Pub Date : 2024-10-22DOI: 10.1016/j.phytochem.2024.114307
Shu-Lan Liu , Xue-Ling Huang , Shun-Hua Zhong , Yong-Hui Ma , Feng Wei , Yu-Ye Zhang , Jin Li , Ke-Jian Pang , Ping Zhao , Xin-Zhou Yang
Seven unreported compounds were isolated from dried flower buds of Ochrocarpus longifolius in this study, including an alkaloid ochrocaracid A (1), five coumarins ochrocarpins I (2), J (3), K (4), L (5), and M (6), and one styryl-2-pyranone compound iresinoacid (7) and nine known compounds (8–16). All these compounds were found in O. longifolius for the first time. Their structural elucidation was achieved through NMR, HR-ESI-MS, and ECD data. Additionally, a glucose uptake-promoting activity assay revealed that compounds 10 (128.21 μM) and 16 (123.15 μM) increased the glucose uptake capacity of L6 cells by 1.49-fold and 1.48-fold, respectively. These bioactive compounds could be potential candidates for further pharmaceutical applications.
本研究从 Ochrocarpus longifolius 的干燥花蕾中分离出了七种未报道的化合物，包括一种生物碱 ochrocaracid A (1)，五种香豆素 ochrocarpins I (2)、J (3)、K (4)、L (5) 和 M (6)，一种苯乙烯基-2-吡喃酮化合物 iresinoacid (7) 以及九种已知化合物 (8-16)。所有这些化合物都是首次在 O. longifolius 中发现。通过 NMR、HR-ESI-MS 和 ECD 数据，这些化合物的结构得以阐明。此外，葡萄糖摄取促进活性测定显示，化合物 10（128.21 μM）和 16（123.15 μM）分别将 L6 细胞的葡萄糖摄取能力提高了 1.49 倍和 1.48 倍。这些生物活性化合物可能成为进一步的药物应用候选化合物。
{"title":"Seven undescribed compounds from dried flower buds of Ochrocarpus longifolius","authors":"Shu-Lan Liu , Xue-Ling Huang , Shun-Hua Zhong , Yong-Hui Ma , Feng Wei , Yu-Ye Zhang , Jin Li , Ke-Jian Pang , Ping Zhao , Xin-Zhou Yang","doi":"10.1016/j.phytochem.2024.114307","DOIUrl":"10.1016/j.phytochem.2024.114307","url":null,"abstract":"<div><div>Seven unreported compounds were isolated from dried flower buds of <em>Ochrocarpus longifolius</em> in this study, including an alkaloid ochrocaracid A (<strong>1</strong>), five coumarins ochrocarpins I (<strong>2</strong>), J (<strong>3</strong>), K (<strong>4</strong>), L (<strong>5</strong>), and M (<strong>6</strong>), and one styryl-2-pyranone compound iresinoacid (<strong>7</strong>) and nine known compounds (<strong>8</strong>–<strong>16</strong>). All these compounds were found in <em>O. longifolius</em> for the first time. Their structural elucidation was achieved through NMR, HR-ESI-MS, and ECD data. Additionally, a glucose uptake-promoting activity assay revealed that compounds <strong>10</strong> (128.21 μM) and <strong>16</strong> (123.15 μM) increased the glucose uptake capacity of L6 cells by 1.49-fold and 1.48-fold, respectively. These bioactive compounds could be potential candidates for further pharmaceutical applications.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114307"},"PeriodicalIF":3.2,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142505942","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 : 2024-10-19DOI: 10.1016/j.phytochem.2024.114308
Warsan Nora Mohamed , Hussain Shakeel Butt , Thomas J. Schmidt , Andrea Angelov Eltvik , Desheng Wu , Karl Egil Malterud , Marit Inngjerdingen , Kari Tvete Inngjerdingen , Helle Wangensteen
Daphne mezereum L. (Thymelaeaceae) was an important medicinal plant in Norway during the 18th and 19th centuries and used against diseases such as diarrhea, swelling, stomach pain, and tuberculosis. Five previously undescribed phenolic compounds, including two biflavonoids with a catechin core structure, two tricoumarins, and one bicoumarin, together with ten known compounds were isolated from a 50% EtOH extract of the bark of D. mezereum. Using NMR, HRESIMS, acid hydrolysis, and circular dichroism spectra, the biflavonoids were identified as 3′-hydroxygenkwanol A and 3′-hydroxydihydrodaphnodorin B, and the coumarins were identified as 3‴-O-acetyltriumbellin, triumbellin 4‴-O-β-d-glucopyranoside, and daphnogitin-7-O-β-d-glucopyranoside. The absolute configuration of dihydrodaphnodorin B was for the first time established as 2R, 3S, 2″S, 3″S. Daphnin, syringin, 3′-hydroxydihydrodaphnodorin B, dihydrodaphnodorin B, and neochamaejasmin A and B were identified as the major secondary metabolites in the extract. Neochamaejasmin A and B showed the most potent inhibition of TNF-α secretion in Con A stimulated peripheral blood mononuclear cells (PBMCs) with 71.3 ± 3.4 and 83.5 ± 11.5% inhibition, respectively, at 50 μM.
