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Volumn 8, Issue 8, 2013, Pages 1101-1103

A concise and efficient total synthesis of α-mangostin and β-Mangostin from Garcinia mangostana

Author keywords

Claisen rearrangement; Total synthesis; Wittig reaction; Mangostin; Mangostin

Indexed keywords

ALICYCLIC COMPOUND; ALPHA MANGOSTIN; DIMETHYLMANGOSTIN; ISOPENTENE DERIVATIVE; MANGOSTIN; PLANT MEDICINAL PRODUCT; UNCLASSIFIED DRUG; XANTHENE;

EID: 84883221374     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1300800818     Document Type: Article
Times cited : (17)

References (24)
  • 2
    • 34250705898 scopus 로고    scopus 로고
    • Characterized mechanism of α-mangostin-induced cell death: Caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells
    • Nakagawa Y, Iinuma M, Naoe T, Nozawa Y, Akao Y. (2007) Characterized mechanism of α-mangostin-induced cell death: Caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells. Bioorganic Medicinal Chemistry, 15, 5620-5628.
    • (2007) Bioorganic Medicinal Chemistry , vol.15 , pp. 5620-5628
    • Nakagawa, Y.1    Iinuma, M.2    Naoe, T.3    Nozawa, Y.4    Akao, Y.5
  • 3
    • 73349098430 scopus 로고    scopus 로고
    • Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen)
    • Han AR, Kim JA, Lantvit DD, Kardono LBS. (2009) Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen). Journal of Natural Products, 72, 2028-2031.
    • (2009) Journal of Natural Products , vol.72 , pp. 2028-2031
    • Han, A.R.1    Kim, J.A.2    Lantvit, D.D.3    Kardono, L.B.S.4
  • 4
    • 64549092413 scopus 로고    scopus 로고
    • α-Mangostin suppresses PC-3 human prostate carcinoma cell metastasis by inhibiting matrix metalloproteinase-2/9 and urokinase-plasminogen expression through the JNK signaling pathway
    • Hung SH, Shen KH, Wu CH, Liu CL, Shi YW. (2009) α-Mangostin suppresses PC-3 human prostate carcinoma cell metastasis by inhibiting matrix metalloproteinase-2/9 and urokinase-plasminogen expression through the JNK signaling pathway. Journal of Agricultural and Food Chemistry, 57, 1291-1298.
    • (2009) Journal of Agricultural and Food Chemistry , vol.57 , pp. 1291-1298
    • Hung, S.H.1    Shen, K.H.2    Wu, C.H.3    Liu, C.L.4    Shi, Y.W.5
  • 6
    • 74249113058 scopus 로고    scopus 로고
    • α-Mangostin, A novel dietary xanthone, suppresses TPA-mediated MMP-2 and MMP-9 expressions through the ERK signaling pathway in MCF-7 human breast adenocarcinoma cells
    • Lee YB, Ko KC, Shi MD, Liao YC, Wu PF, Shih YX, Shih YW. (2010) α-Mangostin, A novel dietary xanthone, suppresses TPA-mediated MMP-2 and MMP-9 expressions through the ERK signaling pathway in MCF-7 human breast adenocarcinoma cells. Journal of Food Science, 75, 13-23.
    • (2010) Journal of Food Science , vol.75 , pp. 13-23
    • Lee, Y.B.1    Ko, K.C.2    Shi, M.D.3    Liao, Y.C.4    Wu, P.F.5    Shih, Y.X.6    Shih, Y.W.7
  • 10
    • 80054999443 scopus 로고    scopus 로고
    • Free radical scavenger properties of α-mangostin: Thermodynamics and kinetics of HAT and RAF mechanisms
    • Martínez A, Galano A, Vargas R. (2011) Free radical scavenger properties of α-mangostin: Thermodynamics and kinetics of HAT and RAF mechanisms. The Journal of Physical Chemistry B, 115, 12591-12598.
    • (2011) The Journal of Physical Chemistry B , vol.115 , pp. 12591-12598
    • Martínez, A.1    Galano, A.2    Vargas, R.3
  • 11
    • 36748999905 scopus 로고    scopus 로고
    • Cardioprotective effect of alpha-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats
    • Sampath PD, Vijayaraghavan K. (2007) Cardioprotective effect of alpha-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats. Journal of Biochemical and Molecular Toxicology, 21, 336-339.
