Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP
A methanol extract of the flowers of <i>Mammea siamensis</i> (Miq.) T. Anders. (Calophyllaceae) showed anti-proliferative activity against human prostate carcinoma LNCaP cells (IC<sub>50</sub> = 2.0 µg/mL). Two new coumarin-related polysubstituted benzofurans, mammeasins P (&...
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MDPI AG
2023-02-01
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| author | Fenglin Luo Yoshiaki Manse Saowanee Chaipech Yutana Pongpiriyadacha Osamu Muraoka Toshio Morikawa |
| author_facet | Fenglin Luo Yoshiaki Manse Saowanee Chaipech Yutana Pongpiriyadacha Osamu Muraoka Toshio Morikawa |
| author_sort | Fenglin Luo |
| collection | DOAJ |
| description | A methanol extract of the flowers of <i>Mammea siamensis</i> (Miq.) T. Anders. (Calophyllaceae) showed anti-proliferative activity against human prostate carcinoma LNCaP cells (IC<sub>50</sub> = 2.0 µg/mL). Two new coumarin-related polysubstituted benzofurans, mammeasins P (<b>1</b>) and Q (<b>2</b>), and a known polysubstituted coumarin mammea B/AC cyclo F (<b>39</b>) were isolated from the extract along with 44 previously reported polysubstituted coumarin constituents (<b>3</b>–<b>38</b> and <b>40</b>–<b>47</b>). The structures of two new compounds (<b>1</b> and <b>2</b>) were determined based on their spectroscopic properties derived from the physicochemical evidence including NMR and MS analyses and taking the plausible generative pathway into account. Among the coumarin constituents, mammeasins A (<b>3</b>, IC<sub>50</sub> = 1.2 µM) and B (<b>4</b>, 0.63 µM), sugangin B (<b>18</b>, 1.5 µM), kayeassamins E (<b>24</b>, 3.0 µM) and G (<b>26</b>, 3.5 µM), and mammeas E/BA (<b>40</b>, 0.88 µM), E/BB (<b>41</b>, 0.52 µM), and E/BC (<b>42</b>, 0.12 µM) showed relatively potent anti-proliferative activity. |
| first_indexed | 2024-03-11T08:18:12Z |
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| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-11T08:18:12Z |
| publishDate | 2023-02-01 |
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| spelling | doaj.art-b1e3370918c3498b97906b31473dd12a2023-11-16T22:36:49ZengMDPI AGPharmaceuticals1424-82472023-02-0116223110.3390/ph16020231Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaPFenglin Luo0Yoshiaki Manse1Saowanee Chaipech2Yutana Pongpiriyadacha3Osamu Muraoka4Toshio Morikawa5Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Osaka, JapanPharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Osaka, JapanPharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Osaka, JapanFaculty of Science and Technology, Rajamangala University of Technology Srivijaya, Thungyai, Nakhon Si Thammarat 80240, ThailandPharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Osaka, JapanPharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Osaka, JapanA methanol extract of the flowers of <i>Mammea siamensis</i> (Miq.) T. Anders. (Calophyllaceae) showed anti-proliferative activity against human prostate carcinoma LNCaP cells (IC<sub>50</sub> = 2.0 µg/mL). Two new coumarin-related polysubstituted benzofurans, mammeasins P (<b>1</b>) and Q (<b>2</b>), and a known polysubstituted coumarin mammea B/AC cyclo F (<b>39</b>) were isolated from the extract along with 44 previously reported polysubstituted coumarin constituents (<b>3</b>–<b>38</b> and <b>40</b>–<b>47</b>). The structures of two new compounds (<b>1</b> and <b>2</b>) were determined based on their spectroscopic properties derived from the physicochemical evidence including NMR and MS analyses and taking the plausible generative pathway into account. Among the coumarin constituents, mammeasins A (<b>3</b>, IC<sub>50</sub> = 1.2 µM) and B (<b>4</b>, 0.63 µM), sugangin B (<b>18</b>, 1.5 µM), kayeassamins E (<b>24</b>, 3.0 µM) and G (<b>26</b>, 3.5 µM), and mammeas E/BA (<b>40</b>, 0.88 µM), E/BB (<b>41</b>, 0.52 µM), and E/BC (<b>42</b>, 0.12 µM) showed relatively potent anti-proliferative activity.https://www.mdpi.com/1424-8247/16/2/231<i>Mammea siamensis</i>mammeasinpolysubstituted coumarincoumarin-related polysubstituted benzofurananti-proliferative activityprostate carcinoma |
| spellingShingle | Fenglin Luo Yoshiaki Manse Saowanee Chaipech Yutana Pongpiriyadacha Osamu Muraoka Toshio Morikawa Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP Pharmaceuticals <i>Mammea siamensis</i> mammeasin polysubstituted coumarin coumarin-related polysubstituted benzofuran anti-proliferative activity prostate carcinoma |
| title | Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP |
| title_full | Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP |
| title_fullStr | Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP |
| title_full_unstemmed | Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP |
| title_short | Structures of Mammeasins P and Q, Coumarin-Related Polysubstituted Benzofurans, from the Thai Medicinal Plant <i>Mammea siamensis</i> (Miq.) T. Anders.: Anti-Proliferative Activity of Coumarin Constituents against Human Prostate Carcinoma Cell Line LNCaP |
| title_sort | structures of mammeasins p and q coumarin related polysubstituted benzofurans from the thai medicinal plant i mammea siamensis i miq t anders anti proliferative activity of coumarin constituents against human prostate carcinoma cell line lncap |
| topic | <i>Mammea siamensis</i> mammeasin polysubstituted coumarin coumarin-related polysubstituted benzofuran anti-proliferative activity prostate carcinoma |
| url | https://www.mdpi.com/1424-8247/16/2/231 |
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