Title:
EXTRACT DERIVED FROM GRAPE RACHIS
Document Type and Number:
WIPO Patent Application WO/2013/081046
Kind Code:
A1
Abstract:
A compound shown by the general formula (1), and an antitumor agent containing this compound as an active ingredient. (A)n1-(B)n2… (1); where n1 represents any integer of 6-20, n2 represents any integer of 1-20, A is a group shown by the general formula (2), B is a group shown by the general formula (3), R1-1-R1-3 represent -O-sugar or the like, R1-4 represents -catechin or the like, R1-5 represents -H or -OH, and R2 represents -O-sugar or the like.
Inventors:
FUJII HIROSHI (JP)
KAWAHARA SEIICHI (JP)
MAKABE HIDEFUMI (JP)
KAWAHARA SEIICHI (JP)
MAKABE HIDEFUMI (JP)
Application Number:
PCT/JP2012/080892
Publication Date:
June 06, 2013
Filing Date:
November 29, 2012
Export Citation:
Assignee:
UNIV SHINSHU (JP)
ST COUSAIR CO LTD (JP)
ST COUSAIR CO LTD (JP)
International Classes:
C07D311/62; A61K31/353; A61K36/00; A61K36/18; A61P13/08; A61P35/00; C12N15/09
Domestic Patent References:
| WO2010108410A1 | 2010-09-30 | |||
| WO2000018416A1 | 2000-04-06 |
Foreign References:
| JPH02187433A | 1990-07-23 | |||
| JP2001097872A | 2001-04-10 | |||
| JP2008508252A | 2008-03-21 |
Other References:
PIRNIYAZOV A.Z. ET AL.: "Polyphenols from Vitis vinifera seeds", CHEMISTRY OF NATURAL COMPOUNDS, vol. 39, no. 4, 2003, pages 349 - 354, XP055075789
PENA-NEIRA A. ET AL.: "A survey of phenolic compounds in Spanish wines of different geographical origin", EUROPEAN FOOD RESEARCH AND TECHNOLOGY, vol. 210, no. 6, 2000, pages 445 - 448, XP055075792
NISHANBAEV S.Z. ET AL.: "New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from Platanus orientalis trunk bark", CHEMISTRY OF NATURAL COMPOUNDS, vol. 46, no. 3, 2010, pages 357 - 362, XP055075794
NISHANBAEV S.Z. ET AL.: "New Oligomeric Proanthocyanidins from Bark of Platanus orientalis", CHEMISTRY OF NATURAL COMPOUNDS, vol. 41, no. 4, 2005, pages 404 - 409, XP019276759
KULIEV Z.A. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii and their biological activity. III", CHEMISTRY OF NATURAL COMPOUNDS, vol. 36, no. 1, 2000, pages 60 - 67, XP008144771
MATAMAROVA K.N. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii. II", CHEMISTRY OF NATURAL COMPOUNDS, vol. 35, no. 1, 1999, pages 39 - 45, XP055075797
ISMAILOV A.E. ET AL.: "Oligomeric proanthocyanidin glycosides of Rhodiola pamiroalaica. II", CHEMISTRY OF NATURAL COMPOUNDS, vol. 35, no. 1, 1999, pages 33 - 38, XP055075799
MATAMAROVA K.N. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii", CHEMISTRY OF NATURAL COMPOUNDS, vol. 34, no. 6, 1998, pages 676 - 682, XP055075800
AOKI K. ET AL.: "Novel inhibitors of poly(ADP- ribose) glycohydrolase", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1158, no. 3, 1993, pages 251 - 256, XP025492665
NAKASHIMA H. ET AL.: "Inhibition of human immunodeficiency viral replication by tannins and related compounds", ANTIVIRAL RESEARCH, vol. 18, no. 1, 1992, pages 91 - 103, XP023794887
KAKIUCHI,N. ET AL.: "Effect of condensed tannins and related compounds on reverse transcriptase", PHYTOTHERAPY RESEARCH, vol. 5, no. 6, 1991, pages 270 - 272, XP055075808
