriantha and their antihepatoma activities","authors":"Meng-Fei Wang , Tian-Ze Li , Yun-Bao Ma , Yong-Cui Wang , Qi-Hao Li , Feng-Jiao Li , Ji-Jun Chen","doi":"10.1016/j.phytochem.2025.114409","DOIUrl":"10.1016/j.phytochem.2025.114409","url":null,"abstract":"<div><div>Artemyriantholidimers A-G (<strong>1</strong>–<strong>7</strong>), seven undescribed guaiane-type sesquiterpenoid dimers (GSDs), and 27 known compounds (<strong>8</strong>–<strong>34</strong>) were isolated from <em>Artemisia myriantha</em> (Asteraceae). Their structures and relative configurations were elucidated based on the comprehensive analyses of UV, IR, MS, NMR data, quantum chemical NMR calculations with DP4+ probability analyses, and the absolute configurations were elucidated by ECD calculations. The undescribed GSDs (<strong>1</strong>–<strong>7</strong>) were presumably formed <em>via</em> Diels-Alder reactions, and compounds <strong>5</strong>–<strong>7</strong> were rare GSDs with <em>α</em>-configuration of H-6'. Compounds <strong>4</strong>–<strong>7</strong> showed significant inhibition on HepG2, Huh7, and SK-Hep-1 cells with IC<sub>50</sub> values ranging from 6.9 to 13.0 μM by antihepatoma assay. The best active compound <strong>5</strong> was deduced to be targeted on the protein AURKA of the p53 signaling pathway by network pharmacological analysis with a high bind affinity of AURKA (total score: −8.98) by molecular docking, and had a K<sub>D</sub> value of 62.4 μM by surface plasmon resonance assay.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114409"},"PeriodicalIF":3.2,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009775","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 : 2025-01-16DOI: 10.1016/j.phytochem.2025.114407
Yu Wei Huang , Jing Guan , Yin Tang , Ren Xiang Tan , Li Ping Lin
Five previously undescribed phenylpyridones, designated as citridones H–L (1–5), along with seven known compounds, were characterized from the rice medium culture of the Cineraria repanda-derived endophytic fungus Penicillium oxalicum. Their structures were elucidated through detailed interpretation of UV, NMR, and HR-ESI-MS data. The absolute configurations of C-2 and C-3 in compounds 1–4 were determined by spectroscopic analysis and ECD calculations, while the C-5′ configurations were established through computational 13C NMR and DP4+ analyses. These compounds represent a novel scaffold of chromone-phenylpyridone hybrids, making only the second report of such compounds from the Penicillium genus and the first to feature a unique (E)-5-methylhepta-1,3-diene group at the C-2 position. Additionally, a biosynthetic pathway for these novel chromone-phenylpyridones is proposed for the first time. Notably, compounds 3 and 4 exhibited cytotoxicity against HCT116 and H1299 cell lines when used in combination, with IC50 values of 4.15 ± 0.34 and 9.07 ± 1.64 μM, respectively. Furthermore, compounds 3, 4 and 5 demonstrated significant inhibitory effects against Staphylococcus aureus, with MIC values of 64, 64 and 8 μg/mL, respectively.
{"title":"Five undescribed chromone-phenylpyridone hybrids from Cineraria repanda-derived Penicillium oxalicum with cytotoxic and antibacterial activity","authors":"Yu Wei Huang , Jing Guan , Yin Tang , Ren Xiang Tan , Li Ping Lin","doi":"10.1016/j.phytochem.2025.114407","DOIUrl":"10.1016/j.phytochem.2025.114407","url":null,"abstract":"<div><div>Five previously undescribed phenylpyridones, designated as citridones <strong>H</strong>–<strong>L</strong> (<strong>1</strong>–<strong>5</strong>), along with seven known compounds, were characterized from the rice medium culture of the <em>Cineraria repanda</em>-derived endophytic fungus <em>Penicillium oxalicum</em>. Their structures were elucidated through detailed interpretation of UV, NMR, and HR-ESI-MS data. The absolute configurations of C-2 and C-3 in compounds <strong>1</strong>–<strong>4</strong> were determined by spectroscopic analysis and ECD calculations, while the C-5′ configurations were established through computational <sup>13</sup>C NMR and DP4+ analyses. These compounds represent a novel scaffold of chromone-phenylpyridone hybrids, making only the second report of such compounds from the <em>Penicillium</em> genus and the first to feature a unique (<em>E</em>)-5-methylhepta-1,3-diene group at the C-2 position. Additionally, a biosynthetic pathway for these novel chromone-phenylpyridones is proposed for the first time. Notably, compounds <strong>3</strong> and <strong>4</strong> exhibited cytotoxicity against HCT116 and H1299 cell lines when used in combination, with IC<sub>50</sub> values of 4.15 ± 0.34 and 9.07 ± 1.64 μM, respectively. Furthermore, compounds <strong>3</strong>, <strong>4</strong> and <strong>5</strong> demonstrated significant inhibitory effects against <em>Staphylococcus aureus</em>, with MIC values of 64, 64 and 8 μg/mL, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114407"},"PeriodicalIF":3.2,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009748","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 : 2025-01-16DOI: 10.1016/j.phytochem.2025.114406
Rodrigo Silva de Andrade , Kaio Aragão Sales , Edileuza Bezerra de Assis , Lucas Silva Abreu , Ana Carolina Ferreira de Albuquerque , Fernando Martins dos Santos Junior , Natália Ferreira de Sousa , Paulo Bruno Araújo Loureiro , Geraldo Moisés Wanderley Amorim , Marianna Vieira Sobral , Marcus Tullius Scotti , Josean Fechine Tavares , Marcelo Sobral da Silva
Eleven previously undescribed macrocyclic humulene sesquiterpenoids, dolichocarpols G−Q (1−11), five undescribed bicyclic, dolichocarpols R−V (12−16) and two undescribed norsesquiterpenes, dolichocarpols W−X (17−18) were isolated from the roots of Anaxagorea dolichocarpa. Their structures were unequivocally determined by the analysis of NMR, HRESIMS, and IR data, along with NMR and ECD quantum-mechanical calculations, followed by the application of the DP4+ method. Most compounds possess an ether bridge between different carbons, whereas compounds 13/14 and 15/16 are diastereomers isomerized at C-7/C-10 and at C-7/C-10/C-12, respectively. The antineuroinflammatory activity of compounds 1−18 was tested in an LPS/IFN-γ-stimulated BV2 microglial cell line. Compounds 1, 5, 8, 9 and 14 significantly reduced nitric oxide (NO) levels in a concentration-dependent manner (25–200 μM). Moreover, possible interactions between these bioactive compounds and inducible nitric oxide synthase (iNOS) were predicted via in silico studies. NO is known as an inflammatory mediator in neurodegenerative diseases; therefore, the effects of these compounds indicate their potential antineuroinflammatory activity.
