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Terrein

BVT-0193-M001 1 mg $110.00
BVT-0193-M005 5 mg $350.00
BVT-0193-M010 10 mg $590.00
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Additional Information

Product Data
Synonyms NSC 291308; 4,5-Dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
Properties
Formula C8H10O3
MW 154.2
CAS 582-46-7
Source/Host Chemicals Isolated from Aspergillus terreus.
Purity ≥98% (HPLC).
Appearance White to off-white solid.
Solubility Soluble in methanol or DMSO.
Identity Determined by 1H-NMR and UV.
InChi Key MHOOPNKRBMHHEC-HZIBQTDNSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
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Product Description

  • Antibacterial. Phytotoxin [3, 4 , 5].
  • Melanogenesis inhibitor by reducing tyrosinase production via extracellular signal-regulated protein kinase (ERK) activation [4, 5].
  • Keratinocyte and epidermis proliferation inhibitor [6, 9].
  • Mycotoxin [7].
  • Anti-inflammatory modulator in pulpal inflammation [8].
  • Angiogenesis inhibitor through angiogenin secretion inhibition [10].
  • Collagen-induced platelet aggregation inhibitor [11].
  • Antioxidant agent that enhances osseointegration by decreasing the level of ROS and having a potentially synergistic effect on osteoblast differentiation [13].
  • Proteasome inhibitor [12, 14].

Product References

  1. Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. A new mould metabolic product-terrein: H. Raistrick & G. Smith; Biochem. J. 29, 606 (1935)
  2. The constitution and stereochemistry of Terrein: D.H.R. Barton & E. Miller; J. Chem. Soc. 1955, 1028 (1955)
  3. Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor: J. Malmstrom, et al.; J. Nat. Prod. 65, 364 (2002)
  4. Terrein: a new melanogenesis inhibitor and its mechanism: S.H. Park, et al.; Cell Mol. Life Sci. 61, 2878 (2004)
  5. Synthesis and melanin biosynthesis inhibitory activity of (+/-)-terrein produced by Penicillium sp. 20135: S. Lee, et al.; Bioorg. Med. Chem. Lett. 15, 471 (2005)
  6. Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivatents: D.S. Kim, et al.; J. Dermatol. Sci. 46, 65 (2007)
  7. Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati: T. O. Larsen, et al.; Med. Mycol. 45, 225 (2007)
  8. Terrein reduces pulpal inflammation in human dental pulp cells: J.C. Lee, et al.; J. Endod. 34, 433 (2008)
  9. Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest: D.S. Kim, et al.; Exp. Dermatol. 17, 312 (2008)
  10. A new terrein glucoside, a novel inhibitor of angiogenin secretion in tumor angiogenesis: M. Arakawa, et al.; J. Antibiot. (Tokyo) 61, 442 (2008)
  11. Inhibitory effects of dihydroterrein and terrein isolated from Aspergillus novofumigatus on platelet aggregation: T. Hosoe, et al.; Mycotoxins 59, 75 (2009)
  12. Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression: S.H. Park, et al.; Exp. Dermatol. 18, 562 (2009)
  13. Enhancement of osteoblast biocompatibility on titanium surface with Terrein treatment: Y.H. Lee, et al.; Cell. Biochem. Funct. 28, 678 (2010)
  14. Studies on terrein as a new class of proteasome inhibitors: M. Demasi, et al.; J. Braz. Chem. Soc. 21, 299 (2010)
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