Steroids and Terpenes

In the diverse and fascinating world of biochemistry, steroids and terpenes represent two distinct yet interconnected classes of organic compounds with profound significance in biology, medicine, and industry. Creative Enzymes offers a wide range of high-quality steroids and terpenes to meet the diverse needs of your applications. With a commitment to innovation and excellence, we ensure that our products meet the highest standards of purity and potency.

Steroids: Structural Powerhouses of Biological Systems

Steroids are a class of organic compounds characterized by a tetracyclic skeleton consisting of three six-membered rings and one five-membered ring. Despite their structural uniformity, steroids are remarkably versatile, with minor modifications resulting in profound biological diversity.

Figure 1: (a) The four-fused-ring steroid skeleton uses letter designations for each ring and the numbering of the carbon atoms. (b) The cholesterol molecule follows this pattern.

Biosynthesis and Core Structure of Steroids

Steroids are synthesized from squalene, a triterpene precursor, via the intermediate lanosterol in animals and cycloartenol in plants. These pathways converge into cholesterol, the primary steroid scaffold in vertebrates. Cholesterol serves as the precursor for a variety of bioactive steroids, including hormones, bile acids, and vitamin D derivatives.

Classification and Functions of Steroids

Steroids can be broadly categorized based on their physiological roles:

• Steroidal Hormones: These include corticosteroids like cortisol, which regulate inflammation and immune response, and sex hormones like testosterone and estrogen, which influence reproduction and secondary sexual characteristics.

Figure 2: Structures and interconversion of the sex-steroids progestagens (green), estrogens (red), and androgens (blue) starting from cholesterol. Arrows indicate metabolizing processes by respective enzymes (gray). CYPs, cytochrome P-450 enzymes; HSD, hydroxysteroid dehydrogenase; SULT, sulfotransferase. (Chatuphonprasert et al., 2018)

• Sterols: Cholesterol, phytosterols, and ergosterols play essential roles in maintaining cell membrane integrity and fluidity.

Figure 3: Structure of major phytosterols. (Shen et al., 2024)

• Bile Acids and Salts: Synthesized in the liver, bile acids like cholic acid facilitate the emulsification and absorption of dietary fats.

Figure 4: Conversion of cholesterol to bile salts and further metabolism of bile salts by bacteria in the intestines. (Brody, 1999)

Physiological Significance of Steroids

Steroids exert their effects primarily by interacting with specific receptors, often acting as ligands for nuclear receptors that modulate gene expression. For example, the binding of cortisol to glucocorticoid receptors initiates transcriptional cascades critical for metabolic homeostasis. Similarly, estrogen interacts with estrogen receptors to influence developmental processes and reproductive health.

Applications of Steroids

Pharmaceutical Industry

• Hormone Replacement Therapy: Synthetic steroids like estrogens, androgens, and corticosteroids are widely used in hormone replacement treatments, addressing conditions such as menopause, hypogonadism, and adrenal insufficiency.
• Anti-inflammatory Drugs: Corticosteroids, such as prednisone and dexamethasone, are pivotal in managing autoimmune diseases, allergies, and inflammatory disorders.
• Cancer Therapy: Steroid-based compounds such as tamoxifen and aromatase inhibitors are used to treat hormone-responsive cancers such as breast and prostate cancer.

Biotechnology and Research

• Cell Biology and Membrane Studies: Cholesterol and its derivatives are critical in understanding cell membrane dynamics and signaling pathways.
• Drug Discovery: Steroids serve as lead molecules for designing novel therapeutic agents, especially for conditions such as osteoporosis, metabolic disorders, and neurological diseases.
• Tissue Engineering: Steroidal compounds are used in the development of biomimetic scaffolds to promote tissue regeneration.

Agriculture

• Plant Growth Regulators: Brassinosteroids, a class of plant steroids, are applied to enhance crop yield, stress tolerance, and resistance to pathogens.
• Veterinary Medicine: Steroid formulations help improve animal growth rates and treat hormonal imbalances in animals.

