References List

 

I. General

  1. Salisbury SA, Forrest HS, Cruse WBT, Kennard O (1979)
    A novel coenzyme from bacterial primary alcohol dehydrogenase.
    Nature 280, 843-844.
  2. Duine JA, Frank J, Van Zeeland JK (1979)
    Glucose dehydrogenase from acinetobacter calcoaceticus: a quinoprotein.
    FEBS letter 108, 443-446.
  3. Smidt CR, Steinberg FM, Rucker RB (1991)
    Physiological importance of pyrroloquinoline quinone.
    Proc Soc Exp Biol Med 197, 19-26.
  4. Stites TE, Mitchel AE, Rucker RB (2000)
    Physiological importance of quinoenzymes and o-quinone family of cofactors.
    J Nutr 130, 719-727.
  5. Rucker R, Chowanadisai W, Nakano M (2009)
    Potential physiological importance of pyrroloquinoline quinone.
    Altern Med Rev 14, 268-277.
    http://www.altmedrev.com/publications/14/3/268.pdf

 

II. Function


(1) Vitamin-like activity in mammals

  1. Killgore J, Smidt C, Duich L, Romero-Chapman N, Tinker D, Reiser K, Melko M, Hyde D, Rucker RB (1989)
    Nutritional importance of pyrroloquinoline quinone.
    Science 245, 850-852.
  2. Steinberg FM, Gershwin ME, Rucker RB (1994)
    Dietary pyrroloquinoline quinone: Growth and immune response in BALB/c mice.
    J Nutr 124, 744-753.
  3. Steinberg F, Stites TE, Anderson P, Storms D, Chan I, Eghbali S, Rucker R (2003)
    Pyrroloquinoline quinone improves growth and reproductive performance in mice fed chemically defined diets.
    Exp Biol Med 228, 160-166.
  4. Stites T, Storms D, Bauerly K, Mah J, Harris C, Fascetti A, Rogers Q, Tchaparian E, Satre M, Rucker RB (2006)
    Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice.
    J Nutr 136, 390-396.
    http://jn.nutrition.org/content/136/2/390.long
  5. Kasahara T, Kato T (2003)
    A new redox-cofactor vitamin for mammals.
    Nature 422, 832.
  6. Felton LM, Anthony C (2005)
    Role of PQQ as a mammalian enzyme cofactor?
    Nature 433, E10.
  7. Rucker R, Storms D, Sheets A, Tchaparian E, Fascetti A (2005)
    Is pyrroloquinoline quinone a vitamin?
    Nature 433, E10-1.
  8. Bauerly KA, Storms DH, Harris CB, Hajizadeh S, Sun MY, Cheung CP, Satre MA, Fascetti AJ, Tchaparian E, Rucker RB (2006)
    Pyrroloquinoline quinone nutritional status alters lysine metabolism and modulates mitochondrial DNA content in the mouse and rat.
    Biochimica Biophysica Acta 1760(11), 1741-1748.
    http://www.ncbi.nlm.nih.gov/pubmed/17029795


(2) Anti-oxidative activity

In vitro anti-oxidative activity

  1. Miyauchi K, Urakami T, Abeta H, Shi H, Noguchi N, Niki E (1994)
    Action of pyrroloquinolinequinol as an antioxidant against lipid peroxidation in solution.
    Antiox Redox Signal 1, 547-554.
  2. Paz MA, Fluckiger R, Gallop PM (1990)
    Redox-cycling is a property of PQQ but not of ascorbate.
    FEBS Lett 264, 283-284.
  3. Ouchi A, NakanoM, Nagaoka S, Mukai K (2009)
    Kinetic study of the antioxidant activity of pyrroloquinolinol (PQQH2, a reduced form of pyrroloquinolinequinone) in micellar solution
    J Agri Food Chem 57, 450-456.
    http://www.ncbi.nlm.nih.gov/pubmed/19108686
  4. ukai K, Ouchi A, Nakano M (2011)
    Kinetic study of the quenching reaction of singlet oxygen by pyrroloquinolinequinole (PQQH2, a reduced form of pyrroloquinolinequinone) in micellar solution.
    J Agri Food Chem in press
    http://www.ncbi.nlm.nih.gov/pubmed/21309575

Anti-oxidative activity at mitochondrial and cellular level

  1. He K, Nukada H, Urakami T, Murphy MP (2003)
    Antioxidant and pro-oxidant properties of pyrroloquinoline quinone (PQQ): implications for its function in biological systems.
    Biochem Pharmacol 65, 67-74.

