Title:
PLANT EXTRACTS ENRICHED WITH IPOLAMIIDE DERIVATIVES AS IMMUNOSUPPRESSANTS FOR TREATING IMMUNOLOGICAL DISORDERS
Document Type and Number:
WIPO Patent Application WO/2018/148816
Kind Code:
A3
Abstract:
The invention describes extracts from plants of the genus Stachytarpheta enriched with ipolamiide derivatives as immunosuppressants for treating immunological disorders. The isolated active compounds and a process of producing these are also disclosed.
Inventors:
GUIMARÃES CRISTIANO RUCH WERNECK (BR)
VITOR CARLOS EDUARDO (BR)
PESSA LISANDRA RAVANELLI (BR)
REIS ROMULO DRAGANI (BR)
MASCARELLO ALESSANDRA (BR)
GAMA FERNANDO HENRIQUE DE SOUZA (BR)
VITOR CARLOS EDUARDO (BR)
PESSA LISANDRA RAVANELLI (BR)
REIS ROMULO DRAGANI (BR)
MASCARELLO ALESSANDRA (BR)
GAMA FERNANDO HENRIQUE DE SOUZA (BR)
Application Number:
PCT/BR2018/050037
Publication Date:
October 18, 2018
Filing Date:
February 19, 2018
Export Citation:
Assignee:
ACHE LABORATORIOS FARMACEUTICOS SA (BR)
International Classes:
C07D311/94; A61K31/201; A61K31/215; A61K31/352; A61P37/06; C07C59/42; C07C69/608
Domestic Patent References:
WO2016128471A1 | 2016-08-18 | |||
WO2008098325A1 | 2008-08-21 | |||
WO2003094946A1 | 2003-11-20 |
Foreign References:
CN103690551A | 2014-04-02 | |||
CN103120699A | 2013-05-29 | |||
EP1145709A1 | 2001-10-17 | |||
EP0045837A1 | 1982-02-17 | |||
US3703543A | 1972-11-21 | |||
DE19644422A1 | 1998-04-30 | |||
EP1371372A1 | 2003-12-17 |
Other References:
ADEBAJO, A. C. ET AL: "Hypoglycaemic constituents of Stachytarpheta cayennensis leaf", PLANTA MEDICA, vol. 73, no. 3, 22 February 2007 (2007-02-22), pages 241 - 250, XP002780026, ISSN: 0032-0943, DOI: 10.1055/s-2007-967125
BIANCO, A. ET AL: "Acid-catalyzed rearrangements of iridoid aglycones. I. Behavior of lamiidol, a nonnatural lamiide derivative", TETRAHEDRON LETTERS, vol. 48, 1978, pages 4829 - 4832, XP002780027, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)85744-0
KHOBRAKOVA, V. B. ET AL: "Immunomodulating Activity of Extract of Gentiana Algida Pall", PHARMACEUTICAL CHEMISTRY JOURNAL, vol. 51, no. 5, August 2017 (2017-08-01), pages 384 - 387, XP002780028, ISSN: 0091-150X, DOI: 10.1007/s11094-017-1618-z
HOKI, KUNIHITO ET AL: "Chiral Molecular Motors Ignited by Femtosecond Pump-Dump Laser Pulses", JOURNAL OF PHYSICAL CHEMISTRY B, vol. 108, no. 15, 2004, pages 4916 - 4921, XP002782769, ISSN: 1520-6106, DOI: 10.1021/jp036437l
KUNIHITO HOKI ET AL: "Mechanism of unidirectional motions of chiral molecular motors driven by linearly polarized pulses", JOURNAL OF CHEMICAL PHYSICS, vol. 119, no. 23, 15 December 2003 (2003-12-15), US, pages 12393 - 12398, XP055488425, ISSN: 0021-9606, DOI: 10.1063/1.1621622
SCHLOEGL, K.; FRIED, M.: "Ferrocenasymmetrie, 1. Mitt.: Darstellung und Racematspaltung von asymmetrischen Aminen und Aldehyden der Ferrocenreihe", MONATSHEFTE FUER CHEMIE, vol. 95, no. 2, 1964, pages 558 - 575, XP002782770, ISSN: 0026-9247
BENKESER, ROBERT A.; BACH, JOSEPH L.: "Factors governing orientation in metalation reactions. III. Metalation of alkylferrocenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 86, no. 5, 1964, pages 890 - 895, XP002782771, ISSN: 0002-7863, DOI: 10.1021/ja01059a029
ORHAN, ILKAY ERDOGAN ET AL: "Immunomodulatory properties of various natural compounds and essential oils through modulation of human cellular immune response", INDUSTRIAL CROPS AND PRODUCTS, vol. 81, 2016, pages 117 - 122, XP002782772, ISSN: 0926-6690, DOI: 10.1016/j.indcrop.2015.11.088
