Abstract
Two monoterpene glycosides, conjugated with gallic acid [globulusin A (1) and B (2)], together with four known compounds, cypellocarpin A (3), eucaglobulin (4), cuniloside (5) and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-d-glucopyranoside (6), were isolated from hot-water extracts of the leaves of Eucalyptus globulus. The structures of compounds 1 and 2 were determined by 1D, 2D NMR and MS spectroscopic analyses. The absolute stereochemistry of 1 was determined by correlating the spectroscopic data with those of synthetic compound 6 with a known configuration. Globulusin A (1) and B (2), cypellocarpin A (3) and eucaglobulin (4), scavenged DPPH free radicals and globulusin A (1) showed a higher antioxidant activity than the other tested compounds, with an IC50 of 3.8microM. Globulusin A (1) and eucaglobulin (4) concentration-dependently suppressed inflammatory cytokine production, tumor-necrosis factor-alpha and interleukin-1beta in cultured human myeloma THP-1 cells co-stimulated with phorbol myristate acetate. These compounds also inhibited melanogenesis in cultured murine melanoma B16F1 cells, without any significant cytotoxicity. These results suggested that globulusin A (1) and eucaglobulin (4), which were isolated as antioxidants from E. globulus, also had anti-inflammatory as well as anti-melanogenesis activity.
MeSH terms
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification
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Antineoplastic Agents, Phytogenic / pharmacology
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Antioxidants / chemistry
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Antioxidants / isolation & purification
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Antioxidants / pharmacology
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Cell Line, Tumor
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Cell Survival / drug effects
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Cyclohexanecarboxylic Acids / chemistry
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Cyclohexanecarboxylic Acids / isolation & purification
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Cyclohexanecarboxylic Acids / pharmacology
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Cytokines / biosynthesis
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Cytokines / drug effects
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Eucalyptus / chemistry*
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Gallic Acid / chemistry
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Gallic Acid / isolation & purification
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Gallic Acid / pharmacology*
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Glucosides / chemistry
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Glucosides / isolation & purification
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Glucosides / pharmacology
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / pharmacology*
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Humans
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Hydrolyzable Tannins / chemistry
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Hydrolyzable Tannins / isolation & purification
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Hydrolyzable Tannins / pharmacology
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Melanins / antagonists & inhibitors
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Melanins / metabolism
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Melanoma, Experimental / drug therapy*
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Melanoma, Experimental / metabolism
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Mice
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Molecular Conformation
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Monoterpenes / chemistry*
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Monoterpenes / isolation & purification
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Monoterpenes / pharmacology*
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Plant Leaves / chemistry*
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Stereoisomerism
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Terpenes / chemistry
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Terpenes / isolation & purification
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Terpenes / pharmacology*
Substances
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2-hydroxy-1,8-cineole beta-d-glucopyranoside
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Anti-Inflammatory Agents, Non-Steroidal
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Antineoplastic Agents, Phytogenic
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Antioxidants
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Cyclohexanecarboxylic Acids
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Cytokines
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Glucosides
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Glycosides
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Hydrolyzable Tannins
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Melanins
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Monoterpenes
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Terpenes
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cypellocarpin A
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eucaglobulin
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globulusin A
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globulusin B
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Gallic Acid