Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus.
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.
Hasegawa
Tatsuya
T
Department of Pharmacognosy and Chemistry of Natural Products, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Takano
Fumihide
F
Takata
Takanobu
T
Niiyama
Masato
M
Ohta
Tomihisa
T
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016207:Cytokines / Q000096:biosynthesis / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005052:Eucalyptus / Q000737:chemistry*; D005707:Gallic Acid / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D047348:Hydrolyzable Tannins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008543:Melanins / Q000037:antagonists & inhibitors / Q000378:metabolism; D008546:Melanoma, Experimental / Q000188:drug therapy* / Q000378:metabolism; D051379:Mice; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
C530093:2-hydroxy-1,8-cineole beta-d-glucopyranoside; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D003509:Cyclohexanecarboxylic Acids; D016207:Cytokines; D005960:Glucosides; D006027:Glycosides; D047348:Hydrolyzable Tannins; D008543:Melanins; D039821:Monoterpenes; D013729:Terpenes; C417927:cypellocarpin A; C429636:eucaglobulin; C530091:globulusin A; C530092:globulusin B; D005707:Gallic Acid