BioViotica

Terrein

Name: Terrein
Brand: BioViotica
SKU: BVT-0193
Price: 130.00 CHF
Availability: InStock

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BVT-0193-M0011 mgCHF 130.00

BVT-0193-M0055 mgCHF 430.00

BVT-0193-M01010 mgCHF 780.00

Specifications / Handling

More Information
Product Details
Synonyms	NSC 291308; 4,5-Dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
Product Type	Chemical
Properties
Formula	C₈H₁₀O₃
MW	154.2
CAS	582-46-7
Source/Host Chemicals	Isolated from Aspergillus terreus.
Purity Chemicals	≥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
Smiles	C\C=C\C1=CC(=O)[C@H](O)[C@H]1O
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.
Documents
Safety Data Sheet	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Scientific Background Information

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-specific References

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)
The constitution and stereochemistry of Terrein: D.H.R. Barton & E. Miller; J. Chem. Soc. 1955, 1028 (1955)
Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor: J. Malmstrom, et al.; J. Nat. Prod. 65, 364 (2002)
Terrein: a new melanogenesis inhibitor and its mechanism: S.H. Park, et al.; Cell Mol. Life Sci. 61, 2878 (2004)
Synthesis and melanin biosynthesis inhibitory activity of (+/-)-terrein produced by Penicillium sp. 20135: S. Lee, et al.; Bioorg. Med. Chem. Lett. 15, 471 (2005)
Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivatents: D.S. Kim, et al.; J. Dermatol. Sci. 46, 65 (2007)
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)
Terrein reduces pulpal inflammation in human dental pulp cells: J.C. Lee, et al.; J. Endod. 34, 433 (2008)
Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest: D.S. Kim, et al.; Exp. Dermatol. 17, 312 (2008)
A new terrein glucoside, a novel inhibitor of angiogenin secretion in tumor angiogenesis: M. Arakawa, et al.; J. Antibiot. (Tokyo) 61, 442 (2008)
Inhibitory effects of dihydroterrein and terrein isolated from Aspergillus novofumigatus on platelet aggregation: T. Hosoe, et al.; Mycotoxins 59, 75 (2009)
Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression: S.H. Park, et al.; Exp. Dermatol. 18, 562 (2009)
Enhancement of osteoblast biocompatibility on titanium surface with Terrein treatment: Y.H. Lee, et al.; Cell. Biochem. Funct. 28, 678 (2010)
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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