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.

Published on Jan 9, 2020in Bioorganic Chemistry4.831
· DOI :10.1016/J.BIOORG.2020.103573
Ting Liu1
Estimated H-index: 1
(SPU: Shenyang Pharmaceutical University),
Miao Wang9
Estimated H-index: 9
(SPU: Shenyang Pharmaceutical University)
+ 6 AuthorsHuiyuan Gao12
Estimated H-index: 12
(SPU: Shenyang Pharmaceutical University)
Sources
Abstract
Abstract In this paper, chemical investigation on the chloroform soluble fraction of seed kernels of Caesalpinia bonduc resulted in the isolation of five new cassane diterpenoids: norcaesalpinin O (1), norcaesalpinin P (2), caesalpinin MQ (3), caesall O/P (4/5) and seven known compounds (6-12). Compounds structures were elucidated by 1H NMR, 13C NMR, 2D NMR, HR-MS and ECD (electronic circular dichroism) spectral analysis. The characters for new compounds with the presence of an aromatized C ring or demethyl group at C-17 position in the structures were found. By means of bioactive screenings, the inhibitory effect on type-4 phosphodiesterase (PDE4, the target protein of asthma disease) and nuclear factor-kappa B (NF-κB) expression were valued. Compound 1 was found to exhibit moderate inhibitory activity on PDE4 and much better binding affinity than other structures by docking studies for interaction analyzing. Compounds 6, 10 and 11 displayed considerable inhibitory strength against NF-κB expression with inhibitory ratio 48.6%, 42.9% and 37.1% at 10 µM, respectively. The isolation of cassane-type diterpenoids with anti-inflammation activity from C. bonduc implied that this plant might be a good source for anti-inflammation agents finding.
📖 Papers frequently viewed together
2 Citations
20192.53Fitoterapia
7 Authors (Qingfeng Ruan, ..., Zhongxiang Zhao)
8 Citations
6 Authors (Guo-Xu Ma, ..., Li-Yan Ma)
24 Citations
References37
Newest
#1Wenhua Jing (SPU: Shenyang Pharmaceutical University)H-Index: 3
#2Xinxin Zhang (SPU: Shenyang Pharmaceutical University)H-Index: 3
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 7 authors...
Abstract Natural products, especially diterpenoids, are enriched with numerous compounds with a broad spectrum of therapeutic indications, suggesting that functional moieties serve as a core pharmacophore. Cassane diterpenoids (CAs), as the main and characteristic constituents of medical plants in the Caesalpinia genus, have been widely studied due to their bioactivities, and >450 compounds have been reported since the 1960s, including 283 compounds that have been reported in the past decade. Th...
13 CitationsSource
#1Gang Xiang (NU: Nanjing University)H-Index: 5
#2Minmin Fan (NU: Nanjing University)H-Index: 6
Last. Qiang Xu (NU: Nanjing University)H-Index: 116
view all 12 authors...
Abstract Although repression of inflammatory gene expression makes glucocorticoids (GCs) powerful anti-inflammatory agents, side effects limit usage and drive the search for improved glucocorticoid receptor (GR) ligands. It has been postulated that the anti-inflammatory effects of GCs are primarily mediated by GR’s activity in transrepressing major inflammation pathways such as NF-κB pathway, whereas their side effects are mostly mediated by GR’s transactivation. In this study, we found that Cae...
11 CitationsSource
#1Ting Liu (University of Texas MD Anderson Cancer Center)H-Index: 3
#2Lingyun Zhang (University of Texas MD Anderson Cancer Center)H-Index: 5
Last. Shao Cong Sun (University of Texas at Austin)H-Index: 79
view all 4 authors...
The transcription factor NF-κB regulates multiple aspects of innate and adaptive immune functions and serves as a pivotal mediator of inflammatory responses. NF-κB induces the expression of various pro-inflammatory genes, including those encoding cytokines and chemokines, and also participates in inflammasome regulation. In addition, NF-κB plays a critical role in regulating the survival, activation and differentiation of innate immune cells and inflammatory T cells. Consequently, deregulated NF...
1,402 CitationsSource
Asthma and chronic obstructive pulmonary disease (COPD) are common chronic respiratory diseases. Both diseases have incompletely distinct pathophysiology, clinical manifestation, and treatment responsiveness. Pulmonary and systemic inflammations are the hallmarks of COPD. Most asthma responds to inhaled corticosteroid (ICS) treatment. In contrast, COPD is a corticosteroid-resistant disease. Bronchodilators are a preferred treatment method of COPD, with the aim of improving symptoms and preventin...
20 CitationsSource
#1Fernanda Paula Roncon Santana (UNIFESP: Federal University of São Paulo)H-Index: 7
#2Nathalia M. Pinheiro (USP: University of São Paulo)H-Index: 10
Last. Carla Máximo Prado (UNIFESP: Federal University of São Paulo)H-Index: 24
view all 9 authors...
