Pub Date : 2024-10-12DOI: 10.1016/j.phytochem.2024.114297
Here we report for the first time the entire 13C-NMR spectral assignments of 119 (out of 127) triterpenoids from the oleo-gum resins of the medicinally important genus Boswellia, which includes the culturally highly valuable Frankincense species. The complete 13C-NMR resonances of these triterpenoids isolated between 1998 and 2024 and their biological activities are presented. 13C-NMR spectroscopy is a highly powerful tool for the characterization of these bioactive natural products. The compounds are arranged according to their skeletons, i.e., ursane, oleanane, lupane, dammarane, and tirucallane triterpenes. This review will be a future reference for the identification of these compounds, which have key medicinal properties in the areas of cytotoxicity and inflammation.
{"title":"Triterpenoids from Frankincense and Boswellia: A focus on their pharmacology and 13C-NMR assignments","authors":"","doi":"10.1016/j.phytochem.2024.114297","DOIUrl":"10.1016/j.phytochem.2024.114297","url":null,"abstract":"<div><div>Here we report for the first time the entire <sup>13</sup>C-NMR spectral assignments of 119 (out of 127) triterpenoids from the oleo-gum resins of the medicinally important genus <em>Boswellia</em>, which includes the culturally highly valuable Frankincense species. The complete <sup>13</sup>C-NMR resonances of these triterpenoids isolated between 1998 and 2024 and their biological activities are presented. <sup>13</sup>C-NMR spectroscopy is a highly powerful tool for the characterization of these bioactive natural products. The compounds are arranged according to their skeletons, i.e., ursane, oleanane, lupane, dammarane, and tirucallane triterpenes. This review will be a future reference for the identification of these compounds, which have key medicinal properties in the areas of cytotoxicity and inflammation.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142437840","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 : 2024-10-05DOI: 10.1016/j.phytochem.2024.114294
Terpenes, volatile compounds known for their aromatic and therapeutic properties, play a pivotal role in shaping the overall chemical profile of Cannabis sativa L. Their biosynthesis in planta occurs in trichomes and involves the 2-C-methyl-D-erythritol 4-phosphate (MEP) and the mevalonic acid (MVA) pathways, responsible for producing the substrates utilized by a family of enzymes, the terpene synthases (TPS), for terpene production. In this work, a comprehensive approach combining chemical analyses of the volatile compounds characterizing the aroma of the inflorescences three C. sativa genotypes collected at three stages of maturity and the transcriptional analyses of key genes involved in the terpene biosynthesis was adopted to study this pathway. The results revealed different terpene profiles among genotypes, which were characterized by peculiar compounds belonging to the sesqui- (CINBOL and Fibrante) or monoterpene (Ermo) categories. Both structural and putative regulatory genes were analysed by RT-qPCR, revealing distinct transcriptional profiles of Terpene Synthases, contributing to the diversity of mono and sesquiterpenes synthesized. Furthermore, the research delved into potential regulatory genes associated with trichome formation, a crucial factor influencing terpene accumulation. This integrated approach highlighted complex mechanisms governing terpene accumulation in cannabis, while also offering potential regulators putatively involved in this pathway.
