Terretonin A

1. Core Information

English Name: Terretonin A
CAS No.: 865092-86-0
Molecular Formula: C26H32O8
Molecular Weight: 472.5 g/mol
SMILE:CC1(C(=O)CCC2(C1=C(C(=O)C3(C2CC(=C)C4(C3C(=O)OC(C4=O)(C)C(=O)OC)C)C)O)C)C

2. International Nomenclature & Identifiers

2.1 IUPAC Name

methyl (2R,4aS,4bR,10aR,10bR,12aR)-6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-9,10,10b,11-tetrahydro-4aH-naphtho[1,2-h]isochromene-2-carboxylate

2.2 InChI

InChI=1S/C26H32O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,17,28H,1,9-11H2,2-8H3/t13-,17-,23-,24+,25-,26-/m1/s1

2.3 InChlKey

GTEJJXOFLPCZGJ-DOFPOEDPSA-N

2.4 Canonical SMILES

CC1(C(=O)CCC2(C1=C(C(=O)C3(C2CC(=C)C4(C3C(=O)OC(C4=O)(C)C(=O)OC)C)C)O)C)C

2.5 Isomeric SMILES

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

Terretonin A is a meroterpenoid isolated from the endophytic fungus Aspergillus terreus. It features a distinctive tetracyclic core and a range of bioactivities.

 

 

4.1 Molecular Genetics of the Biosynthetic Pathway

In 2012, researchers established a gene-targeting system for A. terreus NIH2624 and characterized the Terretonin A biosynthetic gene cluster.[2] Analysis of intermediates and shunt metabolites from mutants revealed the pathway: cytochrome P450 Trt6 oxidizes terrenoic acid to a labile intermediate, which is then rearranged by isomerase Trt14 and processed by the non-heme iron dioxygenase Trt7 to yield Terretonin A.[3]

4.2 Biological Activity

Terretonin A and analogues exhibit diverse bioactivities, including anti-inflammatory and anticancer effects.[4] Recent studies indicate Terretonin A may act as a protective agent against endotoxin-induced acute lung injury (ALI) by modulating SIRT1/Nrf2/NF-κBp65/NLRP3 signaling.[5]

4.3 Discovery of New Analogues

Investigations have identified additional family members such as Terretonins B–D.[2] These compounds broaden the Terretonin portfolio and provide fresh candidates for drug development.

4.4 Evolutionary Relationships

Comparative analyses with the biosynthetic route for austinol—a related fungal metabolite—reveal close evolutionary ties, suggesting shared mechanisms and offering new perspectives on fungal meroterpenoid evolution.[2] Collectively, advances in pathway elucidation, analogue discovery, and functional studies provide a strong foundation for Terretonin A translation.

 

References