Title:
NEOPETROSIDES A AND B, AND SYNTHESIS METHOD THEREOF
Document Type and Number:
WIPO Patent Application WO/2017/209494
Kind Code:
A1
Abstract:
The present invention relates to Neopetroside A (NPS A) and Neopetroside B (NPS B), which are novel pyridine nucleoside compounds obtained by fractioning an ethanol extract of Neopetrosia sp., a marine sponge, with n-butanol (n-BuOH). When applied to myocardial cells, NPS A exhibits the effect of activating oxidative phosphorylation, basal and mitochondrial oxygen consumption rates, ATP-linked respiration, and ATP synthesis, and stimulating glycolysis. When applied to an ischemia reperfusion injury model, NPS A showed the effect of recuperating a left ventricle pressure damaged by ischemia reperfusion and significantly reducing the size of a myocardial injury region. Thus, the compound may be provided as a pharmaceutical composition for the prevention or treatment of ischemia cardiac diseases or as a health functional food for the prevention or amelioration of ischemia cardiac diseases.
More Like This:
Inventors:
HAN JIN (KR)
JEONG SEUNG HUN (KR)
SONG IN-SUNG (KR)
KIM HYOUNG KYU (KR)
KIM NARI (KR)
SHUBINA LARISA K (RU)
MAKARIEVA TATYANA N (RU)
STONIK VALENTIN A (RU)
YASHUNSKY DMITRY V (RU)
NIFANTIEV NIKOLAY E (RU)
JEONG SEUNG HUN (KR)
SONG IN-SUNG (KR)
KIM HYOUNG KYU (KR)
KIM NARI (KR)
SHUBINA LARISA K (RU)
MAKARIEVA TATYANA N (RU)
STONIK VALENTIN A (RU)
YASHUNSKY DMITRY V (RU)
NIFANTIEV NIKOLAY E (RU)
Application Number:
PCT/KR2017/005645
Publication Date:
December 07, 2017
Filing Date:
May 30, 2017
Export Citation:
Assignee:
INJE UNIV INDUSTRY-ACADEMIC COOPERATION FOUNDATION (KR)
International Classes:
C07D405/04; A23L33/10; A61K31/443; C07D405/14
Other References:
FRANCHETTI, P. ET AL.: "Stereoselective Synthesis of Nicotinamide beta-Riboside and Nucleoside Analogs", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 18, 2004, pages 4655 - 4658, XP027347993
FRIEDLOS, F. ET AL.: "Identification of Novel Reduced Pyridinium Derivatives as Synthetic Co-Factors for the Enzyme DT Diaphorase (NAD(P)H Dehydrogenase (quinone), EC 1. 6. 99. 2", BIOCHEMICAL PHARMACOLOGY, vol. 44, no. 1, 1992, pages 25 - 31, XP025567727, DOI: doi:10.1016/0006-2952(92)90033-F
DAVIES, L. C. ET AL.: "Simple Synthesis of the 5-O-Benzoylriboside of 1 ,4-Dihydronicotinic Acid; a Cofactor for DT Diaphorase and Nitroreductase Enzymes", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 311 - 312
SHUBINA, L. K. ET AL.: "Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue", JOURNAL OF NATURAL PRODUCTS, vol. 78, no. 6, 2 June 2015 (2015-06-02), pages 1383 - 1389, XP055447327
GRIBBLE, G. W. ET AL.: "Six-Membered Ring Systems: Pyridine and Benzo Derivatives", PROGRESS IN HETEROCYCLIC CHEMISTRY, vol. 28, no. 1, 23 September 2016 (2016-09-23), pages 682
FRIEDLOS, F. ET AL.: "Identification of Novel Reduced Pyridinium Derivatives as Synthetic Co-Factors for the Enzyme DT Diaphorase (NAD(P)H Dehydrogenase (quinone), EC 1. 6. 99. 2", BIOCHEMICAL PHARMACOLOGY, vol. 44, no. 1, 1992, pages 25 - 31, XP025567727, DOI: doi:10.1016/0006-2952(92)90033-F
DAVIES, L. C. ET AL.: "Simple Synthesis of the 5-O-Benzoylriboside of 1 ,4-Dihydronicotinic Acid; a Cofactor for DT Diaphorase and Nitroreductase Enzymes", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 311 - 312
SHUBINA, L. K. ET AL.: "Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue", JOURNAL OF NATURAL PRODUCTS, vol. 78, no. 6, 2 June 2015 (2015-06-02), pages 1383 - 1389, XP055447327
GRIBBLE, G. W. ET AL.: "Six-Membered Ring Systems: Pyridine and Benzo Derivatives", PROGRESS IN HETEROCYCLIC CHEMISTRY, vol. 28, no. 1, 23 September 2016 (2016-09-23), pages 682
Attorney, Agent or Firm:
TAEBAEK INTELLECTUAL PROPERTY LAW FIRM (KR)
Download PDF: