A new dicaffeoylquinic acid butyl ester from Isertia pittieri

Um, Byung-Hun; Polat, Merve; Lobstein, Annelise; Weniger, Bernard; Aragón, Raúl; Declercq, L.; Anton, Robert

doi:10.1016/s0367-326x(02)00181-8

Cited by 21 publications

(13 citation statements)

References 6 publications

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“…Dicaffeoylquinic acids (DCQAs) are a class of natural polyphenolic compounds widely distributed in plants, such as fennel (Parejo et al, 2004), mugwort flowering tops (Fraisse et al, 2003), coffee (Moreira et al, 2001), sweetpotato leaf (Yoshimoto et al, 2002), Ilex brevicuspis Reisseck (Filip and Ferraro, 2003), Isertia pittieri (Um et al, 2002), and Eleutherococcus senticosus (Tolonen et al, 2002). Structurally, they are characterized by two caffeic acid molecules connected to one quinic acid molecule through ester bonds.…”

Section: In Addition the Anti-hiv (Human Immunodeficiency Virus) Actmentioning

confidence: 99%

“…The efficacy experiments showed that M8, M9, and M12 could inhibit HIV replication with IC 50 values of about 25, 25, and 46 M, respectively. These results suggest that O-methylation and glucuronidation are two important metabolic pathways of 1,5-DCQA, that both rat liver and small intestine can catalyze such reactions by catechol-O-methyltransferase and UDP-glucuronosyltransferases, and that the HIV-1 inhibitory activity of M8, M9, and M12 is comparable to or slightly weaker than that of 1,5-DCQA.Dicaffeoylquinic acids (DCQAs) are a class of natural polyphenolic compounds widely distributed in plants, such as fennel (Parejo et al, 2004), mugwort flowering tops (Fraisse et al, 2003), coffee (Moreira et al, 2001), sweetpotato leaf (Yoshimoto et al, 2002), Ilex brevicuspis Reisseck (Filip and Ferraro, 2003), Isertia pittieri (Um et al, 2002), and Eleutherococcus senticosus (Tolonen et al, 2002). Structurally, they are characterized by two caffeic acid molecules connected to one quinic acid molecule through ester bonds.…”

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confidence: 99%

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Metabolic Profile of 1,5-Dicaffeoylquinic Acid in Rats, an in Vivo and in Vitro Study

Yang¹,

Zhang²,

Dong³

et al. 2005

Drug Metab Dispos

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ABSTRACT:To explore the metabolism of 1,5-dicaffeoylquinic acid (1,5-DCQA) in rats, liquid chromatography-mass spectrometry in parallel to diode-array detection was used for the rapid detection/characterization of the metabolites formed in bile, urine, and plasma of rats following oral administration of 1,5-DCQA (160 mg/kg). The methylation and glucuronidation of 1,5-DCQA occurring in vitro using rat liver and small intestinal microsomes and cytosols were studied in comparison with those occurring in vivo, and the enzymes involved were also determined. In addition, the anti-HIV (human immunodeficiency virus) activity of three important metabolites was preliminarily evaluated in MT-4 cells infected with HIV-1. A total of 22 metabolites in vivo and in vitro were identified, including four isomeric O-mono-methylated metabolites (M8-M11), nine isomeric O-di-methylated metabolites (M3, M6, M22, and M12-M17), four isomeric O-mono-methyl-glucuronidated metabolites (M2 and M19-M21), four isomeric O-di-methyl-glucuronidated metabolites (M1, M4, M5, and M7), and one glucuronidated metabolite (M18).The O-methylation positions of three important metabolites (M8, M9, and M12) were determined (3؆-, 3-, and 3,3؆-) by comparing with synthesized standards. The efficacy experiments showed that M8, M9, and M12 could inhibit HIV replication with IC 50 values of about 25, 25, and 46 M, respectively. These results suggest that O-methylation and glucuronidation are two important metabolic pathways of 1,5-DCQA, that both rat liver and small intestine can catalyze such reactions by catechol-O-methyltransferase and UDP-glucuronosyltransferases, and that the HIV-1 inhibitory activity of M8, M9, and M12 is comparable to or slightly weaker than that of 1,5-DCQA.Dicaffeoylquinic acids (DCQAs) are a class of natural polyphenolic compounds widely distributed in plants, such as fennel (Parejo et al., 2004), mugwort flowering tops (Fraisse et al., 2003), coffee (Moreira et al., 2001), sweetpotato leaf (Yoshimoto et al., 2002), Ilex brevicuspis Reisseck (Filip and Ferraro, 2003), Isertia pittieri (Um et al., 2002), and Eleutherococcus senticosus (Tolonen et al., 2002). Structurally, they are characterized by two caffeic acid molecules connected to one quinic acid molecule through ester bonds. In the past 10 years, DCQAs have been established as an important class of compounds with their potential effects of inhibiting HIV-1 integrase selectively and preventing HIV-1 replication in tissue culture at nontoxic concentrations (McDougall et al., 1998; Robinson et al., 1996a, b;King et al., 1999). HIV-1 integrase is an essential enzyme that mediates integration of the HIV genome into the host chromosomes. Zhu et al. (1999) reported that such inhibition of DCQAs on the HIV-1 integrase is irreversible toward its conserved amino acid residues in the central core domain during catalysis. The combinations of HIV integrase inhibitors with already existing inhibitors for HIV reverse transcriptase and protease have been suggested to be strongly synergetic (Ro...

