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PubMed2005

A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa.

A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.

Carbohydrate Conformation↗
PubMed2006

Radical-scavenging activities of new megastigmane glucosides from Macaranga tanarius (L.) MULL.-ARG.

Four new megastigmane glucosides, named macarangiosides A-D (2-5), together with mallophenol B, lauroside E, methyl brevifolin carboxylate, and hyperin and isoquercitrin as a mixture were isolated from the leaves of Macaranga tanarius (L.) MULL.-ARG. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. Macarangioside A-C (2-4) and mallophenol B were galloylated on glucose moiety and possessed the potent 2,2-diphenyl-picrylhydrazyl (DPPH) radical-scavenging activity.

Alkenes↗
PubMed2005

[Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].

Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine which are biosynthesized via strictosidine, an alkaloidal glucoside, formed from secologanin and tryptamine. In secologanin biosynthesis, the oxidative cleavage process of loganin to secologanin and the hydroxylation of 7-deoxyloganin to loganin have remained unknown enzymologically and mechanistically. Cornoside is a unique glucoside with 4-hydroxy-2,5-cyclohexadien-1-one (benzoquinol) ring and is widespread in families such as Cornaceae, Oleaceae, and Scrophulariaceae but its biosynthesis, especially the oxidative process, remain to be investigated. Shikonin is a red naphthazarin pigment derived from the roots of Lithospermum erythorhizon and produced biotechnologically by cell cultures. Its biosynthesis including the production regulation mechanism has been investigated in detail. However, the naphthazarin ring formation process, probably starting with the hydroxylation of the side chain of geranylhydroquinone, a key intermediate at the late stage of shikonin biosynthesis, remained unknown. In the present review, cytochrome P450 monooxygenases involved in the biosyntheses of three structurally and biosynthetically interesting compounds, secologanin, cornoside, and shikonin, a described together with the results of previous and recent biosynthetic studies. The biosyntheses of related compounds are also discussed.

Cyclohexanones↗
PubMed2006

[Reaction of pyridinium and quinolinium salts having the leaving group at the 2- or 4-position with active methylene compounds].

The reactions of 2- or 4-cyanopyridinium salts with active methylene compounds such as dimethyl malonate, malononitrile, and cyclohexane-1,3-dione affording 2- or 4-(substituted methylene) pyridines are described. Similar reactions of 4-cyano-2-methylthiopyridinium and 4-cyano-2-methylthioquinolinium salts, both of which have two leaving groups, were readily prepared from 4-cyano-1-methyl-2(1H)-pyridone and 4-cyano-1-methyl-2(1H)-quinolone via 4-cyano-1-methyl-2(1H)-thiopyridone and 4-cyano-1-methyl-2(1H)-thioquinolone in two steps, proceeding at the 2- and/or 4-positions on the pyridine or quinoline rings.

Chemistry, Organic↗
PubMed1989

2-cyclohexene-1-one-induced hyperglycemia in the mice.

2-Cyclohexene-1-one (CHX) dose-dependently caused the elevation of blood glucose levels in both fed and fasted mice. Adrenalectomy considerably prevented the elevated blood glucose with CHX, and plasma adrenaline assays revealed about a three- to fifteen-fold rise after CHX treatment. These findings indicate that the CHX-induced hyperglycemia may be largely mediated by adrenaline released from the adrenal medulla.

Adrenalectomy↗
PubMed1989

Brain glutathione and the anti-hypoxic effect of glutathione depletors in mice.

The anti-hypoxic effect (assessed by a standard hypoxia survival test) 3 hr after 2-cyclohexene-1-one (CHX) was completely abolished by injections of L-cysteine after CHX. Under these conditions, brain GSH was depleted to about 50% of the control level in CHX-treated mice and recovered to about 80% of control level following L-cysteine post-treatment. However, D-cysteine could not cause such effects. Intracerebroventricular injection of CHX, which caused a selective depletion of brain GSH, produced an anti-hypoxic effect. Thus, the anti-hypoxic effect may be related to the decrease of brain GSH levels.

Animals↗
PubMed2006

Beneficial action of 2,4,4-trimethyl-3-(15-hydroxypentadecyl)-2-cyclohexen-1-one, a novel long-chain fatty alcohol, on diabetic hypoalgesia and neuropathic hyperalgesia.

