From the ethyl acetate extract of the stem bark of Endodesmia calophylloides (Guttiferae), a novel friedelane triterpenoid named endodesmiadiol (1), as well as the known compounds friedelin (2), canophyllol (3), canophyllal (4), cerin (5), morelloflavone (6), volkensiflavone (7), 8-deoxygartanin (8), 3 beta-acetoxyoleanolic acid (9) and 1,8-dihydroxy-3-isoprenyloxy-6-methylxanthone (10) have been isolated. The structures of these compounds were established by spectroscopic analysis, and the relative configuration of endodesmiadiol (1) was confirmed by X-ray diffraction. The antiplasmodial activity of the isolated compounds was evaluated against the W2 strain of Plasmodium falciparum which is resistant to chloroquine and other antimalarial drugs. All the compounds were found to be active with IC50 values ranging from 7.2 to 23.6 microM. The IC50 of endodesmiadiol was found to be 11.8 microM.
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http://dx.doi.org/10.1248/cpb.56.374 | DOI Listing |
ACS Omega
July 2024
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte ,MG 31270-901, Brazil.
is naturally found in the Atlantic Forest regions of Brazil. Despite the pharmacological potential of plants from the genus, phytochemical studies on this species have not been reported in literature. A new triterpene, 28-hydroxyfriedelane-3,15-dione (), and seven known compounds (friedelan-3-one (), friedelan-3β-ol (), friedelane-3,15-dione (), 15α-hydroxyfriedelan-3-one (), 28-hydroxyfriedelan-3-one (), 30-hydroxyfriedelan-3-one (), and 29-hydroxyfriedelan-3-one ()) were obtained from the hexane extract of leaves.
View Article and Find Full Text PDFChem Biodivers
September 2024
Departamento de Química, Universidade Federal de Minas Gerais, Avenida Presidente Antônio Carlos 6627, Pampulha, Belo Horizonte-MG, 31270-901, Brazil.
Commonly isolated from plants of Celastraceae family, pentacyclic triterpenoids have a broad spectrum of biological activities, such as antitumor, anti-inflammatory, antinociceptive properties, among others. Structural modifications in these triterpenoids can enhance their biological activity, as well as their selectivity, while improving their physicochemical and pharmacokinetic aspects. In this study, eight novel esters were synthesized: four derivatives of 3α-friedelinol (friedelan-3α-yl p-bromobenzoate (1a); friedelan-3α-yl naproxenate (1b); friedelan-3α-yl pent-4-ynoate (1c); friedelan-3α-yl undec-10-ynoate (1d)) and four derivatives of 3β-friedelinol (friedelan-3β-yl p-bromobenzoate (2a); friedelan-3β-yl naproxenate (2b); friedelan-3β-yl pent-4-ynoate (2c); friedelan-3β-yl undec-10-ynoate (2d)).
View Article and Find Full Text PDFMicroorganisms
December 2023
Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Sciences, Kwame Nkrumah University of Science and Technology, PMB, Kumasi, Ghana.
This study investigated the antibacterial, resistance modulation, biofilm inhibition, and efflux pump inhibition potentials of stem extract and its constituents. The antimicrobial activity was investigated by the high-throughput spot culture growth inhibition (HT-SPOTi) and broth microdilution assays. The resistance modulation activity was investigated using the anti-biofilm formation and efflux pump inhibition assays.
View Article and Find Full Text PDFMolecules
November 2023
Department of Biotechnology, Yeungnam University, Gyeongsan 38541, Republic of Korea.
Pharmaceutical companies are investigating more source matrices for natural bioactive chemicals. Friedelin (friedelan-3-one) is a pentacyclic triterpene isolated from various plant species from different families as well as mosses and lichen. The fundamental compounds of these friedelane triterpenoids are abundantly found in cork tissues and leaf materials of diverse plant genera such as Celastraceae, Asteraceae, Fabaceae, and Myrtaceae.
View Article and Find Full Text PDFNew Phytol
February 2024
School of Traditional Chinese Medicine, Capital Medical University, Beijing, 100069, China.
Wilforlide A is one of the main active constituents produced in trace amounts in Tripterygium wilfordii Hook F, which has excellent anti-inflammatory and immune suppressive effects. Despite the seeming structural simplicity of the compound, the biosynthetic pathway of wilforlide A remains unknown. Gene-specific expression analysis and genome mining were used to identify the gene candidates, and their functions were studied in vitro and in vivo.
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