N-Butylidenephthalide – All About Its Structure, Mechanism of Action, and Bioactivity

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N-Butylidenephthalide – All About Its Structure, Mechanism of Action, and Bioactivity

N-Butylidenephthalide is obtained from a chloroform extract of Angelica Sinensis, a Chinese plant. ((Z)-Butylidenephthalide, 3-Butylidenephthalide, Butylidenephthalide) is how it’s spelled.

It aids in various biological functions, including angina reduction, platelet aggregation, proliferation, and non-specific spasmodic.

Structure of N-Butylidenephthalide

3-Butylidene-2-benzofuran-1-one is the IUPAC name for this chemical molecule. It’s a yellow liquid with a strong warm spicy fragrance. It is water-insoluble but soluble in oils and ethanol.

It also has 3-butylidene-1(3H)-isobenzofuranone,3-butylidenephthalide Butylidenephthalide and n-butylidenephthalide.

It has the chemical formula C12H12O2 and a molecular weight of 188.22. It eeps a density of 1.103 g/mL at 25 °C and may be kept as a liquid for up to 2 years at -20 °C in the dark.

n butylidenephthalide
Source: PubChem.Com

How N-Butylidenephthalide is Useful Bioactive Compound?

Among all functional chemicals in Chinese medicinal herbs such as Angelica Sinensis, Ligusticum chuanxiong, and Cnidium Officinale n-butylidenephthalide (BP) is more particular

3-Butylidenephthalide is a phthalide derivative that can treat sensory and olfactory disorders. It exhibits anti-tumour, anti-antiangiogenic, and anti-metastasis properties.

The effects of n-butylidenephthalide have been found to stop cell growth and start apoptosis in glioblastoma cells. Orphan nuclear receptor expression is increased by n-butylidenephthalide.

How Does N-butylidenephthalide Impact Human Bladder Cancer Cells?

Bladder cancer is a prevalent malignancy in the United States and many other countries. According to previous research, around 30% of newly diagnosed superficial bladder tumours are multifocal.

60–70% of these superficial bladder tumours, however, recurred. At the same time, 10–20 per cent of them would proceed to a muscle-invasive or metastatic illness at some point. Chemotherapy and other systemic treatments for bladder cancer have a limited effect.

Although platinum-based chemotherapy is routinely used to treat bladder cancer, invasive bladder cancer requires major cystectomy and systemic chemotherapy.

In most cases, these therapy regimens fail 95 per cent of the time. At least half of invasive bladder cancer patients die of metastases within two years after diagnosis, with a 5-year survival rate of fewer than 10%.

N-butylidenephthalide (BP), derived from Radix Angelica Sinensis (Danggui), has anti-tumorigenic properties in various cancer cells in vivo and in vitro.

The effects of Angelica Sinensis on bladder cancer patients were studied using Taiwan’s National Health Insurance Research Database (NHIRD) database.

The anti-proliferative impact of BP on human bladder cancer cells was examined, and flow cytometry was used to evaluate their cell cycle patterns following BP therapy.

N-butylidenephthalide (BP) caused bladder cancer cells to die by activating the intrinsic mitochondrial route. BP also stopped these cells from migrating and invading, most likely affecting EMT genes.

Additionally, combining BP with a lower cisplatin dosage decreased the development of these bladder cancer cell lines considerably.

Patients exposed to Angelica Sinensis had a lower incidence of bladder cancer, suggesting that BP can act as an adjuvant in treating bladder cancer.

However, the role of blood pressure in bladder cancer therapy is yet unknown, and more research is needed.

Does N-butylidenephthalide Have Antitumor Effects in Glioblastoma Multiforme?

Glioblastoma (GBM) is a fast-growing and severe brain tumour known as a grade IV astrocytoma. It infiltrates surrounding brain tissue but does not usually spread to other organs.

Despite advances in surgical procedures, treatments, and radiotherapies, the prognosis for this kind of disease is still grim. The majority of patients die within 12–18 months of being diagnosed. However, only a tiny number of patients with glioblastoma multiforme survive for three years or more.