The effects of 2,4,4-trimethyl-3-(15-hydroxypentadecyl)-2-cyclohexen-1-one (tCFA15) on diabetic hypoalgesia and neuropathic hyperalgesia were examined. Treatments of streptozotocin (STZ)-pretreated mice with tCFA15 (8 - 40 mg/kg, i.p.) for 7 days significantly reversed the depressed inflammatory nociceptive licking response in the formalin test. In addition, similar drug treatments and dosing in 7-day postoperative neuropathic pain model rats (prepared by the method of Bennett and Xie) yielded a similarly favorable outcome by significantly reversing decreased nociceptive thresholds in the paw pressure test. These results suggest that tCFA15 may have the potential to normalize sensory nerve abnormalities induced in experimental diabetes and nerve injury.

Analgesics↗
PubMed2000

Glycosidic fraction of flue-cured tobacco leaves: its separation and component analysis.

The fraction containing glycosidic components was separated from flue-cured tobacco (Nicotiana tabacum L.) leaves by a facile method. Some components of the fraction were isolated and elucidated to be syringin, coniferin, cichoriin, benzyl-beta-D-glucoside, Blumenol A-beta-D-glucoside, and 5,6-epoxy-5,6-dihydro-3-hydroxy-beta-ionyl-beta-D-glucoside. Syringin and coniferin were detected in the Nicotiana species for the first time.

Benzopyrans↗
PubMed2000

Novel fungal metabolites, demethylsorbicillin and oxosorbicillinol, isolated from Trichoderma sp. USF-2690.

The novel compounds, demethylsorbicillin (1) and oxosorbicillinol (2), were isolated from a fermentation broth of Trichoderma sp. USF-2690. The structures of these compounds, which were determined from spectroscopic evidence, suggest the possibility that methylation at C-6 and oxidation at C-1 and C-6 of sorbicillin were controlled in the early polyketide stage before the formation of oxidized sorbicillin dimers. In a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, 2 gave an ED50 value of 87.7 microM.

Anti-Bacterial Agents↗
PubMed2001

Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.

In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative) analysis for 1 gave m/z 247 as the (M-1)- ion peak. The hydrolysis of synthetic 6-O-acetylsorbicillinol (+/- -2) by 0.05 M KOH and acetylation of product 1 in an aqueous solution indicated that the structure of 1 was (6S)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one, designated sorbicillinol, a quinol that has been postulated to be important in bisorbicillinoid biosynthesis.

Bepridil↗
PubMed2002

Biosynthesis of bisorbicillinoid in Trichoderma sp. USF-2690; evidence for the biosynthetic pathway, via sorbicillinol, of sorbicillin, bisorbicillinol, bisorbibutenolide, and bisorbicillinolide.

An incorporation study of [1-(13)C] and [1,2-(13)C2] labeled sodium acetates into sorbicillinol 1 established a ring closure system between C-1 and C-6 and the positions that were oxidized and/or methylated on a hexaketide chain. Subsequent investigations, using 13C-labeled 1 prepared from [1-(13)C] labeled sodium acetate, clearly demonstrated that both bisorbicillinol 2 and sorbicillin 6 incorporated 13C-labeled 1 into their carbon skeletons. 13C-labeled bisorbicillinols 2 derived from [1-(13)C]- and [2-(13)C]-labeled sodium acetates clearly indicate that these were on the biosynthetic route from 1 to bisorbibutenolide (bislongiquinolide) 3 and bisorbicillinolide 4 via 2 as a branching point in the fungus.

4-Butyrolactone↗
PubMed2002

Old Yellow Enzyme from Candida macedoniensis catalyzes the stereospecific reduction of the C=C bond of ketoisophorone.

Microorganisms were screened for ones that reduced 3,5,5-trimethyl-2-cyclohexene-1,4-dione (ketoisophorone; KIP), and several strains were found to produce (6R)-2,2,6-trimethylcyclohexane-1,4-dione (levodione). The enzyme catalyzing the reduction of the C=C bond of KIP to yield (6R)-levodione was isolated from Candida macedoniensis AKU4588. The results of primary structural analysis and its enzymatic properties suggested that the enzyme might be an Old Yellow Enzyme family protein.

Amino Acid Sequence↗