Title:
METHOD FOR SYNTHESIZING CELOSIANIN II, METHOD FOR SYNTHESIZING BETAXANTHIN, AMYLOID-β POLYMERIZATION INHIBITOR OR THERAPEUTIC OR PROPHYLACTIC AGENT FOR ALZHEIMER'S DISEASE, AMYLOID PEPTIDE AGGREGATION INHIBITOR, AND HIV-1 PROTEASE ACTIVITY INHIBITOR
Document Type and Number:
WIPO Patent Application WO/2021/125352
Kind Code:
A1
Abstract:
The present invention provides: a method for synthesizing celosianin II; a method for synthesizing betaxanthin; an amyloid-β polymerization inhibitor, or a therapeutic or prophylactic agent for Alzheimer's disease; an amyloid peptide aggregation inhibitor; and an HIV-1 protease activity inhibitor. A celosianin II synthesis method according to the present invention was realized through the isolation, from quinua, of a gene having a capability of synthesizing celosianin II. Furthermore, it was confirmed that celosianin II and the like can serve as an active ingredient of: an amyloid-β polymerization inhibitor, or a therapeutic or prophylactic agent for Alzheimer's disease; an amyloid peptide aggregation inhibitor; and an HIV-1 protease activity inhibitor.
Inventors:
MORI MASASHI (JP)
IMAMURA TOMOHIRO (JP)
TAKIZAKI IZUMI (JP)
MIZUNO AKIKO (JP)
HIGASHIMURA YASUKI (JP)
KOGA HIRONORI (JP)
MIZUKOSHI HIROHARU (JP)
IMAMURA TOMOHIRO (JP)
TAKIZAKI IZUMI (JP)
MIZUNO AKIKO (JP)
HIGASHIMURA YASUKI (JP)
KOGA HIRONORI (JP)
MIZUKOSHI HIROHARU (JP)
Application Number:
PCT/JP2020/047581
Publication Date:
June 24, 2021
Filing Date:
December 19, 2020
Export Citation:
Assignee:
MORI MASASHI (JP)
International Classes:
A61P25/28; A61K31/192; A61K31/7056; A61P31/18; A61P43/00; C12N1/15; C12N1/19; C12N1/21; C12N5/10; C12N9/10; C12N15/53; C12N15/54; C12P17/16
Domestic Patent References:
| WO2017122189A1 | 2017-07-20 | |||
| WO2020080503A1 | 2020-04-23 | |||
| WO2020144371A1 | 2020-07-16 |
Foreign References:
| JP2017186335A | 2017-10-12 | |||
| JP2016182044A | 2016-10-20 | |||
| JP2020119563A | 2020-08-06 | |||
| JP2019229647A | 2019-12-19 | |||
| JP2016182044A | 2016-10-20 |
Other References:
NAKATSUKA, T., SASAKI, N., YAMADA, E., FUJITA, K., TAKAHASHI, H., IMAMURA, T., SUZUKI, M., OZEKI, Y., TSUJIMURA, L, SAITO M., SAKA: "Yellow pigment accumulation by reconstruction of betaxanthin biosynthetic pathway", HORTICULTURAL RESEARCH, vol. 12, no. 2, 30 November 2012 (2012-11-30), JP , pages 218, XP009537429, ISSN: 1880-8824
IMAMURA, T. ET AL.: "Isolation of amaranthin synthetase from Chenopodium quinoa and construction of an amaranthin production system using suspension-cultured tobacco BY -2 cells", PLANT BIOTECHNOLOGY JOURNAL, vol. 17, 19 November 2018 (2018-11-19), pages 969 - 981, XP055809833, DOI: 10.1111/pbi.13032
LI-JUNE, M.: "INOR 926 Beeting' Alzheimer's: Inhibition of Cu2+-beta-amyloid mediated oxidation and peroxidation by betanin from sugar beets", ABSTRACTS OF PAPERS; 255TH ACS NATIONAL MEETING & EXPOSITION, NEW ORLEANS, LA, UNITED STATES, MARCH 18-22, 2018, 30 November 2017 (2017-11-30) - 22 March 2018 (2018-03-22), pages INOR 926, XP009537356