{"title":"Insights into terpenes profiling and transcriptional analyses during flowering of different Cannabis sativa L. chemotypes","authors":"","doi":"10.1016/j.phytochem.2024.114294","DOIUrl":"10.1016/j.phytochem.2024.114294","url":null,"abstract":"<div><div>Terpenes, volatile compounds known for their aromatic and therapeutic properties, play a pivotal role in shaping the overall chemical profile of <em>Cannabis sativa</em> L. Their biosynthesis <em>in planta</em> occurs in trichomes and involves the 2-C-methyl-D-erythritol 4-phosphate (MEP) and the mevalonic acid (MVA) pathways, responsible for producing the substrates utilized by a family of enzymes, the terpene synthases (TPS), for terpene production. In this work, a comprehensive approach combining chemical analyses of the volatile compounds characterizing the aroma of the inflorescences three <em>C. sativa</em> genotypes collected at three stages of maturity and the transcriptional analyses of key genes involved in the terpene biosynthesis was adopted to study this pathway. The results revealed different terpene profiles among genotypes, which were characterized by peculiar compounds belonging to the sesqui- (CINBOL and Fibrante) or monoterpene (Ermo) categories. Both structural and putative regulatory genes were analysed by RT-qPCR, revealing distinct transcriptional profiles of <em>Terpene Synthases</em>, contributing to the diversity of mono and sesquiterpenes synthesized. Furthermore, the research delved into potential regulatory genes associated with trichome formation, a crucial factor influencing terpene accumulation. This integrated approach highlighted complex mechanisms governing terpene accumulation in cannabis, while also offering potential regulators putatively involved in this pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142392507","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 : 2024-10-03DOI: 10.1016/j.phytochem.2024.114295
A previously undescribed spirodiketopiperazine-indole alkaloid, chevalierlin (1), two pairs of previously undescribed dihydroisocoumarin enantiomers eurotiumides H–I (2–3), as well as six related known compounds (4–9) were isolated from the culture of a hydrothermal vent associated fungus Aspergillus chevalieri TW132-65. Their structures were unambiguously determined by NMR, mass spectrometry, and ECD calculations. Chevalierlin (1) exhibits moderate cytotoxic activities with IC50 values of 6.20 ± 0.05 μM and 7.68 ± 0.01 μM against Namalwa and Raji cell lines.
{"title":"Chevalierlin: A spirocyclic alkaloid from a hydrothermal vent associated fungus Aspergillus chevalieri TW132-65","authors":"","doi":"10.1016/j.phytochem.2024.114295","DOIUrl":"10.1016/j.phytochem.2024.114295","url":null,"abstract":"<div><div>A previously undescribed spirodiketopiperazine-indole alkaloid, chevalierlin (<strong>1</strong>), two pairs of previously undescribed dihydroisocoumarin enantiomers eurotiumides H–I (<strong>2</strong>–<strong>3</strong>), as well as six related known compounds (<strong>4</strong>–<strong>9</strong>) were isolated from the culture of a hydrothermal vent associated fungus <em>Aspergillus chevalieri</em> TW132-65. Their structures were unambiguously determined by NMR, mass spectrometry, and ECD calculations. Chevalierlin (<strong>1</strong>) exhibits moderate cytotoxic activities with IC<sub>50</sub> values of 6.20 ± 0.05 μM and 7.68 ± 0.01 μM against Namalwa and Raji cell lines.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142378180","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 : 2024-10-02DOI: 10.1016/j.phytochem.2024.114296
Plant-derived natural products remain crucial in drug development. However, the identification of undescribed natural products is becoming increasingly challenging. A comprehensive strategy combining LC–MS with diagnostic ions was proposed for the discovery of undescribed 5-methylcoumarin meroterpenoids. Thirteen undescribed 5-methylcoumarin meroterpenoids, including five pairs of enantiomers (1a/1b and 5a/5b–8a/8b), were isolated from the whole plant of Gerbera piloselloides. Their structures and absolute configurations were unambiguously determined based on their spectroscopic data, calculated and experimental ECD data and X-ray diffraction analysis. Bioassays conducted on scopolamine-induced injury PC12 cells revealed that compounds 5a/5b, 7a/7b and 8a/8b possessed mild protective effects. Additionally, compounds 2 and 8 showed notable IL-6 inhibition in lipopolysaccharide-induced BEAS-2B cells.
