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Natamycin powder is an organic compound with the chemical formula C33H47NO13 and CAS 7681-93-8. It is a nearly white or creamy yellow crystalline powder that is almost insoluble in ethanol and water, slightly soluble in methanol and N, N-dimethylformamide, and soluble in glacial acetic acid and dimethyl sulfoxide. When the pH value is above 9 or below 3, its solubility will increase, and it is very stable in the pH range of most foods.
Natamycin has a certain ability to resist heat treatment, is relatively stable in a dry state, and can withstand short-term high temperatures (100 ℃); However, due to its cyclic chemical structure and sensitivity to ultraviolet radiation, it is not suitable for contact with sunlight. The stability of natamycin activity is affected by pH value, temperature, light intensity, oxidants, and heavy metals, so the product should avoid contact with oxides and sulfur compounds. It is a natural antifungal compound produced by fermentation of Streptomyces, belonging to the class of polyene macrolides. It can effectively inhibit the growth of various molds and yeasts, as well as the production of fungal toxins. It can be widely used for food preservation and antifungal treatment.
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Natamycin powder is a macrolide antibiotic primarily produced through biosynthetic methods. The synthesis process involves multiple steps and complex biochemical reactions. The following are common synthesis methods for natamycin:
The biosynthetic pathway of natamycin
The biosynthesis of natamycin is mainly carried out through the genus Streptomyces, such as Streptomyces natalis and Streptomyces chatanuga. In this process, the polyketide pathway (PKS) plays a crucial role, generating lactone ring structures through condensation reactions.
The polyketide pathway is the core of natamycin biosynthesis, and its catalytic enzymes mainly include PKS class I polyketide synthase. These enzymes contain multiple modules, each with a specific catalytic domain, such as KS (keto synthase), AT (acyltransferase), ACP (acyl carrier protein), etc.
In Streptomyces natalis, the PKS pathway is catalyzed by a series of multifunctional enzymes (PimS0-PimS4). These enzymes are responsible for catalyzing the condensation of acetic acid and carboxylic acid units, forming the skeletal structure of natamycin.
PimS0: As the starting module, its KS domain is inactive, but CoA ligase ACP-KS-AT-ACP catalyzes the formation of acyl adenosine monophosphate from acetic acid, providing acetyl units for subsequent KS domains.
PimS1: Contains 4 modules that complete the first 4 cycles of skeleton chain extension and form the majority of polyene chromophores.
PimS2, PimS3, PimS4: Continue to catalyze the condensation of 8 carboxylic acid module units and perform appropriate structural modifications to form the skeleton of natamycin.
On the basis of the PKS pathway, post modifying enzymes further modify the skeleton structure to form the final natamycin molecule.
PimC, PimD, PimF, PimG, PimJ, and PimK: The proteins encoded by these enzymes are responsible for the post modification of the skeleton ring, such as forming the last double bond of the chromophore, introducing double bonds, and epoxy structures.
PimA, PimB, and PimH: The encoded proteins are responsible for the transport of natamycin, which is excreted from the extracellular space through the ABC transporter system.
PimT, PimE, PimM, and PimR: The encoded proteins are responsible for regulating the expression of natamycin synthesis genes.
The biosynthesis of natamycin involves multiple gene clusters, among which the most important are the Pim gene cluster and the SCN gene cluster.
Pim gene cluster: Contains genes encoding PKS enzymes, post modifying enzymes, and transporters. Compared with the SCN gene cluster, its main difference lies in the gene PimH encoding efflux pumps and the gene PimT encoding amino acid transporters.
SCN gene cluster: Contains genes related to natamycin synthesis, such as scnG (homologous to PimG) and scnL (encoding putative transposase).
Production process of natamycin
The production process of natamycin powder mainly includes steps such as strain cultivation, fermentation, extraction, purification, and drying. The following is a detailed explanation of these steps.
Select high-yielding strains, such as Streptomyces natalensis, for strain cultivation. Inoculate the bacterial strain into a culture medium, which typically includes glucose, sodium chloride, phosphate, etc., to provide the necessary nutrients for the growth and reproduction of the strain.
Mix the culture medium and bacterial strain, and ferment under suitable temperature, pH value, and stirring conditions. During the fermentation process, the strain metabolizes nutrients in the culture medium to produce natamycin.
Fermentation conditions typically include:
Temperature: 28-32 ℃
PH Value: Initial pH 7.3-7.6, Process Control pH 5.8-6.2
Ventilation rate: Initial ventilation rate 18-22m ³/min, 25-30m ³/min after 15 hours, 16-20m ³/min after 100 hours
Mixing speed: initial mixing speed 50-60rpm/min, 8-15 hours 70-80rpm/min, after 15 hours 100-120rpm/min
After fermentation, the fermentation broth is subjected to steps such as centrifugation, filtration, and ultrafiltration to remove bacterial cells and solid impurities, and obtain an extract containing it.
There may be other organic solvents and impurities present in the extraction solution, which require further purification. The purification process usually includes acid-base adjustment, solvent extraction, and anion exchange column chromatography.
