Abstract
Sixteen new prenylated flavonoids, sinoflavonoids P–Z (1–11) and sinoflavonoids NA–NE (12–16), were isolated from the fruit of Sinopodophyllum hexandrum, along with eight known analogues (17–24). Their structures were elucidated on the basis of extensive spectroscopic data (HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC). The cytotoxic activities of compounds 1–18, 20, and 22 were evaluated by MTT assay. Compound 6 showed the most potent cytotoxicity in MCF-7, and HepG2 cell lines, with IC50 values of 6.25 and 3.83 μM, respectively.
Highlights
Preparative high performance liquid chromatography (HPLC) separations were performed on a SEP system (Beijing Sepuruisi scientific Co., Ltd., China) equipped with a variable-wavelength UV detector, using a YMC-Pack ODS-A column (250 × 20 mm, 5 μm)
Prenylated flavonoids are characterized by the presence of lipophilic prenylated group on the parent skeleton
Most of them were tested for the cytotoxic activity in tumor cell lines [2,9,11]
Summary
Its 1H (Table 1, see Figure S53) and 13C-NMR spectra (Table 2, see Figure S54) were quite similar to those of 9, respectively, except for the observation of 2,2-dimethyldihydropyrano group in 14 instead of 3-methyl-2-butenyl in 9 This was further confirmed by their HR-ESI-MS, which gave the same molecular formula C26H28O8 by the quasi-molecular ion peak (m/z 469.1853 [M + H]+ (calcd 469.1862) in 14, m/z 491.1682 [M + Na]+ in 9). Its 1H (Table 1, see Figure S57) and 13C-NMR spectra (Table 2, see Figure S58) were quite similar to those of 14, respectively, except for the observation of one methoxy group δ 3.31 (3H, s), δ 56.9 in 15, suggesting 15 to be a further methyl ether derivative of 14 This was further confirmed by the HR-ESI-MS, which gave the molecular formula C27H30O9 by the quasi-molecularion peak m/z 521.1792 [M + Na]+ (calcd 521.1788), being 14 mass units more than that of 14. With the promising cytotoxicities against two cell lines, compound 6 may be the optimal lead compound for structure optimization studies
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