References
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(a) 10a [synthetic prenyllicoflavone A]: a yellowish viscous liquid; Rf 0.30 (SiO₂, 75% EtOAc-Hexane); ¹H-NMR (300 MHz, acetone-
$d_6$ ) δ 1.75 (s, 3H), 1.77 (s, 9H), 3.39 (d, 4H, J = 7.3 Hz), 5.36 (m, 2H), 6.57 (s, 1H), 6.93 (d, 1H, J = 8.6 Hz), 6.96 (s, 1H), 7.56 (dd, 1H, J = 2.1, 8.6 Hz), 7.79 (d, 1H, J = 2.2 Hz), 7.83 (s, 1H)$^13$ C-NMR (75 MHz, acetone-$d_6$ ) δ 17.4, 25.4, 28.1, 29.5, 103.3, 104.9, 115.6, 117.8, 122.2, 123.6, 124.1, 126.6, 126.8, 128.0, 129.2, 133.6, 133.9, 157.6, 158.7, 162.2, 164.5, 177.3, HRMS (EI) m/z: Found: 390.18285 (Calculated for$C_{25}H_{26}O_{4}M^{+}$ ): 390.18318. -
(b) 10b [synthetic licoflavone A]: a yellowish viscous liquid; Rf 0.32 (SiO₂, 75% EtOAc-Hexane); ¹H-NMR (300 MHz, acetone-d6) δ 1.79 (s, 6H), 3.38 (d, 2H, J = 7.8 Hz), 5.38 (t, 1H), 6.43 (s, 1H), 6.45 (s, 1H), 6.86 (d, 1H, J = 7.8 Hz), 7.38 (s, 1H), 7.41 (d, 1H, J = 8.6 Hz), 7.82 (d, 1H, J = 8.6 Hz), 7.87 (d, 1H, J = 8.6 Hz)
$^13$ CNMR (75 MHz), acetone-$d_6$ ) δ 17.4, 25.4, 29.1, 103.4, 106.3, 117.2, 117.8, 123.2, 124.5, 126.6, 127.9, 128.3, 133.9, 161.6, 161.8, 162.2, 164.0, 177.2, HRMS (EI) m/z: Found: 322.12098 (Calculated for$C_{20}H_{18}O_{4} M^{+}$ ): 322.12054. -
Resorption Pit Assay and Quantitation of Pits: Drops of the osteoclast-like multinucleated cell population
$^{9,10}$ were added on bone slices placed in a 96-well culture dich with and without samples. After incubation for 48 h, bone slices were placed for 30 min in 1 M NaOH and cleaned by ultrasonication to remove adherent cells. The bone slices were then stained with Mayers hematoxylin solution (hematoxylin, 1 g/L; NaIO₃, 0.2 g/L; AlNH₄(SO)₄·12H₂O, 50 g/L; CH₃COOH, 7.5 g/L; pH 2.8) for 50 sec, washed air dried. Resorption pits visualized by Mayers hematoxylin staining were identified by ight microscopy with a X5 objective lens. Using an image analysis sofrware (Imagepro plus, Media Cybernetics, MD, USA), the numbers of pits were counted. - Endocrinology v.123 Takahasi, N.;Akatsu, T.;Udagawa, N.;Sasaki, T.;Yamaguchi, A.;Moseley, J. M.;Martin, T. J.;Suda, T.
- Biochem. Bioph. Res. Co. v.237 Takami, M.;Woo, J.-W.;Takahashi, N.;Suda, T.;Nagai, K.
- Anal. Biochem. v.255 Sugawara, K.;Hmada, M.;Hosoi, S.;Tamaoki, T.
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- Synthesis of Isobavachalcone and Some Organometallic Derivatives vol.2013, pp.2, 2001, https://doi.org/10.1002/ejoc.201201063
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