In glioblastoma, n-Butylidenephthalide (BP) shows antitumor properties. To safeguard the structure of BP, a polycationic liposomal polyethyleneimine (PEI) and polyethene glycol (PEG) complex (LPPC) has been created.

In a research study, Tumor-bearing xenograft mice were treated with BP and BP/LPPC, and their tumour growth, survival, and drug biodistribution were assessed.

Tumour-bearing rats were also given BP and BP/LPPC. Their tumour sizes were measured using magnetic resonance imaging to assess the blood-brain barrier (BBB) and therapeutic medication effects.

Cell uptake, cell cycle, and apoptotic regulators were examined after patients treated with BP/LPPC in vitro to determine the therapeutic process.

BP/LPPC effectively suppressed tumour development and prolonged life in athymic mice. BP/LPPC was shown to pass the blood-brain barrier, resulting in tumour reduction.

Cell cycle arrest in the G 0/G 1 phase was induced by BP/LPPC, which triggered extrinsic and intrinsic cell apoptosis pathways, resulting in cell death.

BP/LPPC was swiftly and efficiently delivered to the tumour location across the BBB, causing cell apoptosis, anti-angiogenic, and anti-metastatic effects both in vivo and in vitro.

Is n-Butylidenephthalide (BP) Helpful in Maintaining Stem Cell Pluripotency and Cells Regeneration?

Stem cells are already being employed in a variety of clinical medicinal applications. Leukaemia, haemophilia, and anaemia are treated using a mix of hematopoietic stem cells (HSCs) and transplanted bone marrow.

Mesenchymal stem cells (MSCs) react to ischemia or injury and revascularization processes.

Embryonic stem cells (ESCs), pluripotent cells produced from the inner cell masses of mammalian blastocysts, can differentiate into embryonic endodermal, mesodermal, and ectodermal cells.

Because of their characteristics to self-renew and differentiate into various specialized cell types, ESCs are thought to have a lot of potential for therapeutic cell treatments.

Human and mouse fibroblasts can make induced pluripotent stem (iPS) cells. Proliferation, morphology, gene expression, surface antigens, the epigenetic state of pluripotent cell-specific genes, and telomerase activity are all identical to ESCs.

The pluripotency of ES and iPS cells makes them interesting candidates for tissue repair and replacement treatments. Still, the inefficiency of reprogramming basic human cells renders patient-specific iPS cells challenging to create from a small starting population.

Since n-Butylidenephthalide (BP) was shown to have a high antitumoral impact in vitro and in vivo, it has been used to stop the development and apoptosis of malignant brain tumours.

While these data suggest that BP might be used as an anticancer agent in clinical settings, nothing is known about how BP affects stem cell activity.

A new study was undertaken to see if a purified component isolated from a traditional Chinese medication may sustain ES and iPS cell pluripotency while boosting the efficiency of iPS cell production.

The study aimed to see if either n-Butylidenephthalide (BP) or Jak2 and Stat3 activation can keep ES and iPS cells pluripotent. According to the findings, the cells retained pluripotency and could develop into three germ layers.

The findings showed that BP might be used instead of LIF in ES cell cultures to keep cells pluripotent following passage.

Is n-Butylidenephthalide (BP) Helpful in Parkinson’s Disease?

Parkinson’s disease (PD) is the second most occurred degenerative central nervous system, affecting motor abilities and cognitive function. Movement problems, such as muscular stiffness, bradykinesia, and tremors, are visible signs of Parkinson’s disease.

However, behavioural and cognitive issues such as dementia, depression, anxiety, and sleep disorders are also present in the latter stages of the illness. There are no effective treatments for the condition currently.

Recent research has focused on finding new medications that might help individuals with Parkinson’s disease halt their deterioration.

However, the long time it takes for neurodegeneration in Parkinson’s disease to occur increases the time and cost of testing possible therapeutic agents in animal models.

A research study was done to see if n-butylidenephthalide might be utilized as a preventative or adjuvant agent for its beneficial effects on Parkinson’s disease.

These findings provide information to traditional Chinese medicine practitioners on using n-butylidenephthalide-containing herbs to treat neuron-related illnesses.

This commonly accessible chemical makes it possible to change the survival and function of DA neurons at a cheap cost and effectiveness.

