Cassane-type Diterpenes from the Seeds of Caesalpinia minax with Their Antineoplastic Activity

Abstract

Five new cassane-type diterpenes, neocaesalpin AA (1), neocaesalpin AB (2), neocaesalpin AC (3), neocaesalpin AD (4) and neocaesalpin AE (5), were isolated from Caesalpinia minax together with three known compounds, 12α-methoxyl,5α,14β-dihydroxy-1α,6α,7β-triacetoxycass-13(15)-en-16,12-olide (6), spirocaesalmin (7) and magnicaesalpin (8). Their structures were elucidated based on 1D and 2D NMR, MS and CD analyses. Compounds 1-6 were tested against Hela, HCT-8, HepG-2, MCF-7 and A549 cancer cells and showed moderate cytotoxicity with IC₅₀ values from 18.4 to 83.9 µM.

Cassane‐Type Diterpenoids from the Seeds of Caesalpinia bonduc (L.) Roxb.

“…Only several cassane‐type diterpenoids were reported with cytotoxic activity ( Supporting Information , Figure S99 ), including caesalpinolides A and B, [31] caesalpins A−D, [21] neocaesalpins S−V, [32] phanginin R, [16] neocaesalpins AA−AC [33] and 12 α ‐methoxy‐5 α ,14 β ‐dihydroxy‐1 α ,6 α ,7 β ‐triacetoxycass‐13(15)‐en‐16,12‐olide [33] . Taken together, the preliminary structure‐activity relationship could be summarized as following: the presence of an acetoxy group at C‐7 or a hydroxy group at C‐6 could decrease the cytotoxic activity.…”

Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells

“…The HRESIMS of 2 indicated the molecular formula as C 22 Tables 1 and 2, also see Supplementary Materials) were very similar to those of caesaljapin methyl ester [20]. In the HMBC spectrum, the correlations from the singlet methyl group (δ H 0.74, s) to C-1 (δ C 39.1), C-5 (δ C 50.5), C-9 (δ C 45.2) and C-10 (δ C 37.0) assigned it as Me-20.…”

“…The HRESIMS of 4, exhibiting the ion peak at m/z 399.1787 [M + Na] + , established the molecular formula as C 21 H 28 O 6 . The UV and IR spectra showed absorptions for a hydroxy group (3436 cm´1) and an α,β-unsaturated butenolide moiety (210 nm; 1729 cm´1) [16,22]. The olefinic proton signal at δ H 5.67 (s, H-15) and downfield carbon signals at δc 79.6 (C-12), 175.5 (C-13), 110.9 (C-15) and 174.0 (C-16) in the NMR spectra further supported the presence of the α,β-unsaturated butenolide moiety (Tables 1 and 2 (Table 1).…”

New Cassane Diterpenes from the seeds of Caesalpinia decapetala

“…Previous studies have shown that this plant contains several classes of compounds, such as diterpenes, triterpenoids, flavonoids, steroids, and phenolic compounds . Among the isolated structures, diterpenes are a group of highly structurally diverse compounds and show significant biological activities, such as antimalarial, antiproliferative, antihelmintic, antibacterial, and antineoplastic effects . Because of these extensive activities, we carried out studies of the cassane diterpenes of the seeds of C. decapetala .…”

“…[2][3][4] Among the isolated structures, diterpenes are a group of highly structurally diverse compounds and show significant biological activities, such as antimalarial, antiproliferative, antihelmintic, antibacterial, and antineoplastic effects. [5][6][7] Because of these extensive activities, we carried out studies of the cassane diterpenes of the seeds of C. decapetala. During the course of this work, five cassane-type diterpenes were isolated from the CHCl 3 extract of C. decapetala, among which caesaldecapes C and D (1-2) were identified as new compounds.…”