Daphne mezereum L.（百里香科）在十八和十九世纪是挪威的一种重要药用植物，可用于治疗腹泻、浮肿、胃痛和肺结核等疾病。从 D. mezereum 树皮的 50% EtOH 提取物中分离出了五种以前未曾描述过的酚类化合物，包括两种具有儿茶素核心结构的双黄酮类化合物、两种三香豆素类化合物和一种双香豆素类化合物，以及十种已知化合物。利用核磁共振、HRESIMS、酸水解和圆二色光谱，双黄酮被鉴定为 3'-hydroxygenkwanol A 和 3'-hydroxydihydrodaphnodorin B，香豆素被鉴定为 3'''-O-acetyltriumbellin, triumbellin 4'''-O-β-D-glucopyranoside 和 daphnogitin-7-O-β-D-glucopyranoside 。首次确定了二氢萘啶 B 的绝对构型为 2R、3S、2''S、3''S。经鉴定，提取物中的主要次生代谢物为水飞蓟素、丁香素、3'-羟基二氢水飞蓟素 B、二氢水飞蓟素 B、新矢车菊素 A 和 B。新蛇床子素 A 和 B 对 Con A 刺激的外周血单核细胞（PBMCs）分泌 TNF-α 的抑制作用最强，在 50 μM 时的抑制率分别为 71.3 ± 3.4% 和 83.5 ± 11.5%。
{"title":"Biflavonoids and bi- and tricoumarins from Daphne mezereum and inhibition of TNF-α secretion","authors":"Warsan Nora Mohamed , Hussain Shakeel Butt , Thomas J. Schmidt , Andrea Angelov Eltvik , Desheng Wu , Karl Egil Malterud , Marit Inngjerdingen , Kari Tvete Inngjerdingen , Helle Wangensteen","doi":"10.1016/j.phytochem.2024.114308","DOIUrl":"10.1016/j.phytochem.2024.114308","url":null,"abstract":"<div><div><em>Daphne mezereum</em> L. (Thymelaeaceae) was an important medicinal plant in Norway during the 18th and 19th centuries and used against diseases such as diarrhea, swelling, stomach pain, and tuberculosis. Five previously undescribed phenolic compounds, including two biflavonoids with a catechin core structure, two tricoumarins, and one bicoumarin, together with ten known compounds were isolated from a 50% EtOH extract of the bark of <em>D</em>. <em>mezereum</em>. Using NMR, HRESIMS, acid hydrolysis, and circular dichroism spectra, the biflavonoids were identified as 3′-hydroxygenkwanol A and 3′-hydroxydihydrodaphnodorin B, and the coumarins were identified as 3‴-<em>O</em>-acetyltriumbellin, triumbellin 4‴-<em>O</em>-β-<span>d</span>-glucopyranoside, and daphnogitin-7-<em>O</em>-β-<span>d</span>-glucopyranoside. The absolute configuration of dihydrodaphnodorin B was for the first time established as 2R, 3S, 2″S, 3″S. Daphnin, syringin, 3′-hydroxydihydrodaphnodorin B, dihydrodaphnodorin B, and neochamaejasmin A and B were identified as the major secondary metabolites in the extract. Neochamaejasmin A and B showed the most potent inhibition of TNF-α secretion in Con A stimulated peripheral blood mononuclear cells (PBMCs) with 71.3 ± 3.4 and 83.5 ± 11.5% inhibition, respectively, at 50 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114308"},"PeriodicalIF":3.2,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472498","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}
Pub Date : 2024-10-18DOI: 10.1016/j.phytochem.2024.114309
Peng-Jun Zhou , Xi-Ying Wu , Ze-Yu Zhao , Yi Zang , Zhong-Shuai Sun , Yue-Ling Li , Na Li , Juan Xiong , Yeun-Mun Choo , Ze-Xin Jin , Jia Li , Jin-Feng Hu
Parrotia subaequalis, an endangered Tertiary relict tree native to China and a member of the Hamamelidaceae family, is one of several host plant species in this family that exhibit unique ecological habits, such as gall formation. Tree galls are the results of complex interactions between gall-inducing insects and their host plant organs. The formation of galls may serve to protect other regions of the plant from potential damage, often through the production of phytoalexins. In this study, a preliminary investigation was carried out on the metabolites of the 90% MeOH extract derived from the closed spherical galls on the twigs of P. subaequalis. Consequently, nine previously undescribed benzofuran-type and dibenzofuran-type phytoalexins (parrotiagallols A−I, 1−9, respectively) were isolated and characterized, along with several known miscellaneous metabolites (10−17). Their chemical structures and absolute configurations were elucidated using spectroscopic methods, a combination of calculated and experimental electronic circular dichroism data, and single crystal X-ray diffraction analyses. Among these compounds, 1 and 2 are identified as neolignan derivatives, while compounds 3−5 are