In vivo anti-oxidative activity

  1. Hamagishi Y, Murata S, Kamei H, Oki T, Adachi O, Ameyama M (1990)
    New biological properties of pyrroloquinoline quinone and its related compounds: Inhibition of chemiluminescence, lipid peroxidation and rat paw edema.
    J Pharm Exp Ther 255, 980-985.


(3) Decrease in heart or brain infarct size

  1. Zhu B, Zhu H, Teerlink JR, Karliner JS (2004)
    Pyrroloquinoline quinone (PQQ) decreases myocardial infarct size and improves cardiac function in rat models of ischemia and ischemia/reperfusion.
    Cardiovasc Drugs Ther 18, 421-431.
  2. Jensen FE, Gardner GJ, Williams AP, Gallop PM, Aizenman E, Rosenberg PA (1994)
    The putative essential nutrient pyrroloquinoline quinone is neuroprotective in a rodent model of hypoxic/ischemic brain injury.
    Neurosci 62, 399-406.
  3. Zhang Y, Feustel P, Kimelberg H K (2006)
    Neuroprotection by pyrroloquinoline quinone (PQQ) in reversible middle cerebral artery occlusion in the adult rat.
    Brain Res 1094, 200-206.
  4. Zhu B, Simonis U, Cecchini G, Zhou H, Li L, Teerlink JR, Karliner JS (2006)
    Comparison of pyrroloquinoline quinone and/or metoprolol on myocardial infarct size and mitochondrial damage in a rat model of ischemia/reperfusion injury.
    J Cardiovas Pharm Ther 11, 119-128.
    http://www.ncbi.nlm.nih.gov/pubmed/16891289
  5. Tao R, Karliner JS, Simonis U, Zheng J, Zhang j, Honbo N, Alano CC (2007)
    Pyrroloquinoline quinone preserves mitochondrial function and prevents oxidative injury in adult rat cardiac myocytes.
    Biochm. Biophys. Res. Com. 363, 257-262.
    http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2844438/pdf/nihms32366.pdf


(4) Regeneration of neurons

  1. Murase K, Hattori A, Kohno M, Hayashi K (1993)
    Stimulation of nerve growth factor synthesis/secretion in mouse astroglial cells by coenzymes.
    Biochem Mol Biol Internat 30, 615-621.
  2. Urakami T, Tanaka A, Yamaguchi K, Tsuji T, Niki E (1995/96)
    Synthesis of esters of coenzyme PQQ and IPQ, and stimulation of nerve growth factor production.
    BioFactors 5, 139-146.
  3. Yamaguchi K, Sasano A, Urakami T, Tsuji T, Kondo K (1993)
    Stimulation of nerve growth factor production by pyrroloquinoline quinone and its derivatives in vitro and in vivo.
    Biosci Biotech Biochem 57, 1231-1233.
  4. Yamaguchi K, Tsuji T, Uemura D, Kondo K (1996)
    Cyclooxygenase induction is essential for NGF synthesis enhancement by NGF inducers in L-M cells.
    Biosci Biotech Biochem 60, 92-94.
  5. Liu S, Li H, Yang J, Peng H, Wu K, Liu Y, Yang J (2005)
    Enhanced rat sciatic nerve regeneration through silicon tubes filled with pyrroloquinoline quinone.
    Microsurgery 25, 329-337.
  6. Li H, Liu S, Peng H, Zhang N (2005)
    Pyrroloquinoline quinone enhances regeneration of transected sciatic nerve in rats.
    Chinese J Traumatol 8, 225-229.
  7. Hirakawa A, Shimizu K, Fukumitsu H, Furukawa S (2009)
    Pyrroloquinoline quinone attenuates iNOS gene expression in the injured spinal cord.
    Biochem Biophys Res Com 378, 308-312.
    http://www.ncbi.nlm.nih.gov/pubmed/19026989