Acid base adjustment: By adjusting the pH value of the extraction solution, natamycin is separated from other impurities.
Solvent extraction: Use organic solvents (such as ethanol, acetone, etc.) to extract the extract and improve the purity of natamycin.
Anion exchange column chromatography: using anion exchange resin for chromatographic separation of the extraction solution to further remove impurities.
Dry the purified natamycin solution to obtain the product. The drying method is usually spray drying or vacuum drying.
Spray drying: spray the natamycin solution into the hot air to evaporate the water rapidly to obtain powder products.
Vacuum drying: Heating and drying the natamycin solution under vacuum conditions to avoid oxidation and deterioration of the product.
Other synthesis methods
In addition to the traditional biosynthetic methods mentioned above, there are also other synthetic methods being studied and explored.
Chemical synthesis is a method of directly synthesizing natamycin powder or its analogues through chemical reactions. However, due to the complex structure and multiple chiral centers of natamycin, chemical synthesis methods are often difficult to obtain high-purity and high-yield products.
Fermentation chemical combination method is a method that combines biological fermentation and chemical synthesis. Firstly, crude or intermediate natamycin is obtained through fermentation, and then further modified and purified through chemical methods. This method can compensate for the shortcomings of biosynthesis in terms of yield and purity, but it also requires higher technological level and cost investment.
Genetic engineering is a method of increasing the yield and purity of natamycin through genetic recombination technology. By constructing high-yield strains of genetically engineered bacteria and optimizing their fermentation conditions, higher yields of natamycin can be obtained. In addition, the structure of it can be modified and optimized through genetic engineering methods to meet different application needs.
Natamycin is a natural, broad-spectrum, highly effective, and safe inhibitor of filamentous fungi such as yeast and mold. It not only inhibits fungi but also prevents the production of fungal toxins. Natamycin is harmless to the human body, difficult to be absorbed by the digestive tract, and microorganisms find it difficult to develop resistance. Additionally, due to its low solubility, it is commonly used for surface preservation of food. Biological preservatives.
Natamycin can prevent cheese from becoming moldy during ripening, thereby limiting the formation of mycotoxins. Because it is difficult to penetrate cheese and only stays on the surface of the cheese, it has an advantage in controlling the growth of mold on the surface of the cheese without affecting the ripening process of the cheese. There are three specific application methods:
(1) Spray 0.05% to 0.28% natamycin onto the surface of cheese products.
(2) Soak the salted cheese in a 0.05% to 0.28% concentration suspension for 2-4 minutes.
(3) Add 0.05% natamycin to the coating covering the cheese.
Mooncakes are rich in nutrients, and the skin, filling, and salted egg yolks often undergo mold growth. Natamycin has a good anti mold effect on mooncakes. When used, the spraying method is generally used: the Natamycin product is formulated into a suspension of 0.02% to 0.04%. After baking the mooncakes and cooling them to room temperature, the Natamycin suspension is sprayed on the surface, periphery, and bottom of the mooncakes to achieve external mold prevention.
Roast raw salted egg yolks in the oven until they are about 70-80% ripe, remove and cool them, then soak them in Natamycin suspension for about 2 minutes to prevent mold growth in the egg yolk filling.
Spraying 100-500ppm natamycin solution on the surface of baked goods such as cakes, white bread, and puff pastry, or spraying natamycin on the surface of unbaked dough, has an ideal anti-mold and preservation effect, without affecting the taste, texture or appearance of the product. Baked goods are prone to mold growth due to their high moisture and carbohydrate content, especially in humid environments.
The method of soaking or spraying meat products can achieve safe and effective mold prevention when using 4mg/cm2 natamycin. Soaking casings in natamycin powder suspension at a concentration of 0.05% to 0.2% (w/V), or using it to soak or spray the surface of sausages that have already been filled with fillings, can effectively prevent mold growth on the sausage surface. Grilled meat, roasted duck and other grilled products, as well as dried fish products, can also extend their shelf life by spraying a 0.05% to 0.1% (w/V) concentration of natamycin suspension.
5. Salad dressing
Salad dressing is a high-fat food that often experiences mold growth after the onset of summer each year. According to literature reports, adding 10ppm natamycin to salad dressing did not cause any deterioration during the experiment, and there was no significant change in microbial count. Salad dressing is similar to cheese and has a higher fat content. Experiments have shown that natamycin has a definite antibacterial effect on high-fat foods.
Soy sauce is a fermented condiment with high water activity, which is prone to yeast growth and "white flowers" (yeast film) on the surface during high-temperature summer, affecting its quality and edible safety.
Adding 15ppm natamycin to soy sauce during the high temperature summer can effectively inhibit the growth and reproduction of yeast and prevent the appearance of white flowers. Combining natamycin and lactobacillus streptomycin for soy sauce mold prevention can achieve a synergistic antibacterial effect, which not only effectively inhibits bacteria and mold, but also reduces the concentration of a single preservative, improving the safety and acceptability of soy sauce.
Due to the high sugar and organic acid content in various fruit juices, they are very suitable for the growth and reproduction of yeast, which can cause spoilage and deterioration of the juice.