SUNNADENIYA, R. ET AL.: "Tyrosine hydroxylation in betalain pigment biosynthesis is performed by cytochrome P450 enzymes in beets (Beta vulgaris", PLOS ONE, vol. 11, no. 2, 2016, pages e0149417, XP055399381, DOI: 10.1371/journal.pone.0149417
POLTURAK, C. ET AL.: "Elucidation of the first committed step in betalain biosynthesis enables the heterologous engineering of betalain pigments in plants", NEW PHYTOLOGIST, vol. 210, 2016, pages 269 - 283, XP055537066, DOI: 10.1111/nph.13796
BOKERN, M . ET AL.: "Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell -suspension cultures of Chenopodium rubrum L.", PLANTA, vol. 184, 1991, pages 261 - 270, XP055836562
JAIN, G.SCHWINN, K.E.GOULD, K.S.: "Betalain induction byl-DOPA application confers photoprotection to saline-exposed leaves of Disphymaaustrale", NEW PHYTOL., vol. 207, 2015, pages 1075 - 1083
POLTURAK, G.GROSSMAN, N.VELA-CORCIA, D.DONG, Y.NUDEL, A.PLINER, M.LEVY, M.ROGACHEV, I.AHARONI, A.: "Engineered gray mold resistance, antioxidant capacity, and pigmentation in betalain-producing crops and ornamentals", PROC. NATL. ACAD. SCI. U. S. A., vol. 114, 2017, pages 9062 - 9067, XP055809832, DOI: 10.1073/pnas.1707176114
KAPADIA, G.J.TOKUDA, H.KONOSHIMA, T.NISHINO, H.: "Chemoprevention of lung and skin cancer by Beta vulgaris (beet) root extract.", CANCER LETT., vol. 100, 1996, pages 211 - 214
IMAMURA, T. ET AL.: "Isolation of amaranthin synthetase from Chenopodium quinoa and construction of an amaranthin production system using suspension-cultured tobacco BY-2 cells", PLANT BIOTECHNOL J, vol. 17, 2019, pages 969 - 981, XP055809833, DOI: 10.1111/pbi.13032
LECHNER, J.F.WANG, L.S.ROCHA, C.M.LARUE, B.HENRY, C.MCINTYRE, C.M.RIEDL, K.M.SCHWARTZ, S.J.STONER, G.D.: "Drinking water with red beetroot food color antagonizes esophageal carcinogenesis in N-nitrosomethylbenzylamine-treated rats", J. MED. FOOD, vol. 13, 2010, pages 733 - 739
MARTINEZ, R.M.LONGHI-BALBINOT, D.T.ZARPELON, A.C.STAURENGO-FERRARI, L.BARACAT, M.M.GEORGETTI, S.R.SASSONIA, R.C.VERRI, W.A., JR.CA: "Anti-inflammatory activity of betalain-rich dye of Beta vulgaris: effect on edema, leukocyte recruitment, superoxide anion and cytokine production", ARCH. PHARM. RES., vol. 38, 2015, pages 494 - 504, XP035445182, DOI: 10.1007/s12272-014-0473-7
RODRIGUEZ, E.B.VIDALLON, M.L.MENDOZA, D.J.REYES, C.T.: "Health-promoting bioactivities of betalains from red dragon fruit (Hylocereus polyrhizus (Weber) Britton and Rose) peels as affected by carbohydrate encapsulation", J. SCI. FOOD AGRIC., vol. 96, 2016, pages 4679 - 4689
TESORIERE, L.BUTERA, D.D'ARPA, D.DIGAUDIO, F.ALLEGRA, M.GENTILE, C.LIVREA, M.A.: "Increased resistance to oxidation of betalain-enriched human low density lipoproteins", FREE RADIC. RES., vol. 37, 2003, pages 689 - 696
TESORIERE, L.ALLEGRA, M.BUTERA, D.LIVREA, M.A.: "Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: potential health effects of betalains in humans", AM. J. CLIN. NUTR., vol. 80, 2004, pages 941 - 945, XP002549924
NUCLEIC ACIDS RES., vol. 10, 1982, pages 6487 - 6500
GANDIA-HERRERO, F.ESCRIBANO, J.GARCIA-CARMONA, F.: "Structural implications on color, fluorescence, and antiradical activity in betalains", PLANTA, vol. 232, 2010, pages 449 - 460, XP019848690
