Novel pathway for N1-acetyl-5-methoxykynuramine: UVB-induced liberation of carbon monoxide from precursor N1-acetyl-N2-formyl-5-methoxykynuramine.


:Irradiation of the melatonin metabolite N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK) with UV light of 254 nm causes the release of carbon monoxide (CO) and, thus, deformylation to N(1)-acetyl-5-methoxykynuramine (AMK). Liberation of CO was demonstrated by reduction of PdCl(2) to metallic palladium, under avoidance of actions by other reductants. Photochemical AMK formation was not due to UV-induced hydroxyl radicals, because the reaction also took place with high efficiency in ethanol and 2-propanol. Moreover, AMK was generated from AFMK by UVB on a dry thin layer chromatographic plate. Although AMK seems to be the major primary product generated by UVB radiation, prolonged exposure of AFMK led to various other products, especially formed by destruction of AMK, as shown by irradiation of this latter compound. With regard to the demonstration of melatonin in skin and substantial amounts of AFMK in keratinocytes, these findings may be of dermatologic relevance.


J Pineal Res


Seever K,Hardeland R




Has Abstract


2008-05-01 00:00:00














  • Immunohistochemical studies on the coexistence of catecholamine-synthesizing enzymes and neuropeptide Y in nerve fibers of the porcine pineal gland.

    abstract::The distribution of nerve fibers immunoreactive (IR) to catecholamine-synthesizing enzymes, tyrosine hydroxylase (TH), dopamine-beta-hydroxylase (D beta H), and phenylethanolamine-N-methyltransferase (PNMT) as well as neuropeptide Y (NPY), in the pineal gland of adult sows was investigated by the use of double-labelin...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Kaleczyc J,Przybylska B,Majewski M,Lewczuk B

    更新日期:1994-08-01 00:00:00

  • Melatonin prevents neural tube defects in the offspring of diabetic pregnancy.

    abstract::Melatonin, an endogenous neurohormone secreted by the pineal gland, has a variety of physiological functions and neuroprotective effects. However, its protective role on the neural tube defects (NTDs) was not very clear. The aim of this study was to investigate the effects of melatonin on the incidence of NTDs (includ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Liu S,Guo Y,Yuan Q,Pan Y,Wang L,Liu Q,Wang F,Wang J,Hao A

    更新日期:2015-11-01 00:00:00

  • Role of melatonin in mucosal gastroprotection against aspirin-induced gastric lesions in humans.

    abstract::Melatonin and its precursor, l-tryptophan, have been shown to exert gastroprotective effects in animals, but their influence on the gastric damage by aspirin (ASA) in humans has been sparingly investigated. In this study, we designed to determine the effects of melatonin and l-tryptophan on ASA-induced gastric mucosal...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Konturek PC,Konturek SJ,Celinski K,Slomka M,Cichoz-Lach H,Bielanski W,Reiter RJ

    更新日期:2010-05-01 00:00:00

  • Melatonin improves insulin resistance and hepatic steatosis through attenuation of alpha-2-HS-glycoprotein.

    abstract::Melatonin plays an important role in regulating circadian rhythms. It also acts as a potent antioxidant and regulates glucose and lipid metabolism, although the exact action mechanism is not clear. The α2-HS-glycoprotein gene (AHSG) and its protein, fetuin-A (FETUA), are one of the hepatokines and are known to be asso...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Heo JI,Yoon DW,Yu JH,Kim NH,Yoo HJ,Seo JA,Kim SG,Choi KM,Baik SH,Choi DS,Kim NH

    更新日期:2018-09-01 00:00:00

  • Comparative aspects of the pineal/melatonin system of poikilothermic vertebrates.

    abstract::The pineal gland of poikilothermic vertebrates originates as an evagination from the diencephalic roof between the habenular and the posterior commissures, and associates with a parapineal organ to form the so-called pineal complex. The pinealocytes may be photosensitive, secretory or intermediate cells between both. ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章,评审


    authors: Filadelfi AM,Castrucci AM

    更新日期:1996-05-01 00:00:00

  • Plasma, cerebrospinal fluid, and brain distribution of 14C-melatonin in rat: a biochemical and autoradiographic study.

    abstract::The distribution of 14C-Melatonin (14C-MT) after systemic injection was studied in the plasma, cerebrospinal fluid (CSF), and brain of rats. Chromatographic analysis (thin-layer chromatography and high-performance liquid chromatography) indicated that the radioactivity from biological samples taken at various times fo...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Vitte PA,Harthe C,Lestage P,Claustrat B,Bobillier P