{"title":"LC–MS coupled with diagnostic ion strategy facilitated the discovery of 5-methylcoumarin meroterpenoids from Gerbera piloselloides","authors":"","doi":"10.1016/j.phytochem.2024.114296","DOIUrl":"10.1016/j.phytochem.2024.114296","url":null,"abstract":"<div><div>Plant-derived natural products remain crucial in drug development. However, the identification of undescribed natural products is becoming increasingly challenging. A comprehensive strategy combining LC–MS with diagnostic ions was proposed for the discovery of undescribed 5-methylcoumarin meroterpenoids. Thirteen undescribed 5-methylcoumarin meroterpenoids, including five pairs of enantiomers (<strong>1a</strong>/<strong>1b</strong> and <strong>5a</strong>/<strong>5b</strong>–<strong>8a</strong>/<strong>8b</strong>), were isolated from the whole plant of <em>Gerbera piloselloides</em>. Their structures and absolute configurations were unambiguously determined based on their spectroscopic data, calculated and experimental ECD data and X-ray diffraction analysis. Bioassays conducted on scopolamine-induced injury PC12 cells revealed that compounds <strong>5a</strong>/<strong>5b</strong>, <strong>7a</strong>/<strong>7b</strong> and <strong>8a</strong>/<strong>8b</strong> possessed mild protective effects. Additionally, compounds <strong>2</strong> and <strong>8</strong> showed notable IL-6 inhibition in lipopolysaccharide-induced BEAS-2B cells.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142375789","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 : 2024-09-29DOI: 10.1016/j.phytochem.2024.114289
In this study, a marine medicinal brown alga Sargassum cristaefolium-derived fungal strain Scytalidium lignicola SC228 has been isolated and identified. Column chromatography of the extracts from liquid-fermented products of the fungal strain was carried out, and led to the purification of eight compounds. Their structures were characterized by spectroscopic analysis, and the absolute configurations were further established by single X-ray diffraction analysis and modified Mosher's method as four previously undescribed compounds, namely scytabenzofurans A–C (1–3), and (3S,4S)-5-chloro-3,4-dihydro-4,6,8-trihydroxy-3-methyl-1H-2-benzopyran-1-one (4), along with four known compounds 5–8. All the isolates were subjected to anti-inflammatory and anti-angiogenic assays. Compounds 1–4, 7, and 8 showed moderate nitric oxide production inhibitory activities in lipopolysaccharide-activated BV-2 microglial cells with IC50 in the range of 19.6 ± 0.1 to 49.0 ± 1.2 μM in comparison with that of curcumin (IC50 = 2.7 ± 0.3 μM). Compounds 5–7 exhibited moderate to potent inhibitory effects on EPCs growth with IC50 in the range of 0.5 ± 0.1 to 42.7 ± 0.9 μM as compared to sorafenib (IC50 = 5.50 ± 1.50 μM).
{"title":"Chemical constituents from marine medicinal brown alga-derived Scytalidium lignicola SC228","authors":"","doi":"10.1016/j.phytochem.2024.114289","DOIUrl":"10.1016/j.phytochem.2024.114289","url":null,"abstract":"<div><div>In this study, a marine medicinal brown alga <em>Sargassum cristaefolium</em>-derived fungal strain <em>Scytalidium lignicola</em> SC228 has been isolated and identified. Column chromatography of the extracts from liquid-fermented products of the fungal strain was carried out, and led to the purification of eight compounds. Their structures were characterized by spectroscopic analysis, and the absolute configurations were further established by single X-ray diffraction analysis and modified Mosher's method as four previously undescribed compounds, namely scytabenzofurans A–C (<strong>1</strong>–<strong>3</strong>), and (3<em>S</em>,4<em>S</em>)-5-chloro-3,4-dihydro-4,6,8-trihydroxy-3-methyl-1<em>H</em>-2-benzopyran-1-one (<strong>4</strong>), along with four known compounds <strong>5</strong>–<strong>8</strong>. All the isolates were subjected to anti-inflammatory and anti-angiogenic assays. Compounds <strong>1</strong>–<strong>4</strong>, <strong>7</strong>, and <strong>8</strong> showed moderate nitric oxide production inhibitory activities in lipopolysaccharide-activated BV-2 microglial cells with IC<sub>50</sub> in the range of 19.6 ± 0.1 to 49.0 ± 1.2 μM in comparison with that of curcumin (IC<sub>50</sub> = 2.7 ± 0.3 μM). Compounds <strong>5</strong>–<strong>7</strong> exhibited moderate to potent inhibitory effects on EPCs growth with IC<sub>50</sub> in the range of 0.5 ± 0.1 to 42.7 ± 0.9 μM as compared to sorafenib (IC<sub>50</sub> = 5.50 ± 1.50 μM).</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142366162","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 : 2024-09-28DOI: 10.1016/j.phytochem.2024.114293
Five undescribed lignans (1–5), along with sixteen known lignans (6–21), were isolated from the roots of Anthriscus sylvestris using small molecule accurate recognition technology (SMART). The structures of the isolated compounds were determined by comprehensive spectroscopic analyses, and the absolute configurations of compounds 3–5 were elucidated by comparison of their calculated and experimental ECD spectra. Compounds 5, 14−15, 19, and 21 exhibited significantly inhibitory effects against hypoxia-stimulated abnormal proliferation of pulmonary arterial smooth muscle cells (PASMCs). Moreover, compounds 5, 14−15, 19, and 21 can significantly restore expression of expression of PASMCs proliferation-related protein, including α-SMA, PCNA, P27, and CyclinD3, which are closely related to cell proliferation.