SCHWARTZ, S.J.VON ELBE, J.H.: "Quantitative determination of individual betacyanin pigments by high-performance liquid chromatography", J. AGRIC. FOOD CHEM., vol. 28, 1980, pages 540 - 543
BOSO, G.ORVELL, C.SOMIA, N.V.: "The nature of the N-terminal amino acid residue of HIV-1 RNase H is critical for the stability of reverse transcriptase in viral particles", J. VIROL., vol. 89, 2015, pages 1286 - 1297
ONO, K.HASEGAWA, K.NAIKI, H.YAMADA, M.: "Anti-amyloidogenic activity of tannic acid and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro", BIOCHIM BIOPHYS ACTA, vol. 1690, 2004, pages 193 - 202, XP004614701, DOI: 10.1016/j.bbadis.2004.06.008
BONTPART, T.CHEYNIER, V.AGEORGES, A.TERRIER, N.: "BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds", NEW PHYTOL, vol. 208, 2015, pages 695 - 707
KIM, D.LANGMEAD, B.SALZBERG, S.L.: "HISAT: a fast spliced aligner with low memory requirements", NAT METHODS, vol. 12, 2015, pages 357 - 360, XP055577566, DOI: 10.1038/nmeth.3317
PERTEA, M. ET AL.: "String Tie enables improved reconstruction of a transcriptome from RNA-seq reads", NAT BIOTECHNOL, vol. 33, 2015, pages 290 - 295
LIAO, Y.SMYTH, G.K.SHI, W.: "feature Counts: an efficient general purpose program for assigning sequence reads to genomic features", BIOINFORMATICS, vol. 30, 2014, pages 923 - 930
IMAMURA, T.TAKAGI, H.MIYAZATO, A.OHKI, S.MIZUKOSHI, H.MORI, M.: "Isolation and characterization of the betalain biosynthesis gene involved in hypocotyl pigmentation of the allotetraploid Chenopodiumquinoa", BIOCHEM. BIOPHYS. RES. COMMUN., vol. 496, 2018, pages 280 - 286
WISE, A.A.LIU, Z.BINNS, A.N.: "Three methods for the introduction of foreign DNA into Agrobacterium", METHODS MOL. BIOL., vol. 343, 2006, pages 43 - 53
HAGIWARA, Y.KOMODA, K.YAMANAKA, T.TAMAI, A.MESHI, T.FUNADA, R.TSUCHIYA, T.NAITO, S.ISHIKAWA, M.: "Subcellular localization of host and viral proteins associated with tobamovirus RNA replication", EMBO J., vol. 22, 2003, pages 344 - 353, XP055109833, DOI: 10.1093/emboj/cdg033
"NCBI", Database accession no. AJD87473
YANG FLIM GPBEGUM AN ET AL.: "Curcumin inhibits formation of amyloid betaoligomers and fibrils, binds plaques, and reduces amyloid in vivo", J BIOLCHEM., vol. 280, no. 7, 2005, pages 5892 - 5901
C.D. LINK: "Expression of human beta-amyloid peptide in transgenic Caenorhabditis elegans", PROC. NATL. ACAD. SCI. U. S. A., vol. 92, 1995, pages 9368 - 9372, XP002065639, DOI: 10.1073/pnas.92.20.9368
E. COHENJ. BIESCHKER.M. PERCIAVALLE ET AL.: "Opposing activities protect against age-onset proteotoxicity", SCIENCE, vol. 313, 2006, pages 1604 - 1610
IMAMURA, T. ET AL.: "Isolation of amaranthin synthetase from Chenopodium quinoa and construction of an amaranthin production system using suspension-cultured tobacco BY -2 cells", PLANT BIOTECHNOLOGY JOURNAL, vol. 17, 19 November 2018 (2018-11-19), pages 969 - 981, XP055809833, DOI: 10.1111/pbi.13032
