L'Acido carnosico si trova in natura nel rosmarino (Rosmarinus officinalis) e nella salvia (Salvia officinalis) ha funzioni antibatteriche, antisettiche, antiossidanti. Appartiene alla classe dei diterpeni.

Il processo di sintesi avviene in diverse fasi:

• Estrazione dalle foglie della pianta di rosmarino con vari solventi, come etanolo o acetone. Le foglie sono immerse nel solvente, che dissolve l'acido carnosico. La soluzione viene quindi filtrata per rimuovere qualsiasi materiale vegetale solido.
• Depurazione.  L'acido carnosico viene purificato dal solvente con tecniche come la cromatografia a colonna, dove la soluzione viene fatta passare attraverso una colonna riempita con un materiale che si lega selettivamente all'acido carnosico. L'acido carnosico può quindi essere estratto dalla colonna utilizzando un solvente diverso.
• Cristallizzazione. L'acido carnosico purificato viene cristallizzato  evaporando il solvente, che fa precipitare l'acido carnosico dalla soluzione in cristalli.

Si presenta in forma di polvere gialla o marrone.

A cosa serve e dove si usa

Medicina

Effetti anti-obesità. L'acido carnosico è stato studiato per il suo potenziale di inibizione dell'adipogenesi (la formazione di cellule grasse) e di promozione della disgregazione dei grassi. Può contribuire a regolare il metabolismo lipidico e a prevenire l'aumento di peso.

Neuroprotettore. Le potenziali applicazioni dell'acido carnosico per il morbo di Alzheimer, il morbo di Parkinson e la COVID-19, attraverso l'inibizione dell'inflammasoma NLRP3 vengono discusse in questo studio (1) inoltre l'acido carnosico ha ridotto l'attivazione aberrante di microglia e astrociti e diminuito la produzione di IL-1β, TNFα e IL-6 matura nel cervello del topo APP/PS1 (2).

Alimentazione

Attività antibatterica e antimicrobica: L'acido carnosico presenta proprietà antimicrobiche che lo rendono efficace contro vari batteri, funghi e virus. È stato studiato per la sua potenziale applicazione nella conservazione degli alimenti e come alternativa agli agenti antimicrobici sintetici.

Cosmetica

Agente antiossidante. Ingrediente che contrasta lo stress ossidativo e che evita danni cellulari. I radicali liberi, i processi infiammatori patologici, le specie reattive dell'azoto e le specie reattive dell'ossigeno sono responsabili del processo di invecchiamento e di molte malattie causate dall'ossidazione.

Sicurezza

Non ha alcuna controindicazione.

Acido carnosico studi

• Formula molecolare: C₂₀H₂₈O₄
• Peso molecolare: 332.44 g/mol
• UNII: LI791SXT24
• CAS: 3650-09-7
• EC Number: 609-253-7
• PubChem Substance ID 329749247
• MDL number MFCD02259459
• Beilstein Registry Number 2707918

Sinonimi: 

• Salvin
• RoseOx
• 11,12-dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-oic acid
• (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid
• (4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic Acid
• 4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-trans)-

Bibliografia_____________________________________________________________________

(1) Satoh, Takumi, Dorit Trudler, Chang-Ki Oh, and Stuart A. Lipton. 2022. "Potential Therapeutic Use of the Rosemary Diterpene Carnosic Acid for Alzheimer’s Disease, Parkinson’s Disease, and Long-COVID through NRF2 Activation to Counteract the NLRP3 Inflammasome" Antioxidants 11, no. 1: 124. https://doi.org/10.3390/antiox11010124

Abstract. Rosemary (Rosmarinus officinalis [family Lamiaceae]), an herb of economic and gustatory repute, is employed in traditional medicines in many countries. Rosemary contains carnosic acid (CA) and carnosol (CS), abietane-type phenolic diterpenes, which account for most of its biological and pharmacological actions, although claims have also been made for contributions of another constituent, rosmarinic acid. This review focuses on the potential applications of CA and CS for Alzheimer’s disease (AD), Parkinson’s disease (PD), and coronavirus disease 2019 (COVID-19), in part via inhibition of the NLRP3 inflammasome. CA exerts antioxidant, anti-inflammatory, and neuroprotective effects via phase 2 enzyme induction initiated by activation of the KEAP1/NRF2 transcriptional pathway, which in turn attenuates NLRP3 activation. In addition, we propose that CA-related compounds may serve as therapeutics against the brain-related after-effects of SARS-CoV-2 infection, termed “long-COVID.” One factor that contributes to COVID-19 is cytokine storm emanating from macrophages as a result of unregulated inflammation in and around lung epithelial and endovascular cells. Additionally, neurological aftereffects such as anxiety and “brain fog” are becoming a major issue for both the pandemic and post-pandemic period. Many reports hold that unregulated NLRP3 inflammasome activation may potentially contribute to the severity of COVID-19 and its aftermath. It is therefore possible that suppression of NLRP3 inflammasome activity may prove efficacious against both acute lung disease and chronic neurological after-effects. Because CA has been shown to not only act systemically but also to penetrate the blood–brain barrier and reach the brain parenchyma to exert neuroprotective effects, we discuss the evidence that CA or rosemary extracts containing CA may represent an effective countermeasure against both acute and chronic pathological events initiated by SARS-CoV-2 infection as well as other chronic neurodegenerative diseases including AD and PD.

(2) Yi-Bin, W., Xiang, L., Bing, Y. et al. Inhibition of the CEBPβ-NFκB interaction by nanocarrier-packaged Carnosic acid ameliorates glia-mediated neuroinflammation and improves cognitive function in an Alzheimer’s disease model. Cell Death Dis 13, 318 (2022). https://doi.org/10.1038/s41419-022-04765-1

Abstract. Neuroinflammation occurs early in Alzheimer’s disease (AD). The initial stage of AD is related to glial dysfunction, which contributes to impairment of Aβ clearance and disruption of synaptic connection. CEBPβ, a member of the CCAAT-enhancer-binding protein (CEBP) family, modulates the expression of inflammation-associated genes, and its expression is elevated in brains undergoing degeneration and injured brains. However, the mechanism underlying CEBPβ-mediated chronic inflammation in AD is unclear. In this study, we observed that increases in the levels of nuclear CEBPβ facilitated the interaction of CEBPβ with the NFκB p65 subunit, increasing the transcription of proinflammatory cytokines in the APP/PS1 mouse brain. Oral administration of nanocarrier-packaged carnosic acid (CA) reduced the aberrant activation of microglia and astrocytes and diminished mature IL-1β, TNFα and IL-6 production in the APP/PS1 mouse brain. CA administration reduced β-amyloid (Aβ) deposition and ameliorated cognitive impairment in APP/PS1 mice. We observed that CA blocked the interaction of CEBPβ with NFκB p65, and chromatin immunoprecipitation revealed that CA reduced the transcription of the NFκB target genes TNFα and IL-6. We confirmed that CA alleviated inflammatory mediator-induced neuronal degeneration and reduced Aβ secretion by inhibiting the CEBPβ-NFκB signalling pathway in vitro. Sulfobutyl ether-beta-cyclodextrin (SBEβCD) was used as the encapsulation agent for the CA-loaded nanocarrier to overcome the poor water solubility and enhance the brain bioavailability of CA. The CA nanoparticles (NPs) had no obvious toxicity. We demonstrated a feasible SBEβCD-based nanodelivery system targeting the brain. Our data provide experimental evidence that CA-loaded NPs are potential therapeutic agents for AD treatment.