{"title":"Targeted isolation of lignans from the roots of Anthriscus sylvestris (L.) Hoffm. by small molecule accurate recognition technology","authors":"","doi":"10.1016/j.phytochem.2024.114293","DOIUrl":"10.1016/j.phytochem.2024.114293","url":null,"abstract":"<div><div>Five undescribed lignans (<strong>1</strong>–<strong>5</strong>), along with sixteen known lignans (<strong>6</strong>–<strong>21</strong>), were isolated from the roots of <em>Anthriscus sylvestris</em> using small molecule accurate recognition technology (SMART). The structures of the isolated compounds were determined by comprehensive spectroscopic analyses, and the absolute configurations of compounds <strong>3</strong>–<strong>5</strong> were elucidated by comparison of their calculated and experimental ECD spectra. Compounds <strong>5</strong>, <strong>14</strong>−<strong>15</strong>, <strong>19</strong>, and <strong>21</strong> exhibited significantly inhibitory effects against hypoxia-stimulated abnormal proliferation of pulmonary arterial smooth muscle cells (PASMCs). Moreover, compounds <strong>5</strong>, <strong>14</strong>−<strong>15</strong>, <strong>19</strong>, and <strong>21</strong> can significantly restore expression of expression of PASMCs proliferation-related protein, including <em>α</em>-SMA, PCNA, P27, and CyclinD3, which are closely related to cell proliferation.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142352062","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 : 2024-09-26DOI: 10.1016/j.phytochem.2024.114292
Fifteen undescribed sesquiterpenoid monomers, including six pairs of sesquiterpenoid enantiomers (1a/1b–3a/3b and 5a/5b–7a/7b) and three analogues (4, 8, and 9), together with two known sesquiterpenoid dimers (10 and 11) were isolated from the whole plant of Chloranthus henryi Hemsl. Their structures were characterized by spectroscopic data analysis, ECD calculations, and single crystal X-Ray diffractions. Compounds 1a and 1b were highly aromatic cadinane-type sesquiterpenoids. At a concentration of 10 μM, compounds 8, 10, and 11 exhibited potent neuroprotective activity against H2O2-induced PC12 cell damage. Compounds 10 and 11 significantly decreased the level of ROS. In addition, compound 11 increased the levels of p-AMPK, p-SIRT1, and SIRT3 in the H2O2-induced PC12 cell damage via activated the AMPK/SIRT signaling pathway.
{"title":"Structurally diversified sesquiterpenoids from Chloranthus henryi and their neuroprotective activities on H2O2 damaged PC12 cells","authors":"","doi":"10.1016/j.phytochem.2024.114292","DOIUrl":"10.1016/j.phytochem.2024.114292","url":null,"abstract":"<div><div>Fifteen undescribed sesquiterpenoid monomers, including six pairs of sesquiterpenoid enantiomers (<strong>1a</strong>/<strong>1b</strong>–<strong>3a</strong>/<strong>3b</strong> and <strong>5a</strong>/<strong>5b</strong>–<strong>7a</strong>/<strong>7b</strong>) and three analogues (<strong>4</strong>, <strong>8</strong>, and <strong>9</strong>), together with two known sesquiterpenoid dimers (<strong>10</strong> and <strong>11</strong>) were isolated from the whole plant of <em>Chloranthus henryi</em> Hemsl. Their structures were characterized by spectroscopic data analysis, ECD calculations, and single crystal X-Ray diffractions. Compounds <strong>1a</strong> and <strong>1b</strong> were highly aromatic cadinane-type sesquiterpenoids. At a concentration of 10 μM, compounds <strong>8</strong>, <strong>10</strong>, and <strong>11</strong> exhibited potent neuroprotective activity against H<sub>2</sub>O<sub>2</sub>-induced PC12 cell damage. Compounds <strong>10</strong> and <strong>11</strong> significantly decreased the level of ROS. In addition, compound <strong>11</strong> increased the levels of <em>p</em>-AMPK, <em>p</em>-SIRT1, and SIRT3 in the H<sub>2</sub>O<sub>2</sub>-induced PC12 cell damage via activated the AMPK/SIRT signaling pathway.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142327706","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 : 2024-09-25DOI: 10.1016/j.phytochem.2024.114290
From Ceratophyllum demersum growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (1–4), acetylvelutins A and B (8 and 9), together with six known compounds, (+)-cyclocolorenone (5), 1-hydroxycyclocolorenone (6), 10-hydroxycyclocolorenone (7), retusin (10), betulinic acid (11), and lupeol (12). The chemical structures and stereochemistry of 1–12 were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (1 and 2), guaiane-type (3), and aromadendrane-type (4–7) sesquiterpenoids have been reported in this genus. Compounds 8 and 9 are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of 1–3 and 5–12, it was found that 12 exhibited the highest potential with an IC50 value of 15.4 ± 1.1 μM. The molecular docking of 3 and 8 was further studied.
