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Synonym name: Deoxypicrosalvinic acid
Catalogue No.: BP0316
Cas No.: 3650-09-7
Formula: C20H28O4
Mol Weight: 332.44
Botanical Source: Salvia officinalis (sage), Salvia canariensis, Salvia apiana and Rosmarinus officinalis (rosemary)
Purity: 90%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams,up to kilograms.
Inquire for bulk scale.
Two studies, led by Stewart Lipton, MD, PhD, from the Burnham Institute for Medical Research, in La Jolla, California, and Takumi Satoh, MD, PhD, from Iwate University, in Japan, which are published in the October 2007 issue of Nature Reviews Neuroscience and online November 8 in the Journal of Neurochemistry, show that CA activates a novel signaling pathway that protects brain cells from free radical damage, seen in stroke and other neurodegenerative conditions such as Parkinson's and Alzheimer's diseases.[1] [2]
Carnosol and carnosic acid have been suggested to account for over 90% of the antioxidant properties of rosemary extract. 2. Purified carnosol and carnosic acid are powerful inhibitors of lipid peroxidation in microsomal and liposomal systems, more effective than propyl gallate. 3. Carnosol and carnosic acid are good scavengers of peroxyl radicals (CCl3O2.) generated by pulse radiolysis, with calculated rate constants of 1-3 x 10(6) M-1 s-1 and 2.7 x 10(7) M-1 s-1 respectively. 4. Carnosic acid reacted with HOCl in such a way as to protect the protein alpha 1-antiproteinase against inactivation. 5. Both carnosol and carnosic acid stimulated DNA damage in the bleomycin assay but they scavenged hydroxyl radicals in the deoxyribose assay. The calculated rate constants for reaction with .OH in the deoxyribose system for carnosol and carnosic acid were 8.7 x 10(10) M-1 s-1 and 5.9 x 10(10) M-1 s-1 respectively. 6. Carnosic acid appears to scavenge H2O2, but it could also act as a substrate for the peroxidase system. 7. Carnosic acid and carnosol reduce cytochrome c but with a rate constant significantly lower than that of O2(-.). [3] From Wikipedia
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Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
77.7600
4.4412
2.2911
.0264
4.4273
5.8857
Low
92.3574
3.7685
No
No
No
No
No
Yes
0.0
Yes
No
No
No
Carnosic acid (CAS No.: 3650-09-7) is a typical natural product of the rosin alkane diterpene class, mainly derived from Rosmarinus officinalis and Salvia officinalis) is separated and obtained. As a natural compound with multiple biological activities, rhamoxic acid demonstrates significant pharmacological potential in antioxidant, anti-tumor, anti-angiogenic effects, and antiviral properties. In recent years, with the deepening of research on neurodegenerative diseases, the mechanisms of rhamoxalic acid and its related molecular targets in neuroprotective fields have gradually been revealed, demonstrating its promising application in neurological diseases such as Alzheimer's and Parkinson's. Moreover, the good safety and low toxicity of rhamoxalic acid make it an important candidate molecule for natural drug development. This paper aims to systematically review the chemical structure, physicochemical properties, plant origin, extraction process, pharmacological activity, and mechanism of action of rhamoxic acid, and, combining druggability parameters and pharmacokinetic characteristics, explores its clinical application potential and future research directions.
Rhamoxic acid belongs to the rosin diterpene compound, with a molecular formula of C20H28O4 and a molecular weight of 332.44. Structurally, rhamnoic acid is composed of rosin-8,11,13-triene bones, with hydroxyl groups replacing it at positions 11 and 12, and carboxyl groups at position 20. This structure imparts strong polarity and a certain lipophilicity, with a LogP value of 4.4412, indicating good lipid solubility that facilitates penetration of cell membranes.
In terms of physicochemical properties, the polar surface area (TPSA) of salvac acid is 77.76 Ų, indicating it has certain polar groups that help molecules bind to biological macromolecules such as proteins. Its low water solubility (0.0264 mg/mL) limits its solubility and bioavailability in the aqueous phase, but its lipid solubility aids membrane penetration. The blood-brain barrier (BBB) has low permeability, suggesting its direct role in the central nervous system may be limited, but its potential to exert neuroprotective effects by modulating relevant targets remains present. The hERG channel inhibition test was negative, indicating a low risk of shamnoic acid cardiotoxicity; Ames-induced mutagenic test results were zero, indicating no significant genotoxicity.
Sageonitic acid is mainly found in Lamiaceae plants Rosemary and sage, with especially abundant content in rosemary leaves. Rosemary and sage, as traditional herbal and spice plants, are widely distributed in the Mediterranean region and are noted for their abundance of diterpenes and phenolic compounds.
There are various methods for extracting rodnulate, with commonly used processes including solvent extraction, ultrasound-assisted extraction, microwave-assisted extraction, and supercritical fluid extraction. Traditional solvent extraction mostly uses ethanol, methanol, or ethyl acetate as solvents to improve extraction efficiency. Ultrasound-assisted extraction promotes cell rupture through sonic vibrations, significantly shortening extraction time and improving yield. Microwave-assisted extraction uses microwave energy to heat plant cells, enhancing solvent penetration and solute dissolution, characterized by rapid and efficient performance. Supercritical carbon dioxide extraction, due to its green and environmentally friendly nature and solvent-free residue advantages, has gradually become the preferred technology for industrial shamvicin extraction.
After extraction, rhamoxalic acid is often separated and purified by liquid chromatography (HPLC), combined with mass spectrometry (MS) and nuclear magnetic resonance (NMR) techniques for structural identification. Higher-purity rodoxic acid provides a reliable material foundation for subsequent pharmacological activity research and drug development.
