메뉴 건너뛰기




Volumn 51, Issue 1, 2005, Pages 48-59

Synthesis of dihydroxyphenacyl glycosides for biological and medicinal study: β-oxoacteoside from Paulownia tomentosa

Author keywords

Oxoacteoside; 2,3 ,4 Trihydroxyacetophenone; Dihydroxyphenacyl glycoside; Phenylpropanoid glycoside; Synthesis

Indexed keywords

ESTERIFICATION; GLUCOSE; PROTEINS; SUGARS; SYNTHESIS (CHEMICAL);

EID: 17044392731     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10086-003-0609-8     Document Type: Article
Times cited : (11)

References (35)
  • 1
    • 0000032930 scopus 로고
    • Evolutionary aspects of caffeoyl ester distribution in dicotyledons
    • Mølgaard P, Ravin H (1988) Evolutionary aspects of caffeoyl ester distribution in dicotyledons. Phytochemistry 27:2411-2421
    • (1988) Phytochemistry , vol.27 , pp. 2411-2421
    • Mølgaard, P.1    Ravin, H.2
  • 2
    • 0028312287 scopus 로고
    • Phenylethanoid glycosides in plants: Structure and biological activity
    • Jiménez C, Riguera R (1994) Phenylethanoid glycosides in plants: structure and biological activity. Nat Prod Rep 11:591-606
    • (1994) Nat Prod Rep , vol.11 , pp. 591-606
    • Jiménez, C.1    Riguera, R.2
  • 3
    • 0142098256 scopus 로고
    • The chemistry of color changes in kiri wood (Paulownia tomentosa Steud) III. A new caffeic acid sugar ester from kiri wood
    • Ota M, Azuma T, Onodera S, Taneda K (1993) The chemistry of color changes in kiri wood (Paulownia tomentosa Steud) III. A new caffeic acid sugar ester from kiri wood (in Japanese). Mokuzai Gakkaishi 39:479-485
    • (1993) Mokuzai Gakkaishi , vol.39 , pp. 479-485
    • Ota, M.1    Azuma, T.2    Onodera, S.3    Taneda, K.4
  • 6
    • 0011383394 scopus 로고
    • The isolation of ketocatechols from insect cuticle and their possible role in sclerotization
    • Anderson SO, Barret FM (1971) The isolation of ketocatechols from insect cuticle and their possible role in sclerotization. J Insect Physiol 17:69-83
    • (1971) J Insect Physiol , vol.17 , pp. 69-83
    • Anderson, S.O.1    Barret, F.M.2
  • 7
    • 0025866442 scopus 로고
    • Phenolic compounds and an analog as superoxide anion scavengers and antioxidants
    • Zhou Y-C, Zheng R-L (1991) Phenolic compounds and an analog as superoxide anion scavengers and antioxidants. Biochem Pharmacol 42:1177-1179
    • (1991) Biochem Pharmacol , vol.42 , pp. 1177-1179
    • Zhou, Y.-C.1    Zheng, R.-L.2
  • 8
    • 0035163075 scopus 로고    scopus 로고
    • Antiproliferative constituents in the plants 7. Leaves of Clerodendron bungei and leaves and bark of C. trichotomum
    • Abe F, Nagao T, Okabe H (2002) Antiproliferative constituents in the plants 7. Leaves of Clerodendron bungei and leaves and bark of C. trichotomum. Biol Pharm Bull 24:1338-1341
    • (2002) Biol Pharm Bull , vol.24 , pp. 1338-1341
    • Abe, F.1    Nagao, T.2    Okabe, H.3
  • 10
    • 0033144471 scopus 로고    scopus 로고
    • Radical scavenging activity of phenylpropanoid glycosides in Caryopteris incana
    • Gao J-J, Igarashi K, Nukina M (1999) Radical scavenging activity of phenylpropanoid glycosides in Caryopteris incana. Biosci Biotech Biochem 63:983-988
    • (1999) Biosci Biotech Biochem , vol.63 , pp. 983-988
    • Gao, J.-J.1    Igarashi, K.2    Nukina, M.3
  • 11
    • 0029992334 scopus 로고    scopus 로고
    • The effect of verbascoside on cyclic 3′,5′-adenosine monophosphate level in isolated rat heart
    • Pennacchio M, Alexander E, Syah YM, Ghisalberti EL (1996) The effect of verbascoside on cyclic 3′,5′-adenosine monophosphate level in isolated rat heart. Eur J Pharmacol 305:169-171
    • (1996) Eur J Pharmacol , vol.305 , pp. 169-171
    • Pennacchio, M.1    Alexander, E.2    Syah, Y.M.3    Ghisalberti, E.L.4
  • 12
    • 0036321124 scopus 로고    scopus 로고
