Complement-Inhibiting Constituents of Bridelia ferruginea Stem Bark

Abstract

A bioassay-guided fractionation of an 80% acetone extract from BRIDELIA FERRUGINEA stem bark showing a dose-dependent inhibitory effect towards both the classical and the alternative pathways of the complement system resulted in the isolation of a biflavanol (gallocatechin-(4'- O-7)-epigallocatechin) ( 1), 3,5-dicaffeoylquinic acid ( 2), 1,3,4,5-tetracaffeoylquinic acid ( 3), and a series of 3-methoxyflavone derivatives, including quercetin 3-methyl ether ( 4), quercetin 3,7,3',4'-tetramethyl ether ( 5), myricetin 3',4',5'-trimethyl ether ( 6; new compound) named ferrugin, myricetin 3,3',4',5'-tetramethyl ether ( 7), myricetin ( 8), and quercetin 3- O-glucoside ( 9) as the active constituents. Especially the biflavanol 1 and the caffeoyl esters of quinic acid 2 and 3 showed a strong inhibitory effect (IC (50) < 10 microM) on the classical pathway, compared to rosmarinic acid. Also on the alternative pathway, the biflavanol 1, the quinic acid derivatives 2 and 3, and some of the 3-methoxyflavones 5, 7 and 8 were more active than rosmarinic acid. The quinic acid derivatives were shown to be inhibitors of the C1 component and the terminal route of the complement system.

The genus Bridelia: A phytochemical and ethnopharmacological review

“…The crude extract exhibited a dose-dependent inhibitory effect on the classical pathway of the complement system. These findings provide some evidence for the traditional use of Bridelia ferruginea for the rheumatic pain treatment in Congo Kinshasa (Cimanga et al, 1999(Cimanga et al, , 2001.…”

“…Tannins, gallocatechin-(4 -O-7) epigallocatechin (1), flavonoids and biflavonoids, caffeoylesters, anticomplement, antioxidant, antiviral, diabetes, anti-inflammatory, antimicrobial activity, effects on rat bladder smooth muscle, quercetin (2), quercetin-3-neohesperidoside (3), rutin (4), myricetin-3-glucoside (5), myricetin-3-rhamnoside (6), 5 -demethoxy-␤-peltatin-5-O-␤-d-glucopyranoside (7), ␤-peltatin-5-O-␤-d-glucopyranoside (8) Cimanga et al (1999Cimanga et al ( , 2001, Tona et al (1998), Adebayo and Ishola (2009), Abubakar et al (2007), Pieters and Vlietinck (2005), Talla et al (2002), Ampofo (1979), Iwu (1980Iwu ( , 1983, Akinpelu et al Olajide et al (1999Olajide et al ( , 2003, Olajide and Makinde Modupe (2000), Rhashid et al (2000), Neuwinger (2000) and Oliver-Bever (1986) Bridelia glauca f. balansae Leaves Bridelionoside, bridelioside, (7R,8S)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-␤-glucopyranoside glochidioboside Sueyoshi et al (2006) and Sueyoshi et al (2007) Bridelia grandis Bark, leaves Oral cavity affection purify breast Antimicrobial activity against oral streptococci, antitrypanosomal and antiplasmodial activity Ngueyem et al (2008), Atindehou et al (2004) …”

Antibacterial, antioxidant and fibroblast growth stimulation activity of crude extracts of Bridelia ferruginea leaf, a wound-healing plant of Nigeria

“…The phytochemical and ethnopharmacological aspects of the genus Bridelia, including Bridelia ferruginea have recently been reviewed by Ngueyem et al (2009). The bark has been widely studied and phytochemical constituents include terpenoids, steroids, tannins, saponins and the flavonoids quercetin-3-glucoside and myricetin-3-glucoside (Addae- Mensah and Achenbach, 1985;Cimanga et al, 1999Cimanga et al, , 2001. Rashid et al (2000) also isolated ␤-peltatin, gallocathechin-(4 -O-7)-epigallocathechin, podophyl- lotoxin and ␤-peltatin-5-O-␤-d-glucopyranoside from the bark.…”

LC determination of citral in Cymbopogon citratus volatile oil

“…It has also been used in chemical synthesis, due its high contents of citral, a natural mixture of two isomeric aldehydes, neral and geranial [2]. The antibacterial and antifungal activities of lemongrass VO and its components have been reported in the literature [3][4][5][6][7][8][9]. Moreover, the literature points that the VO properties are mainly due to its major component, citral [10].…”