classified as 9,10-dinorneolignans. Compound 6 represents a rare 2,3-seco-neolignan, and compounds 7−9 are dihydroxy-dimethyl-dibenzofuran derivatives. Parrotiagallol A (1) showed considerable antibacterial activity against Staphylococcus aureus, with an MIC value of 14 μM. Additionally, parrotiagallol E (5) and methyl gallate (17) exhibited inhibitory effects against ATP-citrate lyase (ACL), a potential therapeutic target for hyperlipidemia, with IC50 values of 5.1 and 9.8 μM, respectively. The findings underscore that galls not only serve as physical defense barriers but also benefit from the chemical defense system of the host plants. These insights provide avenues for exploring potential new therapeutic agents for S. aureus infections and ACL-related diseases, while also promoting scientific conservation strategies for P. subaequalis.
{"title":"Benzofurans and dibenzofurans from galls on twigs of the endangered Chinese endemic tree Parrotia subaequalis and their inhibitory properties against Staphylococcus aureus and ATP-citrate lyase","authors":"Peng-Jun Zhou , Xi-Ying Wu , Ze-Yu Zhao , Yi Zang , Zhong-Shuai Sun , Yue-Ling Li , Na Li , Juan Xiong , Yeun-Mun Choo , Ze-Xin Jin , Jia Li , Jin-Feng Hu","doi":"10.1016/j.phytochem.2024.114309","DOIUrl":"10.1016/j.phytochem.2024.114309","url":null,"abstract":"<div><div><em>Parrotia subaequalis</em>, an endangered Tertiary relict tree native to China and a member of the Hamamelidaceae family, is one of several host plant species in this family that exhibit unique ecological habits, such as gall formation. Tree galls are the results of complex interactions between gall-inducing insects and their host plant organs. The formation of galls may serve to protect other regions of the plant from potential damage, often through the production of phytoalexins. In this study, a preliminary investigation was carried out on the metabolites of the 90% MeOH extract derived from the closed spherical galls on the twigs of <em>P. subaequalis</em>. Consequently, nine previously undescribed benzofuran-type and dibenzofuran-type phytoalexins (parrotiagallols A−I, <strong>1</strong>−<strong>9</strong>, respectively) were isolated and characterized, along with several known miscellaneous metabolites (<strong>10</strong>−<strong>17</strong>). Their chemical structures and absolute configurations were elucidated using spectroscopic methods, a combination of calculated and experimental electronic circular dichroism data, and single crystal X-ray diffraction analyses. Among these compounds, <strong>1</strong> and <strong>2</strong> are identified as neolignan derivatives, while compounds <strong>3</strong>−<strong>5</strong> are classified as 9,10-dinorneolignans. Compound <strong>6</strong> represents a rare 2,3-<em>seco</em>-neolignan, and compounds <strong>7</strong>−<strong>9</strong> are dihydroxy-dimethyl-dibenzofuran derivatives. Parrotiagallol A (<strong>1</strong>) showed considerable antibacterial activity against <em>Staphylococcus aureus</em>, with an MIC value of 14 <em>μ</em>M. Additionally, parrotiagallol E (<strong>5</strong>) and methyl gallate (<strong>17</strong>) exhibited inhibitory effects against ATP-citrate lyase (ACL), a potential therapeutic target for hyperlipidemia, with IC<sub>50</sub> values of 5.1 and 9.8 <em>μ</em>M, respectively. The findings underscore that galls not only serve as physical defense barriers but also benefit from the chemical defense system of the host plants. These insights provide avenues for exploring potential new therapeutic agents for <em>S. aureus</em> infections and ACL-related diseases, while also promoting scientific conservation strategies for <em>P</em>. <em>subaequalis</em>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114309"},"PeriodicalIF":3.2,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472497","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 : 2024-10-16DOI: 10.1016/j.phytochem.2024.114298
