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Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages.
Bioorg Med Chem. 2005 Apr 01; 13(7):2381-8.BM

Abstract

Four kaempferol glycosides were isolated from the leaves of Cinnamomum osmophloeum Kaneh, a Taiwan endemic tree. These compounds namely, kaempferitrin (1), kaempferol 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (2), kaempferol 3-O-beta-D-apiofuranosyl-(1-->2)-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (3), and kaempferol 3-O-beta-D-apiofuranosy-(1-->4)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (4). The structure of compound 2 was determined by spectroscopic analyses and acid hydrolysis. The isolates 1-4 were evaluated as inhibitors of some macrophage functions involved in the inflammatory process. These four compounds inhibited lipopolysaccharide (LPS) and interferon (IFN)-gamma-induced nitric oxide (NO), and cytokines [tumor necrosis factor (TNF)-alpha and interleukin (IL)-12] in a dose-dependent manner. The concentration of 50% inhibition (IC(50)) of NO by compounds 1, 3, 4 were 40, 15, 20microM, respectively. In parallel, these concentrations were approximately in a similar manner to that observed for TNF-alpha and IL-12 production. However, compound 2 inhibited NO and cytokines production by 30% at 100microM concentration. On the other hand, compounds 3 and 4 showed no inhibitory effect on the production of NO from macrophages, when inducible NO synthase was already expressed by the stimulation with LPS and IFN-gamma. Taken together, our results provide evidence that isolates of C. osmophloeum possess an anti-inflammatory potential which constitutes a previously unrecognized biological activity.

Authors+Show Affiliations

Fang SH
Department of Microbiology, School of Medicine, China Medical University, Taichung 400, Taiwan, ROC.
Rao YK
No affiliation info available
Tzeng YM
No affiliation info available

MeSH

AnimalsCarbohydrate ConformationCinnamomumDose-Response Relationship, DrugFemaleFlavonolsGlycosidesInflammation MediatorsInterferon-gammaInterleukin-12LipopolysaccharidesMacrophage ActivationMacrophagesMiceMice, Inbred BALB CMolecular Sequence DataNitric OxideNitric Oxide SynthasePlant LeavesStructure-Activity RelationshipTumor Necrosis Factor-alpha

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15755640

Citation

Fang, Shih-Hua, et al. "Inhibitory Effects of Flavonol Glycosides From Cinnamomum Osmophloeum On Inflammatory Mediators in LPS/IFN-gamma-activated Murine Macrophages." Bioorganic & Medicinal Chemistry, vol. 13, no. 7, 2005, pp. 2381-8.
Fang SH, Rao YK, Tzeng YM. Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages. Bioorg Med Chem. 2005;13(7):2381-8.
Fang, S. H., Rao, Y. K., & Tzeng, Y. M. (2005). Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages. Bioorganic & Medicinal Chemistry, 13(7), 2381-8.
Fang SH, Rao YK, Tzeng YM. Inhibitory Effects of Flavonol Glycosides From Cinnamomum Osmophloeum On Inflammatory Mediators in LPS/IFN-gamma-activated Murine Macrophages. Bioorg Med Chem. 2005 Apr 1;13(7):2381-8. PubMed PMID: 15755640.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages. AU - Fang,Shih-Hua, AU - Rao,Yerra Koteswara, AU - Tzeng,Yew-Min, PY - 2004/08/16/received PY - 2005/01/26/accepted PY - 2005/3/10/pubmed PY - 2005/9/2/medline PY - 2005/3/10/entrez SP - 2381 EP - 8 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 13 IS - 7 N2 - Four kaempferol glycosides were isolated from the leaves of Cinnamomum osmophloeum Kaneh, a Taiwan endemic tree. These compounds namely, kaempferitrin (1), kaempferol 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (2), kaempferol 3-O-beta-D-apiofuranosyl-(1-->2)-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (3), and kaempferol 3-O-beta-D-apiofuranosy-(1-->4)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (4). The structure of compound 2 was determined by spectroscopic analyses and acid hydrolysis. The isolates 1-4 were evaluated as inhibitors of some macrophage functions involved in the inflammatory process. These four compounds inhibited lipopolysaccharide (LPS) and interferon (IFN)-gamma-induced nitric oxide (NO), and cytokines [tumor necrosis factor (TNF)-alpha and interleukin (IL)-12] in a dose-dependent manner. The concentration of 50% inhibition (IC(50)) of NO by compounds 1, 3, 4 were 40, 15, 20microM, respectively. In parallel, these concentrations were approximately in a similar manner to that observed for TNF-alpha and IL-12 production. However, compound 2 inhibited NO and cytokines production by 30% at 100microM concentration. On the other hand, compounds 3 and 4 showed no inhibitory effect on the production of NO from macrophages, when inducible NO synthase was already expressed by the stimulation with LPS and IFN-gamma. Taken together, our results provide evidence that isolates of C. osmophloeum possess an anti-inflammatory potential which constitutes a previously unrecognized biological activity. SN - 0968-0896 UR - https://www.unboundmedicine.com/medline/citation/15755640/Inhibitory_effects_of_flavonol_glycosides_from_Cinnamomum_osmophloeum_on_inflammatory_mediators_in_LPS/IFN_gamma_activated_murine_macrophages_ DB - PRIME DP - Unbound Medicine ER -
Grapherence [↓11]

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