LI-JUNE, M.: "INOR 926 Beeting' Alzheimer's: Inhibition of Cu2+-beta-amyloid mediated oxidation and peroxidation by betanin from sugar beets", ABSTRACTS OF PAPERS; 255TH ACS NATIONAL MEETING & EXPOSITION, NEW ORLEANS, LA, UNITED STATES, MARCH 18-22, 2018, 30 November 2017 (2017-11-30) - 22 March 2018 (2018-03-22), pages INOR 926, XP009537356
SUNNADENIYA, R. ET AL.: "Tyrosine hydroxylation in betalain pigment biosynthesis is performed by cytochrome P450 enzymes in beets (Beta vulgaris", PLOS ONE, vol. 11, no. 2, 2016, pages e0149417, XP055399381, DOI: 10.1371/journal.pone.0149417
POLTURAK, C. ET AL.: "Elucidation of the first committed step in betalain biosynthesis enables the heterologous engineering of betalain pigments in plants", NEW PHYTOLOGIST, vol. 210, 2016, pages 269 - 283, XP055537066, DOI: 10.1111/nph.13796
BOKERN, M . ET AL.: "Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell -suspension cultures of Chenopodium rubrum L.", PLANTA, vol. 184, 1991, pages 261 - 270, XP055836562
JAIN, G.SCHWINN, K.E.GOULD, K.S.: "Betalain induction byl-DOPA application confers photoprotection to saline-exposed leaves of Disphymaaustrale", NEW PHYTOL., vol. 207, 2015, pages 1075 - 1083
POLTURAK, G.GROSSMAN, N.VELA-CORCIA, D.DONG, Y.NUDEL, A.PLINER, M.LEVY, M.ROGACHEV, I.AHARONI, A.: "Engineered gray mold resistance, antioxidant capacity, and pigmentation in betalain-producing crops and ornamentals", PROC. NATL. ACAD. SCI. U. S. A., vol. 114, 2017, pages 9062 - 9067, XP055809832, DOI: 10.1073/pnas.1707176114
KAPADIA, G.J.TOKUDA, H.KONOSHIMA, T.NISHINO, H.: "Chemoprevention of lung and skin cancer by Beta vulgaris (beet) root extract.", CANCER LETT., vol. 100, 1996, pages 211 - 214
IMAMURA, T. ET AL.: "Isolation of amaranthin synthetase from Chenopodium quinoa and construction of an amaranthin production system using suspension-cultured tobacco BY-2 cells", PLANT BIOTECHNOL J, vol. 17, 2019, pages 969 - 981, XP055809833, DOI: 10.1111/pbi.13032
LECHNER, J.F.WANG, L.S.ROCHA, C.M.LARUE, B.HENRY, C.MCINTYRE, C.M.RIEDL, K.M.SCHWARTZ, S.J.STONER, G.D.: "Drinking water with red beetroot food color antagonizes esophageal carcinogenesis in N-nitrosomethylbenzylamine-treated rats", J. MED. FOOD, vol. 13, 2010, pages 733 - 739
MARTINEZ, R.M.LONGHI-BALBINOT, D.T.ZARPELON, A.C.STAURENGO-FERRARI, L.BARACAT, M.M.GEORGETTI, S.R.SASSONIA, R.C.VERRI, W.A., JR.CA: "Anti-inflammatory activity of betalain-rich dye of Beta vulgaris: effect on edema, leukocyte recruitment, superoxide anion and cytokine production", ARCH. PHARM. RES., vol. 38, 2015, pages 494 - 504, XP035445182, DOI: 10.1007/s12272-014-0473-7
RODRIGUEZ, E.B.VIDALLON, M.L.MENDOZA, D.J.REYES, C.T.: "Health-promoting bioactivities of betalains from red dragon fruit (Hylocereus polyrhizus (Weber) Britton and Rose) peels as affected by carbohydrate encapsulation", J. SCI. FOOD AGRIC., vol. 96, 2016, pages 4679 - 4689
TESORIERE, L.BUTERA, D.D'ARPA, D.DIGAUDIO, F.ALLEGRA, M.GENTILE, C.LIVREA, M.A.: "Increased resistance to oxidation of betalain-enriched human low density lipoproteins", FREE RADIC. RES., vol. 37, 2003, pages 689 - 696