Qianqian Yin , Gang Chen , Jinle Hao , Bin Lin , Qingqi Meng , Libin Xu , Di Zhou , Yue Hou , Ning Li
Eight cyclopenta[b]benzofurans (1, 2, 4, and 5-9) and eight cyclopenta[bc]benzopyrans (3, 10–16), including a revised (4) and three undescribed compounds (1–3), were isolated from the twigs and leaves of Aglaia edulis (Roxb.) Wall. Their structures were determined by a combination of spectral analysis in conjunction with NMR and ECD calculations. Moreover, based on the findings from 13C NMR calculations and DP4+ statistical analysis, an empirical guideline was established to differentiate the structures of cyclopenta[bc]benzopyrans and cyclopenta[b]benzofurans by aggregating chemical shift data from known compounds. This guideline facilitated the proposal of structural revisions for three previously reported analogs (R-1, R-2, R-3). Biological assay indicated that cyclopenta[b]benzofuran flavalines (2, and 4–8) could significantly inhibit NO production in LPS-induced BV-2 cells with IC50 values from 0.002 to 0.05 μM.
{"title":"Flavaglines with anti-neuroinflammatory activity from Aglaia edulis (Roxb.) Wall. and structure revision of related flavaglines","authors":"Qianqian Yin , Gang Chen , Jinle Hao , Bin Lin , Qingqi Meng , Libin Xu , Di Zhou , Yue Hou , Ning Li","doi":"10.1016/j.phytochem.2024.114298","DOIUrl":"10.1016/j.phytochem.2024.114298","url":null,"abstract":"<div><div>Eight cyclopenta[<em>b</em>]benzofurans (<strong>1</strong>, <strong>2</strong>, <strong>4</strong>, and <strong>5</strong>-<strong>9</strong>) and eight cyclopenta[<em>bc</em>]benzopyrans (<strong>3</strong>, <strong>10</strong>–<strong>16</strong>), including a revised (<strong>4</strong>) and three undescribed compounds (<strong>1</strong>–<strong>3</strong>), were isolated from the twigs and leaves of <em>Aglaia edulis</em> (Roxb.) Wall. Their structures were determined by a combination of spectral analysis in conjunction with NMR and ECD calculations. Moreover, based on the findings from <sup>13</sup>C NMR calculations and DP4+ statistical analysis, an empirical guideline was established to differentiate the structures of cyclopenta[<em>bc</em>]benzopyrans and cyclopenta[<em>b</em>]benzofurans by aggregating chemical shift data from known compounds. This guideline facilitated the proposal of structural revisions for three previously reported analogs (<strong>R-1</strong>, <strong>R-2</strong>, <strong>R-3</strong>). Biological assay indicated that cyclopenta[<em>b</em>]benzofuran flavalines (<strong>2</strong>, and <strong>4–8</strong>) could significantly inhibit NO production in LPS-induced BV-2 cells with IC<sub>50</sub> values from 0.002 to 0.05 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114298"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472500","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 : 2024-10-16DOI: 10.1016/j.phytochem.2024.114301
Corentin Conart, Henrik Toft Simonsen
The liverwort Frullania tamarisci (L.) Dumort produces large amounts of terpenoids, among others the sesquiterpene alcohol tamariscol. Tamariscol has an earthy woody fragrance, and the use in perfurmes and production of it was patented in 1984. The microbial terpene synthase-like (MTPSL) enzyme FtMTPSL6 is shown to be responsible for the biosynthesis of tamariscol. FtMTPSL6 was obtained through RNA sequencing of wild growing F. tamarisci along with six other MTPSLs (FtMTPSL1-7). The biochemical activity was determined for three of them, and two others where metabolic active, but the product could not be identified. The three characterized enzymes are the tamariscol synthase (FtMTPSL6), copaene synthase (FtMTPSL1) and gurjunene synthase (FtMTPSL3). Thus, the biosynthesis of the economically attractive compound tamariscol is established, and this opens up for further exploitation of this molecule.