(5) Protection of neurons

  1. Aizenman E, Hartnett K, Zhong C, Gallop PM, Rosenberg PA (1992)
    Interaction of putative essential nutrient pyrroloquinoline quinone with the N-methyl-D-aspartate receptor redox modulatory site.
    J Neurosci 12, 2362-2369.
  2. Sanchez RM, Wang C, Gardner G, Orlando L, Tauck DL, Rosenberg PA, Aizenman E, Jensen FE (2000)
    Novel role for the NMDA receptor redox modulatory site in the pathophysiology of seizures.
    J Neurosci 20, 2409-2417.
  3. Zhang Y, Rosenberg PA (2002)
    The essential nutrient pyrroloquinoline quinone may act as a neuroprotectant by suppressing peronitrite formation.
    Eur J Neurosci 16, 1015-1024.
  4. Kobayashi M, Kim J, Kobayashi N, Han S, Nakamura C, Ikebukuro K, Sode K (2006)
    Pyrroloquinoline quinone (PQQ) prevents fibril formation of alpha-synuclein.
    Biochem Biophys Res Com 349, 1139-44.
  5. Hara H, Hiramatsu H, Adachi T (2007)
    Pyrroloquinoline quinone is a potent neuroprotective nutrient against 6-hydroxydopamine-induced neurotoxicity.
    Neurochem Res 32, 489-495.
  6. Ohwada K, Takeda H, Yamazaki M, Ishogai H, Nakano M, Shimomura M, Fukui K, Urano S (2008)
    Pyrroloquinoline quinine (PQQ) prevents cognitive deficit caused by oxidative stress in rats.
    J Clin Biochem Nutri 42, 29-34.
    http://www.jstage.jst.go.jp/article/jcbn/42/1/29/_pdf
  7. Nunome K, Miyazaki S, NakanoM, Iguchi-Ariga S, Ariga H (2008)
    Pyrroloquinoline quinone prevents oxidative stress-induced neuronal death probably through changes in oxidative status of DJ-1.
    Biol. Pharma. Bull. 31(7), 1321-1326.
    http://www.jstage.jst.go.jp/article/bpb/31/7/1321/_pdf
  8. Takatsu H, Owada K, Abe K, Nakano M, Urano S (2009)
    Effect of vitamin E on learning and memory deficit in aged rats.
    J Nutr Sci Vitaminol 55, 389-393.
    http://www.ncbi.nlm.nih.gov/pubmed/19926923
  9. Zhang JJ, Zhang RF, Meng XK (2009)
    Protective effect of pyrroloquinoline quinone against Aβ-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.
  10. Kim J, Kobayashi M, Fukuda M, Ogasawara D, Kobayashi N, Han S, Nakamura C, Inada M, Miyaura C, Ikebukuro K, Sode K (2010)
    Pyrroloquinoline quinone inhibits the fibrillation of amyloid proteins.
    Prion 4(1):26-31.
  11. Kim J, Harada R, Kobayashi M, Kobayashi N, Sode K (2010)
    The inhibitory effect of pyrroloquinoline quinone on the amyloid formation and cytotoxicity of truncated alpha-synuclein.
    Molecular Neurodegeneration 5, 20.


