AUTHOR=Morikawa Toshio , Luo Fenglin , Manse Yoshiaki , Sugita Hidemi , Saeki Shunsuke , Chaipech Saowanee , Pongpiriyadacha Yutana , Muraoka Osamu , Ninomiya Kiyofumi 

TITLE=Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity

JOURNAL=Frontiers in Chemistry

VOLUME=8

YEAR=2020

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2020.00199

DOI=10.3389/fchem.2020.00199

ISSN=2296-2646

ABSTRACT=<p>Geranylated coumarin constituents, kayeassamin I (<bold>1</bold>) and mammeasins E (<bold>2</bold>) and F (<bold>3</bold>) were newly isolated from the methanol extract of the flowers of <italic>Mammea siamensis</italic> (Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (<bold>23</bold>), deacetylmammea E/AA cyclo D (<bold>31</bold>), deacetylmammea E/BB cyclo D (<bold>32</bold>), mammea A/AA cyclo F (<bold>34</bold>), and mammea A/AC cyclo F (<bold>35</bold>). These compounds (<bold>1</bold>–<bold>3</bold>) were obtained as an inseparable mixture (<italic>ca</italic>. 1:1 ratio) of the 3″<italic>R</italic> and 3″<italic>S</italic> forms, respectively. Among the isolated coumarins from the extract, mammeasins E (<bold>2</bold>, 22.6 μM), A (<bold>4</bold>, 19.0 μM), and B (<bold>5</bold>, 24.0 μM), kayeassamins E (<bold>9</bold>, 33.8 μM), F (<bold>10</bold>, 15.9 μM), and G (<bold>11</bold>, 17.7 μM), surangin C (<bold>13</bold>, 5.9 μM), and mammeas A/AA (<bold>17</bold>, 19.5 μM), E/BB (<bold>22</bold>, 16.8 μM), and A/AA cyclo F (<bold>34</bold>, 23.6 μM), were found to inhibit testosterone 5α-reductase.</p>