{"title":"Chemical constituents with their alpha-glucosidase inhibitory activity from the whole plant of Ceratophyllum demersum","authors":"","doi":"10.1016/j.phytochem.2024.114290","DOIUrl":"10.1016/j.phytochem.2024.114290","url":null,"abstract":"<div><div>From <em>Ceratophyllum demersum</em> growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (<strong>1</strong>–<strong>4</strong>), acetylvelutins A and B (<strong>8</strong> and <strong>9</strong>), together with six known compounds, (+)-cyclocolorenone (<strong>5</strong>), 1-hydroxycyclocolorenone (<strong>6</strong>), 10-hydroxycyclocolorenone (<strong>7</strong>), retusin (<strong>10</strong>), betulinic acid (<strong>11</strong>), and lupeol (<strong>12</strong>). The chemical structures and stereochemistry of <strong>1</strong>–<strong>12</strong> were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (<strong>1</strong> and <strong>2</strong>), guaiane-type (<strong>3</strong>), and aromadendrane-type (<strong>4</strong>–<strong>7</strong>) sesquiterpenoids have been reported in this genus. Compounds <strong>8</strong> and <strong>9</strong> are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of <strong>1</strong>–<strong>3</strong> and <strong>5</strong>–<strong>12</strong>, it was found that <strong>12</strong> exhibited the highest potential with an IC<sub>50</sub> value of 15.4 ± 1.1 μM. The molecular docking of <strong>3</strong> and <strong>8</strong> was further studied.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142327707","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 : 2024-09-24DOI: 10.1016/j.phytochem.2024.114291
Five previously undescribed indole alkaloids, maeruines A−E (1−5), bearing imino-2H-thieno[2,3-b]indol-3(8H)-one skeleton, were obtained from the stems of Maerua siamensis. Their chemical structures were elucidated using spectroscopic techniques [NMR, MS, IR, and UV], and single-crystal X-ray diffraction. Maeruine D (4) displayed selective cyclooxygenase-2 (COX-2) inhibitory activity in vitro with an IC50 of 29.72 ± 6.36 μM. Molecular dynamics simulations revealed that maeruine D could form a stable complex with human COX-2, predominantly driven by hydrophobic interactions. In addition, five amino-acid residues including Val349, Leu352, Leu384, Val523, and Ala527 were identified as hot-spot ones, which may lead to high binding affinity and selectivity. Furthermore, it exhibited cytotoxicity against HT-29 colorectal cancer cells with an IC50 of 29.32 ± 4.76 μM, and, at 0.1−10 μM, significantly inhibited their proliferation, induced by the proinflammatory cytokine interleukin-1β (IL-1β), in a dose-dependent manner.