    更新日期:1988-01-01 00:00:00

  • The effect of melatonin on cellular activation processes in human blood.

    abstract::The pineal hormone melatonin, due to its lipophilic nature, has access to every cell and every part of a cell in the body, suggesting that it could exert effects on blood immune cells. The regulation of the activation of monocytes may be important in a number of diseases, especially pathophysiological conditions assoc...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Fjaerli O,Lund T,Osterud B

    更新日期:1999-01-01 00:00:00

  • Melatonin alleviates secondary brain damage and neurobehavioral dysfunction after experimental subarachnoid hemorrhage: possible involvement of TLR4-mediated inflammatory pathway.

    abstract::Previous studies proved that melatonin protected against secondary brain damage by modulating oxidative stress after experimental subarachnoid hemorrhage (SAH), but it has not been evaluated yet about its effects on inflammatory pathway and secondary cognitive dysfunction in SAH model. This study was undertaken to eva...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Wang Z,Wu L,You W,Ji C,Chen G

    更新日期:2013-11-01 00:00:00

  • Overexpression of rice serotonin N-acetyltransferase 1 in transgenic rice plants confers resistance to cadmium and senescence and increases grain yield.

    abstract::While ectopic overexpression of serotonin N-acetyltransferase (SNAT) in plants has been accomplished using animal SNAT genes, ectopic overexpression of plant SNAT genes in plants has not been investigated. Because the plant SNAT protein differs from that of animals in its subcellular localization and enzyme kinetics, ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Lee K,Back K

    更新日期:2017-04-01 00:00:00

  • Absence of circadian rhythm in the disposition of melatonin in the cow.

    abstract::Five adult pasture-bred Prim Holstein cows were used to document the time invariance of melatonin disposition in the cow. Melatonin was administered by an intravenous route as a bolus (5 micrograms/kg of body weight) at either 1430 or 2230. Data were analysed according to a three-compartment open model with melatonin ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Berthelot X,Ravault JP,Concordet D,Ferney J,Toutain PL

    更新日期:1993-10-01 00:00:00

  • Specific binding of 2-[125I]iodomelatonin by rat spleen crude membranes: day-night variations and effect of pinealectomy and continuous light exposure.

    abstract::Melatonin binding sites were characterized in rat spleen crude membranes. The specific binding of 2-[125I]iodomelatonin by spleen crude membranes fulfills all the criteria for binding to a receptor site. Thus, binding was dependent on time and temperature, stable, specific, and increased under constant light exposure ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Rafii-El-Idrissi M,Calvo JR,Giordano M,Guerrero JM

    更新日期:1996-01-01 00:00:00

  • Melatonin attenuates the neuronal NADPH-d/NOS expression in the nodose ganglion of acute hypoxic rats.

    abstract::Excessive production of nitric oxide (NO) may play a detrimental role in the process of hypoxia-related neuropathology. This study explored whether treatment with melatonin would attenuate the neuropathological changes in the vagal ganglia following a severe hypoxic insult. Thirty minutes prior to hypoxia treatment, y...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Chang HM,Ling EA,Chen CF,Lue H,Wen CY,Shieh JY

    更新日期:2002-03-01 00:00:00

  • Sexually dimorphic effects of melatonin on prolactin cell function in male and female syrian hamsters.

    abstract::The purpose of this study was to determine and compare the effects of chronic melatonin treatment in vivo on several aspects of prolactin (PRL) cell activity (PRL synthesis, storage, and release) in vitro in male and female Syrian hamsters. Adult male and female hamsters were maintained on long photoperiod and treated...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Blask DE

    更新日期:1989-01-01 00:00:00

  • Chemoneuroendocrine therapy of metastatic breast cancer with persistent thrombocytopenia with weekly low-dose epirubicin plus melatonin: a phase II study.

    abstract::Thrombocytopenia is a frequent complication of cancer and constitutes an absolute contraindication for chemotherapy. Recent studies have demonstrated that platelet generation may be influenced by both cytokines and neurohormones. In particular, the pineal indole melatonin has been proven to enhance platelet number in ...

    journal_title:Journal of pineal research

    pub_type: 临床试验,杂志文章


    authors: Lissoni P,Tancini G,Paolorossi F,Mandalà M,Ardizzoia A,Malugani F,Giani L,Barni S

    更新日期:1999-04-01 00:00:00

  • Protective effect of melatonin on Ca2+ homeostasis and contractility in acute cholecystitis.

