New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity
<i>Lansium domesticum</i> Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have...
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MDPI AG
2023-02-01
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| author | Tri Mayanti Zulfikar Sarah Fawziah Al Arofatus Naini Rani Maharani Kindi Farabi Nurlelasari Muhammad Yusuf Desi Harneti Dikdik Kurnia Unang Supratman |
| author_facet | Tri Mayanti Zulfikar Sarah Fawziah Al Arofatus Naini Rani Maharani Kindi Farabi Nurlelasari Muhammad Yusuf Desi Harneti Dikdik Kurnia Unang Supratman |
| author_sort | Tri Mayanti |
| collection | DOAJ |
| description | <i>Lansium domesticum</i> Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E (<b>1</b>) and F (<b>2</b>), from the fruit peels of <i>L. domesticum</i> Corr., along with a new tetranortriterpenoid, kokosanolide G (<b>3</b>), from the seeds of <i>L. domesticum</i> Corr. The structural determination of compounds <b>1–3</b> was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds <b>1–3</b> with the literature data. The cytotoxic properties of compounds <b>1–3</b> were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds <b>1</b> and <b>3</b>, with IC<sub>50</sub> values of 45.90 and 18.41 μg/mL, respectively, while compound <b>2</b> showed no activity (IC<sub>50</sub> 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound <b>1</b> is presumably the reason for its better cytotoxic activity compared with that of compound <b>2</b>. Compound <b>3</b> showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from <i>L. domesticum</i> indicate the significant value of this plant as a source of new compounds. |
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| spelling | doaj.art-b51c25a12f144ca3ae2e3d0bff4273e32023-11-17T08:12:33ZengMDPI AGMolecules1420-30492023-02-01285214410.3390/molecules28052144New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic ActivityTri Mayanti0Zulfikar1Sarah Fawziah2Al Arofatus Naini3Rani Maharani4Kindi Farabi5Nurlelasari6Muhammad Yusuf7Desi Harneti8Dikdik Kurnia9Unang Supratman10Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, Indonesia<i>Lansium domesticum</i> Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E (<b>1</b>) and F (<b>2</b>), from the fruit peels of <i>L. domesticum</i> Corr., along with a new tetranortriterpenoid, kokosanolide G (<b>3</b>), from the seeds of <i>L. domesticum</i> Corr. The structural determination of compounds <b>1–3</b> was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds <b>1–3</b> with the literature data. The cytotoxic properties of compounds <b>1–3</b> were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds <b>1</b> and <b>3</b>, with IC<sub>50</sub> values of 45.90 and 18.41 μg/mL, respectively, while compound <b>2</b> showed no activity (IC<sub>50</sub> 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound <b>1</b> is presumably the reason for its better cytotoxic activity compared with that of compound <b>2</b>. Compound <b>3</b> showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from <i>L. domesticum</i> indicate the significant value of this plant as a source of new compounds.https://www.mdpi.com/1420-3049/28/5/2144<i>Lansium domesticum</i>MeliaceaeMCF-7onoceranoid triterpenetetranortriterpenoid |
| spellingShingle | Tri Mayanti Zulfikar Sarah Fawziah Al Arofatus Naini Rani Maharani Kindi Farabi Nurlelasari Muhammad Yusuf Desi Harneti Dikdik Kurnia Unang Supratman New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity Molecules <i>Lansium domesticum</i> Meliaceae MCF-7 onoceranoid triterpene tetranortriterpenoid |
| title | New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity |
| title_full | New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity |
| title_fullStr | New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity |
| title_full_unstemmed | New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity |
| title_short | New Triterpenoids from <i>Lansium domesticum</i> Corr. cv <i>kokossan</i> and Their Cytotoxic Activity |
| title_sort | new triterpenoids from i lansium domesticum i corr cv i kokossan i and their cytotoxic activity |
| topic | <i>Lansium domesticum</i> Meliaceae MCF-7 onoceranoid triterpene tetranortriterpenoid |
| url | https://www.mdpi.com/1420-3049/28/5/2144 |
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