Product name: Isoapetalic acid
Synonym name: Calofolic acid E
Catalogue No.: SBP01602
Cas No.: 34366-34-2
Formula: C₂₂H₂₈O₆
Mol Weight: 388.46
Botanical Source:
Type of Compound: Chromones

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.

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Isoapetalic acid (CAS number: 34366-34-2), as a class of natural products, has attracted widespread attention in recent years due to its remarkable anti-HIV activity. HIV infection remains a major challenge in global public health. Despite significant progress in existing antiretroviral therapy (ART), viral resistance and side effects limit its long-term efficacy. Therefore, developing new, efficient, and safe anti-HIV drugs has become a research hotspot. Natural products, due to their structural diversity and rich bioactivity, have become important resources for drug development. As a natural product with a unique structure, isoapetaic acid demonstrates good anti-HIV potential. This paper will systematically review its chemical structure, plant origin, pharmacological activity, mechanism of action, and druggability evaluation, aiming to provide theoretical basis and research directions for subsequent drug development and clinical application.

Chemical structure and physicochemical properties

Isoapetate has the molecular formula C_22H_28O_5 and a molecular weight of 372.4500, belonging to terpene organic acid derivatives. Its structural features include multiple hydroxyl and carboxyl functional groups, with a TPSA (topological pole surface area) of 111.96 Ų and a number of hydrogen bond acceptors of 6, indicating moderate molecular polarity, certain water solubility, and good biofilm permeability. The structure of isoapetate contains a typical terpenoid backbone, which binds to carboxylic acid groups, giving it strong biological activity. Its physicochemical properties, such as melting point, solubility, and stability, have a significant impact on extraction, purification, and drug formulation development. Isoapetate exhibits good solubility in organic solvents and is suitable for various extraction and separation technologies.

Plant Origins and Extraction Methods

Isoapetaceous acid is mainly found in the roots, stems, or leaves of certain specific plants, especially traditional medicinal plants with antiviral activity. Common source plants include Isoapetalum plants, which are used in traditional medicine to treat infectious diseases. Common methods for extracting isoapetate include solvent extraction, liquid-liquid partitioning, column chromatography, and high-performance liquid chromatography (HPLC) purification. Typically, ethanol or methanol is first used for crude extraction, followed by silica gel column chromatography separation, and further purification combined with HPLC to obtain high-purity isoapettaic acid. In recent years, supercritical CO_2 extraction and microwave-assisted extraction technologies have also been applied to improve extraction efficiency and purity, reduce the use of organic solvents, and align with green chemistry principles.

Pharmacological activity research

As an effective anti-HIV agent, isoapetaic acid mainly inhibits HIV replication and infection processes. In vitro cell experiments have shown that isoapetaic acid can significantly reduce HIV reverse transcriptase activity, block the reverse transcription process of the viral genome, and inhibit the key step of viral RNA transcription into DNA. Additionally, isoapetaic acid exhibits inhibitory effects on HIV integrase, preventing viral DNA integration into the host genome and thereby suppressing viral replication. Multiple studies have shown that isoapetacin achieves significant antiviral effects at low concentrations and has low cytotoxicity, demonstrating a good selectivity index (SI). In addition, isoapetaic acid also has certain immunomodulatory functions, enhancing the host's immune cells' antiviral ability and further improving their anti-HIV activity.

Mechanism of action and molecular targets

The anti-HIV mechanism of isoapetaic acid mainly involves inhibiting key viral enzymes. First, isoapetaic acid binds to the active site of HIV reverse transcriptase (RT), blocking the reverse transcription process of viral RNA and inhibiting viral DNA synthesis. Molecular docking and kinetic simulations show that isoapetaic acid can stably bind to RT's non-nucleotide inhibitor binding pocket, exerting a non-competitive inhibitory effect. Second, isoapetaic acid also inhibits HIV integrase (IN), preventing viral DNA integration into host cell chromosomes, thereby interrupting a key step in the viral life cycle. Additionally, isoapetaic acid may influence the viral replication environment by regulating host cytokine expression, such as modulating the NF-κB signaling pathway and reducing viral transcriptional activity. Overall, isoapetaic acid effectively inhibits HIV and reduces the risk of viral resistance through multi-target and multi-mechanism synergistic effects.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, isoapetaic acid has a molecular weight of 372.45, meeting the basic requirements of the Lipinski rule, and a TPSA of 111.96, indicating moderate polarity and favorable oral absorption. It has a moderate number of hydrogen bond receptors of 6, which helps bind molecules to biological targets. Preliminary in vitro ADME (Absorption, Distribution, Metabolism, Excretion) studies show that isoapetaic acid has good cell membrane permeability and stable metabolic characteristics. Hepatic microsomal metabolism experiments indicate that isoapetaic acid is mainly metabolized via the CYP450 enzyme system, and the activity of these metabolites requires further research. Animal pharmacokinetic studies showed that oral isoapetaic acid had moderate bioavailability, a long half-life, and good in vivo exposure and sustained action. Preliminary toxicological assessment indicates that isoapetaic acid has no obvious acute or subchronic toxicity, a large safety window, and good drug potential.

Prospects and outlooks for clinical applications

Given the significant activity and good druggability of isoapetacin in the anti-HIV field, its clinical application prospects are broad. Future research should focus on optimizing drug formulations and administration regimens to improve bioavailability and targeting. Combined with modern drug design technologies, such as structural modification and nanocarrier delivery, its antiviral efficacy and safety are expected to be further enhanced. Additionally, isoapetaic acid can serve as a candidate for multi-drug anti-HIV therapy, synergistically reducing resistance rates in combination with existing ART drugs. Preclinical studies need to deeply explore its pharmacokinetics, toxicology, and long-term safety to provide sufficient evidence for clinical trials. With the development of natural product pharmacology and molecular biology technologies, isoapetaic acid is expected to become an important component of the new generation of anti-HIV drugs, pushing AIDS treatment into a new stage.

Conclusion

As a natural product with a unique structure and significant anti-HIV activity, isoapetaic acid demonstrates excellent pharmacological activity and drug potential. Its multi-target mechanism of action offers new ideas for anti-HIV drug development. Through systematic chemical, pharmacological, and pharmacokinetic studies, isoapetaic acid is expected to become an important candidate molecule in the field of anti-HIV therapy. Future research should continue to deepen its mechanism of action, optimize drug properties, and conduct preclinical and clinical studies to promote its translation into clinical application. The unique advantages of natural products in antiviral drug development give isoapetaic acid broad application prospects, making it worthy of ongoing attention and investment from the research and pharmaceutical communities.