Orsellinic acid is a common salicylic acid unit in the biosynthesis of secondary metabolites in actinomycetes, fungi and lichens, formally isolated from Chaetomium cochliodes in 1959. Orsellinic acid is a key biosynthetic intermediate of many depside metabolites in lichen and fungi with over 100 citations in Scifinder up to 2016. Orsellinic acid is also an important polar co-metabolite present in many fungi, notably Trichomonacea, however its contribution to overall bioactivity is not well understood. Orsellinic acid is a useful standard for bioassay and analytical techniques for dereplication of common co-metabolites.
| Molecular Formula | C8H8O4 |
| Mechanism of Action | The precise mechanism of action is not fully elucidated, but it is thought to modulate the activity of enzymes and receptors involved in the inflammatory response. It may also interact with signaling pathways, including NF-kB and MAPK, to regulate the expression of inflammatory mediators. |
| Eukaryotic Cell Culture Applications |
Orsellinic Acid prevents PARP cleavage induced by platelet-activating factor (PAF) in PC12-AC cells and PAF-induced cytotoxicity in PAF receptor null (Pafr-/-) mouse cerebellar granule cells when used at a concentration of 1 μg/ml (Ryan et al, 2007). Orsellinic Acid can be used for bone regeneration (osteogenesis). When the compound was incorporated into Gel/nHAp/nCS biocomposite scaffolds at 80 μM it promoted differentiation of osteoblasts via cell adhesion mediated signaling pathway, compared with that shown by Gel/nHAp/nCS alone. This means that Orsellinic Acid has potential for clinical applications in bone regeneration (ref). Researchers found it was cyto-friendly to mouse mesenchymal stem cells (mMSCs, C3H10T1/2). |
| References |
Birkinshaw JH and Gowlland A (1962) Studies in the biochemistry of micro-organisms. 110. Production and biosynthesis of orsellinic acid by Penicillium madriti G. Smith. Biochem. J. 84(2):342-3247 PMID 13869400 Lopes TI, Coelho RG, Yoshida NC, Honda NK (2008) Radical-scavenging activity of orsellinates. Chem Pharm Bull (Tokyo). 56(11):1551-1554 PMID 18981604 Ryan SD et al (2007) Platelet activating factor-induced neuronal apoptosis is initiated independently of its G-protein coupled PAF receptor and is inhibited by the benzoate Orsellinic Acid. J. Neurochem. 103(1):88-97 PMID 17877634 Smith G, Birkinshaw JH and Gowland A (1964) Production and biosynthesis of Orsellinic acid by Penicillium madriti G. Biochem. J. 84:342 Van Eijk GW, Van Leeuwenhoek A (1969) Isolation and identification of Orsellinic Acid and penicillic acid produced by Penicillium fennelliae Stolk 35:497 Yadav LR, Balagangadharan K, Lavanya K, Selvamurugan N (2022) Orsellinic acid-loaded chitosan nanoparticles in gelatin/nanohydroxyapatite scaffolds for bone formation in vitro. Life Sci.299:120559 PMID 35447131 |
