New cassane-type diterpenoids from kernels of Caesalpinia bonduc (Linn.) Roxb. and their inhibitory activities on phosphodiesterase (PDE) and nuclear factor-kappa B (NF-κB) expression

Liu, Ting; Wang, Miao; Qi, Shizhou; Shen, Xuehui; Wang, Ying; Jing, Wenhua; Yang, Yiren; Li, Xianzhe; Gao, Huiyuan

doi:10.1016/j.bioorg.2020.103573

Cited by 19 publications

(18 citation statements)

References 35 publications

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“…The stems of this plant are commonly used in folk medicine to treat rheumatic arthralgia, cough as well as traumatic bleeding. [15] In this report, eight undescribed CA (1)(2)(3)(4)(5)(6)(7)(8), along with seven known compounds (9)(10)(11)(12)(13)(14)(15) were obtained (Figure 1). These CA were firstly found from C. cucullata, and their structural characteristics were summarized and possible biogenetic relationship was deduced.…”

Section: Background and Originality Contentmentioning

confidence: 90%

“…The structures of known compounds were elucidated in the light of spectroscopic data and references. Thus, compounds (9)(10)(11)(12)(13)(14)(15) were defined as 6-hydroxyvouacapane ( 9), [17] 6-acetoxyvouacapane (10), [17] vouacapenan ( 11), [18] sucutinirane C ( 12), [19] deacetylsucutinirane C ( 13), [20] (5α)-vouacapa-8( 14),9(11)-diene ( 14), [19] and taepeenin L ( 15), [18] respectively. Fifteen small polar CA were firstly reported from C. cucullata and their structural features were summarized.…”

Section: Concise Reportmentioning

confidence: 99%

“…obtained some CA with novel structures and anti‐inflammatory activity. [ 11‐14 ] Accordingly, in our continuing search for much more structurally diverse CA to treat inflammatory diseases, the systematic chemical investigation on the petroleum ether extract of seed kernels of Caesalpinia cucullata Roxb. was firstly performed.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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New Cassane Diterpenoids from the Seed Kernels of Caesalpinia cucullata, Exhibit Anti‐inflammatory Effect in vitro by Inhibiting iNOS Enzymatic Activity

et al. 2021

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Inflammation is a complex biological response to stimulation. Natural cassane diterpenoids from Caesalpinia genus exhibit significant anti-inflammation activity. Eight new cassane diterpenoids (1-8) along with seven known ones (9-15) were obtained from the seed kernels of Caesalpinia cucullata Roxb. This is the first report on chemical investigation of the seed kernels of C. cucullata, and the cassane diterpenes were found in this plant for the first time. Their structures were elucidated based on the extensive spectroscopic analyses, and the absolute configurations were identified by ECD calculation and X-ray crystallography. All compounds were evaluated for their anti-inflammation activity by inhibiting NO production in LPS-induced RAW 264.7 cells. Compounds 1-2 and 9-11 exhibited effective inhibitory activity with inhibition rate more than 50%. The iNOS enzyme activity and molecular docking experiments were performed to explore the preliminary mechanism. Eventually, a potential anti-inflammatory mechanism revealed that the bioactive cassane inhibited overproduction of NO by targeting key residues in the iNOS active cavity to reduce iNOS enzymatic activation.

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Section: Background and Originality Contentmentioning

confidence: 90%

Section: Concise Reportmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

See 1 more Smart Citation

New Cassane Diterpenoids from the Seed Kernels of Caesalpinia cucullata, Exhibit Anti‐inflammatory Effect in vitro by Inhibiting iNOS Enzymatic Activity

et al. 2021

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“…Roxb., (family: Leguminosae, genus: Caesalpinia) is widely distributed in tropical and subtropical regions. As a traditional folk medicine, it is often used to treat fever, dysentery, and asthma [ 12 , 13 ]. Phytochemical analysis showed that the plant contains mainly polyphenols, flavonoids, saponins, and terpenoids.…”

