Two new cassane-type diterpenoids from the seed kernels of Caesalpinia bonduc (Linn.) Roxb. and their anti-inflammatory activity

Published on Mar 4, 2021in Natural Product Research2.158
· DOI :10.1080/14786419.2021.1896511
Ting Liu1
Estimated H-index: 1
(SPU: Shenyang Pharmaceutical University),
Xiang Li (SPU: Shenyang Pharmaceutical University)+ 2 AuthorsHuiyuan Gao12
Estimated H-index: 12
(SPU: Shenyang Pharmaceutical University)
Sources
Abstract
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...
References17
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#1Flaure Rosette Ehawa Essoung (University Institute of Technology, Burdwan University)H-Index: 2
#2Brice M. Mba’ning (University of Yaoundé)H-Index: 4
Last. Russell J. CoxH-Index: 44
view all 10 authors...
Methanolic extracts of liana of Caesalpinia welwitschiana and leaves of C. bonduc were found to possess moderate antifeedant and ovicidal activities against Tuta absoluta. Bioassay-guided isolation...
1 CitationsSource
#1Ting Liu (SPU: Shenyang Pharmaceutical University)H-Index: 1
#2Miao Wang (SPU: Shenyang Pharmaceutical University)H-Index: 9
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 9 authors...
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...
2 CitationsSource
#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
#1Qin Liu (SYSU: Sun Yat-sen University)H-Index: 3
#2Bai Bai (SYSU: Sun Yat-sen University)H-Index: 4
Last. Zhimin Zhao (SYSU: Sun Yat-sen University)H-Index: 6
view all 7 authors...
AbstractFour fractions were prepared from the crude extract of Caesalpinia minax Hance and the inhibitory activity of nitric oxide (NO) production release of RAW 264.7 cells stimulated by lipopolysaccharide (LPS) was evaluated. The ethyl acetate (EtOAc) fraction showed obvious inhibitory effect. Bioassay-guided fractionation led to the isolation of three new cassane diterpenes, caesalmin X (1), caesalmin Y (2) and caesalmin Z (3), together with 19 known cassane diterpenoids (4–22). Their structu...
6 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: 40
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
#1Ruijuan Dong (SPU: Shenyang Pharmaceutical University)H-Index: 1
#2Jiuzhi Yuan (SPU: Shenyang Pharmaceutical University)H-Index: 2
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 7 authors...
Cassane skeletons are rare in nature, but often possess valuable medicinal properties. A furanoditerpenoid with an unusual A-seco-rearranged cassane skeleton, neocaesalminin A, and five furanoditerpenoids were isolated from seeds of Caesalpinia minax Hance, along with six known cassane derivatives, 7-O-acetyl-bonducellpin C, caesalmin F, caesalmin C, ζ-caesalmin, caesalmin E1 and caesalpinin K. Compound structures were determined by spectroscopy (HR-ESI-MS, UV, IR, 1D NMR, 2D NMR), X-ray crystal...
21 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Jun Luo (CPU: China Pharmaceutical University)H-Index: 22
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 6 authors...
Abstract Seven new cassane diterpenoids ( 1 – 7 ), along with three known compounds ( 8 – 10 ), were isolated from the seed kernels of Caesalpinia bonduc . The structures were elucidated by extensive 1D and 2D NMR (HSQC, HMBC and ROESY) and mass (HRESIMS) spectroscopic data analyses. The structure and absolute configuration of compound 1 were confirmed by a single-crystal X-ray diffraction experiment. All isolates were tested for their cytotoxicity against HepG-2, MCF-7 and MG-63 cells, and 8 – ...
13 CitationsSource
#1Jiming Wu (SPU: Shenyang Pharmaceutical University)H-Index: 3
#1Jiming Wu (SPU: Shenyang Pharmaceutical University)H-Index: 1
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 7 authors...
Abstract A bioassay-guided study led to the isolation of seven new cassane furanoditerpenes, designated as spirocaesalmin B (1), caesalpinin M1 (2), caesalpinin M2 (3), caesalmin E1 (4), caesalmin E2 (5), caesalmin E3 (6), caesalpinin F1 (7) and three known compounds neocaesalpin A(8), neocaesalpin L(9), neocaesalpin L1(10) from the seeds of Caesalpinia minax Hance. Compound structures were determined on the basis of extensive spectroscopic analyses, including X-ray crystallographic analysis, HR...
29 CitationsSource
#1Guo-Xu Ma (Peking Union Medical College)H-Index: 11
#2Jing-Quan YuanH-Index: 9
Last. Xudong XuH-Index: 21
view all 13 authors...
Eight new cassane-type diterpenes, caesalpins A–H (1–8), were isolated from the ethyl acetate extract of Caesalpinia minax. Compound 1 displayed significant antiproliferative activity against HepG-2 (IC50 4.7 μM) and MCF-7 (IC50 2.1 μM) cells, and compounds 2 and 4 exhibited selective cytotoxic activities against MCF-7 (IC50 7.9 μM) and AGS (IC50 6.5 μM) cells.
31 CitationsSource
#1Dayanand M KannurH-Index: 2
#2Mukta Paranjpe (Braunschweig University of Technology)H-Index: 4
view all 5 authors...
In the present work, Caesalpinia bonduc seed coat extract (CBSCE) has been evaluated for anti-inflammatory and analgesic activity C. bonduc seeds have been attributed with anti-inflammatory and analgesic properties in the folklore medicine. Here in our study, we have tried to carry out the systematic evaluation of the seed coat extract of C. bonduc to substantiate these claims. C. bonduc seed coat was extracted with 95% ethanol and concentrated; further, the extract was screened for anti-inflamm...
14 CitationsSource
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