New Cassane-Type Diterpenoids of &lt;i&gt;Caesalpinia echinata&lt;/i&gt; (Leguminosae) Exhibiting NF-κB Inhibitory Activities

Mitsui, Taichi; Ishihara, Risa; Hayashi, Ken‐ichiro; Sunadome, Mitsuhisa; Matsuura, Nobuo; Nozaki, Hirōshi

doi:10.1248/cpb.c13-00812

Cited by 16 publications

(5 citation statements)

References 16 publications

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“…The absolute configuration of 4 was deduced from the CD curve of its γ-lactone chromophore. The negative π-π* Cotton effect at 228 nm (∆ε-9.6) indicated an S configuration at C-12 [17,25], thus confirming the proposed structure of compound 4.…”

Section: Identification Of New Compoundssupporting

confidence: 63%

“…Moreover, the NOE cross-peak of H-12/H-11α (δ H 2.60, m) indicated H-12 was also α-oriented. Among the cassane diterpenoids isolated from the genus Caesalpinia, about twenty compounds contain an α,β-unsaturated butenolide moiety fused on ring C, all of which possess the same configuration at C-12 [16,[23][24][25]. The substituents at C-12 could be a hydrogen atom, hydroxy, methoxy, ethoxy and acetyl group.…”

Section: Identification Of New Compoundsmentioning

confidence: 99%

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

et al. 2016

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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 IC 50 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.

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Section: Identification Of New Compoundssupporting

confidence: 63%

Section: Identification Of New Compoundsmentioning

confidence: 99%

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

et al. 2016

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“…Previous reports have described the anti-inflammatory potential of natural cassane diterpenoids from different species of Caesalpinia sp . This activity was showed by inhibition of nitric oxide production and interleukin-1 (IL-1), interleukin-6 (IL-6) protein expression, , and other inflammatory protein mediators, such as cyclooxygenase-2 (COX-2) , or nuclear factor κB (NF-κB). , Yodsaoue et al reported the inhibition of NO release induced by pulcherrin Q, a cassane diterpenoid isolated from the roots of C. pulcherrima , possessing potent NO inhibitory properties, with an IC 50 value of 2.9 μM . Liu et al confirmed that caesalmin A and caesalpinins D and H extracted from the seeds of C. minax displayed a moderate NO inhibitory effect, with IC 50 values around 25.40 μM. , …”

Section: Resultsmentioning

confidence: 99%

Semisynthesis and Evaluation of Anti-Inflammatory Activity of the Cassane-Type Diterpenoid Taepeenin F and of Some Synthetic Intermediates

et al. 2022

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A new strategy for the semisynthesis of the aromatic cassane-type diterpene taepeenin F (6) is reported. The introduction of the methyl group at C-14, characteristic of the target compound, was achieved via dienone 13, easily prepared from abietic acid (10), the major compound in renewable rosin. Biological assays of selected compounds are reported. The antiproliferative activity against HT29, B16-F10, and HepG2 tumor cell lines has been investigated. Salicylaldehyde 21 was the most active compound (IC50 = 7.72 μM). Products 16 and 21 displayed apoptotic effects in B16-F10 cells, with total apoptosis rates of 46 and 38.4%, respectively. This apoptotic process involves a significant arrest of the B16-F10 cell cycle, blocking the G0/G1 phase. Dienone 16 did not cause any loss of the mitochondrial membrane potential (MMP), while salicylaldehyde 21 caused a partial loss of the MMP. The anti-inflammatory activity of the selected compounds was investigated with the LPS-stimulated RAW 264.7 macrophages. All compounds showed potent NO inhibition, with percentages between 80 and 99% at subcytotoxic concentrations. Dienone 16 inhibited LPS-induced differentiation of RAW 264.7 cells, by increasing the proportion of cells in the S phase. In addition, salicylaldehyde 21 had effects on the cell cycle, recovering the cells from the G0/G1 full arrest produced in response to LPS action.

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“…A large number of cassane diterpenoids have been obtained from Caesalpinia (Fabaceae) species including the caesalls A-M (e.g. A 23) from C. bonduc, 102,103 the echinalides A-G from C. echinata, 104 and the caesalfurfuric acids from C. furfuracea. 105 Various studies of C. minax have afforded the caesalpins I and J, 106 neocaesalpins N and AF-AH, 107,108 the anti-malarial lactam, caesalminine A 24, 109 and the unusual nor-cassane, norcaesalpinin I 25.…”

Section: Pimaranes Cassanes and Related Diterpenoidsmentioning

confidence: 99%

Diterpenoids of terrestrial origin

Hanson

2015

Nat. Prod. Rep.

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New Cassane-Type Diterpenoids of <i>Caesalpinia echinata</i> (Leguminosae) Exhibiting NF-κB Inhibitory Activities

Cited by 16 publications

References 16 publications

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

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

Semisynthesis and Evaluation of Anti-Inflammatory Activity of the Cassane-Type Diterpenoid Taepeenin F and of Some Synthetic Intermediates

Diterpenoids of terrestrial origin

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