Abstract
The chemical study on the seeds of Caesalpinia sappan led to the isolation of five new cassane diterpenoids, phanginins R‒T (1–3) and caesalsappanins M and N (4 and 5), together with seven known compounds 6–12. Their structures were elucidated on the basis of NMR and HRESIMS analyses. The absolute configurations of compounds 1 and 4 were determined by the corresponding CD spectra. All the isolated compounds were tested for their cytotoxicity against ovarian cancer A2780 and HEY, gastric cancer AGS, and non-small cell lung cancer A549 cells. Compound 1 displayed significant toxicity against the four cell lines with the IC50 values of 9.9 ± 1.6 µM, 12.2 ± 6.5 µM, 5.3 ± 1.9 µM, and 12.3 ± 3.1 µM, respectively. Compound 1 induced G1 phase cell cycle arrest in A2780 cells. Furthermore, compound 1 dose-dependently induced A2780 cells apoptosis as evidenced by Hoechst 33342 staining, Annexin V positive cells, the up-regulated cleaved-PARP and the enhanced Bax/Bcl-2 ratio. What’s more, compound 1 also promoted the expression of the tumor suppressor p53 protein. These findings indicate that cassane diterpenoids might have potential as anti-cancer agents, and further in vivo animal studies and structural modification investigation are needed.
Highlights
Cancer is one of the major causes of mortality and death worldwide
The chloroform-soluble fraction of the 80% ethanol extract of C. sappan was purified by column chromatography over silica gel, MCI gel and preparative HPLC to afford twelve cassane diterpenoids, chromatography over silica gel, MCI gel and preparative HPLC to afford twelve cassane diterpenoids, including fivefive new
The human ovarian cancer A2780 cells were acquired from KeyGEN Biotech (Nanjing, Jiangsu, China), HEY cells were kindly provided by Dr Wen-An Qiang
Summary
Cancer is one of the major causes of mortality and death worldwide. The 2014 World Cancer. Expectorant, andhave has exhibited a wide range of activities, including diterpenoids anti-inflammation on the seeds of C. sappan led to isolation of a series of cassane-type with[7], potent anti-influenza virus [8], anti-allergy [9], anti-oxidation [10]. In systematic searching for cytotoxic agents, the chloroform-soluble fraction from the ethanol diterpenoids with potent cytotoxic effect [12,13,14,15,16,17]. Extract of the seeds of C. sappan was chemically investigated, resulting in the isolation of twelve cassane. In systematic searching for cytotoxic agents, the chloroform-soluble fraction from the ethanol diterpenoids, including five new ones, phanginins R‒T (1‒3) and caesalsappanins M and N (4 and 5), extract of the seeds of C. sappan was chemically investigated, resulting in the isolation of twelve cassane and seven knownincluding ones, tomocin. The pro-apoptotic property of compound 1 was further investigated
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