(6) Human syudy

  1. Nakano M, Ubukata K, Yamamoto T, Yamaguchi H (2009)
    Effect of pyrroloquinoline quinone (PQQ) on mental status of middle-aged and elderly persons.
    FOOD style21 13, 50-53 (Japanese)


(7) Nutrigenomics

  1. Chowanadisai W, Bauerly KA, Tchaparian E, Wong A, Cortopassi GA, Rucker RB (2010)
    Pyrroloquinoline quinone stimulates mitochondrial biogenesis through cAMP response element-binding protein phosphorylation and increased PGC-1alpha expression.
    J Biol Chem. 285(1):142-52.
    http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2804159/?tool=pubmed
  2. Identification of transcriptional networks responding to pyrroloquinoline quinone dietary supplementation and their influence on thioredoxin expression, and the JAK/STAT and MAPK pathways.
    Biochem J. 429(3):515-26.
    http://www.biochemj.org/bj/429/0515/4290515.pdf


(8) Other activities

  1. Tsuchida T, Yasuyama T, Higuchi K, Watanabe A, Urakami T, Akaike T, Sato K, Maeda H (1993)
    The protective effect of pyrroloquinoline quinone and its derivatives against carbon tetrachloride-induced liver injury of rats.
    J. Gastroenterol Hepatol 8, 342-347.
  2. Nishigori H, Yasunaga M, Mizumura M, Lee JW, Iwatsuru M (1989)
    Preventive effects of pyrroloquinoline quinone on formation of cataract and decline of lenticular and hepatic glutathione of developing chick embryo after glucocorticoid treatment.
    Life Sci 45, 593-598.
  3. Hobara N, Watanabe A, Kobayashi M, Tsuji T, Gomita Y, Araki Y (1988)
    Quinone derivatives lower blood and liver acetaldehyde but not ethanol concentratios following ethanol loading to rats.
    Pharmacol 37, 264-267.
  4. Kumazawa T, Hiwasa T, Takaguchi M, Suzuki O, Sato K (2007)
    Activation of Ras signaling pathways by pyrroloquinoline quinone in NIH3T3 mouse fibroblasts.
    Int J Mol Med 19, 765-770.
  5. Ishii T, Akagawa M, Naito Y, Handa O, Takagi T, Mori T, Kumazawa S, Yoshikawa T, Nakayama T (2010)
    Pro-oxidant action of pyrroloquinoline quinone: characterization of protein oxidative modifications.
    Biosci Biotechnol Biochem. 74(3):663-6.
  6. Shankar BS, Pandey R, Amin P, Misra HS, Sainis KB (2010)
    Role of glutathione in augmenting the anticancer activity of pyrroloquinoline quinone (PQQ).
    Redox Rep. 15(4):146-54.

 

III. Measurements

  1. Kumazawa T, Sato K, Seno H, Ishii A, Suzuki O (1995)
    Levels of pyrroloquinoline quinone in various foods.
    Biochem J 307, 331-333.
  2. Mitcell AE, Johnes AD, Mercer RS, Rucker RB (1999)
    Characterization of pyrroloquinoline quinone amino acid derivatives by electrospray ionization mass spectrometry and detection in human milk.
    Anal Biochem 269, 317-325.
  3. Kumazawa T, Seno H, Urakami T, Matsumoto T, Suzuki O (1992)
    Trace levels of pyrroloquinoline quinone in human and rat samples detected by gas chromatography/mass spectrometry.
    Biochim Biophys Acta 1156, 62-66.
  4. Noji N, Nakamura T, Kitahata N, Taguchi K, Kudo T, Yoshida S, Tsujimoto M, Sugiyama T, Asami T (2007)
    Simple and sensitive method for Pyrroloquinoline quinone (PQQ) analysis in various foods using liquid chromatography/electrospray-ionization tandem mass spectrometry.
    J. Agric. Food Chem. 55, 7258-7263
    http://www.ncbi.nlm.nih.gov/pubmed/17685628

 

IV. ADME

  1. Smidt CR, Unkefer CJ, Houck DR, Rucker RB (1991)
    Intesitinal absorption and tissue distribution of [14C]pyrroloquinoline quinone in mice.
    Proc Soc Exp Biol Med 197, 27-31.