Glucosinolates

Glucosinolates is degraded to isothiocyanate, thiocyanate, nitrile and other degradation products by its degradation enzyme, myrosinase, which protects the plant from insects and some pathogenic bacteria. In addition, these degradation products also have strong anti-cancer activity, which is beneficial to human health. With increasing research into their chemical structures, biosynthesis pathways, and potential applications, glucosinolates are a cornerstone in the fields of natural product chemistry, biochemistry, and applied health sciences. BOC Sciences offers high-quality glucosinolates products, as well as extraction and synthesis services, catering to both research and industrial needs.

What are Glucosinolates?

Cruciferous plants such as broccoli, rape, and mustard have been shown to have many health benefits, thanks to the fact that cruciferous plants are rich in glucosinolates, a secondary metabolite of sulfide, whose degradation produces isothiocyanates (ITCs) that have been shown to have antioxidant, gastrointestinal cancer-preventive, and other properties. and other functions. Under normal conditions, thioglucoside exists in inert form in plant vesicles, while black mustard enzyme, an enzyme capable of degrading it to produce active substances, exists in the cytoplasm of plant cells. When the plant is chewed by insects or ingested by human beings, the thioglucoside will be released, and active ITCs will be produced through the degradation of black mustard enzyme. ITCs can help plants to kill insects and antimicrobials, so thioglucosides are very important for plants and human health. However, black mustard enzyme will be inactivated under high temperature, so in vegetables treated with high temperature, black mustard enzyme has lost its activity, and the human body can only obtain active ITCs through the metabolism of GSs by intestinal symbiotic bacteria.

Glucosinolates Examples

More than 130 distinct glucosinolate structures have been identified, with a variety of side chains that define their chemical and biological properties. Some of the most well-known glucosinolates include:

• Sinigrin: Found in mustard and horseradish, sinigrin is a precursor to allyl isothiocyanate, a compound known for its pungent aroma and antimicrobial properties.
• Glucoraphanin: Present in broccoli and related vegetables, glucoraphanin is converted into sulforaphane, a potent inducer of Phase II detoxification enzymes, which plays a role in cancer prevention.
• Progoitrin: Predominantly found in turnips and cabbage, progoitrin is metabolized into goitrin, a substance that can impact thyroid function when consumed in large quantities.

Each glucosinolate has its own distinct profile of biological activities, which vary based on the side chain structure and how it is metabolized.

Glucosinolate Structure

The fundamental structure of glucosinolates consists of a β-D-glucose unit linked to a thiohydroximate-O-sulfonate group. This structure is attached to a variable side chain that is derived from an amino acid. The chemical composition of the side chain determines the specific properties and biological activities of each glucosinolate. The side chain may be aliphatic, aromatic, or indolic, and this variation is key in influencing how the glucosinolate behaves both within the plant and when metabolized in the human body. The chemical diversity of glucosinolates allows for their broad range of applications in agriculture, health, and nutrition.

Structural formula of Glucosinolate(GLs). (Abdel-Massih, R.M.; et al, 2023)

Glucosinolates in Plants

Glucosinolates are primarily concentrated in cruciferous plants such as cabbage, broccoli, cauliflower, kale, and mustard. These plants are part of the Brassicaceae family, which is characterized by its high glucosinolate content. Glucosinolates are stored in vacuoles within the plant's cells and are typically concentrated in roots, seeds, and leaves. In some species, they are also found in specific idioblasts or specialized plant cells that are distinct from the surrounding tissue.

Glucosinolates in Plant Defense Mechanisms

Glucosinolates play an important role in plant defense mechanisms, particularly against herbivores, pathogens, and pests. Upon damage to the plant tissue—whether by herbivory or physical injury—glucosinolates are hydrolyzed by the enzyme myrosinase, producing toxic breakdown products such as isothiocyanates (ITCs), nitriles, and epithionitriles. These breakdown products are deterrents to herbivores and exhibit antimicrobial properties that protect the plant from pathogens and diseases.

Glucosinolate Metabolism

• The Myrosinase-Glucosinolate System: The myrosinase-glucosinolate system is central to the biological activity of glucosinolates. In their intact form, glucosinolates are inactive, but when plant tissue is damaged, myrosinase, an enzyme stored separately in plant cells, hydrolyzes glucosinolates into bioactive compounds, such as isothiocyanates (ITCs), nitriles, thiocyanates, and indole-3-carbinol. Isothiocyanates, especially, exhibit antimicrobial, anticancer, and antioxidant properties, often through the induction of Phase II detoxification enzymes that enhance carcinogen elimination.
• Factors Influencing Metabolism: The metabolism of glucosinolates is influenced by factors like pH, iron ions (Fe²⁺), and plant proteins such as the epithiospecifier protein (ESP). Low pH and the presence of iron favor nitrile formation, while neutral pH supports ITC production. The glucosinolate side chains also play a key role in determining the breakdown products.

