Bridged cassane derivatives from the seeds of Caesalpinia sappan L. and their cytotoxic activities

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“…Caesanamides A 8 and B 9 , from the seeds of Caesalpinia sappan , are cassane alkaloids with unprecedented ring systems. 5 The structure of caesanamide A 8 was confirmed by X-ray analysis. The structure of veragranine A 10 , from Veratrum grandiflorum , was also confirmed by X-ray analysis.…”

Guided Isolation of New Cytotoxic Cassane Diterpenoids from Caesalpinia sappan

“…[12] The 1 H-NMR data exhibited characteristic resonances for a pair of methyl doublet protons at δ H 1.09 (6H, d, J = 7.3, H 3 -17), three methoxy signals at δ H 3.17 (6H, s, 12-OCH 3 ), 3.69/3.71 (3H, s, 18-OCH 3 ), a group of oxygenated methylene groups at δ H 3.93/ 4.10 (2H, dd, J = 11.3, 2.4, H-20) and dioxymethine groups at 5.25/5.42 (1H, s, H-19), together with an α,β-unsaturated butenolide at δ H 5.25 (2H, s, H-15). Analysis of 13 C-NMR data with the aid of a HSQC spectrum showed two sets of carbons, including a methyl group (δ C 11.4/11.5), two methoxy carbon signals (δ C 50.9/50.9, 52.0/52.1), seven methylene groups (δ C 21.0/21.0, 23.3/24.5, 28.8/35.1, 29.5/30.0, 37.3/37.4, 38.0/38.1, 62.3/66.9), five methine groups (δ C 35. ).…”

“…The cell cycle and apoptosis analyses of compound 1 at various concentrations were assessed by propidium iodide (PI) and Annexin V-FITC/PI staining which be previously reported. [13,32]…”

“…[21] Currently, cytotoxic cassane derivatives with diverse bridge features that separated from C. sappan in our previous research have been found to display potential inhibitory effects on tumor cells by inducing apoptosis. [13] Nevertheless, a large number of compounds that exist in raw medicinal material at low concentrations have not been completely discovered. In order to prioritize the isolation of undescribed cassanes rapidly, a MS/MS-based molecular networking [22,23] analysis of C. sappan was carried out to explore more uncovered chemical constituents.…”

“…Previous investigations on chemical constituents of C. sappan have reported a large number of naturally occurring molecules including cassanes, [3–7] flavones, [8] coumarins [9] . Among of these components, cassanes, as the typical and effective substances, [7] have been proved to exert extensive biological activities in terms of anti‐inflammatory effects on colitis, [10] arthritis [11] and asthma, [12] inhibitory effects on cancer cell lines, [13] renal fibrosis, [14] bacterial and glioblastoma, [15] especially in antiproliferative and anti‐inflammatory [16–19] . In the course of our ongoing search for bioactive cassanes with unique structures and promising tumor cells proliferation inhibitors, a series of diterpenoids and alkaloids have obtained from our studies on six Caesalpinia plants of C. bonduc , [12] C. sappan , [13] C. mimosoides , [14] C. sinensis , [19] C. minax , [20] C. cucullata [21] .…”