Terrein
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MedKoo CAT#: 329866

CAS#: 582-46-7

Description: Terrain, also known as NSC 291308, is a fungal metabolite with diverse biological activities. Terrein reduces age-related inflammation induced by oxidative stress through Nrf2/ERK1/2/HO-1 signalling in aged HDF cells. (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts.

Chemical Structure

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Terrein
CAS# 582-46-7
Instruction

Theoretical Analysis

MedKoo Cat#: 329866
Name: Terrein
CAS#: 582-46-7
Chemical Formula: C8H10O3
Exact Mass: 154.06
Molecular Weight: 154.165
Elemental Analysis: C, 62.33; H, 6.54; O, 31.13

Price and Availability

Size Price Availability Quantity
1mg USD 465 2 Weeks
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Synonym: (+)Terrein; Terrain; NSC 291308; NSC-291308; NSC291308.

IUPAC/Chemical Name: 4S,5R-dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one

InChi Key: MHOOPNKRBMHHEC-HZIBQTDNSA-N

InChi Code: InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

SMILES Code: O=C1C=C(/C=C/C)[C@H](O)[C@H]1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 154.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zaehle C, Gressler M, Shelest E, Geib E, Hertweck C, Brock M. Terrein biosynthesis in Aspergillus terreus and its impact on phytotoxicity. Chem Biol. 2014 Jun 19;21(6):719-31. doi: 10.1016/j.chembiol.2014.03.010. Epub 2014 May 8. PubMed PMID: 24816227.

2: Lee YH, Lee SJ, Jung JE, Kim JS, Lee NH, Yi HK. Terrein reduces age-related inflammation induced by oxidative stress through Nrf2/ERK1/2/HO-1 signalling in aged HDF cells. Cell Biochem Funct. 2015 Oct;33(7):479-86. doi: 10.1002/cbf.3145. Epub 2015 Sep 28. PubMed PMID: 26416516.

3: Mandai H, Omori K, Yamamoto D, Tsumura T, Murota K, Yamamoto S, Mitsudo K, Ibaragi S, Sasaki A, Maeda H, Takashiba S, Suga S. Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts. Bioorg Med Chem. 2014 Oct 1;22(19):5338-44. doi: 10.1016/j.bmc.2014.07.047. Epub 2014 Aug 7. PubMed PMID: 25151086.

4: Yin Y, Xu B, Li Z, Zhang B. Enhanced production of (+)-terrein in fed-batch cultivation of Aspergillus terreus strain PF26 with sodium citrate. World J Microbiol Biotechnol. 2013 Mar;29(3):441-6. doi: 10.1007/s11274-012-1196-x. Epub 2012 Oct 21. PubMed PMID: 23085955.

5: Yin Y, Ding Y, Feng G, Li J, Xiao L, Karuppiah V, Sun W, Zhang F, Li Z. Modification of artificial sea water for the mass production of (+)-terrein by Aspergillus terreus strain PF26 derived from marine sponge Phakellia fusca. Lett Appl Microbiol. 2015 Dec;61(6):580-7. doi: 10.1111/lam.12496. PubMed PMID: 26394071.

6: Zhao C, Guo L, Wang L, Zhu G, Zhu W. Improving the yield of (+)-terrein from the salt-tolerant Aspergillus terreus PT06-2. World J Microbiol Biotechnol. 2016 May;32(5):77. doi: 10.1007/s11274-016-2029-0. Epub 2016 Apr 2. PubMed PMID: 27038947.

7: Chen YF, Wang SY, Shen H, Yao XF, Zhang FL, Lai D. The marine-derived fungal metabolite, terrein, inhibits cell proliferation and induces cell cycle arrest in human ovarian cancer cells. Int J Mol Med. 2014 Dec;34(6):1591-8. doi: 10.3892/ijmm.2014.1964. Epub 2014 Oct 13. PubMed PMID: 25318762.

8: Porameesanaporn Y, Uthaisang-Tanechpongtamb W, Jarintanan F, Jongrungruangchok S, Thanomsub Wongsatayanon B. Terrein induces apoptosis in HeLa human cervical carcinoma cells through p53 and ERK regulation. Oncol Rep. 2013 Apr;29(4):1600-8. doi: 10.3892/or.2013.2288. Epub 2013 Feb 15. PubMed PMID: 23417151.

