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Synonym name: Norloganin
Catalogue No.: BP0883
Cas No.: 22255-40-9
Formula: C16H24O10
Mol Weight: 376.358
Botanical Source: Swertia caroliniensis and Dipsacus asperoides
Purity: 95%~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.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Loganic acid( 0.7% solution) has a strong intraocular pressure (IOP)-hypotensive effect, it exhibits both sides effect on superoxide generation. Loganic acid also has protective effects on atherosclerosis risk factors in hypercholesterolemic rabbits, it shows significant anti-inflammatory effects decreasing TNF-α and IL-6 activity in serum.
References:
Nat Prod Res. 2013;27(10):911-5.
Anti-inflammatory effect of three iridoids in human neutrophils.
To verify the anti-inflammatory potency of iridoids, three iridoids (two natural, Loganic acid: LA; geniposide: GE; and an artefact, 7(S)-n-butyl morroniside: BM) were investigated in vitro on the inhibition of superoxide generation in human neutrophils.
METHODS AND RESULTS:
All compounds showed inhibitory effect on fMLP-induced superoxide generation in a concentration-dependent manner with the following order: BM>LA>GE. BM exhibits potent inhibitory activity on superoxide anion induced by PMA, while LA and GE showed weak effect. When AA was used as stimulus, the generation of superoxide anion was suppressed by BM in a concentration-dependent manner.
CONCLUSIONS:
LA and GE exhibit both sides effect on superoxide generation.
Phytomedicine. 2014 Nov 15;21(13):1774-84.
The protective effect of the Cornus mas fruits (cornelian cherry) on hypertriglyceridemia and atherosclerosis through PPARα activation in hypercholesterolemic rabbits.
Cornelian cherry (Cornus mas L.) fruits have been used in traditional cuisine and in folk medicine in various countries. This study was conducted to evaluate the constituents and impact of cornelian cherry (C. mas L.) fruits lyophilisate on lipid levels, PPARα protein expression, atheromatous changes in the aorta, oxido-redox state, and proinflammatory cytokines in hypercholesterolemic rabbits.
METHODS AND RESULTS:
The HPLC-MS method was used for determining active constituents in cornelian cherry. In a subsequent in vivo study the protective effect of the cornelian cherry on diet-induced hyperlipidemia was studied using a rabbit model fed 1% cholesterol. Cornelian cherry (100mg/kg b.w.) or simvastatin (5mg/kg b.w.) were administered orally for 60 days. Two iridoids - Loganic acid and cornuside - and five anthocyanins were identified as the main constituents of the cornelian cherry. The administering of the cornelian cherry led to a 44% significant decrease in serum triglyceride levels, as well as prevented development of atheromatous changes in the thoracic aorta. Cornelian cherry significantly increased PPARα protein expression in the liver, indicating that its hypolipidemic effect may stem from enhanced fatty acid catabolism. Simvastatin treatment did not affect PPAR-α expression. Moreover, the cornelian cherry had a significant protective effect on diet-induced oxidative stress in the liver, as well as restored upregulated proinflammatory cytokines serum levels.
CONCLUSIONS:
In conclusion, we have shown Loganic acid to be the main iridoid constituent in the European cultivar of the cornelian cherry, and proven that the cornelian cherry could have protective effects on diet-induced hypertriglicerydemia and atherosclerosis through enhanced PPARα protein expression and via regulating oxidative stress and inflammation.
HPLC of Loganic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
166.1400
-1.2267
-3.2645
48.5428
.4201
.4423
Low
37.1359
4.7288
Yes
No
No
No
No
No
0.0
Yes
Yes
Yes
Yes
Loganic acid (CAS No.: 22255-40-9) is a typical cycloether terpene natural product, mainly isolated from the fruit of Cornus officinalis. As an important plant secondary metabolite, marchanilate has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activities. Numerous studies have shown that marchanyanin has significant anti-inflammatory, antioxidant, and cell-protective effects, especially showing good potential in regulating inflammatory responses and redox homeostasis. Additionally, marchanyanin can regulate diet-induced atherosclerotic processes, demonstrating its promising application in cardiovascular disease prevention and treatment. This paper will systematically review the chemical structure and physicochemical properties of marchanyanide, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and explore its clinical application prospects and future development directions.