{"title":"Tamariscol biosynthesis in Frullania tamarisci","authors":"Corentin Conart, Henrik Toft Simonsen","doi":"10.1016/j.phytochem.2024.114301","DOIUrl":"10.1016/j.phytochem.2024.114301","url":null,"abstract":"<div><div>The liverwort <em>Frullania tamarisci</em> (L.) Dumort produces large amounts of terpenoids, among others the sesquiterpene alcohol tamariscol. Tamariscol has an earthy woody fragrance, and the use in perfurmes and production of it was patented in 1984. The microbial terpene synthase-like (MTPSL) enzyme <em>Ft</em>MTPSL6 is shown to be responsible for the biosynthesis of tamariscol. <em>Ft</em>MTPSL6 was obtained through RNA sequencing of wild growing <em>F. tamarisci</em> along with six other MTPSLs (<em>Ft</em>MTPSL1-7). The biochemical activity was determined for three of them, and two others where metabolic active, but the product could not be identified. The three characterized enzymes are the tamariscol synthase (<em>Ft</em>MTPSL6), copaene synthase (<em>Ft</em>MTPSL1) and gurjunene synthase (<em>Ft</em>MTPSL3). Thus, the biosynthesis of the economically attractive compound tamariscol is established, and this opens up for further exploitation of this molecule.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114301"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472501","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}
Pub Date : 2024-10-16DOI: 10.1016/j.phytochem.2024.114305
Kai Guo , Shi-Hong Luo , Yan-Chun Liu , Ting-Ting Zhou , Yan Liu , Sheng-Hong Li
Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of Leucosceptrum canum. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. In vitro immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-γ were evaluated. Among them, 11α-H-leucosceptroid C, 5,13-dehydro-11α-H-leucosceptroid C, 5,13-dehydro-11β-hydroxy-leucosceptroid C, and 5,13-dehydro-11α-hydroxy-leucosceptroid C significantly inhibited IFN-γ secretion with IC50 values of 12.55–23.62 μM. More remarkable inhibitory effects against IFN-γ secretion were observed for 5,13-dehydro-11β-hydroxy-leucosceptroid D, leucosceptroid U, 14-epi-leucosceptroid U, leucosceptroid V, and 14-epi-leucosceptroid V, with IC50 values of 4.32–9.47 μM.
从 Leucosceptrum canum 的叶子中分离出了十种未曾描述过的具有对偶环戊烯酮分子的 leucosceptrane-type sesterterpenoids。通过综合光谱分析（包括一维和二维核磁共振以及 HRMS）和 ECD 计算，阐明了它们的结构，包括绝对构型。评估了这些酯萜类化合物对 T 细胞增殖和细胞因子 IFN-γ 分泌的体外免疫抑制作用。其中 11α-H-leucosceptroid C、5,13-dehydro-11α-H-leucosceptroid C、5,13-dehydro-11β-hydroxy-leucosceptroid C 和 5,13-dehydro-11α-hydroxy-leucosceptroid C 能显著抑制 IFN-γ 的分泌，其 IC50 值为 12.55-23.62 μM。5,13-脱氢-11β-羟基-亮腺受体 D、亮腺受体 U、14-表-亮腺受体 U、亮腺受体 V 和 14-表-亮腺受体 V 对 IFN-γ 分泌的抑制作用更为明显，IC50 值为 4.32-9.47 μM。
{"title":"Immunosuppressive leucosceptrane-type sesterterpenoids with antipodal cyclopentenones isolated from Leucosceptrum canum","authors":"Kai Guo , Shi-Hong Luo , Yan-Chun Liu , Ting-Ting Zhou , Yan Liu , Sheng-Hong Li","doi":"10.1016/j.phytochem.2024.114305","DOIUrl":"10.1016/j.phytochem.2024.114305","url":null,"abstract":"<div><div>Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of <em>Leucosceptrum canum</em>. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. <em>In vitro</em> immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-<em>γ</em> were evaluated. Among them, 11<em>α</em>-<em>H</em>-leucosceptroid C, 5,13-dehydro-11<em>α</em>-<em>H</em>-leucosceptroid C, 5,13-dehydro-11<em>β</em>-hydroxy-leucosceptroid C, and 5,13-dehydro-11<em>α</em>-hydroxy-leucosceptroid C significantly inhibited IFN-<em>γ</em> secretion with IC<sub>50</sub> values of 12.55–23.62 μM. More remarkable inhibitory effects against IFN-<em>γ</em> secretion were observed for 5,13-dehydro-11<em>β</em>-hydroxy-leucosceptroid D, leucosceptroid U, 14-<em>epi</em>-leucosceptroid U, leucosceptroid V, and 14-<em>epi</em>-leucosceptroid V, with IC<sub>50</sub> values of 4.32–9.47 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114305"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472505","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 : 2024-10-16DOI: 10.1016/j.phytochem.2024.114299