To explore the innovative antiparkinson potential of n-butylidenephthalide in the prevention and treatment of PD, more research into the specific mechanism by which n-butylidenephthalide preserves DA neuron function in different animal PD models is needed.

Does n-butylidenephthalide Help to Inhibit Angiogenesis?

Angiogenesis is the synthesis of new blood vessels from existing blood vessels. Excessive, inadequate, or aberrant angiogenesis has been shown to contribute to the pathophysiology of cardiovascular illnesses in recent years (CVDs).

Angiogenesis modulation using angiogenesis inhibitors or stimulators thus becomes a promising technique for treating CVDs.

Radix Angelica Sinensis (also known as Bangui or dong Quai) is a traditional Chinese medicine commonly used in composite formulas to treat Asia’s cardiovascular disease and gynaecological dysfunction.

Radix A. Sinensis has previously been shown to have anti-atherosclerotic, cardioprotective, and endothelial-protective properties.

The alkylphthalide n-butylidenephthalide (BP), produced from the volatile oil of Radix A. Sinensis (VOAS), has antiplatelet, anti-anginal, and anticancer properties.

The effects of Radix A. Sinensis (VOAS) and n-butylidenephthalide (BP), one of the bioactive components in VOAS, on angiogenesis in vitro and in vivo were examined in the current research work.

On Matrigel, VOAS inhibited human umbilical vein endothelial cell proliferation, migration, and capillary-like tube formation, suggesting that it had anti-angiogenic actions. Anti-angiogenic properties of BP were discovered by reduction of cell cycle progression and promotion of apoptosis.

According to further research, BP suppressed endothelial sprouting in an ex vivo mouse aortic ring model and was a powerful inhibitor of the growth of zebrafish subintestinal arteries in vivo.

Frequently Asked Questions (FAQs):

Q. Does N-Butylidenephthalide Act as An Anticancer Drug?

A. Hepatoma, brain tumours, and colon cancer are all inhibited by N-Butylidenephthalide (BP), a natural compound. The action of BP is quickly lost following dissolving in an aqueous solution due to its fragile structure.

Q. What Is the Purpose of Using Angelica Sinensis?

A. The dried root of Angelica Sinensis (Danggui) enriches the blood, increases blood circulation, and modifies the immune system in Chinese medicine. It’s also used to treat persistent constipation in the aged and disabled and menstruation irregularities.

Q. Is Angelica Sinensis Is Same as Danggui?

A. Dong Quai, or Angelica Sinensis, is a fragrant shrub with a cluster of little white blooms. Carrots and celery are in the same botanical family as the flower. Its root is dried and used medicinally in China, Korea, and Japan. For almost 2,000 years, Dong Quai has been utilized as herbal medicine.

Q. What Is the Use of Stem Cells?

A. Stem cells are already being used in several clinical therapeutic applications. Hematopoietic stem cells (HSCs) and transplanted bone marrow are used to treat leukaemia, haemophilia, and anaemia.

Q. Is N-Butylidenephthalide Helpful In Bladder Cancer?

A. Angelica Sinensis-exposed patients had a decreased risk of bladder cancer, suggesting that BP might be an adjuvant in treating bladder cancer.

Q. What Is Glioblastoma GBM?

A. Glioblastoma (GBM), a grade IV astrocytoma, is a fast-growing and aggressive brain tumour. It infiltrates the brain’s surrounding tissue but seldom spreads to other organs.

Despite advancements in surgical techniques, treatments, and radiotherapies, the prognosis for this kind of cancer remains bleak.

The Bottom Line

Angelica root has been utilized in Europe and East Asia for millennia as a traditional herbal treatment. The two species of angelica are Angelica archangelica and Angelica Sinensis. The most important organic component recovered from the plant of potential advantages has been N-Butylidenephthalide.

The chemical has also been examined and shown to have a wide range of medicinal properties. It has antitumor properties and is involved in cell apoptosis. It has anti-proliferative properties.

It has also shown promising pharmacological outcomes in treating Parkinson’s disease. So far, the medication has shown to have significant therapeutic benefits. In any case, the breadth is broad, and much more research is required.

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