{"title":"Dolichocarpols G−X: Previously undescribed macrocyclic humulene sesquiterpenoids from Anaxagorea dolichocarpa","authors":"Rodrigo Silva de Andrade , Kaio Aragão Sales , Edileuza Bezerra de Assis , Lucas Silva Abreu , Ana Carolina Ferreira de Albuquerque , Fernando Martins dos Santos Junior , Natália Ferreira de Sousa , Paulo Bruno Araújo Loureiro , Geraldo Moisés Wanderley Amorim , Marianna Vieira Sobral , Marcus Tullius Scotti , Josean Fechine Tavares , Marcelo Sobral da Silva","doi":"10.1016/j.phytochem.2025.114406","DOIUrl":"10.1016/j.phytochem.2025.114406","url":null,"abstract":"<div><div>Eleven previously undescribed macrocyclic humulene sesquiterpenoids, dolichocarpols G−Q (<strong>1</strong>−<strong>11</strong>), five undescribed bicyclic, dolichocarpols R−V (<strong>12</strong>−<strong>16</strong>) and two undescribed norsesquiterpenes, dolichocarpols W−X (<strong>17</strong>−<strong>18</strong>) were isolated from the roots of <em>Anaxagorea dolichocarpa</em>. Their structures were unequivocally determined by the analysis of NMR, HRESIMS, and IR data, along with NMR and ECD quantum-mechanical calculations, followed by the application of the DP4+ method. Most compounds possess an ether bridge between different carbons, whereas compounds <strong>13</strong>/<strong>14</strong> and <strong>15</strong>/<strong>16</strong> are diastereomers isomerized at C-7/C-10 and at C-7/C-10/C-12, respectively. The antineuroinflammatory activity of compounds <strong>1</strong>−<strong>18</strong> was tested in an LPS/IFN-γ-stimulated BV2 microglial cell line. Compounds <strong>1</strong>, <strong>5</strong>, <strong>8</strong>, <strong>9</strong> and <strong>14</strong> significantly reduced nitric oxide (NO) levels in a concentration-dependent manner (25–200 μM). Moreover, possible interactions between these bioactive compounds and inducible nitric oxide synthase (iNOS) were predicted via <em>in silico studies</em>. NO is known as an inflammatory mediator in neurodegenerative diseases; therefore, the effects of these compounds indicate their potential antineuroinflammatory activity.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114406"},"PeriodicalIF":3.2,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009788","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 : 2025-01-15DOI: 10.1016/j.phytochem.2025.114405
Xiuli Wang , Yang Xu , Zhiqi Zhang , Hua Li , Lixia Chen
Delphinium forrestii var. viride is a plant of the genus Delphinium in the family Ranunculaceae. The chemical composition of the 95% ethanol extract of the whole herb of D. forrestii var. viride was investigated. 7 previously undescribed C19-type diterpenoid alkaloids along with 5 known ones were isolated from D. forrestii var. viride. Based on chemical evidence and spectral data analysis (UV, optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of new compounds were elucidated. All compounds were also tested for anti-inflammatory effects. Our work has enriched the chemical diversity of D. forrestii var. viride and the Delphinium genus, providing valuable information for further research.
{"title":"C19-diterpenoid alkaloids isolated from Delphinium forrestii var. viride","authors":"Xiuli Wang , Yang Xu , Zhiqi Zhang , Hua Li , Lixia Chen","doi":"10.1016/j.phytochem.2025.114405","DOIUrl":"10.1016/j.phytochem.2025.114405","url":null,"abstract":"<div><div><em>Delphinium forrestii</em> var. <em>viride</em> is a plant of the genus <em>Delphinium</em> in the family Ranunculaceae. The chemical composition of the 95% ethanol extract of the whole herb of <em>D. forrestii</em> var. <em>viride</em> was investigated. 7 previously undescribed C<sub>19</sub>-type diterpenoid alkaloids along with 5 known ones were isolated from <em>D. forrestii</em> var. <em>viride</em>. Based on chemical evidence and spectral data analysis (UV, optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of new compounds were elucidated. All compounds were also tested for anti-inflammatory effects. Our work has enriched the chemical diversity of <em>D. forrestii</em> var. <em>viride</em> and the <em>Delphinium</em> genus, providing valuable information for further research.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114405"},"PeriodicalIF":3.2,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143009782","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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