Glucosinolate Synthesis

Glucosinolate Biosynthesis

The biosynthesis of glucosinolates occurs through a multistep pathway in plants, primarily in the endoplasmic reticulum. The process begins with the amino acid precursors, which are then modified to form a sulfur-containing structure that is characteristic of glucosinolates. The pathway can be divided into several stages, including:

• Amino acid modification: The amino acid methionine is often the precursor for the synthesis of glucosinolates. Other amino acids, such as tryptophan and phenylalanine, also contribute to the diversity of side chains in glucosinolates.
• Sulfation: The sulfur atoms in glucosinolates are introduced at this stage. This is a crucial step, as sulfur is key to the biological activity of glucosinolates.
• Attachment of side chains: The side chains, which can be alkyl, alkenyl, or indole, are added at this stage. These side chains greatly influence the properties and biological effects of the glucosinolate.
• Final assembly: The modified amino acids are assembled into the final glucosinolate structure, which is then stored in vacuoles.

This complex biosynthesis pathway ensures that plants can produce a wide variety of glucosinolates, each with distinct biological and chemical properties.

Glucosinolates Extraction

The extraction of glucosinolates from plant material is a challenging process due to their hydrophilic nature. Conventional extraction methods, such as solvent extraction or steam distillation, often fail to provide high yields of glucosinolates due to their solubility and stability in aqueous environments. As a result, more sophisticated techniques are being explored to improve efficiency and scalability.

One such method is ultrasound-assisted extraction (UAE), which uses high-frequency sound waves to disrupt plant tissues and release glucosinolates more effectively. Another promising technique is microwave-assisted extraction (MAE), which employs microwave radiation to rapidly heat and break down plant tissues, facilitating glucosinolate extraction.

Despite these advancements, the extraction of pure glucosinolates at an industrial scale remains a challenge due to the need for high-purity extraction processes and the substantial costs associated with these techniques. BOC Sciences continues to innovate and optimize extraction methods to ensure the scalability of glucosinolate production.

Glucosinolates Benefits

Anticancer Properties

Glucosinolates, particularly isothiocyanates (ITCs), are known for their anticancer effects. ITCs induce apoptosis and inhibit cell cycle progression in cancer cells. They also activate Phase II detoxification enzymes, helping to eliminate carcinogens from the body.

Antimicrobial and Antifungal Activities

Glucosinolates and their breakdown products, such as ITCs, have antimicrobial properties, inhibiting bacteria like E. coli and Salmonella and demonstrating fungicidal effects against plant pathogens. These qualities make glucosinolates useful in food preservation and crop protection.

Anti-inflammatory and Antioxidant Effects

Glucosinolates also exhibit anti-inflammatory and antioxidant effects. Breakdown products like indole-3-carbinol and ITCs reduce pro-inflammatory cytokines and oxidative stress, contributing to the prevention of chronic diseases such as arthritis and cardiovascular issues.

Applications of Glucosinolates

Pharmaceutical and Nutraceutical Applications

In the pharmaceutical and nutraceutical industries, glucosinolates are incorporated into products for their anticancer, antimicrobial, and anti-inflammatory properties. ITCs, indole-3-carbinol, and other glucosinolate derivatives are being investigated as dietary supplements for the prevention of chronic diseases and for use as pharmaceutical agents in cancer therapy.

Agricultural Applications

The antimicrobial and pest-repellent properties of glucosinolates make them valuable in agriculture. Glucosinolates are used as natural pesticides and biofumigants to control soilborne diseases and pests. For example, mustard seeds, which are rich in glucosinolates, are used to fumigate soil and suppress the growth of harmful pathogens. This eco-friendly approach reduces the need for chemical pesticides, which have harmful environmental impacts.

Food Industry Applications

In the food industry, glucosinolates and their breakdown products are valued for their health-promoting effects. They are often included in functional foods and supplements due to their anticancer, antioxidant, and anti-inflammatory properties. BOC Sciences provides high-quality glucosinolate derivatives for the development of functional food products aimed at enhancing human health.

Advantages of BOC Sciences' Glucosinolates

At BOC Sciences, we are committed to providing high-quality glucosinolates that meet the evolving needs of research, industry, and health applications. Our expertise in natural product synthesis, extraction techniques, and biosynthesis pathways positions us as a leading supplier of glucosinolates with distinct advantages over other providers in the market.

• High Purity and Consistency: BOC Sciences provides glucosinolates with unmatched purity, achieved through optimized extraction and purification methods. This ensures reliable and reproducible results, meeting strict pharmaceutical and agricultural standards.
• Diverse Product Range: We offer a wide array of glucosinolates and breakdown products, including ITCs, indole-3-carbinol, and nitriles. Custom synthesis services allow for tailored compounds to meet specific research needs, ensuring flexibility for various applications.
• Cost-Effective Solutions: Our large-scale production and optimized processes provide high-quality glucosinolates at competitive prices, passing savings to customers without compromising quality or efficacy.
• Expert Support and Customization Services: BOC Sciences offers expert support for formulation development, biosynthesis optimization, and application guidance, assisting clients in achieving their research and product development goals.

• Phenylpropanoids
• Triterpenoids
• Other Terpenoid
• Impurities
• Lignans
• Other Quinones