9: Zhang F, Mijiti M, Ding W, Song J, Yin Y, Sun W, Li Z. (+) Terrein inhibits human hepatoma Bel 7402 proliferation through cell cycle arrest. Oncol Rep. 2015 Mar;33(3):1191-200. doi: 10.3892/or.2015.3719. Epub 2015 Jan 14. PubMed PMID: 25592371.

10: Shibata A, Ibaragi S, Mandai H, Tsumura T, Kishimoto K, Okui T, Hassan NM, Shimo T, Omori K, Hu GF, Takashiba S, Suga S, Sasaki A. Synthetic Terrein Inhibits Progression of Head and Neck Cancer by Suppressing Angiogenin Production. Anticancer Res. 2016 May;36(5):2161-8. PubMed PMID: 27127118.

11: Gressler M, Meyer F, Heine D, Hortschansky P, Hertweck C, Brock M. Phytotoxin production in Aspergillus terreus is regulated by independent environmental signals. Elife. 2015 Jul 14;4. pii: e07861. doi: 10.7554/eLife.07861. PubMed PMID: 26173180; PubMed Central PMCID: PMC4528345.

12: Xu B, Yin Y, Zhang F, Li Z, Wang L. Operating conditions optimization for (+)-terrein production in a stirred bioreactor by Aspergillus terreus strain PF-26 from marine sponge Phakellia fusca. Bioprocess Biosyst Eng. 2012 Nov;35(9):1651-5. doi: 10.1007/s00449-012-0735-z. Epub 2012 Apr 24. PubMed PMID: 22527032.

13: Liao WY, Shen CN, Lin LH, Yang YL, Han HY, Chen JW, Kuo SC, Wu SH, Liaw CC. Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus. J Nat Prod. 2012 Apr 27;75(4):630-5. doi: 10.1021/np200866z. Epub 2012 Feb 23. PubMed PMID: 22360613.

14: Gressler M, Hortschansky P, Geib E, Brock M. A new high-performance heterologous fungal expression system based on regulatory elements from the Aspergillus terreus terrein gene cluster. Front Microbiol. 2015 Mar 16;6:184. doi: 10.3389/fmicb.2015.00184. eCollection 2015. PubMed PMID: 25852654; PubMed Central PMCID: PMC4360782.

15: Lee YH, Lee NH, Bhattarai G, Oh YT, Yu MK, Yoo ID, Jhee EC, Yi HK. Enhancement of osteoblast biocompatibility on titanium surface with Terrein treatment. Cell Biochem Funct. 2010 Dec 2;28(8):678-85. doi: 10.1002/cbf.1708. Epub 2010 Oct 29. PubMed PMID: 21104936.

16: Park SH, Kim DS, Kim WG, Ryoo IJ, Lee DH, Huh CH, Youn SW, Yoo ID, Park KC. Terrein: a new melanogenesis inhibitor and its mechanism. Cell Mol Life Sci. 2004 Nov;61(22):2878-85. PubMed PMID: 15558216.

17: Lee JC, Yu MK, Lee R, Lee YH, Jeon JG, Lee MH, Jhee EC, Yoo ID, Yi HK. Terrein reduces pulpal inflammation in human dental pulp cells. J Endod. 2008 Apr;34(4):433-7. doi: 10.1016/j.joen.2008.01.015. PubMed PMID: 18358890.

18: Park SH, Kim DS, Lee HK, Kwon SB, Lee S, Ryoo IJ, Kim WG, Yoo ID, Park KC. Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression. Exp Dermatol. 2009 Jun;18(6):562-6. doi: 10.1111/j.1600-0625.2009.00847.x. PubMed PMID: 19493001.

19: Kim DS, Lee HK, Park SH, Lee S, Ryoo IJ, Kim WG, Yoo ID, Na JI, Kwon SB, Park KC. Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest. Exp Dermatol. 2008 Apr;17(4):312-7. Epub 2007 Nov 2. PubMed PMID: 17979972.

20: Boruta T, Bizukojc M. Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542. J Biotechnol. 2014 Apr 10;175:53-62. doi: 10.1016/j.jbiotec.2014.01.038. Epub 2014 Feb 15. PubMed PMID: 24534845.