TY - JOUR
T1 - Five new 2-(2-phenylethyl)chromone derivatives from agarwood
AU - Shibata, Shunsuke
AU - Sugiyama, Takuji
AU - Uekusa, Yoshinori
AU - Masui, Ryo
AU - Narukawa, Yuji
AU - Kiuchi, Fumiyuki
N1 - Funding Information:
This work was supported in part by Keio Gijyuku Academic Development Funds and MEXT-Supported Program for the Strategic Research Foundation at Private Universities.
Publisher Copyright:
© 2020, The Japanese Society of Pharmacognosy.
PY - 2020/6/1
Y1 - 2020/6/1
N2 - Agarwood has been used as an incense and in traditional medicines as aphrodisiac, sedative, cardiotonic, and carminative. In this study, five new 2-(2-phenylethyl)chromones (2, 13–16) and eleven known compounds (1, 3–12) were isolated from the agarwood. The structures of the new compounds were determined by 1H-, 13C-, and two-dimensional NMR together with electronic circular dichroism (ECD) spectroscopy. All isolated compounds were evaluated for the phosphodiesterase (PDE) 3A and 5A1 inhibitory activity by the fluorescence polarization method. Dimeric 2-(2-phenylehyl)chromones (13, 14, 16) had potent inhibitory activity to PDE 5A1 with IC50 values of micro molar range (13: 4.2 μM, 14: 7.9 μM, 16: 4.3 μM), whereas they had weak activity to PDE 3A. In contrast, compound (15), which has a phenylpropionic acid moiety instead of the 2-(2-phenylethyl)chromone moiety in the dimers, showed moderate inhibition of both PDE 3A (IC50: 42.6 μM) and PDE 5A1 (IC50: 15.1 μM).
AB - Agarwood has been used as an incense and in traditional medicines as aphrodisiac, sedative, cardiotonic, and carminative. In this study, five new 2-(2-phenylethyl)chromones (2, 13–16) and eleven known compounds (1, 3–12) were isolated from the agarwood. The structures of the new compounds were determined by 1H-, 13C-, and two-dimensional NMR together with electronic circular dichroism (ECD) spectroscopy. All isolated compounds were evaluated for the phosphodiesterase (PDE) 3A and 5A1 inhibitory activity by the fluorescence polarization method. Dimeric 2-(2-phenylehyl)chromones (13, 14, 16) had potent inhibitory activity to PDE 5A1 with IC50 values of micro molar range (13: 4.2 μM, 14: 7.9 μM, 16: 4.3 μM), whereas they had weak activity to PDE 3A. In contrast, compound (15), which has a phenylpropionic acid moiety instead of the 2-(2-phenylethyl)chromone moiety in the dimers, showed moderate inhibition of both PDE 3A (IC50: 42.6 μM) and PDE 5A1 (IC50: 15.1 μM).
KW - 2-(2-phenylethyl)chromone
KW - Agarwood
KW - Aquilaria
KW - Phosphodiesterase inhibitor
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U2 - 10.1007/s11418-020-01410-z
DO - 10.1007/s11418-020-01410-z
M3 - Article
C2 - 32335822
AN - SCOPUS:85084152063
SN - 1861-0293
VL - 74
SP - 561
EP - 570
JO - Journal of Natural Medicines
JF - Journal of Natural Medicines
IS - 3
ER -