    abstract::Impaired Ca2+ homeostasis and smooth muscle contractility co-exist in acute cholecystitis (AC) leading to gallbladder dysfunction. There is no pharmacological treatment for this pathological condition. Our aim was to evaluate the effects of melatonin treatment on Ca2+ signaling pathways and contractility altered by ch...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Gomez-Pinilla PJ,Camello PJ,Pozo MJ

    更新日期:2008-04-01 00:00:00

  • Melatonin excretion is not related to sleep in the elderly.

    abstract::We examined the association between 6-sulphatoxymelatonin (6-SMT) excretion and sleep in 68 volunteers 60-79 years of age who complained of insomnia or depression. An Actillume wrist monitor was worn for 5-7 consecutive days and nights in home-living conditions. Activity was used to estimate total sleep time (TST) and...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Youngstedt SD,Kripke DF,Elliott JA

    更新日期:1998-04-01 00:00:00

  • Melatonin restores the cytochrome oxidase reactivity in the nodose ganglia of acute hypoxic rats.

    abstract::This study aimed to elucidate whether melatonin would exert beneficial effects on the neuronal functions of the nodose ganglion (NG) following acute hypoxic insult. The cytochrome oxidase (COX) and the nicotinamine adenine dinucleotide phosphate diaphorase (NADPH-d) histochemistry along with the nitric oxide synthase ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Chang HM,Tseng CY,Wei IH,Lue JH,Wen CY,Shieh JY

    更新日期:2005-09-01 00:00:00

  • Melatonin regulates the rhythmic migration of neutrophils in live zebrafish.

    abstract::The circadian clock plays a vital role in physiology and behavior such as the sleep-wake cycle and blood pressure and hormone levels. Immune responses also display circadian rhythmicity and particularly pineal melatonin contributes to immunological processes. Little attention, however, is given to mechanisms underlyin...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Ren DL,Li YJ,Hu BB,Wang H,Hu B

    更新日期:2015-05-01 00:00:00

  • Cloning and characterization of a Chlamydomonas reinhardtii cDNA arylalkylamine N-acetyltransferase and its use in the genetic engineering of melatonin content in the Micro-Tom tomato.

    abstract::Melatonin is found in a wide variety of plant species. Several investigators have studied the physiological roles of melatonin in plants. However, its role is not well understood because of the limited information on its biosynthetic pathway. To clarify melatonin biosynthesis in plants, we isolated a cDNA-coded arylal...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Okazaki M,Higuchi K,Hanawa Y,Shiraiwa Y,Ezura H

    更新日期:2009-05-01 00:00:00

  • Antioxidative protection in a high-melatonin organism: the dinoflagellate Gonyaulax polyedra is rescued from lethal oxidative stress by strongly elevated, but physiologically possible concentrations of melatonin.

    abstract::Lethal oxidative stress was investigated in the dinoflagellate Gonyaulax polyedra by measuring the dying-peak of bioluminescence during circadian phases of low physiological light emission, low bioluminescence capacity, and low sensitivity to stimulatory agents. Measurements were carried out in constant darkness after...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Antolín I,Obst B,Burkhardt S,Hardeland R

    更新日期:1997-11-01 00:00:00

  • Melatonin enhances antioxidant action of alpha-tocopherol and ascorbate against NADPH- and iron-dependent lipid peroxidation in human placental mitochondria.

    abstract::Human placental mitochondria might be a significant source of NADPH- and iron-dependent production of reactive oxygen species (ROS). Preeclampsia is believed to be a consequence of overproduction of ROS in human placenta. The experimental results presented here show that melatonin inhibits NADPH- and iron-dependent li...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Milczarek R,Hallmann A,Sokołowska E,Kaletha K,Klimek J

    更新日期:2010-09-01 00:00:00

  • Melatonin nephroprotective action in Zucker diabetic fatty rats involves its inhibitory effect on NADPH oxidase.

    abstract::Excessive activity of NADPH oxidase (Nox) is considered to be of importance for the progress of diabetic nephropathy. The aim of the study was to elucidate the effect of melatonin, known for its nephroprotective properties, on Nox activity under diabetic conditions. The experiments were performed on three groups of an...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Winiarska K,Dzik JM,Labudda M,Focht D,Sierakowski B,Owczarek A,Komorowski L,Bielecki W

    更新日期:2016-01-01 00:00:00

  • Elevated production of melatonin in transgenic rice seeds expressing rice tryptophan decarboxylase.