HATANO T. ET AL.: "Effects of interaction of tannins with co-existing substances. VII. Inhibitory effects of tannins and related polyphenols on xanthine oxidase", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 38, no. 5, 1990, pages 1224 - 1229, XP009085886
HATANO,T. ET AL.: "Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl- 2-picrylhydrazyl radical", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 37, no. 8, 1989, pages 2016 - 2021, XP000907239
FUKUCHI K. ET AL.: "Inhibition of herpes simplex virus infection by tannins and related compounds", ANTIVIRAL RESEARCH, vol. 11, no. 5-6, 1989, pages 285 - 297, XP023893379
SAKAGAMI,H. ET AL.: "Stimulation of granulocytic cell iodination by tannins and related compounds", ANTICANCER RES, vol. 10, no. 6, 1990, pages 1523 - 1531
SAKAGAMI,H. ET AL.: "Stimulation of monocyte iodination and IL-1 production by tannins and related compounds", ANTICANCER RES, vol. 12, no. 2, 1992, pages 377 - 387
MAKHMATKULOV,A.B. ET AL.: "Proanthocyanidins of Polygonum coriarium. II", KHIMIYA PRIRODNYKH SOEDINENII, 1994, pages 233 - 244
KIDERLEN,A.F. ET AL.: "Tannins and related compounds: killing of amastigotes of Leishmania donovani and release of nitric oxide and tumour necrosis factor alpha in macrophages in vitro", Z NATURFORSCH C, vol. 56, no. 5-6, 2001, pages 444 - 454, XP009116790
KARVELA,E. ET AL.: "Deployment of response surface methodology to optimise recovery of grape (Vitis vinifera) stem polyphenols", TALANTA, vol. 79, no. 5, 2009, pages 1311 - 1321, XP026374920
ZGA N. ET AL.: "Preparative purification of antiamyloidogenic stilbenoids from Vitis vinifera (Chardonnay) stems by centrifugal partition chromatography", J CHROMATOGR B ANALYT TECHNOL BIOMED LIFE SCI, vol. 877, no. 10, 2009, pages 1000 - 1004, XP026010978
MAKRIS, D.P. ET AL.: "Characterisation of certain major polyphenolic antioxidants in grape (Vitis vinifera cv. Roditis) stems by liquid chromatography-mass spectrometry", EUROPEAN FOOD RESEARCH AND TECHNOLOGY, vol. 226, no. 5, 2008, pages 1075 - 1079, XP019585021
PUSSA T. ET AL.: "Survey of grapevine Vitis vinifera stem polyphenols by liquid chromatography-diode array detection-tandem mass spectrometry", J AGRIC FOOD CHEM, vol. 54, no. 20, 2006, pages 7488 - 7494, XP055075823
PENA-NEIRA A. ET AL.: "A survey of phenolic compounds in Spanish wines of different geographical origin", EUROPEAN FOOD RESEARCH AND TECHNOLOGY, vol. 210, no. 6, 2000, pages 445 - 448, XP055075792
NISHANBAEV S.Z. ET AL.: "New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from Platanus orientalis trunk bark", CHEMISTRY OF NATURAL COMPOUNDS, vol. 46, no. 3, 2010, pages 357 - 362, XP055075794
NISHANBAEV S.Z. ET AL.: "New Oligomeric Proanthocyanidins from Bark of Platanus orientalis", CHEMISTRY OF NATURAL COMPOUNDS, vol. 41, no. 4, 2005, pages 404 - 409, XP019276759
KULIEV Z.A. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii and their biological activity. III", CHEMISTRY OF NATURAL COMPOUNDS, vol. 36, no. 1, 2000, pages 60 - 67, XP008144771
MATAMAROVA K.N. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii. II", CHEMISTRY OF NATURAL COMPOUNDS, vol. 35, no. 1, 1999, pages 39 - 45, XP055075797
ISMAILOV A.E. ET AL.: "Oligomeric proanthocyanidin glycosides of Rhodiola pamiroalaica. II", CHEMISTRY OF NATURAL COMPOUNDS, vol. 35, no. 1, 1999, pages 33 - 38, XP055075799
