The concise, efficient synthesis of α-mangostin is described in eight simple steps with 8.3% overall yield. Highlights include a practical approach to construct the isopentene groups and other diverse groups at C–2 and C–8 of the xanthene skeleton through Claisen rearrangement and Wittig reaction. Meanwhile the first total synthesis of β-mangostin is presented with a similar approach.
AkaoY., NakagawaY., NozawaY. (2008) Anti-cancer effects of xanthones from pericarps of mangosteen. International Journal of Molecular Sciences, 9, 355–370.
2.
NakagawaY., IinumaM., NaoeT., NozawaY., AkaoY. (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.
3.
HanA.R., KimJ.A., LantvitD.D., KardonoL.B.S. (2009) Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen). Journal of Natural Products, 72, 2028–2031.
4.
HungS.H., ShenK.H., WuC.H., LiuC.L., ShiY.W. (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.
5.
SuksamrarnS., KomutibanO., RatananukulP., ChimnoiN., LartpornmatuleeN., SuksamrarnA. (2006) Cytotoxic prenylated xanthones from the young fruit of Garcinia mangostana. Chemical and Pharmaceutical Bulletin, 54, 301–305.
6.
LeeY.B., KoK.C., ShiM.D., LiaoY.C., WuP.F., ShihY.X., ShihY.W. (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.
7.
AbundisE.M., GarcíaN., CorreaF., ReséndizS.H., ChaverriJ.P., ZazuetaC. (2010) Effects of α-mangostin on mitochondrial energetic metabolism. Mitochondrion, 10, 151–157.
8.
TaherM., SusantiD., RezaliM.F., ZohnF.S.A., IchwanS.J.A., AlkhamaisehS.I., AhmadF. (2012) Apoptosis, antimicrobial and antioxidant activities of phytochemicals from Garcinia malaccensis Hk.f. Asian Pacific Journal of Tropical Medicine, 5, 136–141.
9.
ChaverríJ.P., FermínL.M.R., AmayaE.G.N., IbarraM.O., CamposO.N., CuahutencosO.G., CruzL.R., MataR. (2009) ROS scavenging capacity and neuroprotective effect of α-mangostin against 3-nitropropionic acid in cerebellar granule neurons. Experimental and Toxicologic Pathology, 61, 491–501.
10.
MartínezA., GalanoA., VargasR. (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.
11.
SampathP.D., VijayaraghavanK. (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.
12.
QuanX.F., WangY., MaX.F., LiangY., TianW.X., MaQ.Y., JiangH.Z., ZhaoY.X. (2012) α-Mangostin induces apoptosis and suppresses differentiation of 3T3-L1 cells via inhibiting fatty acid synthase. PLOS ONE, 7. e33376.
13.
CotterillP.J., ScheinmannF. (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.
14.
LeeH.H. (1981) Synthesis of the mangostins. Journal of the Chemical Society, Perkin Transactions 1, 3205–3213.
15.
IikuboK., IshikawaY., AndoN., UmezawaK. (2002) The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase. Tetrahedron Letters, 43, 291–293.
16.
ZhangQ., ChenY., XiaP., XiaY., YangZ.Y., YuD., NatschkeS.L.M., LeeK. 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.
17.
MuscarellaM., KimberM.C., MoodyC.J. (2008) Synthesis of ptaeroxylin (desoxykarenin): An unusual chromone from the sneezewood tree Ptaeroxylon obliquum. Synlett, 14, 2101–2102.
18.
MandalS.K., RoyS.C. (2007) Titanocene(III) mediated radical cyclizations of epoxides for the synthesis of medium-sized cyclic ethers. Tetrahedron, 63, 11341–11348.
19.
XieX., LemckeT., GussioR., ZaharevitzD.W., LeostM., MeijerL., KunickC. (2005) Epoxide-containing side chains enhance antiproliferative activity of paullones. European Journal of Medicinal Chemistry, 40, 655–661.
20.
JeffersonA., ScheinmannF. (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.
21.
RajuG.G. (2009) A process for production-mangostin.Patent WO2009/093259 A2.
22.
BennettG.J., LeeH.H., DasN.P. (1990) Biosynthesis of mangostin. Journal of the Chemical Society, Perkin Transactions 1, 10, 2671–2676.
23.
GunasekeraS.P., SultanbawaM.U.S., BalasubramaniamS. (1973) Mangostin from the barks of Hydnocarpus species. Phytochemistry, 12, 232–233.
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
