PhytochemistryPub Date : 2024-10-05DOI: 10.1016/j.phytochem.2024.114294
Flavia Fulvio , Ylenia Pieracci , Roberta Ascrizzi , Laura Bassolino , Guido Flamini , Roberta Paris
{"title":"Insights into terpenes profiling and transcriptional analyses during flowering of different Cannabis sativa L. chemotypes","authors":"Flavia Fulvio , Ylenia Pieracci , Roberta Ascrizzi , Laura Bassolino , Guido Flamini , Roberta Paris","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":"229 ","pages":"Article 114294"},"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}
PhytochemistryPub Date : 2024-10-03DOI: 10.1016/j.phytochem.2024.114295
Jihua Wei , Xuexia Chen , Yihan Ma , Bin Wu
{"title":"Chevalierlin: A spirocyclic alkaloid from a hydrothermal vent associated fungus Aspergillus chevalieri TW132-65","authors":"Jihua Wei , Xuexia Chen , Yihan Ma , Bin Wu","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":"229 ","pages":"Article 114295"},"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}
PhytochemistryPub Date : 2024-10-02DOI: 10.1016/j.phytochem.2024.114296
Shi-lin Chen , Ha Gao , Chen-xu Zhao, Tao Zhang, Zhong-mei Zou
{"title":"LC–MS coupled with diagnostic ion strategy facilitated the discovery of 5-methylcoumarin meroterpenoids from Gerbera piloselloides","authors":"Shi-lin Chen , Ha Gao , Chen-xu Zhao, Tao Zhang, Zhong-mei Zou","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":"229 ","pages":"Article 114296"},"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}
PhytochemistryPub Date : 2024-09-29DOI: 10.1016/j.phytochem.2024.114289
Hsiao-Yang Hsi , George Hsiao , Shih-Wei Wang , Shu-Jung Huang , Tzong-Huei Lee
{"title":"Chemical constituents from marine medicinal brown alga-derived Scytalidium lignicola SC228","authors":"Hsiao-Yang Hsi , George Hsiao , Shih-Wei Wang , Shu-Jung Huang , Tzong-Huei Lee","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":"229 ","pages":"Article 114289"},"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}
PhytochemistryPub Date : 2024-09-28DOI: 10.1016/j.phytochem.2024.114293
Yan-ling Liu , Yan-gang Cao , Ya-juan Zheng , Ying Niu , Lan Chen , Xu Chen , Xin-yi Ma , Xiang-da Li , Xiao-ke Zheng , Wei-sheng Feng
{"title":"Targeted isolation of lignans from the roots of Anthriscus sylvestris (L.) Hoffm. by small molecule accurate recognition technology","authors":"Yan-ling Liu , Yan-gang Cao , Ya-juan Zheng , Ying Niu , Lan Chen , Xu Chen , Xin-yi Ma , Xiang-da Li , Xiao-ke Zheng , Wei-sheng Feng","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":"229 ","pages":"Article 114293"},"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}
PhytochemistryPub Date : 2024-09-26DOI: 10.1016/j.phytochem.2024.114292
Meng-Li He , Lian-Lian Xu , Yang Liu , Yan-Ping Gao , Yong-Ming Luo , Rong-Cai Yue , Fang-You Chen
{"title":"Structurally diversified sesquiterpenoids from Chloranthus henryi and their neuroprotective activities on H2O2 damaged PC12 cells","authors":"Meng-Li He , Lian-Lian Xu , Yang Liu , Yan-Ping Gao , Yong-Ming Luo , Rong-Cai Yue , Fang-You Chen","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":"229 ","pages":"Article 114292"},"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}
{"title":"Chemical constituents with their alpha-glucosidase inhibitory activity from the whole plant of Ceratophyllum demersum","authors":"Thuc-Huy Duong , Thammarat Aree , Thi-Kim-Dung Le , Van-Son Dang , Ngoc-Hong Nguyen , Jirapast Sichaem","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":"229 ","pages":"Article 114290"},"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}
{"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":"Sasiwimon Nukulkit , Nonthaneth Nalinratana , Thammarat Aree , Utid Suriya , Rutt Suttisri , Nitra Nuengchamnong , Hsun-Shuo Chang , Chaisak Chansriniyom","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":"229 ","pages":"Article 114291"},"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}
PhytochemistryPub Date : 2024-09-19DOI: 10.1016/j.phytochem.2024.114288
Yang Xu , Jinxia Chen , Yuxia Li , Dejuan Sun , Hua Li , Lixia Chen
{"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":"Yang Xu , Jinxia Chen , Yuxia Li , Dejuan Sun , Hua Li , Lixia Chen","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":"229 ","pages":"Article 114288"},"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}
PhytochemistryPub Date : 2024-09-12DOI: 10.1016/j.phytochem.2024.114272
Yuka Yoshizawa, Akihito Yokosuka, Mina Inomata, Tomoki Iguchi, Yoshihiro Mimaki
{"title":"Steroidal constituents in the whole plants of Helleborus niger and their cytotoxic activity in vitro","authors":"Yuka Yoshizawa, Akihito Yokosuka, Mina Inomata, Tomoki Iguchi, Yoshihiro Mimaki","doi":"10.1016/j.phytochem.2024.114272","DOIUrl":"10.1016/j.phytochem.2024.114272","url":null,"abstract":"<div><p>Phytochemical investigation of the whole plants of <em>Helleborus niger</em> L. (Ranunculaceae) resulted in the isolation of five undescribed compounds, including one bufadienolide (<strong>1</strong>), two bufadienolide rhamnosides (<strong>2</strong> and <strong>3</strong>), and two ecdysteroids (<strong>12</strong> and <strong>13</strong>), along with eight known compounds (<strong>4</strong>–<strong>11</strong>). The chemical structures of <strong>1</strong>–<strong>3</strong>, <strong>12</strong>, and <strong>13</strong> were determined by spectroscopic studies, including 2D NMR, and chromatographic and spectroscopic analyses of the hydrolyzed products. Compounds <strong>1</strong>–<strong>13</strong> were evaluated for their cytotoxic activity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, SBC-3 human small-cell lung cancer cells, and TIG-3 human normal diploid lung cells. Compounds <strong>1</strong>–<strong>12</strong> showed cytotoxic activity against HL-60, A549, and SBC-3 cells, with IC<sub>50</sub> values ranging from 0.0016 to 6.1 μM. Bufadienolide rhamnoside <strong>2</strong> exhibited potent cell proliferation inhibitory activity against SBC-3 cells after 24–48 h of treatment and apoptosis-inducing activity in SBC-3 cells via an intrinsic pathway after 72 h of treatment. The JFCR39 panel screening of <strong>2</strong> suggests that the molecular target of <strong>2</strong> is Na<sup>+</sup>,K<sup>+</sup>-ATPase.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"229 ","pages":"Article 114272"},"PeriodicalIF":3.2,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142242852","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}