    • Enhancement of contraction of rat mesenteric artery by acteoside: Role of endothelial nitric oxide
    • Tam W-Y, Chen Z-Y, He Z-D, Yao X, Lau C-W, Huang Y (2002) Enhancement of contraction of rat mesenteric artery by acteoside: role of endothelial nitric oxide. J Nat Prod 65:990-995
    • (2002) J Nat Prod , vol.65 , pp. 990-995
    • Tam, W.-Y.1    Chen, Z.-Y.2    He, Z.-D.3    Yao, X.4    Lau, C.-W.5    Huang, Y.6
  • 13
    • 0034949716 scopus 로고    scopus 로고
    • Relaxing effects of Ligstrum purpurascens extract and purified acteoside in rat aortic rings
    • Wong IYF, Huang Y, He Z-D, Lau C-W, Chen Z-Y (2001) Relaxing effects of Ligstrum purpurascens extract and purified acteoside in rat aortic rings. Planta Medica 67:317-321
    • (2001) Planta Medica , vol.67 , pp. 317-321
    • Wong, I.Y.F.1    Huang, Y.2    He, Z.-D.3    Lau, C.-W.4    Chen, Z.-Y.5
  • 14
    • 0036178169 scopus 로고    scopus 로고
    • In vitro modulation of telomerase activity, telomere length and cell cycle in MKN45 cells by verbascoside
    • Zhang F, Jia Z, Deng Z, Wei Y, Zheng R, Yu L (2002) In vitro modulation of telomerase activity, telomere length and cell cycle in MKN45 cells by verbascoside. Planta Medica 68:115-118
    • (2002) Planta Medica , vol.68 , pp. 115-118
    • Zhang, F.1    Jia, Z.2    Deng, Z.3    Wei, Y.4    Zheng, R.5    Yu, L.6
  • 16
    • 0035432087 scopus 로고    scopus 로고
    • HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum
    • Kim HJ, Woo E-R, Shin C-G, Hwang DJ, Park H, Lee YS (2001) HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. Arch Pharm Res 24:286-291
    • (2001) Arch Pharm Res , vol.24 , pp. 286-291
    • Kim, H.J.1    Woo, E.-R.2    Shin, C.-G.3    Hwang, D.J.4    Park, H.5    Lee, Y.S.6
  • 18
    • 0032784301 scopus 로고    scopus 로고
    • Total synthesis of the phenylpropanoid glycoside, acteoside
    • Kawada T, Asano R, Hayashida S, Sakuno T (1999) Total synthesis of the phenylpropanoid glycoside, acteoside. J Org Chem 64:9268-9271
    • (1999) J Org Chem , vol.64 , pp. 9268-9271
    • Kawada, T.1    Asano, R.2    Hayashida, S.3    Sakuno, T.4
  • 19
    • 0033855989 scopus 로고    scopus 로고
    • Synthesis of conandroside: A dihydroxyphenylethyl glycoside from Conandron ramaidioides
    • Kawada T, Asano R, Hayashida S, Makino K, Sakuno T (2000) Synthesis of conandroside: a dihydroxyphenylethyl glycoside from Conandron ramaidioides. Eur J Org Chem 15:2723-2727
    • (2000) Eur J Org Chem , vol.15 , pp. 2723-2727
    • Kawada, T.1    Asano, R.2    Hayashida, S.3    Makino, K.4    Sakuno, T.5
  • 22
    • 0142129939 scopus 로고    scopus 로고
    • Role of caffeic glucoside esters in defense-repair processing of trees II: Synthesis of 2-(3,4-dihydroxyphenyl)-ethyl 3-O-α-L-rhamnopyranosyl- β-D-glucopyranoside
    • Ota M, Takahashi K, Kofujita H (1998) Role of caffeic glucoside esters in defense-repair processing of trees II: synthesis of 2-(3,4-dihydroxyphenyl)- ethyl 3-O-α-L-rhamnopyranosyl-β-D-glucopyranoside. J Wood Sci 44:320-326
    • (1998) J Wood Sci , vol.44 , pp. 320-326
    • Ota, M.1    Takahashi, K.2    Kofujita, H.3
  • 23
    • 0142134906 scopus 로고    scopus 로고
    • Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside
    • Kawada T, Asano R, Makino K, Sakuno T (2002) Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside. J Wood Sci 48: 512-515
    • (2002) J Wood Sci , vol.48 , pp. 512-515
    • Kawada, T.1    Asano, R.2    Makino, K.3    Sakuno, T.4
  • 25
    • 0016040837 scopus 로고
    • Results and problems of O-glycoside synthesis
    • Wulff G, Röhle G (1974) Results and problems of O-glycoside synthesis. Angew Chem Int Ed Engl 13:157-216
    • (1974) Angew Chem Int Ed Engl , vol.13 , pp. 157-216
    • Wulff, G.1    Röhle, G.2
  • 26
    • 0001205939 scopus 로고