TESORIERE, L.ALLEGRA, M.BUTERA, D.LIVREA, M.A.: "Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: potential health effects of betalains in humans", AM. J. CLIN. NUTR., vol. 80, 2004, pages 941 - 945, XP002549924
NUCLEIC ACIDS RES., vol. 10, 1982, pages 6487 - 6500
GANDIA-HERRERO, F.ESCRIBANO, J.GARCIA-CARMONA, F.: "Structural implications on color, fluorescence, and antiradical activity in betalains", PLANTA, vol. 232, 2010, pages 449 - 460, XP019848690
SCHWARTZ, S.J.VON ELBE, J.H.: "Quantitative determination of individual betacyanin pigments by high-performance liquid chromatography", J. AGRIC. FOOD CHEM., vol. 28, 1980, pages 540 - 543
BOSO, G.ORVELL, C.SOMIA, N.V.: "The nature of the N-terminal amino acid residue of HIV-1 RNase H is critical for the stability of reverse transcriptase in viral particles", J. VIROL., vol. 89, 2015, pages 1286 - 1297
ONO, K.HASEGAWA, K.NAIKI, H.YAMADA, M.: "Anti-amyloidogenic activity of tannic acid and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro", BIOCHIM BIOPHYS ACTA, vol. 1690, 2004, pages 193 - 202, XP004614701, DOI: 10.1016/j.bbadis.2004.06.008
BONTPART, T.CHEYNIER, V.AGEORGES, A.TERRIER, N.: "BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds", NEW PHYTOL, vol. 208, 2015, pages 695 - 707
KIM, D.LANGMEAD, B.SALZBERG, S.L.: "HISAT: a fast spliced aligner with low memory requirements", NAT METHODS, vol. 12, 2015, pages 357 - 360, XP055577566, DOI: 10.1038/nmeth.3317
PERTEA, M. ET AL.: "String Tie enables improved reconstruction of a transcriptome from RNA-seq reads", NAT BIOTECHNOL, vol. 33, 2015, pages 290 - 295
LIAO, Y.SMYTH, G.K.SHI, W.: "feature Counts: an efficient general purpose program for assigning sequence reads to genomic features", BIOINFORMATICS, vol. 30, 2014, pages 923 - 930
IMAMURA, T.TAKAGI, H.MIYAZATO, A.OHKI, S.MIZUKOSHI, H.MORI, M.: "Isolation and characterization of the betalain biosynthesis gene involved in hypocotyl pigmentation of the allotetraploid Chenopodiumquinoa", BIOCHEM. BIOPHYS. RES. COMMUN., vol. 496, 2018, pages 280 - 286
WISE, A.A.LIU, Z.BINNS, A.N.: "Three methods for the introduction of foreign DNA into Agrobacterium", METHODS MOL. BIOL., vol. 343, 2006, pages 43 - 53
HAGIWARA, Y.KOMODA, K.YAMANAKA, T.TAMAI, A.MESHI, T.FUNADA, R.TSUCHIYA, T.NAITO, S.ISHIKAWA, M.: "Subcellular localization of host and viral proteins associated with tobamovirus RNA replication", EMBO J., vol. 22, 2003, pages 344 - 353, XP055109833, DOI: 10.1093/emboj/cdg033
"NCBI", Database accession no. AJD87473
YANG FLIM GPBEGUM AN ET AL.: "Curcumin inhibits formation of amyloid betaoligomers and fibrils, binds plaques, and reduces amyloid in vivo", J BIOLCHEM., vol. 280, no. 7, 2005, pages 5892 - 5901
C.D. LINK: "Expression of human beta-amyloid peptide in transgenic Caenorhabditis elegans", PROC. NATL. ACAD. SCI. U. S. A., vol. 92, 1995, pages 9368 - 9372, XP002065639, DOI: 10.1073/pnas.92.20.9368
E. COHENJ. BIESCHKER.M. PERCIAVALLE ET AL.: "Opposing activities protect against age-onset proteotoxicity", SCIENCE, vol. 313, 2006, pages 1604 - 1610
Attorney, Agent or Firm:
SHOJI Takashi et al. (JP)
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