Jinchun Nie , Shuang Guo , Didi Wang , Zhenwei Li , Daidi Zhang , Wei Li , De-an Guo
Aspongpyridiniums A−J (1−10), ten previously undescribed amino acid-derived pyridinium salts were isolated and identified from the n-BuOH fraction of the 50% MeOH extract of insect species Aspongopus chinensis, well-known for its use in traditional Chinese medicine for the treatment of pain, indigestion and kidney diseases. Their structures were determined by extensive spectroscopic data as well as electronic circular dichroism calculations and comparisons. Aspongpyridiniums A−J are structurally characterized by a unique 1,3,4-trisubstituted pyridinium skeleton with a variable functional group derived from an amino acid unit. In bioassays, Compounds 5 and 10 exhibited certain inhibitory activities against α-glucosidase, while 1−10 showed moderate to weak acetylcholinesterase inhibitory effects.
{"title":"Aspongpyridiniums A−J, amino acid-derived pyridinium salts from insect species Aspongopus chinensis","authors":"Jinchun Nie , Shuang Guo , Didi Wang , Zhenwei Li , Daidi Zhang , Wei Li , De-an Guo","doi":"10.1016/j.phytochem.2024.114299","DOIUrl":"10.1016/j.phytochem.2024.114299","url":null,"abstract":"<div><div>Aspongpyridiniums A−J (<strong>1</strong>−<strong>10</strong>), ten previously undescribed amino acid-derived pyridinium salts were isolated and identified from the <em>n</em>-BuOH fraction of the 50% MeOH extract of insect species <em>Aspongopus chinensis</em>, well-known for its use in traditional Chinese medicine for the treatment of pain, indigestion and kidney diseases. Their structures were determined by extensive spectroscopic data as well as electronic circular dichroism calculations and comparisons. Aspongpyridiniums A−J are structurally characterized by a unique 1,3,4-trisubstituted pyridinium skeleton with a variable functional group derived from an amino acid unit. In bioassays, Compounds <strong>5</strong> and <strong>10</strong> exhibited certain inhibitory activities against <em>α</em>-glucosidase, while <strong>1</strong>−<strong>10</strong> showed moderate to weak acetylcholinesterase inhibitory effects.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114299"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472496","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 : 2024-10-16DOI: 10.1016/j.phytochem.2024.114302
Chuntong Li , Deduo Xu , Zhancai Zheng , Wenquan Lu , Yingbo Yang , Wansheng Chen , Zhijun Wu
Thirty-six compounds were isolated from extract of the stem bark of Illicium burmanicum, including twelve previously undescribed prenylated C6–C3 compounds and a norsesquiterpene lactone: illicidione D (1), illicidione E (2), illicidione F (3), illicidione G (4), (2R,4S,11R)-12-O-ethylillifunone C (5), (2R,4S,11R)-illifunone C-12-O-β-d-glucopyranoside (6), (2R,4S,11R)-2-hydroxyillifunone C (7), 4-epi-2,3-dehydroillifunone C (8), illiburmanone A (9), illiburmanone B (10), illiburmanlactone A (11), (2S,4S,5S,11R)-2,3-dihydroillicione E (12), and illiburmanolside A (13). Their structures were determined based on extensive spectroscopic data analyses, including MS, NMR, and ECD spectra. The anti-inflammatory activity of the isolated compounds (1–36) was evaluated, and compounds 7, 12, 14, and 18 exhibited inhibitory effects in RAW 264.7 cells induced by LPS.
