Three new cassane furanoditerpenoids ( 1- 3), together with 13 known cassane diterpenes ( 4- 16), were isolated from the EtOAc extract of the seed kernels of Caesalpinia bonduc. Their structures were elucidated on the basis of spectroscopic analysis, mainly NMR and MS. Compounds 1- 3 exhibited good antimalarial activity against the multidrug-resistant K1 strain of Plasmodium falciparum, while compound 4 was inactive. None of the compounds were cytotoxic against any of the tumor cell lines tested.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/np070330y | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Total Syntheses of Cassane Furanoditerpenoids and Their Stimulation of Cellular Respiration in Brown Adipocytes.
J Am Chem Soc
October 2023
ETH Zurich, Vladimir-Prelog-Weg 3, HCI, 8093 Zurich, Switzerland.
We report the first and enantioselective total syntheses of (+)-1-deacetylcaesalmin C, (+)-δ-caesalpin, (+)-norcaesalpinin MC, and (+)-norcaesalpinin P. Salient features of the synthetic strategy are an exo-selective intramolecular Diels-Alder reaction of a furanoquinone monoketal and subsequent chemoselective reduction of the resulting pentacyclic furfuryl ketal, furnishing a keystone intermediate. The latter enables access to the collection of natural products through implementation of stereoselective oxidations.
View Article and Find Full Text PDFHPLC profiles and spectroscopic data of cassane-type furanoditerpenoids.
Data Brief
December 2018
Graduate School of Biosphere Science, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan.
The data presented here are related to the research paper entitled "Hydroxylated furanoditerpenoids from the pupal case produced by the bruchid beetle inside the seed of " (Akihara et al., 2018) [1]. In this data article, we provide high-performance liquid chromatography (HPLC) profiles of seven undescribed hydroxylated furanoditerpenoids, caesalsauteolide, 2-hydroxycaesaljapin, 2,7-dihydroxycaesaljapin, 2-hydroxycaesalacetal, caesalsauterol, 6-acetylcaesalsauterol, norcaesalsauterol isolated from the pupal cases produced by and four known compounds, caesaljaponin A (Kamikawa et al.
View Article and Find Full Text PDFHydroxylated furanoditerpenoids from pupal cases produced by the bruchid beetle Sulcobruchus sauteri inside the seeds of Caesalpinia decapetala.
Phytochemistry
December 2018
Graduate School of Biosphere Science, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan. Electronic address:
Seven undescribed hydroxylated cassane-type furanoditerpenoids were isolated from pupal cases formed from the secretion/excretion of the larvae of the wild bruchid seed beetle Sulcobruchus sauteri in infested Caesalpinia decapetala seeds, and their structures were elucidated by interpreting their spectra. The hydroxylated furanoditerpenoids found in the pupal cases were not present in the seeds of the host plant. Caesalacetal and caesaljapin obtained from the intact seeds exhibited larvicidal activity against the larvae of Aedes albopictus, while the hydroxylated furanoditerpenoids isolated from the pupal cases were inactive.
View Article and Find Full Text PDFDiterpenoids of the Cassane Type from Caesalpinia decapetala.
J Nat Prod
December 2016
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation and Department of Pharmacology, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
Eighteen compounds, including eight new cassane-type furanoditerpenoids, 3β-hydroxyphanginin H (1), 3β-acetoxyphanginin H (2), 7β-acetoxyphanginin H (3), 7β-hydroxyphanginin H (4), 4-epi-3β-hydroxycaesalpinilinn (5), 4-epi-3β-acetoxycaesalpinilinn (6), 20-acetoxytaepeenin D (7), and tomocin E (8), along with 10 known compounds (9-18) were isolated from the roots of Caesalpinia decapetala. Compounds 1-13 were isolated from C. decapetala for the first time.
View Article and Find Full Text PDFCassane diterpenoids from the roots of Caesalpinia decapetala var. japonica and structure revision of caesaljapin.
Phytochemistry
January 2016
Graduate School of Biosphere Science, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan. Electronic address:
Two cassane-type furanoditerpenoids, designated caesalacetal and caesalpinetate, and a norditerpenoid designated caesalpinone were isolated from the roots of Caesalpinia decapetala var. japonica along with seven known diterpenoids. Structures were elucidated by interpretation of their spectroscopic data, and the absolute structure of caesalacetal was confirmed by X-ray crystallographic analysis.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!