Pulmonary inflammation is a hallmark of many respiratory diseases such as asthma, chronic obstructive pulmonary disease (COPD), and acute respiratory syndrome distress (ARDS). Most of these diseases are treated with anti-inflammatory therapy in order to prevent or to reduce the pulmonary inflammation. Herbal medicine-derived natural products have been used in folk medicine and scientific studies to evaluate the value of these compounds have grown in recent years. Many substances derived from pla...
27 CitationsSource
#1Marco Bigoni (University of Milano-Bicocca)H-Index: 18
#2Marco Turati (University of Milano-Bicocca)H-Index: 10
Last. Antonio TorselloH-Index: 36
view all 14 authors...
Anterior cruciate ligament (ACL) reconstruction restores knee stability but does not reduce the incidence of posttraumatic osteoarthritis induced by inflammatory cytokines. The aim of this research was to longitudinally measure IL-1β, IL-6, IL-8, IL-10, and TNF-α levels in patients subjected to ACL reconstruction using bone-patellar tendon-bone graft. Synovial fluid was collected within 24–72 hours of ACL rupture (acute), 1 month after injury immediately prior to surgery (presurgery), and 1 mont...
291 CitationsSource
#1Patricia Angeli da Silva Pigati (USP: University of São Paulo)H-Index: 4
#2Renato Fraga Righetti (USP: University of São Paulo)H-Index: 13
Last. Iolanda F.L.C. Tibério (USP: University of São Paulo)H-Index: 24
view all 13 authors...
Background: Previously, we showed that treatment with the Rho-kinase inhibitor Y-27632 was able to control airway responsiveness, inflammation, remodeling, and oxidative stress in an animal model of asthma, suggesting that this drug is beneficial in asthma. However, studies evaluating the effects of these inhibitors in conjunction with corticosteroids on chronic pulmonary inflammation have not been conducted. Therefore, we evaluated the effects of treatment with the Rho-kinase inhibitor Y-27632,...
26 CitationsSource
#1Carolyn Chee (University of Nottingham)H-Index: 4
#2Luckni Sellahewa (Royal Derby Hospital)H-Index: 1
Last. Joseph M PappachanH-Index: 20
view all 3 authors...
Inhaled corticosteroids (ICS) are the cornerstones in the management of bronchial asthma and some cases of chronic obstructive pulmonary disease. Although ICS are claimed to have low side effect profiles, at high doses they can cause systemic adverse effects including bone diseases such as osteopenia, osteoporosis and osteonecrosis. Corticosteroids have detrimental effects on function and survival of osteoblasts and osteocytes, and with the prolongation of osteoclast survival, induce metabolic b...
30 CitationsSource
Although the dysglycemic effects of systemic glucocorticoid therapy are well known, the effect of inhaled corticosteroids (ICS) on carbohydrate metabolism is still a subject of debate. The systemic bioavailability of ICS is claimed to be minimal and the side effects negligible. However, some large retrospective cohort studies showed a definite association between ICS use and incident diabetes or worsening glycemic control in pre-existing diabetes. There are no professional-body recommended guide...
20 CitationsSource
#1Vishnu Sannarangappa (Modbury Hospital)H-Index: 1
#2Ryan Jalleh (Modbury Hospital)H-Index: 1
Inhaled corticosteroids (ICS) have been used as first line treatment of asthma for many decades. ICS are a form of exogenous glucocorticosteroids that can suppress the endogenous production of glucocorticosteroids, a condition known as adrenal suppression (AS). As a result, cessation, decreasing the dose or changing the type of ICS may trigger features of adrenal insufficiency (AI). AI may cause a spectrum of presentations varying from vague symptoms of fatigue to potentially life threatening ac...
19 CitationsSource
Cited By2
Newest
#1Gokhan Zengin (Selçuk University)H-Index: 44
#2Mohamad Fawzi Mahomoodally (UoM: University of Mauritius)H-Index: 26
Last. Małgorzata Polz-Dacewicz (Medical University of Lublin)H-Index: 15
view all 11 authors...
Abstract Caesalpinia bonduc and C. decapeleta var. japonica have great of importance in traditional medicine systems but scientific information’s are still lack for their potentials. To explore their bioactivity, we assessed the antioxidant, enzyme inhibitory abilities of the dichloromethane (DCM), ethyl acetate, methanol, and water extracts prepared from the leaves and bark. The cytotoxicity and anticancer properties of the extracts were also assessed in vitro. The water extract of C. decapelet...
Source
#1Ting Liu (SPU: Shenyang Pharmaceutical University)H-Index: 1
#2Xiang Li (SPU: Shenyang Pharmaceutical University)
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 5 authors...
In this study, phytochemical investigation on the chloroform soluble fraction of seed kernels of Caesalpinia bonduc led to the isolation of two new cassane-type diterpenoids, norcaesalpinin Q (1) a...
Source
#1Miao Wang (SPU: Shenyang Pharmaceutical University)H-Index: 9
#2Yiren Yang (SPU: Shenyang Pharmaceutical University)H-Index: 4
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 8 authors...
1 CitationsSource