从 Illicium burmanicum 的茎皮提取物中分离出了 36 种化合物，包括 12 种以前未曾描述过的前烯化 C6-C3 化合物和一种后半萜内酯：伊利西酮 D (1)、伊利西酮 E (2)、伊利西酮 F (3)、伊利西酮 G (4)、(2R,4S,11R)-12-O-乙基illifunone C (5)、(2R,4S,11R)-illifunone C-12-O-β-d-glucopyranoside (6)、(2R,4S、11R)-2-hydroxyillifunone C (7)、4-epi-2,3-dehydroillifunone C (8)、illiburmanone A (9)、illiburmanone B (10)、illiburmanlactone A (11)、(2S,4S,5S,11R)-2,3-dihydroillicione E (12) 和 illiburmanolside A (13)。它们的结构是根据大量的光谱数据分析（包括 MS、NMR 和 ECD 光谱）确定的。对分离出的化合物（1-36）的抗炎活性进行了评估，化合物 7、12、14 和 18 对 LPS 诱导的 RAW 264.7 细胞有抑制作用。
{"title":"Chemical constituents from the stem bark of Illicium burmanicum and their anti-inflammatory activity","authors":"Chuntong Li , Deduo Xu , Zhancai Zheng , Wenquan Lu , Yingbo Yang , Wansheng Chen , Zhijun Wu","doi":"10.1016/j.phytochem.2024.114302","DOIUrl":"10.1016/j.phytochem.2024.114302","url":null,"abstract":"<div><div>Thirty-six compounds were isolated from extract of the stem bark of <em>Illicium burmanicum,</em> including twelve previously undescribed prenylated C6–C3 compounds and a norsesquiterpene lactone: illicidione D (<strong>1</strong>), illicidione E (<strong>2</strong>), illicidione F (<strong>3</strong>), illicidione G (<strong>4</strong>), (2<em>R</em>,4<em>S</em>,11<em>R</em>)-12-<em>O</em>-ethylillifunone C (<strong>5</strong>), (2<em>R</em>,4<em>S</em>,11<em>R</em>)-illifunone C-12-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (<strong>6</strong>), (2<em>R</em>,4<em>S</em>,11<em>R</em>)-2-hydroxyillifunone C (<strong>7</strong>), 4-<em>epi</em>-2,3-dehydroillifunone C (<strong>8</strong>), illiburmanone A (<strong>9</strong>), illiburmanone B (<strong>10</strong>), illiburmanlactone A (<strong>11</strong>), (2<em>S</em>,4<em>S</em>,5<em>S</em>,11<em>R</em>)-2,3-dihydroillicione E (<strong>12</strong>), and illiburmanolside A (<strong>13</strong>). Their structures were determined based on extensive spectroscopic data analyses, including MS, NMR, and ECD spectra. The anti-inflammatory activity of the isolated compounds (<strong>1</strong>–<strong>36</strong>) was evaluated, and compounds <strong>7</strong>, <strong>12</strong>, <strong>14</strong>, and <strong>18</strong> exhibited inhibitory effects in RAW 264.7 cells induced by LPS.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114302"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472504","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}
Eleven undescribed steroids, bipolaristeroids A–K, and one known compound, demethylincisterol A3, were isolated from the fungus Bipolaris maydis. Bipolaristeroid A is a 5,6-seco-9,10-seco-steroid with a rearranged B ring, in which the A and C rings are connected by an ester bond. Bipolaristeroid B is a rearranged 1(10 → 6)-abeosteroid with an aromatic B ring. Their planar structures and absolute configuration were determined using NMR, HRESIMS, DP4+ analysis, ECD calculation, and single-crystal X-ray diffraction. Bipolaristeroid A shows excellent inhibitory effects against the cancer cell lines HepG2, A549, SW620, and C4–2B with IC50 values of 7.94, 5.11, 5.13, and 3.83 μM, respectively.
