In this study, phytochemical investigation on the chloroform soluble fraction of seed kernels of led to the isolation of two new cassane-type diterpenoids, norcaesalpinin Q () and caesalpinin MR (), together with seven known compounds (-). The structures of the new compounds were elucidated on the basis of extensive NMR spectroscopic and mass spectrometric analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. All compounds were evaluated for inhibitory effects against NO production of RAW264.7 cells induced by LPS, and compounds , and could inhibited the production of NO at the concentration of 50 µM.
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http://dx.doi.org/10.1080/14786419.2021.1896511 | DOI Listing |
Phytochemistry
September 2024
Key Laboratory of Ethnic Medicine Resource Chemistry, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, 650504, China. Electronic address:
Eight previously undescribed diterpenoids, caesamins A-H (1-8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl.
View Article and Find Full Text PDFFitoterapia
March 2024
School of Pharmaceutical Sciences, Zhejiang Chinese Medical University, No. 260 Baichuan Street, Hangzhou 311402, People's Republic of China. Electronic address:
The phytochemical investigation of the pericarps of Caesalpinia bonduc led to the isolation and identification of five new cassane-type alkaloids: caesalminines C - G (1-5) and six new diterpenoids: caesalbonducin K - P (6-11), along with seven known compounds (12-18). Compounds 1-5 were identified as a group of rare alkaloids possessing a tetracyclic cassane-type diterpenoid skeleton with a lactam D-ring instead of a typical furan or lactone moiety. The structures of 1-11 were elucidated on the basis of 1D and 2D NMR including HSQC, HMBC, COSY and NOESY, and other spectroscopic analyses.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2023
Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
The first total synthesis of heavily oxidized cassane-type diterpenoid neocaesalpin A (1) is disclosed. At the heart of the synthesis lies an intermolecular Diels-Alder reaction that rapidly assembles the target framework from commercial materials. A carefully orchestrated sequence of oxidations secured the desired oxygenation pattern.
View Article and Find Full Text PDFJ Nat Prod
October 2022
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain.
A new strategy for the semisynthesis of the aromatic cassane-type diterpene taepeenin F () is reported. The introduction of the methyl group at C-14, characteristic of the target compound, was achieved via dienone , easily prepared from abietic acid (), the major compound in renewable rosin. Biological assays of selected compounds are reported.
View Article and Find Full Text PDFMolecules
September 2022
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain.
A set of thirteen cassane-type diterpenes was synthesized and an expedient synthetic route was used to evaluate 14-desmethyl analogs of the most active tested cassane. The anti-inflammatory activities of these 13 compounds were evaluated on a lipopolysaccharide (LPS)-activated RAW 264.7 cell line by inhibition of nitric oxide (NO) production, some of them reaching 100% NO inhibition after 72 h of treatment.
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