    abstract::A major goal of plant biotechnology is to improve the nutritional qualities of crop plants through metabolic engineering. Melatonin is a well-known bioactive molecule with an array of health-promoting properties, including potent antioxidant capability. To generate melatonin-rich rice plants, we first independently ov...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Byeon Y,Park S,Lee HY,Kim YS,Back K

    更新日期:2014-04-01 00:00:00

  • Melatonin, hydroxyl radical-mediated oxidative damage, and aging: a hypothesis.

    abstract::Melatonin is a very potent and efficient endogenous radical scavenger. The pineal indolamine reacts with the highly toxic hydroxyl radical and provides on-site protection against oxidative damage to biomolecules within every cellular compartment. Melatonin acts as a primary non-enzymatic antioxidative defense against ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章,评审


    authors: Poeggeler B,Reiter RJ,Tan DX,Chen LD,Manchester LC

    更新日期:1993-05-01 00:00:00

  • Effect of short photoperiod on hypothalamic methionine-enkephalin and LHRH content and serum beta-endorphin-like immunoreactivity (beta-end LI) levels in golden hamsters.

    abstract::Adult female golden hamsters were used to study the effect of short photoperiod on the endogenous opioid system and the effect of pinealectomy on the serum beta-endorphin-like immunoreactivity (beta-end LI) levels. Hamsters were housed under either long photoperiod (14L:10D) or short photoperiod (2L:22D) and the regul...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Kumar MS,Besch EL,Millard WJ,Sharp DC,Leadem CA

    更新日期:1984-01-01 00:00:00

  • JAK2/STAT3 activation by melatonin attenuates the mitochondrial oxidative damage induced by myocardial ischemia/reperfusion injury.

    abstract::Ischemia/reperfusion injury (IRI) is harmful to the cardiovascular system and causes mitochondrial oxidative stress. Numerous data indicate that the JAK2/STAT3 signaling pathway is specifically involved in preventing myocardial IRI. Melatonin has potent activity against IRI and may regulate JAK2/STAT3 signaling. This ...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Yang Y,Duan W,Jin Z,Yi W,Yan J,Zhang S,Wang N,Liang Z,Li Y,Chen W,Yi D,Yu S

    更新日期:2013-10-01 00:00:00

  • Analgesic effects of melatonin: a review of current evidence from experimental and clinical studies.

    abstract::Melatonin is an endogenous indoleamine, produced mainly by the pineal gland. Melatonin has been proven to have chronobiotic, antioxidant, antihypertensive, anxiolytic and sedative properties. There are also experimental and clinical data supporting an analgesic role of melatonin. In experimental studies, melatonin sho...

    journal_title:Journal of pineal research

    pub_type: 杂志文章,评审


    authors: Wilhelmsen M,Amirian I,Reiter RJ,Rosenberg J,Gögenur I

    更新日期:2011-10-01 00:00:00

  • Effects of melatonin on mammary gland lesions in transgenic mice overexpressing N-ras proto-oncogene.

    abstract::The oncostatic effects of melatonin on the mammary gland have been studied in transgenic mice carrying the N-ras proto-oncogene under the control of the MMTV-LTR. Female (4-week-old) virgin mice with positive transgenic pedigrees were injected with melatonin (200 micrograms/mouse/ day, five times a week) or vehicle la...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Mediavilla MD,Güezmez A,Ramos S,Kothari L,Garijo F,Sánchez Barceló EJ

    更新日期:1997-03-01 00:00:00

  • Elevated environmental temperature alters the responses of the reproductive and thyroid axes of female Syrian hamsters to afternoon melatonin injections.

    abstract::Female Syrian hamsters were kept in a light (14:10 h light:dark cycle, lights on 0600 h)- and temperature (22 or 30 degrees C)-controlled room; some groups were treated with an afternoon s.c. injection of melatonin (6.25, 12.5, or 25 micrograms/day) for 11 or 14 weeks. The melatonin-induced suppression of the reproduc...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Reiter RJ,Li K,Gonzalez-Brito A,Tannenbaum MG,Vaughan MK,Vaughan GM,Villanua MA

    更新日期:1988-01-01 00:00:00

  • Permeability of the pineal gland of the rat to lanthanum: significance of dark pinealocytes.

    abstract::The permeability of the pineal gland to lanthanum was investigated by means of transmission electron microscopy and X-ray microanalysis. Different pineal cell populations were studied. Light pinealocytes as well as glial cells were not permeated by the tracer lanthanum, which normally stays extracellularly. Dark pinea...

    journal_title:Journal of pineal research

    pub_type: 杂志文章


    authors: Humbert W,Pévet P

    更新日期:1992-03-01 00:00:00