KOBAYASHI, YUKO ET AL: "Inhibitory effects of geranium essential oil and its major component, citronellol, on degranulation and cytokine production by mast cells", BIOSCIENCE, BIOTECHNOLOGY AND BIOCHEMISTRY, vol. 80, no. 6, 2016, pages 1172 - 1178, XP002782773, ISSN: 1347-6947, DOI: 10.1080/09168451.2016.1148573
LEE, JE-HYUK ET AL: "Anti-inflammatory activities of Chopi (Zanthoxylum piperitum A.P. DC) essential oil: Suppression of the inducible nitric oxide synthase and cellular adhesion", FOOD SCIENCE AND BIOTECHNOLOGY, vol. 18, no. 6, 2009, pages 1371 - 1378, XP002782774, ISSN: 1226-7708
LEE, JE-HYUK ET AL: "Composition and anti-inflammatory activities of Zanthoxylum schinifolium essential oil: suppression of inducible nitric oxide synthase, cyclooxygenase-2, cytokines and cellular adhesion", JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, vol. 89, no. 10, 2009, pages 1762 - 1769, XP002782775, ISSN: 0022-5142, DOI: 10.1002/jsfa.3653
YU, XIA ET AL: "A new linear monoterpene from the Chinese mangrove plant Cerbera manghas L", JOURNAL OF CHINESE PHARMACEUTICAL SCIENCES, vol. 18, no. 3, 2009, pages 232 - 235, XP009506549, ISSN: 1003-1057
ELMASRI, WAEL A. ET AL: "Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, vol. 30, no. 18, 2016, pages 2033 - 2042, XP002782776, ISSN: 0951-4198, DOI: 10.1002/rcm.7681
BADEN, CHRISTIAN ULRICH ET AL: "Differing patterns of sequestration of iridoid glycosides in the Mecininae (Coleoptera, Curculionidae)", CHEMOECOLOGY, vol. 22, no. 2, 2012, pages 113 - 118, XP002782777, ISSN: 0937-7409, DOI: 10.1007/s00049-012-0103-0
AKKOL, ESRA KUPELI ET AL: "Antinociceptive and anti-inflammatory activities of some Linaria species from Turkey", PHARMACEUTICAL BIOLOGY, vol. 47, no. 3, 2009, pages 188 - 194, XP002782778, ISSN: 1388-0209, DOI: 10.1080/13880200802465165
VICCINI ET AL: "Ipolamiide and fulvoipolamiide from Stachytarpheta glabra (Verbenaceae): A structural and spectroscopic characterization", JOURNAL OF MOLECULAR STRUCTURE, ELSEVIER, AMSTERDAM, NL, vol. 875, no. 1-3, 1 March 2008 (2008-03-01), pages 27 - 31, XP022508309, ISSN: 0022-2860, DOI: 10.1016/J.MOLSTRUC.2007.03.056
LEITAO, GILDA GUIMARAES ET AL: "Step-gradient CCC separation of phenylpropanoid and iridoid glycosides from roots of Stachytarpheta cayennensis", JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, vol. 28, no. 12-13, 2005, pages 2053 - 2060, XP002782779, ISSN: 1082-6076, DOI: 10.1081/JLC-200063672
SCHAPOVAL, ELFRIDES E. S.: "Antiinflammatory and antinociceptive activities of extracts and isolated compounds from Stachytarpheta cayennensis", JOURNAL OF ETHNOPHARMACOLOGY, vol. 60, no. 1, 1998, pages 53 - 59, XP002782780, ISSN: 0378-8741, DOI: 10.1016/S0378-8741(97)00136-0
BIANCO, A. ET AL: "Acid-catalyzed rearrangements of iridoid aglycones. I. Behavior of lamiidol, a nonnatural lamiide derivative", TETRAHEDRON LETTERS, vol. 48, 1978, pages 4829 - 4832, XP002780027, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(01)85744-0
KHOBRAKOVA, V. B. ET AL: "Immunomodulating Activity of Extract of Gentiana Algida Pall", PHARMACEUTICAL CHEMISTRY JOURNAL, vol. 51, no. 5, August 2017 (2017-08-01), pages 384 - 387, XP002780028, ISSN: 0091-150X, DOI: 10.1007/s11094-017-1618-z
HOKI, KUNIHITO ET AL: "Chiral Molecular Motors Ignited by Femtosecond Pump-Dump Laser Pulses", JOURNAL OF PHYSICAL CHEMISTRY B, vol. 108, no. 15, 2004, pages 4916 - 4921, XP002782769, ISSN: 1520-6106, DOI: 10.1021/jp036437l
KUNIHITO HOKI ET AL: "Mechanism of unidirectional motions of chiral molecular motors driven by linearly polarized pulses", JOURNAL OF CHEMICAL PHYSICS, vol. 119, no. 23, 15 December 2003 (2003-12-15), US, pages 12393 - 12398, XP055488425, ISSN: 0021-9606, DOI: 10.1063/1.1621622
