Product name: 6-aldehydo-Isoophiopogonone A
Synonym name:
Catalogue No.: BP4716
Cas No.: 112500-90-0
Formula: C₁₉H₁₄O₇
Mol Weight: 354.314
Botanical Source:
Type of Compound: Flavonoids

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

Natural products, as an important source of drug discovery, play an irreplaceable role in the field of anti-tumor drug development. 6-aldehydo-isoophiopogonone A (CAS No.: 112500-90-0) is a novel natural flavonoid compound that has attracted widespread attention in recent years due to its remarkable antitumor activity. This compound was mainly isolated from the traditional Chinese medicinal material Ophiopogon isomaopogon, demonstrating multi-target and multi-mechanism anticancer potential, especially in regulating tumor cell apoptosis, inhibiting tumor invasion and metastasis, and modulating the tumor microenvironment.

This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of 6-aldehyde isoosopogon flavonoid A, druggability evaluation and pharmacokinetic characteristics, and to look ahead to its clinical application prospects, providing theoretical basis and research reference for further development and clinical translation of this compound.

Chemical structure and physicochemical properties

6-Aldehyde-based isomyponic flavonoid A belongs to the flavonoid class of compounds, with a molecular formula of C_20H_18O_6 and a molecular weight of 354.3140. Its structural features include a typical flavonoid backbone with aldehyde functional groups at position 6, giving it unique biological activity. The compound has a LogP value of 2.0854, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. The topological pole surface area (TPSA) is 106.2 Ų, indicating certain polarity that may affect its absorption and bioavailability.

Low water solubility (0.0315 mg/mL) indicates limited solubility in the aqueous phase, and formulation optimization may be needed to improve bioavailability. The blood-brain barrier has a relatively low penetration ability, suggesting its distribution in the central nervous system is limited, which helps reduce toxic side effects in the central nervous system. The hERG channel inhibition test results were negative, indicating that the compound carries a low risk of cardiotoxicity. The Ames-induced mutagenic test result was 0.6, indicating a low genotoxicity risk and good safety.

Plant Origins and Extraction Methods

6-Aldehyde-based Ophiopogon flavonoid A mainly comes from the Liliaceae plant Ophiopogon japonicus, which is widely used in traditional Chinese medicine for nourishing yin, moistening the lungs, clearing heat, and generating fluids. The rhizome of Isomaton contains abundant flavonoids and saponins, with 6-aldehyde isoOphiopogon flavonoid A being one of the important active components.

The extraction method typically uses organic solvent extraction combined with column chromatography separation technology. The specific steps include:

1. After crushing the dried Ophiopogon rhizome, reflux extraction is performed with ethanol or methanol, and the extract is concentrated to obtain the crude extract.
2. The crude extract was separated and purified by silica gel column chromatography or reversed-phase high-performance liquid chromatography (RP-HPLC).
3. Structural identification of purified products was performed using technologies such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).

In recent years, new technologies such as ultrasound-assisted extraction and supercritical fluid extraction have also been applied to extract this compound, improving extraction efficiency and purity.

Pharmacological activity research

Numerous in vitro and in vivo studies have shown that 6-aldehyde isomorphogon flavonoid A has significant antitumor activity, manifesting as inhibiting tumor cell proliferation, inducing apoptosis, blocking the tumor cell cycle, and inhibiting tumor invasion and metastasis.

Anti-tumor cell proliferation

6-Aldehyde isomorphogon flavonoid A can significantly inhibit the proliferation of various tumor cell lines (such as breast cancer, lung cancer, liver cancer, etc.), with IC_50 values generally below 10 μM. This action is closely related to its interference with cell cycle regulation of protein expression and can induce G1 or G2/M phase blockade.

Induces apoptosis

This compound promotes mitochondrial pathway-mediated cell apoptosis by regulating the expression of BCL2 family proteins (including the anti-apoptotic protein BCL2 and the pro-apoptotic protein MCL1). The activity of caspase-3 and caspase-9 related to apoptosis was significantly enhanced, suggesting that they exert cytotoxicity by activating endogenous apoptosis pathways.

Inhibits tumor invasion and metastasis

6-Aldehyde isomorphogon flavonoid A can downregulate the expression of matrix metalloproteinase MMP2, inhibiting tumor cell migration and invasion capabilities. Additionally, by inhibiting tumor-related signaling pathways, it reduces interactions between tumor cells and stroma, blocking the process of tumor metastasis.

Anti-tumor microenvironment regulation

This compound can inhibit the expression of the tumor hypoxia-inducing factor HIF1A, improve the hypoxia state of the tumor microenvironment, and reduce tumor cell drug resistance and invasiveness. At the same time, it regulates tumor-related inflammatory responses and enhances the immune system's ability to recognize and clear tumors.

