Cassane diterpenoids from the aerial parts of Caesalpinia pulcherrima and their antibacterial and anti-glioblastoma activity

Discovery of diversified cassane diterpenoids as potent antibacterial agents from Caesaplinia pulcherrima and their mechanisms

“…Further analysis of the 1 H– 1 H COSY (correlated spectroscopy), HSQC, and HMBC (heteronuclear multiple bond correlation) correlations (Fig. 2) suggested that rings A and B in 1 are closely related to those of pulcherritam A, also discovered from C. pulcherrima by us 19 . In the HMBC spectra, the correlations of H‐11 ( δ H 7.36, s) with C‐8 ( δ C 122.9), C‐10 ( δ C 43.5), C‐12 ( δ C 154.2), and C‐13 ( δ C 126.7), and of Me‐17 ( δ H 2.35, s) with C‐8, C‐9 ( δ C 141.5), C‐11 ( δ C 106.3), C‐12, C‐13, and C‐14 ( δ C 129.0) verified the conjugation of a benzene ring (ring C) with the fused furan ring, which suggested that 1 was a cassane‐type furanoditerpenoid featuring an aromatic C ring.…”

“…Crystal data for 1: C 31 H 34 O 8 (M = 534.58 g mol −1 ): orthorhombic, space group P2 1 2 1 2 1 (no. 19), a = 8.74700(10) Å, b = 14.0951(2) Å, c = 21.8126(3) Å, V = 2689.27(6) Å 3 , Z = 4, T = 150.00(10) K, μ(Cu K⊍) = 0.780 mm −1 , Dcalc = 1.320 g cm −3 , 13 069 reflections measured (7.468°≤ 2Θ ≤ 144.152°), 5175 unique (R int = 0.0207, R sigma = 0.0196), which were used in all calculations. The final R 1 was 0.0378 (I > 2⊞(I)) and wR 2 was 0.0972 (all data).…”

“…Most of these alkaloids exhibited significant antibacterial and antiglioblastoma activity. 19 Inspired by this research, we have identified C. pulcherrima from Yunnan Province as a major plants for antibacterial investigation. 19,20 In searching for suitable antibacterial and antifeedant agents from Chinese medicinal plants, the crude extract of C. pulcherrima was found to have strong antibacterial activity in the preliminary study.…”

“…19 Inspired by this research, we have identified C. pulcherrima from Yunnan Province as a major plants for antibacterial investigation. 19,20 In searching for suitable antibacterial and antifeedant agents from Chinese medicinal plants, the crude extract of C. pulcherrima was found to have strong antibacterial activity in the preliminary study. Here, the antibacterial ingredients, cassane diterpenoids, were isolated from the stem of C. pulcherrima through a bioassayguided method (Fig.…”

Guided Isolation of New Cytotoxic Cassane Diterpenoids from Caesalpinia sappan

“…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] .…”