{"title":"当地特有的 Haplophyllum megalanthum Bornm.及其新分离的生物碱和木脂素的细胞毒性","authors":"","doi":"10.1016/j.bse.2024.104901","DOIUrl":null,"url":null,"abstract":"<div><p>In this study, two previously unreported lignans [4′-<em>O</em>-demetylsuchilactone-8′-ol (<strong>1</strong>), 7-<em>O</em>-(3-methyl-2,3-dihydroxy-butyl)isodaurinol] (<strong>2</strong>), four new alkaloids (haplomegalanthine (<strong>3</strong>), megalantin (<strong>4</strong>), megalanthamide (<strong>5</strong>), glycoisohaplopine (<strong>6</strong>) and thirty-five known compounds (<strong>7–41</strong>) were isolated from <em>Haplophyllum megalanthum</em> Bornm. (Rutaceae). Pinoresinol (<strong>23</strong>), epipinoresinol (<strong>24</strong>), indole-3-carbaldehyde (<strong>29</strong>), <em>N</em>-[2-(4-hydroxyphenyl)ethyl]-3-methylbut-2-enamide (<strong>34</strong>), 7,8-dimethoxyfuroquinoline-4-one (<strong>35</strong>), <em>cis</em>-khellactone (<strong>36</strong>), 4,4′-dihydroxy-3,3′,9-trimethoxy-9,9′-epoxylignan (<strong>37</strong>), ulopterol (<strong>39</strong>) and <em>trans</em>-decursidinol (<strong>40</strong>) were identified for the first time in the genus <em>Haplophyllum</em>. Also, 4′-<em>O</em>-demethylsuchilactone (<strong>16</strong>) and <em>N</em>-(4-hydroxyphenethyl)benzamide (<strong>32</strong>) were found for the first time within the family Rutaceae. Structures of the compounds were elucidated by the use of HRMS, UHPLC-MS and 1D/2D NMR analyses. Furthermore, cytotoxic activity of the crude extract and previously unreported compounds (1–3, 5, 6) on colon cancer cell line HT29 were tested by the MTT method. IC<sub>50</sub> values were determined for these five compounds and the crude extract as 18.48 ± 0.94 μg/ml, 52.62 ± 7.27 μg/ml, 23.15 ± 6.70 μg/ml, 21.45 ± 2.48 μg/ml, 5.06 ± 0.19 μg/ml and 2.82 ± 0.012 μg/ml, respectively.</p><p>The present report is the first detailed phytochemical investigation of the title plant pointing out that it comprises a rich source of diverse chemical constituents including new compounds with promising cytotoxic activity.</p></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cytotoxicity of endemic Haplophyllum megalanthum Bornm. and its newly isolated alkaloids and lignans\",\"authors\":\"\",\"doi\":\"10.1016/j.bse.2024.104901\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In this study, two previously unreported lignans [4′-<em>O</em>-demetylsuchilactone-8′-ol (<strong>1</strong>), 7-<em>O</em>-(3-methyl-2,3-dihydroxy-butyl)isodaurinol] (<strong>2</strong>), four new alkaloids (haplomegalanthine (<strong>3</strong>), megalantin (<strong>4</strong>), megalanthamide (<strong>5</strong>), glycoisohaplopine (<strong>6</strong>) and thirty-five known compounds (<strong>7–41</strong>) were isolated from <em>Haplophyllum megalanthum</em> Bornm. (Rutaceae). Pinoresinol (<strong>23</strong>), epipinoresinol (<strong>24</strong>), indole-3-carbaldehyde (<strong>29</strong>), <em>N</em>-[2-(4-hydroxyphenyl)ethyl]-3-methylbut-2-enamide (<strong>34</strong>), 7,8-dimethoxyfuroquinoline-4-one (<strong>35</strong>), <em>cis</em>-khellactone (<strong>36</strong>), 4,4′-dihydroxy-3,3′,9-trimethoxy-9,9′-epoxylignan (<strong>37</strong>), ulopterol (<strong>39</strong>) and <em>trans</em>-decursidinol (<strong>40</strong>) were identified for the first time in the genus <em>Haplophyllum</em>. Also, 4′-<em>O</em>-demethylsuchilactone (<strong>16</strong>) and <em>N</em>-(4-hydroxyphenethyl)benzamide (<strong>32</strong>) were found for the first time within the family Rutaceae. Structures of the compounds were elucidated by the use of HRMS, UHPLC-MS and 1D/2D NMR analyses. Furthermore, cytotoxic activity of the crude extract and previously unreported compounds (1–3, 5, 6) on colon cancer cell line HT29 were tested by the MTT method. IC<sub>50</sub> values were determined for these five compounds and the crude extract as 18.48 ± 0.94 μg/ml, 52.62 ± 7.27 μg/ml, 23.15 ± 6.70 μg/ml, 21.45 ± 2.48 μg/ml, 5.06 ± 0.19 μg/ml and 2.82 ± 0.012 μg/ml, respectively.</p><p>The present report is the first detailed phytochemical investigation of the title plant pointing out that it comprises a rich source of diverse chemical constituents including new compounds with promising cytotoxic activity.</p></div>\",\"PeriodicalId\":8799,\"journal\":{\"name\":\"Biochemical Systematics and Ecology\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-09-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Biochemical Systematics and Ecology\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0305197824001194\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197824001194","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Cytotoxicity of endemic Haplophyllum megalanthum Bornm. and its newly isolated alkaloids and lignans
In this study, two previously unreported lignans [4′-O-demetylsuchilactone-8′-ol (1), 7-O-(3-methyl-2,3-dihydroxy-butyl)isodaurinol] (2), four new alkaloids (haplomegalanthine (3), megalantin (4), megalanthamide (5), glycoisohaplopine (6) and thirty-five known compounds (7–41) were isolated from Haplophyllum megalanthum Bornm. (Rutaceae). Pinoresinol (23), epipinoresinol (24), indole-3-carbaldehyde (29), N-[2-(4-hydroxyphenyl)ethyl]-3-methylbut-2-enamide (34), 7,8-dimethoxyfuroquinoline-4-one (35), cis-khellactone (36), 4,4′-dihydroxy-3,3′,9-trimethoxy-9,9′-epoxylignan (37), ulopterol (39) and trans-decursidinol (40) were identified for the first time in the genus Haplophyllum. Also, 4′-O-demethylsuchilactone (16) and N-(4-hydroxyphenethyl)benzamide (32) were found for the first time within the family Rutaceae. Structures of the compounds were elucidated by the use of HRMS, UHPLC-MS and 1D/2D NMR analyses. Furthermore, cytotoxic activity of the crude extract and previously unreported compounds (1–3, 5, 6) on colon cancer cell line HT29 were tested by the MTT method. IC50 values were determined for these five compounds and the crude extract as 18.48 ± 0.94 μg/ml, 52.62 ± 7.27 μg/ml, 23.15 ± 6.70 μg/ml, 21.45 ± 2.48 μg/ml, 5.06 ± 0.19 μg/ml and 2.82 ± 0.012 μg/ml, respectively.
The present report is the first detailed phytochemical investigation of the title plant pointing out that it comprises a rich source of diverse chemical constituents including new compounds with promising cytotoxic activity.
期刊介绍：
Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology).
In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.
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