{"title":"Maeruines A−E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation","authors":"","doi":"10.1016/j.phytochem.2024.114291","DOIUrl":"10.1016/j.phytochem.2024.114291","url":null,"abstract":"<div><div>Five previously undescribed indole alkaloids, maeruines A−E (<strong>1</strong>−<strong>5</strong>), bearing imino-2<em>H</em>-thieno[2,3-<em>b</em>]indol-3(8<em>H</em>)-one skeleton, were obtained from the stems of <em>Maerua siamensis</em>. Their chemical structures were elucidated using spectroscopic techniques [NMR, MS, IR, and UV], and single-crystal X-ray diffraction. Maeruine D (<strong>4</strong>) displayed selective cyclooxygenase-2 (COX-2) inhibitory activity <em>in vitro</em> with an IC<sub>50</sub> of 29.72 ± 6.36 μM. Molecular dynamics simulations revealed that maeruine D could form a stable complex with human COX-2, predominantly driven by hydrophobic interactions. In addition, five amino-acid residues including Val349, Leu352, Leu384, Val523, and Ala527 were identified as hot-spot ones, which may lead to high binding affinity and selectivity. Furthermore, it exhibited cytotoxicity against HT-29 colorectal cancer cells with an IC<sub>50</sub> of 29.32 ± 4.76 μM, and, at 0.1−10 μM, significantly inhibited their proliferation, induced by the proinflammatory cytokine interleukin-1β (IL-1β), in a dose-dependent manner.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142323189","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 : 2024-09-19DOI: 10.1016/j.phytochem.2024.114288
Sophora flavescens Aiton is a plant in the Leguminosae family. As a traditional Chinese medicine, it is used to treat eczema, bloody stool, skin pruritus, and so on. By studying non-alkaloid components in the roots of S. flavescens, we obtained a total of 49 compounds (1–49), including three undescribed flavonoids (13, 15 and 18), five undescribed isopentenyl flavonoids (32, 34, 38, 39 and 48), two known coumarins (1–2), three phenolic acids (3–5), one known isopentenyl flavonoids (19–31, 33, 35–37, 40–47 and 49). On the basis of chemical evidences and spectral data analysis (UV, ECD, Optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of undescribed compounds were elucidated. The inhibitory effect of compounds 1–49 on LPS induced NO production in RAW 264.7 cells was detected. Compounds 11, 19, 21–24, and 28–30 showed significant inhibitory effects, and the IC50 values of compounds 11 and 22 even reached 4.58 ± 0.66 and 4.53 ± 0.66 μM. This study suggests that flavonoids may be the main component that exerts anti-inflammatory effects in the non-alkaloid extraction layer of the extract from the roots of S. flavescens.
{"title":"Non-alkaloid components with inhibitory activity against LPS induced NO production in RAW 264.7 cells isolated from the roots of Sophora flavescens","authors":"","doi":"10.1016/j.phytochem.2024.114288","DOIUrl":"10.1016/j.phytochem.2024.114288","url":null,"abstract":"<div><p><em>Sophora flavescens</em> Aiton is a plant in the Leguminosae family. As a traditional Chinese medicine, it is used to treat eczema, bloody stool, skin pruritus, and so on. By studying non-alkaloid components in the roots of <em>S. flavescens</em>, we obtained a total of 49 compounds (<strong>1</strong>–<strong>49</strong>), including three undescribed flavonoids (<strong>13</strong>, <strong>15</strong> and <strong>18</strong>), five undescribed isopentenyl flavonoids (<strong>32</strong>, <strong>34</strong>, <strong>38</strong>, <strong>39</strong> and <strong>48</strong>), two known coumarins (<strong>1</strong>–<strong>2</strong>), three phenolic acids (<strong>3</strong>–<strong>5</strong>), one known isopentenyl flavonoids (<strong>19</strong>–<strong>31</strong>, <strong>33</strong>, <strong>35</strong>–<strong>37</strong>, <strong>40</strong>–<strong>47</strong> and <strong>49</strong>). On the basis of chemical evidences and spectral data analysis (UV, ECD, Optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of undescribed compounds were elucidated. The inhibitory effect of compounds <strong>1</strong>–<strong>49</strong> on LPS induced NO production in RAW 264.7 cells was detected. Compounds <strong>11</strong>, <strong>19</strong>, <strong>21</strong>–<strong>24</strong>, and <strong>28</strong>–<strong>30</strong> showed significant inhibitory effects, and the IC<sub>50</sub> values of compounds <strong>11</strong> and <strong>22</strong> even reached 4.58 ± 0.66 and 4.53 ± 0.66 μM. This study suggests that flavonoids may be the main component that exerts anti-inflammatory effects in the non-alkaloid extraction layer of the extract from the roots of <em>S. flavescens.</em></p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142271791","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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