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

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

doi:10.3389/fchem.2020.00199

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

Front Chem. 2020 Mar 20:8:199. doi: 10.3389/fchem.2020.00199. eCollection 2020.

Authors

Toshio Morikawa¹, Fenglin Luo¹, Yoshiaki Manse¹, Hidemi Sugita¹, Shunsuke Saeki¹, Saowanee Chaipech^{1

2}, Yutana Pongpiriyadacha³, Osamu Muraoka¹, Kiyofumi Ninomiya¹

Affiliations

¹ Pharmaceutical Research and Technology Institute, Kindai University, Osaka, Japan.
² Faculty of Agro-Industry, Rajamangala University of Technology Srivijaya, Nakhon Si Thammarat, Thailand.
³ Faculty of Science and Technology, Rajamangala University of Technology Srivijaya, Nakhon Si Thammarat, Thailand.

Abstract

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

Keywords: 5α-reductase inhibitor; Mammea siamensis; calophyllaceae; geranylated coumarin; mammeasin.