    • (2007) Journal of Biochemical and Molecular Toxicology , vol.21 , pp. 336-339
    • Sampath, P.D.1    Vijayaraghavan, K.2
  • 12
    • 84863264712 scopus 로고    scopus 로고
    • α-Mangostin induces apoptosis and suppresses differentiation of 3T3-L1 cells via inhibiting fatty acid synthase
    • Quan XF, Wang Y, Ma XF, Liang Y, Tian WX, Ma QY, Jiang HZ, Zhao YX. (2012) α-Mangostin induces apoptosis and suppresses differentiation of 3T3-L1 cells via inhibiting fatty acid synthase. PLOS ONE, 7. e33376.
    • (2012) PLOS ONE , vol.7
    • Quan, X.F.1    Wang, Y.2    Ma, X.F.3    Liang, Y.4    Tian, W.X.5    Ma, Q.Y.6    Jiang, H.Z.7    Zhao, Y.X.8
  • 13
    • 0002644396 scopus 로고
    • Studies in the xanthone series. Part 13. Structural and synthetic studies on toxyloxanthone B
    • Cotterill PJ, Scheinmann F. (1980) Studies in the xanthone series. Part 13. Structural and synthetic studies on toxyloxanthone B. Journal of the Chemical Society, Perkin Transactions 1, 2353-2357.
    • (1980) Journal of the Chemical Society, Perkin Transactions , vol.1 , pp. 2353-2357
    • Cotterill, P.J.1    Scheinmann, F.2
  • 15
    • 0037033232 scopus 로고    scopus 로고
    • The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase
    • Iikubo K, Ishikawa Y, Ando N, Umezawa K. (2002) The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase. Tetrahedron Letters, 43, 291-293.
    • (2002) Tetrahedron Letters , vol.43 , pp. 291-293
    • Iikubo, K.1    Ishikawa, Y.2    Ando, N.3    Umezawa, K.4
  • 16
    • 7044254915 scopus 로고    scopus 로고
    • Anti-AIDS agents. Part 62: Anti-HIV activity of 2′-substituted 4-methyl-3′, 4′-di-O-(?)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs
    • Zhang Q, Chen Y, Xia P, Xia Y, Yang ZY, Yu D, Natschke SLM, Lee, K. H. (2004) Anti-AIDS agents. Part 62: Anti-HIV activity of 2′-substituted 4-methyl-3′, 4′-di-O-(?)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs. Bioorganic and Medicinal Chemistry Letters, 14, 5855-5857.
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , pp. 5855-5857
    • Zhang, Q.1    Chen, Y.2    Xia, P.3    Xia, Y.4    Yang, Z.Y.5    Yu, D.6    Natschke, S.L.M.7    Lee, K.H.8
  • 17
    • 51149095789 scopus 로고    scopus 로고
    • Synthesis of ptaeroxylin (desoxykarenin): An unusual chromone from the sneezewood tree Ptaeroxylon obliquum
    • Muscarella M, Kimber MC, Moody CJ. (2008) Synthesis of ptaeroxylin (desoxykarenin): An unusual chromone from the sneezewood tree Ptaeroxylon obliquum. Synlett, 14, 2101-2102.
    • (2008) Synlett , vol.14 , pp. 2101-2102
    • Muscarella, M.1    Kimber, M.C.2    Moody, C.J.3
  • 18
    • 34848890900 scopus 로고    scopus 로고
    • Titanocene(III) mediated radical cyclizations of epoxides for the synthesis of medium-sized cyclic ethers
    • Mandal SK, Roy SC. (2007) Titanocene(III) mediated radical cyclizations of epoxides for the synthesis of medium-sized cyclic ethers. Tetrahedron, 63, 11341-11348.
    • (2007) Tetrahedron , vol.63 , pp. 11341-11348
    • Mandal, S.K.1    Roy, S.C.2
  • 20
    • 37049107492 scopus 로고
    • Synthesis of the ozonolysis product from dimethylmangostin, 1-hydroxy-3, 6, 7-trimethoxy-2, 8-bis(2-oxoethyl) xanthone: Some carbon-13 nuclear magnetic resonance spectra of xanthones
    • Jefferson A, Scheinmann F. (1977) Synthesis of the ozonolysis product from dimethylmangostin, 1-hydroxy-3, 6, 7-trimethoxy-2, 8-bis(2-oxoethyl) xanthone: Some carbon-13 nuclear magnetic resonance spectra of xanthones. Journal of the Chemical Society, Perkin Transactions 1, 2158-2162.
    • (1977) Journal of the Chemical Society, Perkin Transactions , vol.1 , pp. 2158-2162
    • Jefferson, A.1    Scheinmann, F.2


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