    • Isopropylidene derivatives
    • Schmidt OT (1963) Isopropylidene derivatives. Methods Carbohyd Chem 2:318-325
    • (1963) Methods Carbohyd Chem , vol.2 , pp. 318-325
    • Schmidt, O.T.1
  • 27
    • 0022636075 scopus 로고
    • New method for the synthesis of glycosides and oligosaccharides - Are there alternatives to the königs-knorr method?
    • Schmidt RR (1986) New method for the synthesis of glycosides and oligosaccharides - are there alternatives to the königs-knorr method? Angew Chem Int Ed Engl 25:212-235
    • (1986) Angew Chem Int Ed Engl , vol.25 , pp. 212-235
    • Schmidt, R.R.1
  • 28
    • 0000889527 scopus 로고
    • A mild method for the hydrolysis of acetal groups attached to sugars and nucleosides
    • Christensen JE, Goodman L (1968) A mild method for the hydrolysis of acetal groups attached to sugars and nucleosides. Carbohydr Res 7:510-512
    • (1968) Carbohydr Res , vol.7 , pp. 510-512
    • Christensen, J.E.1    Goodman, L.2
  • 29
    • 33751385862 scopus 로고
    • An extremely simple, convenient, and selective method for acetylating primary alcohols in the presence of secondary alcohols
    • Ishihara K, Kurihara H, Yamamoto H (1993) An extremely simple, convenient, and selective method for acetylating primary alcohols in the presence of secondary alcohols. J Org Chem 58:3791-3793
    • (1993) J Org Chem , vol.58 , pp. 3791-3793
    • Ishihara, K.1    Kurihara, H.2    Yamamoto, H.3
  • 30
    • 33845378280 scopus 로고
    • Proton-transfer steps in steglich esterification: A very practical new method for macrolactonization
    • Boden EP, Keck GE (1985) Proton-transfer steps in steglich esterification: a very practical new method for macrolactonization. J Org Chem 50:2394-2395
    • (1985) J Org Chem , vol.50 , pp. 2394-2395
    • Boden, E.P.1    Keck, G.E.2
  • 31
    • 17044372705 scopus 로고
    • Synthesis of ω-hydroxyacetoguaiacone and guaiacylethylenediol (1,2)
    • Omori S, Yoshida E (1982) Synthesis of ω-hydroxyacetoguaiacone and guaiacylethylenediol (1,2) (in Japanese). Bulletin of the Iwate University Forests 13:69-82
    • (1982) Bulletin of the Iwate University Forests , vol.13 , pp. 69-82
    • Omori, S.1    Yoshida, E.2
  • 32
    • 84980126406 scopus 로고
    • Über derivate des brezcatechins
    • Voswinckel H (1909) Über derivate des brezcatechins. Ber Dtsch Chem Ges 42:4651-4654
    • (1909) Ber Dtsch Chem Ges , vol.42 , pp. 4651-4654
    • Voswinckel, H.1
  • 33
    • 84986669074 scopus 로고
    • Preparative bioorganic chemistry, XVI: Synthesis of 3,4′- dihydroxypropiophenone 3-β-D-glucopyranoside, a constituent of Betula platyphylla var. japonica, by enzymatic transglucosylation
    • Mori K, Qian Z-H, Watanabe S (1992) Preparative bioorganic chemistry, XVI: synthesis of 3,4′-dihydroxypropiophenone 3-β-D-glucopyranoside, a constituent of Betula platyphylla var. japonica, by enzymatic transglucosylation. Liebigs Ann Chem 485-487
    • (1992) Liebigs Ann Chem , pp. 485-487
    • Mori, K.1    Qian, Z.-H.2    Watanabe, S.3
  • 34
    • 0000825928 scopus 로고
    • Photooxidation of hexamethylbenzene and related aromatic systems
    • Wasserman HH, Mariano PS, Keehn PM (1971) Photooxidation of hexamethylbenzene and related aromatic systems. J Org Chem 36:1765-1769
    • (1971) J Org Chem , vol.36 , pp. 1765-1769
    • Wasserman, H.H.1    Mariano, P.S.2    Keehn, P.M.3
  • 35
    • 0000064019 scopus 로고
    • Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo 17-ketones and its reaction mechanism
    • Numazawa M, Nagaoka M (1982) Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo 17-ketones and its reaction mechanism. J Org Chem 47:4024-4029
    • (1982) J Org Chem , vol.47 , pp. 4024-4029
    • Numazawa, M.1    Nagaoka, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.