SCHLOEGL, K.; FRIED, M.: "Ferrocenasymmetrie, 1. Mitt.: Darstellung und Racematspaltung von asymmetrischen Aminen und Aldehyden der Ferrocenreihe", MONATSHEFTE FUER CHEMIE, vol. 95, no. 2, 1964, pages 558 - 575, XP002782770, ISSN: 0026-9247
BENKESER, ROBERT A.; BACH, JOSEPH L.: "Factors governing orientation in metalation reactions. III. Metalation of alkylferrocenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 86, no. 5, 1964, pages 890 - 895, XP002782771, ISSN: 0002-7863, DOI: 10.1021/ja01059a029
ORHAN, ILKAY ERDOGAN ET AL: "Immunomodulatory properties of various natural compounds and essential oils through modulation of human cellular immune response", INDUSTRIAL CROPS AND PRODUCTS, vol. 81, 2016, pages 117 - 122, XP002782772, ISSN: 0926-6690, DOI: 10.1016/j.indcrop.2015.11.088
KOBAYASHI, YUKO ET AL: "Inhibitory effects of geranium essential oil and its major component, citronellol, on degranulation and cytokine production by mast cells", BIOSCIENCE, BIOTECHNOLOGY AND BIOCHEMISTRY, vol. 80, no. 6, 2016, pages 1172 - 1178, XP002782773, ISSN: 1347-6947, DOI: 10.1080/09168451.2016.1148573
LEE, JE-HYUK ET AL: "Anti-inflammatory activities of Chopi (Zanthoxylum piperitum A.P. DC) essential oil: Suppression of the inducible nitric oxide synthase and cellular adhesion", FOOD SCIENCE AND BIOTECHNOLOGY, vol. 18, no. 6, 2009, pages 1371 - 1378, XP002782774, ISSN: 1226-7708
LEE, JE-HYUK ET AL: "Composition and anti-inflammatory activities of Zanthoxylum schinifolium essential oil: suppression of inducible nitric oxide synthase, cyclooxygenase-2, cytokines and cellular adhesion", JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, vol. 89, no. 10, 2009, pages 1762 - 1769, XP002782775, ISSN: 0022-5142, DOI: 10.1002/jsfa.3653
YU, XIA ET AL: "A new linear monoterpene from the Chinese mangrove plant Cerbera manghas L", JOURNAL OF CHINESE PHARMACEUTICAL SCIENCES, vol. 18, no. 3, 2009, pages 232 - 235, XP009506549, ISSN: 1003-1057
ELMASRI, WAEL A. ET AL: "Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, vol. 30, no. 18, 2016, pages 2033 - 2042, XP002782776, ISSN: 0951-4198, DOI: 10.1002/rcm.7681
BADEN, CHRISTIAN ULRICH ET AL: "Differing patterns of sequestration of iridoid glycosides in the Mecininae (Coleoptera, Curculionidae)", CHEMOECOLOGY, vol. 22, no. 2, 2012, pages 113 - 118, XP002782777, ISSN: 0937-7409, DOI: 10.1007/s00049-012-0103-0
AKKOL, ESRA KUPELI ET AL: "Antinociceptive and anti-inflammatory activities of some Linaria species from Turkey", PHARMACEUTICAL BIOLOGY, vol. 47, no. 3, 2009, pages 188 - 194, XP002782778, ISSN: 1388-0209, DOI: 10.1080/13880200802465165
VICCINI ET AL: "Ipolamiide and fulvoipolamiide from Stachytarpheta glabra (Verbenaceae): A structural and spectroscopic characterization", JOURNAL OF MOLECULAR STRUCTURE, ELSEVIER, AMSTERDAM, NL, vol. 875, no. 1-3, 1 March 2008 (2008-03-01), pages 27 - 31, XP022508309, ISSN: 0022-2860, DOI: 10.1016/J.MOLSTRUC.2007.03.056
LEITAO, GILDA GUIMARAES ET AL: "Step-gradient CCC separation of phenylpropanoid and iridoid glycosides from roots of Stachytarpheta cayennensis", JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, vol. 28, no. 12-13, 2005, pages 2053 - 2060, XP002782779, ISSN: 1082-6076, DOI: 10.1081/JLC-200063672
SCHAPOVAL, ELFRIDES E. S.: "Antiinflammatory and antinociceptive activities of extracts and isolated compounds from Stachytarpheta cayennensis", JOURNAL OF ETHNOPHARMACOLOGY, vol. 60, no. 1, 1998, pages 53 - 59, XP002782780, ISSN: 0378-8741, DOI: 10.1016/S0378-8741(97)00136-0
Attorney, Agent or Firm:
DANIEL ADVOGADOS (BR)
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