The use of natamycin can increase the storage stability of non-alcoholic beverages. The application of 20ppm natamycin in grape juice can prevent juice fermentation caused by yeast contamination, and adding 100ppm can completely terminate fermentation activity. Orange juice, due to fungal contamination under natural conditions, usually spoils after one week of storage. With the addition of natamycin, even at a dose as low as 1.25 ppm, the shelf life can be as long as 8 weeks when stored at 2 ° C to 4 ° C. The antibacterial effect of natamycin is related to the storage temperature. Concentrated orange juice stored at 10 ℃ can inhibit yeast growth at 10ppm; Storing at room temperature requires 20ppm natamycin to have antibacterial effect.
The 30ppm natamycin in apple juice can prevent fermentation for up to 6 weeks, and the original flavor of the juice remains unchanged. Natamycin at a concentration of 70mg/kg in tomato juice has a good anti mold and preservation effect on tomato juice.
The application in rice cakes and Mantou can prevent mildew and effectively extend the shelf life. Natamycin used in condiments such as vinegar can prevent spoilage caused by mold and yeast. In beer and wine, 2.5mg/kg natamycin can greatly extend the shelf life.
The product is used to treat fungal infections, including Candida, Aspergillus, and Fusarium, and is also used in eye drops or oral medications. In these applications, the human body absorbs less natamycin. When taken orally, it is hardly absorbed from the gastrointestinal tract, making it unsuitable as a systemic infectious drug. Natamycin is also used in eye drops, with a 5% content suitable for treating fungal blepharitis, conjunctivitis, and keratitis caused by microorganisms, including Fusarium oxysporum keratitis.
Natamycin powder, as a broad-spectrum, efficient, and safe antifungal agent produced by fermentation of Streptomyces natalis and other microorganisms, has shown broad development prospects in multiple fields. The following is a detailed analysis of its development prospects:
Market demand growth：With the increasing concern of consumers for food safety and health, the requirements for food preservatives are also becoming higher and higher.
Technological progress and industrial upgrading：With the continuous development of biotechnology, the fermentation process of natamycin will be further optimized, increasing yield and reducing production costs.
Policy support and international cooperation：Governments around the world are increasingly emphasizing food safety and health, and will introduce more policy measures that are conducive to the development of natural preservatives such as natamycin.
Market Challenges and Response Strategies：With the continuous expansion of the natamycin market, competition will become increasingly fierce.
I. Discovery and Nomenclature (1950s)
In 1954, Dutch scientist Jacques Waisvisz isolated Streptomyces natalensis from soil near Pietermaritzburg in Natal, South Africa. In 1955, the research team led by A.P. Struyk first extracted an antifungal active substance from the fermentation broth of this strain, which was named Pimaricin in 1957, derived from the name of the local discovered city.
In 1959, American researchers obtained Tennecetin from Streptomyces chatanoogensis separated from Tennessee soil, which was later confirmed to be identical to pimaricin. In the 1960s, the World Health Organization (WHO) uniformly designated the compound as Natamycin, standardizing the naming criteria for antibiotics derived from Streptomyces.
II. Structural Analysis and Mechanism Research (1960s–1980s)
In 1966, scholars identified the 26-membered macrolide tetraene structure of natamycin. Its stereochemical configuration was fully elucidated in 1990, clarifying the molecular basis for binding with sterols in fungal cell membranes. In 1978, the U.S. FDA approved natamycin for clinical antifungal treatment, including infections caused by Candida and Aspergillus. In 1982, it was further recognized as GRAS (Generally Recognized As Safe), permitting its application as a food preservative in cheese and other food commodities.
III. Industrialization and Global Application Expansion (1990s–2000s)
In 1997, the Chinese Ministry of Health approved natamycin as a food preservative and incorporated it into the GB 2760 national standard. During this period, continuous optimization of fermentation technology, including strain mutagenesis and fermentation parameter regulation, greatly increased production yield and reduced manufacturing costs, promoting its widespread use in dairy products, meat products and baked foods. After 2000, natamycin was included in the WHO List of Essential Medicines, establishing it as one of the core natural agents for global antifungal therapy and food preservation.
IV. Technological Upgrading and Emerging Application Exploration (2010s–Present)
In recent years, synthetic biology has been applied to modify Streptomyces strains, effectively improving the fermentation efficiency and product purity of the product. Its application scope has expanded from traditional food preservation and ophthalmic antifungal therapy to feed mildew prevention and daily chemical antibacterial fields. Meanwhile, researches on nano-delivery systems and compound formulations are constantly advancing, aiming to enhance its bioavailability and application adaptability, and further consolidate its core position in the field of natural antifungal agents.
FAQ
Is natamycin in food safe?
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Natamycin is generally considered safe to eat and is approved by the FDA and WHO as a natural preservative, often used in dairy and meats to prevent mold. While it has a high safety profile, it is an antifungal medication, and some, including Whole Foods, ban it due to concerns about high-level consumption.
What is the toxicity of natamycin?
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Safety. Natamycin does not have acute toxicity. In animal studies, the lowest LD 50 found was 2.5–4.5 g/kg.
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