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Product name: Yohimbic acid
Synonym name: Yohimbine acid; Yohimbinic acid; Yohimbolcarboxylic acid
Catalogue No.: BP4358
Cas No.: 522-87-2
Formula: C20H24N2O3
Mol Weight: 340.423
Botanical Source:
Type of Compound:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Yohimbic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
76.5600
.6363
.5949
.3574
.8638
9.8335
Low
64.9999
3.8630
No
No
No
No
No
No
0.0
No
No
No
No
Yohimbic acid (CAS No.: 522-87-2), as a natural product derivative, has attracted widespread attention in the field of pharmacology in recent years. Its structure is an amphoteric demethylated derivative of yohimbine, exhibiting unique biological activity, especially showing potential therapeutic value in research on vasodilation and osteoarthritis (OA). Yuhengic acid not only plays an important role in regulating targets related to male sexual dysfunction but also, due to its excellent safety and druggability parameters, has become a hot topic in natural product pharmacology research. This paper aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of yohenic acid, providing theoretical basis and reference for subsequent in-depth research and drug development.
The molecular formula of yohenic acid is C21H28N2O4, with a molecular weight of 340.4230. Its structure is based on the yohegine framework and formed through amphoteric demethylation modification, giving it unique physicochemical properties. The LogP value of yohesic acid is 0.6363, indicating moderate lipophilicity, which facilitates cell membrane penetration but is not prone to excessive accumulation in lipid environments. The polar surface area (TPSA) is 76.5600, indicating good solubility in polar environments. Water solubility is 0.3574, indicating that yohesic acid has a certain solubility in the aqueous phase, which is beneficial for absorption and distribution in the body.
The low permeability of yohesic acid at the blood-brain barrier suggests that its role in the central nervous system may be limited, which helps reduce central nervous system side effects. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic test results were 0.0, indicating that yohesic acid has no obvious genotoxicity and is relatively safe.
Yochen acid mainly comes from the bark of the yochen tree (Pausinystalia yohimbe), a plant widely distributed in the tropical regions of West Africa. The bark of the yoheng tree contains various alkaloids, and yochenic acid, as a derivative of yoheng alkaloids, is usually obtained through chemical modification or biosynthesis.
Traditional extraction methods include solvent extraction, acid-base extraction, and column chromatography separation. Modern technologies such as ultrasound-assisted extraction, microwave-assisted extraction, and high-performance liquid chromatography (HPLC) purification have significantly improved the extraction efficiency and purity of yohenic acid. During extraction, controlling pH and temperature is a key factor in ensuring yohemic acid's stability and activity.
Yohesic acid exhibits multiple pharmacological activities, showing significant potential especially in vasodilation and osteoarthritis treatment studies.
Vasodilation
Yohanic acid regulates the signaling pathways of vascular smooth muscle cells, promotes nitric oxide (NO) production, dilates blood vessels, and lowers blood pressure. In vitro experiments have shown that yohenic acid can enhance the activity of endothelial-type nitric oxide synthase (eNOS), promote NO release, and improve hemodynamic status.
Osteoarthritis (OA) research potential
In OA models, yohenic acid exhibits anti-inflammatory and cartilage-protective effects. It alleviates joint inflammatory responses by inhibiting inflammatory mediators such as tumor necrosis factor α (TNF-α) and interleukin-1β (IL-1β). Additionally, yohenic acid can regulate matrix metalloproteinase (MMPs) activity, slow down cartilage matrix degradation, and slow the progression of OA.
Male sexual dysfunction
Yohenic acid acts on various molecular targets related to male sexual function, such as CNR1, AR, NOS1, PDE5A, DRD2, HTR1A, ADRA2A, NOS3, SRD5A2, and ADRA2B. By modulating these targets, yohesic acid can improve blood supply, enhance nerve conduction and hormone regulation, and improve sexual performance.
The pharmacological effects of yohesic acid depend on its ability to regulate multiple targets and mainly involve the following mechanisms:
Neurotransmitter regulation
Yohesic acid regulates neurotransmitter release in the central nervous system by acting on dopamine D2 receptor (DRD2) and 5-hydroxytryptamine 1A receptor (HTR1A), improving libido and sexual function.
Vasodilation mechanism
Yohesic acid enhances nitric oxide synthase (NOS3) activity in endothelial cells, promotes NO synthesis, activates the guanylate cyclase (sGC)-cGMP signaling pathway, leads to relaxation of vascular smooth muscle, and results in vasodilation.
Androgen receptor (AR) regulation
The regulatory effect of yohesic acid on AR helps maintain male hormone levels and promotes the recovery of sexual function.
Phosphodiesterase 5A (PDE5A) inhibition
By partially inhibiting PDE5A, yohesic acid prolongs the duration of cGMP action and enhances vasodilatory effects, similar to the mechanism of action of PDE5 inhibitors.
Adrenaline receptor regulation
Yohesic acid regulates α2A and α2B adrenergic receptors (ADRA2A, ADRA2B), affects the sympathetic nervous system, and modulates blood flow and neural excitability.
Anti-inflammatory mechanisms in osteoarthritis
By inhibiting inflammatory factors and regulating matrix metalloproteinase activity, yohesic acid reduces joint inflammation and cartilage damage, providing protection.
Yohesic acid has excellent druggability characteristics:
In terms of pharmacokinetics, yohesic acid exhibits good oral absorption and in vivo distribution characteristics. Its metabolic pathway mainly occurs through hepatic enzyme systems, and its metabolites are safe. Excretion is mainly completed by the kidneys. The half-life of yohesic acid is moderate, supporting a reasonable dosing frequency.
Yohesic acid shows broad clinical application prospects in the fields of male sexual dysfunction and osteoarthritis. Its multi-target modulation capability and good safety provide strong support for the development of novel therapeutic drugs.
Treatment of male sexual dysfunction
By regulating multiple mechanisms such as neurotransmitters, vasodilation, and hormone receptors, yohesic acid is expected to become a novel drug for treating erectile dysfunction, decreased libido, and other conditions. Compared to existing PDE5 inhibitors, yohenic acid may have a more comprehensive mechanism of action and fewer side effects.
Adjunctive treatment for osteoarthritis
The anti-inflammatory and cartilage-protective effects of yohesic acid offer new treatment approaches for OA patients. In the future, combined with existing drugs, compound formulations can be developed to enhance efficacy and improve patients' quality of life.
Drug development and optimization
Designing and synthesizing derivatives based on yohenic acid skeletal structures, and optimizing their pharmacodynamic and pharmacokinetic properties, will be an important direction for future research. At the same time, it conducts in-depth analysis of its mechanism of action, conducts preclinical and clinical studies, and promotes its clinical translation.
Safety and tolerability studies
Although yohesic acid demonstrates good safety, it still requires systematic evaluation of its long-term toxicological characteristics and potential drug interactions to ensure clinical application.
As a amphoteric demethylation derivative of yohestine, yohesic acid, with its unique chemical structure and multi-target pharmacological activity, shows broad research and application prospects in areas such as vasodilation, male sexual dysfunction, and osteoarthritis. Its excellent druggability parameters and safety provide a solid foundation for the development of natural product drugs. In the future, through in-depth mechanistic research and clinical validation, yohesic acid is expected to become an emerging drug for treating related diseases, bringing great hope to patients. The continued development of natural product pharmacology will further promote innovative drug research and development of yohenic acid and its derivatives, promoting the rational use and value enhancement of natural product resources.
Shenshuai
Wenjing
Hedandan
