Terrein
1. Core Information
English Name: Terrein
Chinese Name: Terrein (Tu Qumei Tong)
CAS No.: 582-46-7
Molecular Formula: C8H10O3
Molecular Weight: 154.16 g/mol
SMILE:CC=CC1=CC(=O)C(C1O)O
2. International Nomenclature & Identifiers
2.1 IUPAC Name
(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
2.2 InChI
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
2.3 InChlKey
MHOOPNKRBMHHEC-HZIBQTDNSA-N
2.4 Canonical SMILES
CC=CC1=CC(=O)C(C1O)O
2.5 Isomeric SMILES
C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O
3. Spectroscopic Data
3.1 13C Nuclear Magnetic Resonance (13C NMR)
3.2 1H Nuclear Magnetic Resonance (1H NMR)
4. Research Progress on Terrein
Terrein is a bioactive metabolite isolated from Aspergillus terreus. Recent investigations highlight its potential roles in melanogenesis inhibition, anticancer activity, and antibacterial applications.
4.1 Inhibition of Melanogenesis
Terrein is a potent inhibitor of melanogenesis, with up to tenfold greater activity than kojic acid. It accelerates ERK activation in melanophore cells and selectively suppresses MITF expression, yielding skin-brightening effects without directly inhibiting tyrosinase—reducing cytotoxicity relative to traditional agents. Owing to complementary mechanisms, combining Terrein with established inhibitors can further enhance outcomes.
4.2 Antitumor Activity
Studies show Terrein inhibits proliferation across multiple cancer cell lines. In human tongue squamous cell carcinoma SCC9, Terrein suppresses growth in a dose- and time-dependent manner by arresting cells in G2/M phase. It also induces apoptosis in breast cancer cells and reduces invasiveness, supporting its potential as an anticancer lead.
4.3 Antibacterial Properties
Terrein disrupts quorum sensing and c-di-GMP synthesis in Pseudomonas aeruginosa, reducing virulence factor production and biofilm formation. These findings position Terrein as a prospective anti-infective agent.
4.4 Biosynthesis & Chemical Synthesis
Progress has been made in elucidating Terrein biosynthesis. Heterologous expression of the biosynthetic gene cluster in Saccharomyces cerevisiae and Aspergillus nidulans yields the metabolite, enabling structure confirmation via LC-MS and NMR. Complementary studies—fungal gene knockouts, mutant feeding, E. coli expression of enzymes, and substrate derivatization—further clarify pathway logic. Parallel efforts to refine chemical synthesis are improving yields and purity for potential industrial production.
4.5 Future Perspectives
Continued research will clarify Terrein’s safety, efficacy, and synergistic potential with existing therapies across dermatology, oncology, and anti-infective treatments. Deeper insight into its biosynthesis and scalable synthesis will further enable translational and industrial applications. Overall, Terrein’s multifaceted bioactivity makes it an attractive candidate for pharmaceutical, cosmetic, and antimicrobial innovation.
References
[1] http://www.kehuaai.com/productInfo/174960
[2] https://www.biobw.org/Technology/bio-w-9441.html
[3] Qiao Yuben. Research on active natural products from three fungi and Caesalpinia sappan, and biosynthesis of Terrein. Huazhong University of Science and Technology, 2020. DOI:10.27157/d.cnki.ghzku.2020.001721
[4] Huang Xuenian, Tang Shen, Lü Xuefeng. Advances and prospects of synthetic biology for industrial filamentous fungus Aspergillus terreus. Synthetic Biology, 2020, 1(02):187-211.