Maxianinin is a cycloalkene ether terpene compound with a molecular formula of C16H24O10 and a molecular weight of 376.3580. Its structural features include a cycloalkene ether framework connected to multiple hydroxyl and carboxyl functional groups, giving it high polarity and water solubility. The topological surface area (TPSA) of marchanoside is 166.14 Ų, indicating strong polarity and hydrogen bond donor/acceptor capability, which facilitates stable binding with biomacromolecules. Its LogP value is -1.2267, indicating low lipid solubility, consistent with its good water solubility (around 48.54 mg/mL), which has significant implications for oral absorption and internal distribution.
In terms of physicochemical properties, marchanoside is difficult to cross the blood-brain barrier (BBB), which may limit its direct application in central nervous system diseases but reduces the risk of CN toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenicity test was zero, indicating good genotoxicity safety. Overall, the physicochemical properties of marchanyanine have laid a solid foundation for further pharmacological research and drug development.
Cornus officinalis is mainly found in the fruit of Cornus officinalis, a plant of the Cornus officinalis, which is widely used in traditional Chinese medicine and has effects such as tonifying the kidneys and consolidating essence, astringing essence, and stopping diarrhea. Besides cornelian cherry, some other plants such as Strychnos nux-vomica also contain small amounts of strychnos, but the main source is the fruit of Cornus officinalis.
The extraction method typically uses water or alcohol solvents for extraction combined with column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and other technologies for purification. In recent years, modern extraction technologies such as ultrasound-assisted extraction and microwave-assisted extraction have been applied to improve the extraction efficiency and purity of marchanotide. The typical process generally includes: crushing dried cornelian cherry fruit, extracting it with 70% ethanol or pure water, filtering and concentrated the extract, then using a silica gel column or C18 reverse-phase column for separation and purification, ultimately obtaining high-purity marchanolate crystals or powder.
Machchan acid exhibits significant anti-inflammatory effects, effectively inhibiting the expression and release of various inflammatory mediators. Both in vitro cell and in vivo inflammation models have confirmed that it alleviates inflammatory responses by inhibiting the NF-κB signaling pathway, reducing the expression of pro-inflammatory factors such as TNF-α, IL-6, and IL-1β. Related targets include NFKB1, TNF, IL-6, STAT3, CASP1, etc., demonstrating their multi-target regulatory characteristics. Additionally, marchanyanine can regulate inflammation-related ion channels such as TRPV1 and TRPA1, further modulating neuro-immune interactions during inflammation.
Maxianic acid has a powerful free radical scavenging ability, effectively eliminating reactive oxygen species (ROS) such as superoxide anions and hydroxyl radicals, thereby reducing oxidative stress damage. By activating the Nrf2 signaling pathway, it promotes the expression of downstream antioxidant enzymes such as HO-1 and NQO1, thereby enhancing the cell's antioxidant defense capacity. Additionally, marchanoside has a significant protective effect against heavy metal-mediated cytotoxicity, reducing oxidative damage and apoptosis induced by heavy metals.
In the diet-induced atherosclerosis model, machinyanin can regulate lipid metabolism, reduce vascular endothelial damage, suppress inflammatory responses and oxidative stress, and slow the progression of atherosclerosis. Its mechanism involves multiple pathways including anti-inflammatory, antioxidant, and lipid metabolism regulation, demonstrating potential value in cardiovascular disease prevention and treatment.
Preliminary studies have also found that xianyanin has certain potential in regulating immune function, antibacterial effects, and neuroprotection, but the related mechanisms still require further exploration.