从真菌 Bipolaris maydis 中分离出了 11 种未曾描述过的类固醇（双极甾醇 A-K）和一种已知化合物（去甲基双极甾醇 A3）。双极性甾体 A 是一种 5,6-seco-9,10-seco-甾体，具有重新排列的 B 环，其中 A 环和 C 环通过酯键连接。双极性类固醇 B 是一种重新排列的 1(10→6)-类固醇，带有一个芳香的 B 环。利用核磁共振、HRESIMS、DP4+分析、ECD计算和单晶X射线二折射测定了它们的平面结构和绝对构型。双极性甾体A对HepG2、A549、SW620和C4-2B癌细胞株有很好的抑制作用，IC50值分别为7.94、5.11、5.13和3.83 μM。
{"title":"Bipolaristeroid A, a 5,6-seco-9,10-seco-steroid with cytotoxic activity from the fungus Bipolaris maydis","authors":"Yong Shen , Lianghu Gu , Qun Zhou , Xiaotian Zhang, Mengru Yu, Qin Li, Yu Liang, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1016/j.phytochem.2024.114303","DOIUrl":"10.1016/j.phytochem.2024.114303","url":null,"abstract":"<div><div>Eleven undescribed steroids, bipolaristeroids A–K, and one known compound, demethylincisterol A<sub>3</sub>, were isolated from the fungus <em>Bipolaris maydis</em>. Bipolaristeroid A is a 5,6-seco-9,10-seco-steroid with a rearranged B ring, in which the A and C rings are connected by an ester bond. Bipolaristeroid B is a rearranged 1(10 → 6)-abeosteroid with an aromatic B ring. Their planar structures and absolute configuration were determined using NMR, HRESIMS, DP4+ analysis, ECD calculation, and single-crystal X-ray diffraction. Bipolaristeroid A shows excellent inhibitory effects against the cancer cell lines HepG2, A549, SW620, and C4–2B with IC<sub>50</sub> values of 7.94, 5.11, 5.13, and 3.83 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114303"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472499","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 : 2024-10-16DOI: 10.1016/j.phytochem.2024.114304
Xue Tang , Xian-Jing Zhang , Jing-Feng Pan , Kai Guo , Chun-Lin Tan , Qiao-Zhuo Zhang , Li-Ping Long , Rui-Feng Ding , Xue-Mei Niu , Yan Liu , Sheng-Hong Li
Plant enzymes often present advantages in the synthesis of natural products with specific configurations. Farnesene is a pharmacologically active sesquiterpene with three natural Z/E configurations, among which the enzyme selectively responsible for the biosynthesis of (3Z,6E)-α-farnesene remains elusive. Herein, a sesquiterpene synthase TwSTPS1 biosynthesizing (3Z,6E)-α-farnesene as the major product was identified from Taxus wallichiana through genome mining. Utilizing molecular dynamics simulations and mutation analysis, the catalytic mechanism of TwSTPS1, especially Z/E configuration control, was explored. Moreover, the crucial residues associated with the specific catalytic activity of TwSTPS1 was elucidated through mutagenesis experiments. The findings contribute to our understanding of the Z/E configuration control by plant terpene synthases and also provide an alternative tool for manipulating (3Z,6E)-α-farnesene production using synthetic biology.
{"title":"Z/E configuration controlled by a Taxus sesquiterpene synthase facilitating the biosynthesis of (3Z,6E)-α-farnesene","authors":"Xue Tang , Xian-Jing Zhang , Jing-Feng Pan , Kai Guo , Chun-Lin Tan , Qiao-Zhuo Zhang , Li-Ping Long , Rui-Feng Ding , Xue-Mei Niu , Yan Liu , Sheng-Hong Li","doi":"10.1016/j.phytochem.2024.114304","DOIUrl":"10.1016/j.phytochem.2024.114304","url":null,"abstract":"<div><div>Plant enzymes often present advantages in the synthesis of natural products with specific configurations. Farnesene is a pharmacologically active sesquiterpene with three natural <em>Z</em>/<em>E</em> configurations, among which the enzyme selectively responsible for the biosynthesis of (3<em>Z</em>,6<em>E</em>)-<em>α</em>-farnesene remains elusive. Herein, a sesquiterpene synthase TwSTPS1 biosynthesizing (3<em>Z</em>,6<em>E</em>)-<em>α</em>-farnesene as the major product was identified from <em>Taxus wallichiana</em> through genome mining. Utilizing molecular dynamics simulations and mutation analysis, the catalytic mechanism of TwSTPS1, especially <em>Z/E</em> configuration control, was explored. Moreover, the crucial residues associated with the specific catalytic activity of TwSTPS1 was elucidated through mutagenesis experiments. The findings contribute to our understanding of the <em>Z</em>/<em>E</em> configuration control by plant terpene synthases and also provide an alternative tool for manipulating (3<em>Z</em>,6<em>E</em>)-<em>α</em>-farnesene production using synthetic biology.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114304"},"PeriodicalIF":3.2,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142472502","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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