Four new cassane-type diterpenoids from the seed kernels of Caesalpinia cucullata Roxb.

Published on May 5, 2021in Natural Product Research2.158
· DOI :10.1080/14786419.2021.1919107
Miao Wang9
Estimated H-index: 9
(SPU: Shenyang Pharmaceutical University),
Tianliang Zhu (SPU: Shenyang Pharmaceutical University)+ 3 AuthorsHuiyuan Gao12
Estimated H-index: 12
(SPU: Shenyang Pharmaceutical University)
The first investigation of chemical composition in seed kernels of Caesalpinia cucullata Roxb. resulted in the separation of four new cassane diterpenes, including three furanoditerpenes (1, 2 and 4) and one tricyclic type (3). It was the first found cassane diterpenoids from this plant. Their gross structures were elucidated by means of comprehensive spectroscopic analysis (UV, IR, NMR, HRESIMS) as well as electronic circular dichroism (ECD) calculation. The compound 1 possess a rare isomerized dihydrofuran ring in structure framework. In bioassay, compounds 1-4 exhibited moderate anti-inflammatory activity by inhibiting production of NO in LPS-induced RAW 264.7 cells.
📖 Papers frequently viewed together
10 Authors (Guo-Xu Ma, ..., Xudong Xu)
15 Citations
#1Xuesong LiangH-Index: 3
#2Dewen BiH-Index: 3
Last. Liqin WangH-Index: 8
view all 4 authors...
1 CitationsSource
#1Qingfeng Ruan (Guangzhou University of Chinese Medicine)H-Index: 6
#2Xing-Hong Zhou (Guangzhou University of Chinese Medicine)H-Index: 5
Last. Zhongxiang Zhao (Guangzhou University of Chinese Medicine)H-Index: 13
view all 7 authors...
Abstract Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1–6), together with 28 known compounds (7–34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first exa...
9 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...
18 CitationsSource
#1Zheng-Feng Wu (UM: University of Macau)H-Index: 2
#2Han Bao (UM: University of Macau)H-Index: 4
Last. Ligen Lin (UM: University of Macau)H-Index: 27
view all 10 authors...
Abstract Phytochemical investigation on the seeds of Caesalpinia sappan led to the isolation of five new cassane-type diterpenoids, named 11-oxo-phanginin A ( 1 ), caesalsappanins O–Q ( 2 – 4 ) and phanginin U ( 5 ), together with five known compounds. The structures of the new compounds were elucidated by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. All the new compounds showed moderate cytotoxic effects on human breast cancer MCF-7 and human colon cancer HCT11...
10 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 – ...
17 CitationsSource
#1Yong Zheng (CAS: Chinese Academy of Sciences)H-Index: 8
#2Shuwei ZhangH-Index: 18
Last. Li-Jiang XuanH-Index: 19
view all 5 authors...
Fourteen new cassane diterpenoids, caesalminaxins A–L (1–14), and three known compounds were isolated from the seeds of Caesalpinia minax. Among the new diterpenoids, compounds 3 and 4 possess a rare spiro C/D ring system. The C-16 epimeric mixture 1/2 has an unprecedented carbon skeleton, presumably derived from 3 by cleavage of the C-13–C-14 bond. Compound 5 is the first example of a cassane diterpenoid with a spiro A/B ring system. The structures of the compounds were elucidated on the basis ...
32 CitationsSource
#1Mario A. Gómez-Hurtado (UMSNH: Universidad Michoacana de San Nicolás de Hidalgo)H-Index: 8
#2Fany E. Álvarez-Esquivel (UMSNH: Universidad Michoacana de San Nicolás de Hidalgo)H-Index: 1
Last. Rosa E. del Río (UMSNH: Universidad Michoacana de San Nicolás de Hidalgo)H-Index: 12
view all 11 authors...
Abstract The dichloromethane extract from the leaves of Caesalpinia platyloba provided cassane diterpenes whose structures were determined as (−)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane (1), (−)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene (3), and (−)-(5S,6R,8S,9S,10R,13E)-6-acetoxycassa-13,15-diene (4). Compound 1 was chemically correlated with (−)-(5S,6R,8S,9S,10R,14R)-6-hydroxyvouacapane (2), (+)-(5S,8S,9S,10R,14R)-6-oxovouacapane (5), and (+)-(5S,6S,8S,9S,10R,14R)-6-acetoxyvouacap...
17 CitationsSource
#3Li Cao (Peking Union Medical College)H-Index: 4
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, 12 α -methoxyl,5 α ,14 β -dihydroxy-1 α ,6 α ,7 β -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...
27 CitationsSource
#1Rita A. Dickson ('KCL': King's College London)H-Index: 12
#2Peter J. Houghton ('KCL': King's College London)H-Index: 74
Last. Peter J. Hylands ('KCL': King's College London)H-Index: 25
view all 3 authors...
Abstract Bioactivity-guided fractionation of the light petroleum extract of Caesalpinia benthamiana (= Mezoneuron benthamianum ) root bark has led to the isolation of two cassane diterpenoids, designated as benthaminin 1 and 2. A third compound, a deoxy form of caesaldekarin C (also referred to as methyl vouacapenate) which has previously been isolated from Caesalpinia major , C. bonducella , Vouacapoua americana and V. macropetala , was also isolated, together with β-sitosterol and stigmastenon...
84 CitationsSource
#1Surya Kant Kalauni (University of Toyama)H-Index: 5
#2Suresh Awale (University of Toyama)H-Index: 38
Last. Shigetoshi Kadota (University of Toyama)H-Index: 76
view all 8 authors...
Malaria is one of the most life-threatening infectious diseases worldwide and claims the millions of peoples life each year. The appearance of drug-resistance Plasmodium falciparum has made the treatment of malaria increasingly problematic, and thus, it is a dire need to search the new alternatives of current drugs. In the present study, 44 cassane- and norcassane-type diterpenes isolated from Caesalpinia crista of Myanmar and Indonesia were evaluated for their antimalarial activity against the ...
67 CitationsSource
Cited By1