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Section: In Addition the Anti-hiv (Human Immunodeficiency Virus) Actmentioning

confidence: 99%

mentioning

confidence: 99%

Metabolic Profile of 1,5-Dicaffeoylquinic Acid in Rats, an in Vivo and in Vitro Study

Yang¹,

Zhang²,

Dong³

et al. 2005

Drug Metab Dispos

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“…Compounds (1-4) were identified as; caffeic acid, 17) 4,5-dicaffeoylquinic acid, 18) 3,5-dicaffeoylquinic acid, 19) and 3,5-dicaffeoylquinic acid methyl ester, 19,20) respectively, by comparing their spectral (MS, NMR) data with literature values (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

The Anti-oxidative and Anti-inflammatory Effects of Caffeoyl Derivatives from the Roots of Aconitum koreanum R. RAYMOND

Park

Choi

et al. 2009

Biological & Pharmaceutical Bulletin

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Free radicals can cause oxidative damage by oxidizing biomolecules and this results in cell death and tissue damage as is observed in atherosclerosis, cancer, emphysema, cirrhosis, and arthritis. 1) Oxidative damage plays a critical pathological role in human diseases, and thus, anti-oxidative supplements are important because they reduce oxidative damage in the human body. 2)Inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) are known to contribute to inflammatory response via the production of nitric oxide (NO) and prostaglandins.3,4) These two enzymes, which mediated inflammatory events, are highly expressed by proinflammatory cytokines, such as, interferon-g (IFN-g) and tumor necrosis factor a (TNF-a), and by lipopolysaccharide (LPS), a component of the outer membranes of Gram-negative bacteria. 5)Thus, the screening of components that suppress these proteins and their mRNAs has proven to be a useful strategy for identifying therapeutics capable of combating inflammatory diseases. 6,7) As part of our on-going screening program to search antioxidative and anti-inflammatory natural products, 8) we examined the roots of Aconitum koreanum (RAK), which was traditionally used to treat pain, rheumatic arthralgia, epilepsia, furunculus, acne, vertigo, tetanus, and cardialgia.9,10) In addition, diterpene alkaloids, which have been shown to have anti-arrhythmic 11) and myorelaxant 12) effects, also have been isolated from this plant. Furthermore, RAK has been reported to possess analgesic and anti-inflammatory effects. 13)Thus, we undertook to search the components in RAK that scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals and inhibit NO production and the expression of iNOS and COX-2. MATERIALS AND METHODSGeneral Experiment TLC was carried out using precoated silica gel 60 F 254 plates (Merck, Darmstadt, Germany) and ethylacetate-water-acetic acid (10 : 9 : 1, volume ratio) or chloroform-methanol-water (6 : 4 : 1, volume ratio). The spots were detected using UV (254 nm) and by spraying with FeCl 3 and 10% H 2 SO 4 , followed by heating. Compounds were identified by 1 H-and Extraction, Isolation, and Identification The roots of Aconitum koreanum (3 kg) were extracted three times with 80% aqueous acetone at room temperature. After removing the acetone under vacuum, the residual aqueous solution was filtered. The filtrate was then concentrated (328 g) and applied to an Amberlite XAD-2 column (20-50 mesh, 2000 g, 10ϫ100 cm) (Fluka AG, Buchs, Switzerland) eluted with water containing increasing proportions of MeOH, to afford 6 sub-fractions. Repeated column chromatography of fraction 5, which showed anti-oxidative activity with an IC 50 value of 22.66Ϯ2.23 mg/ml compared with a positive control, L-ascorbic acid (IC 50 ϭ13.92Ϯ3.87 mg/ml) (data not shown) on a Sephadex LH-20 column (25-100 mm, 800 g, 6ϫ75 cm) (Pharmacia, Uppsala, Sweden) eluted with 60% MeOH resulted in two sub-fractions (5-1, 5-2). Sub-fraction 5-1 was further separated on a Sephadex LH-20 column (25-100 mm, 800 g, 6ϫ75 cm) el...

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“…The quinic acid esters were identified by their 1 H and 13 C NMR and UV data (Um et al, 2002;Lavault and Richomme, 2004). KCl was identified by X-ray diffraction analysis.…”

Section: Phytochemical Studymentioning

confidence: 99%