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Chemical Compound Review

Brassinin     N-(1H-indol-3-ylmethyl)-1- methylsulfanyl...

Synonyms: Brassinine, UPCMLD-DP058, Brassinin, 1, AC1MHYXY, AGN-PC-0092RH, ...
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High impact information on Brassinine

  • Two dietary components capable of mediating chemopreventive activity in animal models by modulation of drug-metabolizing enzymes are sulforaphane, an aliphatic isothiocyanate, and brassinin, an indole-based dithiocarbamate, both found in cruciferous vegetables [1].
  • Structure-activity study of brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors [2].
  • Cyclobrassinin is a biologically derived product of the oxidative cyclization of brassinin, and was as active as the parent compound in inhibiting the formation of preneoplastic mammary lesions in culture; however, 2-methylbrassinin was not significantly active in this process [3].
  • Biosynthetic studies using tetra- and pentadeuterated precursors established that indolyl-3-acetaldoxime (22) and brassinin (4) are precursors of brassicanate A (10) and rutalexin (11) and that cyclobrassinin (23) is a biosynthetic precursor of rutalexin (11), whereas tryptamine (24) is not a precursor of rutabaga phytoalexins [4].
  • Previous collaborative work by our group has led to the discovery of several plant isolates and derivatives with activities in in vivo models of cancer chemoprevention, including deguelin, resveratrol, bruceantin, brassinin, 4'-bromoflavone, and oxomate [5].

Biological context of Brassinine


Anatomical context of Brassinine

  • We tested antiproliferative activity of selected cruciferous phytoalexins including brassinin, 1-methoxybrassinin, (+/-)-spirobrassin, (+/-)-1-methoxyspirobrassinin and (+/-)-1-methoxyspirobrassinol, in leukemic Jurkat cell [8].
  • Isobrassinin (2-(S-methyldithiocarbamoylaminomethyl)indole (7a), a regioisomer of the cruciferous phytoalexin brassinin (1), exerted marked antiproliferative effects on the HeLa, A431 and MCF7 cell lines (>78.6% inhibition at 30muM) [9].
  • In the present study, we synthesized several analogs of brassinin and evaluated their effectiveness in the mouse mammary gland organ culture model [6].

Associations of Brassinine with other chemical compounds


Gene context of Brassinine

  • In addition, it was established that tetradeuterated brassinin was incorporated into the phytoalexin brassilexin in B. juncea and B. rapa [11].
  • The effects of brassinin may, in part, be mediated by induction of phase II detoxifying enzymes such as quinone reductase [6].

Analytical, diagnostic and therapeutic context of Brassinine

  • As judged by these tumor inhibition studies in conjunction with potential to induce phase II enzymes in mice or cell culture, brassinin may be effective as a chemopreventive agent during both the initiation and promotion phases of carcinogenesis [3].
  • We have analyzed 23 crucifer phytoalexins (e.g. brassinin, dioxibrassinin, cyclobrassinin, brassicanals A and C) by HPLC with diode array detection and electrospray ionization mass spectrometry (HPLC-DAD-ESI-MS) using both negative and positive ion modes [12].
  • Previously, we showed that brassinin significantly inhibited dimethylbenz(a)anthracene (DMBA)-induced mammary lesions in organ culture [6].


  1. Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Gerhäuser, C., You, M., Liu, J., Moriarty, R.M., Hawthorne, M., Mehta, R.G., Moon, R.C., Pezzuto, J.M. Cancer Res. (1997) [Pubmed]
  2. Structure-activity study of brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors. Gaspari, P., Banerjee, T., Malachowski, W.P., Muller, A.J., Prendergast, G.C., DuHadaway, J., Bennett, S., Donovan, A.M. J. Med. Chem. (2006) [Pubmed]
  3. Cancer chemopreventive activity of brassinin, a phytoalexin from cabbage. Mehta, R.G., Liu, J., Constantinou, A., Thomas, C.F., Hawthorne, M., You, M., Gerhüser, C., Pezzuto, J.M., Moon, R.C., Moriarty, R.M. Carcinogenesis (1995) [Pubmed]
  4. Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity. Pedras, M.S., Montaut, S., Suchy, M. J. Org. Chem. (2004) [Pubmed]
  5. Natural inhibitors of carcinogenesis. Kinghorn, A.D., Su, B.N., Jang, D.S., Chang, L.C., Lee, D., Gu, J.Q., Carcache-Blanco, E.J., Pawlus, A.D., Lee, S.K., Park, E.J., Cuendet, M., Gills, J.J., Bhat, K., Park, H.S., Mata-Greenwood, E., Song, L.L., Jang, M., Pezzuto, J.M. Planta Med. (2004) [Pubmed]
  6. Structure-activity relationships of brassinin in preventing the development of carcinogen-induced mammary lesions in organ culture. Mehta, R.G., Liu, J., Constantinou, A., Hawthorne, M., Pezzuto, J.M., Moon, R.C., Moriarty, R.M. Anticancer Res. (1994) [Pubmed]
  7. Development of a method for mRNA differential display in filamentous fungi: comparison of mRNA differential display reverse transcription polymerase chain reaction and cDNA amplified fragment length polymorphism in Leptosphaeria maculans. Gellatly, K.S., Ash, G.J., Taylor, J.L. Can. J. Microbiol. (2001) [Pubmed]
  8. Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells. Pilátová, M., Sarisský, M., Kutschy, P., Mirossay, A., Mezencev, R., Curillová, Z., Suchý, M., Monde, K., Mirossay, L., Mojzis, J. Leuk. Res. (2005) [Pubmed]
  9. Isobrassinin and its analogues: Novel types of antiproliferative agents. Csom??s, P., Zupk??, I., R??thy, B., Fodor, L., Falkay, G., Bern??th, G. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  10. Botanicals in cancer chemoprevention. Park, E.J., Pezzuto, J.M. Cancer Metastasis Rev. (2002) [Pubmed]
  11. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Pedras, M.S., Nycholat, C.M., Montaut, S., Xu, Y., Khan, A.Q. Phytochemistry (2002) [Pubmed]
  12. Detection, characterization and identification of crucifer phytoalexins using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. Pedras, M.S., Adio, A.M., Suchy, M., Okinyo, D.P., Zheng, Q.A., Jha, M., Sarwar, M.G. Journal of chromatography. A. (2006) [Pubmed]
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