MATAMAROVA K.N. ET AL.: "Oligomeric proanthocyanidin glycosides of Clementsia semenovii", CHEMISTRY OF NATURAL COMPOUNDS, vol. 34, no. 6, 1998, pages 676 - 682, XP055075800
AOKI K. ET AL.: "Novel inhibitors of poly(ADP- ribose) glycohydrolase", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1158, no. 3, 1993, pages 251 - 256, XP025492665
NAKASHIMA H. ET AL.: "Inhibition of human immunodeficiency viral replication by tannins and related compounds", ANTIVIRAL RESEARCH, vol. 18, no. 1, 1992, pages 91 - 103, XP023794887
KAKIUCHI,N. ET AL.: "Effect of condensed tannins and related compounds on reverse transcriptase", PHYTOTHERAPY RESEARCH, vol. 5, no. 6, 1991, pages 270 - 272, XP055075808
HATANO T. ET AL.: "Effects of interaction of tannins with co-existing substances. VII. Inhibitory effects of tannins and related polyphenols on xanthine oxidase", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 38, no. 5, 1990, pages 1224 - 1229, XP009085886
HATANO,T. ET AL.: "Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl- 2-picrylhydrazyl radical", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 37, no. 8, 1989, pages 2016 - 2021, XP000907239
FUKUCHI K. ET AL.: "Inhibition of herpes simplex virus infection by tannins and related compounds", ANTIVIRAL RESEARCH, vol. 11, no. 5-6, 1989, pages 285 - 297, XP023893379
SAKAGAMI,H. ET AL.: "Stimulation of granulocytic cell iodination by tannins and related compounds", ANTICANCER RES, vol. 10, no. 6, 1990, pages 1523 - 1531
SAKAGAMI,H. ET AL.: "Stimulation of monocyte iodination and IL-1 production by tannins and related compounds", ANTICANCER RES, vol. 12, no. 2, 1992, pages 377 - 387
MAKHMATKULOV,A.B. ET AL.: "Proanthocyanidins of Polygonum coriarium. II", KHIMIYA PRIRODNYKH SOEDINENII, 1994, pages 233 - 244
KIDERLEN,A.F. ET AL.: "Tannins and related compounds: killing of amastigotes of Leishmania donovani and release of nitric oxide and tumour necrosis factor alpha in macrophages in vitro", Z NATURFORSCH C, vol. 56, no. 5-6, 2001, pages 444 - 454, XP009116790
KARVELA,E. ET AL.: "Deployment of response surface methodology to optimise recovery of grape (Vitis vinifera) stem polyphenols", TALANTA, vol. 79, no. 5, 2009, pages 1311 - 1321, XP026374920
ZGA N. ET AL.: "Preparative purification of antiamyloidogenic stilbenoids from Vitis vinifera (Chardonnay) stems by centrifugal partition chromatography", J CHROMATOGR B ANALYT TECHNOL BIOMED LIFE SCI, vol. 877, no. 10, 2009, pages 1000 - 1004, XP026010978
MAKRIS, D.P. ET AL.: "Characterisation of certain major polyphenolic antioxidants in grape (Vitis vinifera cv. Roditis) stems by liquid chromatography-mass spectrometry", EUROPEAN FOOD RESEARCH AND TECHNOLOGY, vol. 226, no. 5, 2008, pages 1075 - 1079, XP019585021
PUSSA T. ET AL.: "Survey of grapevine Vitis vinifera stem polyphenols by liquid chromatography-diode array detection-tandem mass spectrometry", J AGRIC FOOD CHEM, vol. 54, no. 20, 2006, pages 7488 - 7494, XP055075823
Attorney, Agent or Firm:
MOEGI PATENT OFFICE (JP)
Patent business corporation It burns and is ぎ特許事務所. (JP)
Patent business corporation It burns and is ぎ特許事務所. (JP)
Download PDF:
Claims: