Terretonin

1. Core Information[1]

English Name: Terretonin
CAS No.: 71911-90-5
Molecular Formula: C26H32O9
Molecular Weight: 488.5 g/mol
SMILE:CC1(C(=O)CCC2(C1=C(C(=O)C3(C2(CC(=C)C4(C3C(=O)OC(C4=O)(C)C(=O)OC)C)O)C)O)C)C 

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

methyl (2S,4aS,4bR,10aR,10bR,12aS)-6,10b-dihydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4a,9,10,11-tetrahydronaphtho[1,2-h]isochromene-2-carboxylate

2.2 InChI

InChI=1S/C26H32O9/c1-12-11-26(33)22(4)10-9-13(27)21(2,3)15(22)14(28)17(29)24(26,6)16-18(30)35-25(7,20(32)34-8)19(31)23(12,16)5/h16,28,33H,1,9-11H2,2-8H3/t16-,22+,23+,24-,25-,26+/m0/s1

2.3 InChlKey

CYHGEJACRPDZDP-RSQIKLETSA-N

2.4 Canonical SMILES

CC1(C(=O)CCC2(C1=C(C(=O)C3(C2(CC(=C)C4(C3C(=O)OC(C4=O)(C)C(=O)OC)C)O)C)O)C)C

2.5 Isomeric SMILES

C[C@@]12CCC(=O)C(C1=C(C(=O)[C@]3([C@]2(CC(=C)[C@@]4([C@@H]3C(=O)O[C@](C4=O)(C)C(=O)OC)C)O)C)O)(C)C

 

 

 

3. Spectroscopic Data

3.1 ¹³C Nuclear Magnetic Resonance (¹³C NMR)

 

3.2 ¹H Nuclear Magnetic Resonance (¹H NMR)

 

4. Research Progress on Terretonin

Terretonin is a fungal meroterpenoid derived from Aspergillus terreus with growing relevance in medicine. Key findings include:

 

 

4.1 Antibacterial Activity

Terretonin N—a derivative—exhibits notable activity against Gram-positive bacteria, surpassing gentamicin in assays against S. warneri.[2] This positions Terretonin scaffolds as promising antibiotic leads.

4.2 Antitumor Potential

Terretonin analogues such as those isolated from Aspergillus ustus demonstrate antiproliferative effects.[3] These meroterpenoids may serve as starting points for anticancer drug discovery.

4.3 Anti-inflammatory Prospects

Although detailed studies are limited, the structural class suggests anti-inflammatory potential, aligning with activities observed for related terpenoids.

4.4 Drug Development

Terretonin’s unique framework and bioactivity profile make it an attractive lead for medicinal chemistry programs aimed at optimizing pharmacological efficacy and pharmacokinetics.

4.5 Scientific Utility

Terretonin also functions as a probe for studying fungal metabolism, biosynthetic machinery, and mechanistic pharmacology. Overall, its antibacterial, anticancer, and anti-inflammatory profiles—combined with its structural novelty—underscore broad translational potential.

 

 

 

References