Mechanism of action and molecular targets

The antitumor effects of 6-aldehyde isomypon flavonoid A involve multiple signaling pathways and molecular targets, reflecting its multi-target drug characteristics.

MCL1 and BCL2

As key anti-apoptotic proteins, MCL1 and BCL2 play important roles in tumor cell survival. 6-Aldehyde-based isomyotong flavonoid A disrupts mitochondrial membrane stability and induces apoptosis by downregulating the expression of MCL1 and BCL2.

STAT3 signaling pathway

STAT3 plays a central role in tumor cell proliferation, immune evasion, and drug resistance. This compound can inhibit the phosphorylation activation of STAT3, block its transcriptional activity, and reduce the proliferation and survival ability of tumor cells.

MMP2

MMP2 acts as a matrix-degrading enzyme in tumor cells, promoting tumor invasion and metastasis. 6-Aldehyde isomypon flavonoid A significantly inhibits the expression and activity of MMP2, reducing tumor cell migration ability.

TOP1 and TOP2A

DNA topoisomerases TOP1 and TOP2A play key roles in DNA replication and transcription. This compound blocks normal replication of tumor cell DNA by inhibiting the activity of TOP1 and TOP2A, inducing cell cycle arrest and apoptosis.

HIF1A

HIF1A regulates tumor hypoxia responses, promoting angiogenesis and metabolic reprogramming. 6-Aldehyde isomorphogon A inhibits HIF1A expression, improves the tumor hypoxic microenvironment, and reduces tumor drug resistance.

MAPK1 and ESR1

MAPK1 (ERK2) is involved in cell proliferation signaling, and ESR1 (estrogen receptor α) is especially important in breast cancer. This compound regulates MAPK1 and ESR1, helping to inhibit tumor cell proliferation and the development of hormone-dependent tumors.

CYP19A1

Aromatase CYP19A1 catalyze estrogen synthesis and promote hormone-dependent tumor growth. 6-Aldehyde isomyponic Flavonoid A exerts anti-breast cancer effects by inhibiting CYP19A1 activity, lowering estrogen levels.

Druggability evaluation and pharmacokinetics

The druggability parameters of 6-aldehyde-based isomypogon flavonoid A indicate that it has promising potential for drug development. A moderate LogP value indicates good membrane permeability. Low water solubility is a major challenge in drug formulation development, requiring improved solubility and bioavailability through technologies such as nanocarriers, liposomes, or solid dispersions.

The blood-brain barrier has a low penetration capacity, reducing the risk of central nervous system side effects. hERG channel inhibition negative, reducing the risk of cardiotoxicity. Ames trial results showed that it carries a low risk of genotoxicity and is relatively safe.

Pharmacokinetic studies show that this compound is absorbed orally quickly, has a moderate half-life, and is mainly metabolized by the liver. Its metabolic pathway mainly involves the CYP450 enzyme system, especially CYP3A4, suggesting a possible risk of drug interactions. It is widely distributed in the body, but its concentration in brain tissue is relatively low. Excretion is mainly through bile and urine.

Prospects and outlooks for clinical applications

Based on the significant antitumor activity and good safety shown by 6-aldehyde-based isomypon flavonoid A across various tumor cell lines, its future clinical development prospects are broad. It holds particular potential value in adjuvant therapy for common malignant tumors such as breast, lung, and liver cancer.

Future research should focus on the following aspects:

1. Dosage form development and route optimization: To address its poor water solubility, develop efficient delivery systems to improve bioavailability and targeting.
2. In-depth mechanistic research: Further clarifying its multi-target mechanisms, especially its interactions with the tumor immune microenvironment, providing theoretical support for combination therapy.
3. Pharmacokinetic and toxicology systematic evaluation: Comprehensive in vivo metabolism, distribution, and long-term safety assessments to ensure clinical drug safety.
4. Preclinical animal model validation: Validating anti-tumor efficacy and tolerability through various tumor animal models, promoting clinical trials.
5. Exploration of combination drug strategies: Combine existing chemotherapy drugs or immunomodulators to evaluate synergistic effects, enhance treatment efficacy, and reduce the occurrence of resistance.

Conclusion

6-Aldehyde-based isomypong flavonoid A, as a natural flavonoid compound with multi-target antitumor activity, demonstrates excellent pharmacological activity and drug development potential. By regulating tumor cell apoptosis, inhibiting invasion and metastasis, and improving the tumor microenvironment, it has become a strong candidate for anti-tumor drug development. In the future, through in-depth mechanistic research, dosage form optimization, and systematic pharmacokinetic and toxicological evaluations, it is expected to promote clinical translation and benefit a wide range of cancer patients.

With continuous advances in natural product pharmacology and modern medicinal chemistry technologies, research on 6-aldehyde isomypogon flavonoid A will provide valuable experience and new ideas for the development of natural flavonoid antitumor drugs, promoting innovation and application of natural products in tumor treatment.