Rhamoxic acid has a wide range of pharmacological activities, covering antioxidant, anti-tumor, anti-angiogenesis, antiviral, and neuroprotective aspects.
As a natural phenolic antioxidant, shamoxic acid can effectively eliminate free radicals, inhibit lipid peroxidation, and protect cells from oxidative stress damage. Its hydroxyl and carboxyl structures give it strong electron donor capacity, capable of neutralizing reactive oxygen species (ROS) and nitrogen radicals (RNS). In vitro studies have shown that rhamoxic acid significantly increases intracellular antioxidant enzyme activity (such as superoxide dismutase SOD and glutathione peroxidase GPx), lowers oxidative damage markers, and delays cellular aging.
Multiple in vitro and in vivo studies have shown that rhamoxic acid inhibits various tumor cell lines, including breast cancer, colon cancer, lung cancer, and others. Its antitumor mechanism involves inducing apoptosis, inhibiting cell proliferation, blocking tumor angiogenesis, and regulating the tumor microenvironment. Rhamoxalic acid can downregulate VEGF expression, inhibit angiogenesis, and limit tumor nutrient supply and growth. Additionally, rhamoxalic acid exerts its antitumor effects by regulating NF-κB, PI3K/Akt, and MAPK signaling pathways.
Rhamoxalic acid has shown certain activity in anti-HIV research, inhibiting HIV reverse transcriptase and protease activity, thereby blocking the viral replication cycle. Its multi-target mechanism of action makes it a potential candidate for antiviral drug development.
Neuroprotection is a hot area in satirical acid research. Oxidative stress and neuroinflammation are common pathological foundations in many neurodegenerative diseases; shamoxic acid alleviates neuronal damage through antioxidant and anti-inflammatory effects. In vitro and animal model studies have shown that ratoxic acid can reduce neurotoxicity induced by β-amyloid protein (Aβ), reduce neuronal apoptosis, and improve cognitive function. Its protective effect on dopaminergic neurons in Parkinson's disease models has also been confirmed.
The multi-target mechanism of rhamoxalic acid forms the basis of its pharmacological activity, especially involving multiple key proteins and signaling pathways in neuroprotection.
Salvanoic acid activates nuclear factor red lineage-related factor 2 (NRF2), promotes the expression of antioxidant enzyme genes, and enhances cellular antioxidant capacity. At the same time, it inhibits the NF-κB signaling pathway, reduces the release of pro-inflammatory cytokines, and alleviates neuroinflammation.
In summary, rhamoxalic acid exerts its neuroprotective and antitumor effects through multi-target and multi-pathway synergistic effects.
The druggability parameters of rhamoxalic acid indicate that it has certain potential for drug development. Molecular weight 332.44 meets the Lipinski rule, and LogP 4.44 suggests good lipid solubility, which facilitates cell membrane penetration, but its low water solubility (0.0264 mg/mL) may limit oral bioavailability. Its TPSA is 77.76, and moderate polarity helps bind to target proteins.
The blood-brain barrier has low permeability, suggesting its limited ability to directly enter the central nervous system, but it can still exert neuroprotective effects by modulating the peripheral nervous system or by indirect mechanisms. The negative inhibition of hERG channels and the absence of mutagenicity in the Ames test indicate that rhamoxic acid is relatively safe and carries low risks of cardiotoxicity and genotoxicity.
Pharmacokinetic studies show that oral absorption of rhamoxic acid is limited, and metabolism in the body mainly occurs through hepatic enzyme systems, with metabolites mostly being hydroxylated and glucuronic acid conjugates. Its half-life is moderate, making it suitable for routine administration. To improve bioavailability, the development of novel drug delivery systems such as nanocarriers, liposomes, and solid dispersions has become a research hotspot.
As a versatile natural product, rhamoxic acid shows broad clinical application prospects thanks to its remarkable antioxidant, antitumor, and neuroprotective effects. In the field of neurodegenerative diseases, rhamoxic acid is expected to become an adjunctive treatment for diseases such as Alzheimer's and Parkinson's, alleviating pathological progression and improving patients' cognitive and motor functions. Its antitumor properties also offer new ideas for cancer treatment, especially in combination chemotherapy and targeted therapy, where synergistic effects may be achieved.
However, the clinical transformation of rhamoxic acid still faces many challenges, including poor water solubility, low bioavailability, and insufficient blood-brain barrier permeability. Future research should focus on optimizing delivery routes and dosage form design to enhance pharmacokinetic performance. At the same time, in-depth analysis of its mechanism of action, especially molecular networks related to neuroprotection, will provide a theoretical basis for precision drug development.
In addition, systematic preclinical safety evaluation and clinical trial design are also key to achieving the clinical application of rhamnolate. Multidisciplinary collaboration combining modern medicinal chemistry, pharmacology, and pharmacoformulation will drive shamoxic acid from the laboratory to clinical practice, benefiting patients.
As a naturally occurring diterpenoid compound with a unique structure and rich pharmacological activity, rhamoxic acid has become a hot topic in natural product pharmacology research due to its antioxidant, antitumor, and neuroprotective functions. Its multi-target mechanism of action offers new approaches for the treatment of various diseases. Despite limitations such as water solubility and bioavailability, the clinical potential of rhamoxic acid is becoming increasingly evident with continuous advances in extraction and purification technologies and drug delivery systems. In the future, further optimization of its druggability and in-depth research on mechanisms will lay a solid foundation for the drug development and clinical application of rhamoxalic acid, promoting it to become an important player in the field of natural medicines.
Shenshuai
Wenjing
Hedandan