The pharmacological effects of marchanyanin mainly work by regulating inflammatory and oxidative stress-related signaling pathways. Its core mechanisms include:
Inhibition of NF-κB signaling pathway: NF-κB is a key transcription factor in inflammatory responses. Marchanotide inhibits the phosphorylation and degradation of IκBα, blocks NF-κB nuclear translocation, and reduces the expression of pro-inflammatory factors such as TNF-α, IL-6, PTGS2 (COX-2), achieving anti-inflammatory effects.
Activation of the Nrf2 signaling pathway: As the main regulator of cellular antioxidant defense, marchaninyl promotes the transfer of Nrf2 from the cytoplasm to the nucleus, inducing the expression of antioxidant enzyme genes and enhancing cellular resistance to oxidative stress.
Regulation of inflammation-related targets: including STAT3, CASP1 (inflammasome component), TRPV1/TRPA1 (inflammation-related ion channels), NOS2 (induced nitric oxide synthase), PTGS1 (COX-1), etc. Through the synergistic action of multiple targets, marchanotide achieves comprehensive regulation of inflammatory responses.
Free Radical Scavenging and Cell Protection: Marchanoside directly scavenges ROS, protecting mitochondrial function and preventing apoptosis and necrosis, especially showing significant protective effects in cell damage induced by heavy metal toxicity.
In summary, marchanyanin, with its multi-target and multi-pathway mechanism, demonstrates excellent pharmacological activity and potential therapeutic value.
Druggability evaluation of marchanoside shows it has good safety and pharmacokinetic characteristics:
Oral activity: Machchannicotin has good water solubility and moderate molecular weight, supporting its feasibility for oral administration. Although the low LogP value indicates limited lipophilusity, its polar structure facilitates absorption mediated by intestinal transporters.
Low blood-brain barrier penetration: This limits its application in central nervous system diseases but simultaneously reduces the risk of CN toxicity.
No cardiotoxicity risk: hERG channel inhibition test was negative, reducing the risk of potential arrhythmias.
No genotoxicity: Ames test results show no mutagenicity, meeting safety requirements.
Pharmacokinetic characteristics: Currently, there is limited research on in vivo metabolism and excretion of marchanyanin. Preliminary data indicate good bioavailability and a long half-life in animals, but further systematic research is needed.
Potential for drug interactions: Due to its multihydroxyl structure, it may interact with certain drug-metabolizing enzymes or transporters, requiring special attention in future research.
Based on the multiple pharmacological activities of marchanolate, especially its anti-inflammatory, antioxidant, and cardiovascular protective effects, it holds broad clinical application prospects in various disease fields in the future:
Chronic inflammatory diseases: such as rheumatoid arthritis and inflammatory bowel disease, where marchanolate modulates the NF-κB and Nrf2 pathways, making it a promising candidate for safe and effective anti-inflammatory drugs.
Cardiovascular diseases: For atherosclerosis and hyperlipidemia, marchanoside can be used as an adjunct therapy to slow disease progression.
Oxidative stress-related diseases: Including diabetes and its complications, neurodegenerative diseases, etc., the antioxidant effects of marchaninic acid provide a potential therapeutic basis.
Heavy Metal Poisoning and Environmental Toxicology Applications: Its cell-protective effects make it a potential drug for the prevention and treatment of heavy metal toxicity.
Future research should focus on preclinical pharmacokinetics, toxicological evaluation, and clinical trial design for marchanyanin, to further clarify its safety and efficacy. In addition, structural modification of marchanyanin and the development of drug delivery systems will also drive its clinical translation.
As a natural cycloene ether terpene with multiple targets and mechanisms, marchanotide demonstrates rich pharmacological activity and promising drug development potential. Its mechanisms of action in anti-inflammation, antioxidant, and cardiovascular protection have gradually been clarified, and it demonstrates good safety and oral activity. Although challenges in pharmacokinetics and clinical applications still exist, advances in modern drug development technology make marchanoside a key candidate for natural product drug development. Future systematic pharmacological mechanism research, structural optimization, and clinical validation will provide a solid foundation for its clinical application, promoting its widespread use in the field of natural medicines.
Shenshuai
Wenjing
Hedandan
