Endodesmiadiol, a friedelane triterpenoid, and other antiplasmodial compounds from Endodesmia calophylloides.

Chem Pharm Bull (Tokyo)

Laboratoire de Substances Naturelles et Synthèse Organique, Département de Chimie Organique, Faculté des Sciences, Université de Yaoundé I, BP 812 Yaoundé, Cameroun.

Published: March 2008

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.

Download full-text PDF

Source
http://dx.doi.org/10.1248/cpb.56.374DOI Listing

Publication Analysis

Top Keywords

friedelane triterpenoid
8
endodesmia calophylloides
8
compounds
5
endodesmiadiol
4
endodesmiadiol friedelane
4
triterpenoid antiplasmodial
4
antiplasmodial compounds
4
compounds endodesmia
4
calophylloides ethyl
4
ethyl acetate
4

Similar Publications

Isolation and Biological Evaluation of Triterpenes from Leaves.

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 PDF

Synthesis and Cytotoxic Activity of Friedelinyl Esters.

Chem 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 PDF

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 PDF

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 PDF

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.

View Article and Find Full Text PDF

Want 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!