Section: Introductionmentioning

confidence: 99%

Diterpenoid Caesalmin C Delays Aβ-Induced Paralysis Symptoms via the DAF-16 Pathway in Caenorhabditis elegans

Zhang

Bai

Cui

et al. 2022

IJMS

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Alzheimer’s disease (AD) is the most prevalent neurodegenerative disease in the world. However, there is no effective drug to cure it. Caesalmin C is a cassane-type diterpenoid abundant in Caesalpinia bonduc (Linn.) Roxb. In this study, we investigated the effect of caesalmin C on Aβ-induced toxicity and possible mechanisms in the transgenic Caenorhabditis elegans AD model. Our results showed that caesalmin C significantly alleviated the Aβ-induced paralysis phenotype in transgenic CL4176 strain C. elegans. Caesalmin C dramatically reduced the content of Aβ monomers, oligomers, and deposited spots in AD C. elegans. In addition, mRNA levels of sod-3, gst-4, and rpt-3 were up-regulated, and mRNA levels of ace-1 were down-regulated in nematodes treated with caesalmin C. The results of the RNAi assay showed that the inhibitory effect of caesalmin C on the nematode paralysis phenotype required the DAF-16 signaling pathway, but not SKN-1 and HSF-1. Further evidence suggested that caesalmin C may also have the effect of inhibiting acetylcholinesterase (AchE) and upregulating proteasome activity. These findings suggest that caesalmin C delays the progression of AD in C. elegans via the DAF-16 signaling pathway and that it could be developed into a promising medication to treat AD.

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“…The C. bonducella is extensively used in folk medicines 5 for the treatment of filarial infection, common cold, tumor, fever, asthma, dysentery, and diabetes in India and China. [5][6][7] The extract of leaves, seeds and seeds kernel of C. bonducella have been studied for antitumor activity, 8 anti-inflammatory effects, 7 an increase of contractile force, 9 contractile activity of uterine smooth muscle, 10 antioxidants, 6,8 and antihyperglycemic. 6 No study has been reported antiurolithiatic effect of C. bonducella seed.…”

Section: Introductionmentioning

confidence: 99%

Antiurolithiasis, Antioxidant, Anti-inflammatory, Analgesic, and Diuretic Activity of Ethanolic Extract of Seeds of Caesalpinia bonducella

Kumar

Nandi

Kumar

et al. 2021

JPHI

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Antioxidant activityDPPH assay: 7.89 mg of DPPH was dissolved in 100 ml 99.5% ethanol to make 0.2 mmol/L DPPH solution and incubated in dark for 2 hr. The EECB at various concentrations (25, 50, 100, and 200 µg/ml) were diluted with ethanol to get testing sample solution. 200µl of EECB, 1ml of DPPH solution and 800 μl of Tris-HCl buffer (pH 7.4) were mixed in test tube and kept at 25°C for 45 min. The absorbance was recorded at 517 nm by UV-Visible spectrophotometric (Systronics Double Beam

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New cassane-type diterpenoids from kernels of Caesalpinia bonduc (Linn.) Roxb. and their inhibitory activities on phosphodiesterase (PDE) and nuclear factor-kappa B (NF-κB) expression

Cited by 19 publications

References 35 publications

New Cassane Diterpenoids from the Seed Kernels of Caesalpinia cucullata, Exhibit Anti‐inflammatory Effect in vitro by Inhibiting iNOS Enzymatic Activity

New Cassane Diterpenoids from the Seed Kernels of Caesalpinia cucullata, Exhibit Anti‐inflammatory Effect in vitro by Inhibiting iNOS Enzymatic Activity

Diterpenoid Caesalmin C Delays Aβ-Induced Paralysis Symptoms via the DAF-16 Pathway in Caenorhabditis elegans

Antiurolithiasis, Antioxidant, Anti-inflammatory, Analgesic, and Diuretic Activity of Ethanolic Extract of Seeds of Caesalpinia bonducella

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