Sports and Fitness Industry

• Performance Enhancement: Anabolic steroids are controversially used to enhance muscle growth, strength, and athletic performance, although this use is strictly regulated.

Terpenes: Nature's Fragrant Architects

In stark contrast to the rigidity of the steroid nucleus, terpenes exhibit a vast structural and functional diversity. Synthesized from isoprene units (C5H8), these hydrocarbons are ubiquitous in nature and are often associated with the distinctive aromas and flavors of plants.

Biosynthesis and Classification of Terpenes

The biosynthesis of terpenes occurs via the mevalonate pathway or the methylerythritol phosphate (MEP) pathway, depending on the organism and cellular compartment. Through these pathways, isoprene units are assembled into larger molecules, leading to the classification of terpenes based on the number of isoprene units:

• Monoterpenes (C10): Examples include limonene and menthol, often associated with essential oils.
• Sesquiterpenes (C15): Compounds like farnesene and humulene contribute to the aromatic profiles of hops and spices.
• Diterpenes (C20): Molecules such as retinoids and gibberellins play vital roles in vision and plant growth, respectively.
• Triterpenes (C30): Squalene, the precursor to steroids, falls into this category.
• Tetraterpenes (C40): Carotenoids like β-carotene are crucial for photosynthesis and as dietary antioxidants.

Figure 5: Terpene: classification A) and examples of monoterpenes B), sesquiterpenes C), diterpenes D), triterpenes E). (Adamczyk, 2016)

Ecological and Biological Roles of Terpenes

Terpenes serve as signaling molecules, defense compounds, and metabolic intermediates:

• Plant Defense: Many terpenes act as natural insect repellents or pollinator attractants. For example, pyrethrins, insecticides derived from monoterpenes, protect plants from herbivory.
• Antimicrobial Properties: Sesquiterpenes like artemisinin exhibit potent antimalarial activity, underscoring their medicinal potential.
• Physiological Regulation: In humans, diterpene derivatives such as retinoic acid regulate cellular differentiation and embryonic development.

Applications of Terpenes

Pharmaceuticals

• Drug Precursors: Terpenes such as artemisinin (anti-malarial) and paclitaxel (anti-cancer) are critical active compounds in modern medicine.
• Anti-inflammatory and Antimicrobial Agents: Terpenes like menthol and limonene exhibit potent anti-inflammatory, analgesic, and antimicrobial properties.
• Neuroprotective Agents: Certain terpenoids, such as cannabinoids (derived from terpenes), are used in the treatment of neurological disorders such as epilepsy and multiple sclerosis.

Figure 6: Reported and traditional therapeutic application of terpenes and terpenoids. (Kumar et al., 2022)

Food and Beverage Industry

• Flavor and Fragrance Enhancers: Monoterpenes (e.g., limonene, pinene) are widely used to create natural flavors and fragrances in foods and beverages.
• Nutritional Supplements: Terpenoids such as carotenoids (e.g., β-carotene, lutein) are added to enhance the nutritional value and antioxidant properties of food products.

Cosmetics and Personal Care

• Aromatherapy and Essential Oils: Terpenes form the basis of essential oils, which are used for stress relief, relaxation, and wellness.
• Skin Care Products: Terpenes such as squalene and β-caryophyllene are incorporated into moisturizers, sunscreens and anti-aging products for their moisturizing and anti-inflammatory properties.

Agriculture

• Natural Pesticides and Herbicides: Terpenes such as pyrethrins and limonoids are used as environmentally friendly pesticides.
• Plant Resistance: Terpenes enhance the natural defense mechanisms of crops against pests and environmental stress.

Industrial Applications

• Biofuels: Terpenes are being explored as sustainable alternatives to fossil fuels due to their high energy density and renewable nature.
• Solvents and Cleaning Agents: Limonene is widely used in environmentally friendly cleaning products and solvents.
• Polymer and Resin Production: Terpenes such as colophony and turpentine are key materials in adhesives, paints and coatings.

Biotechnology and Research

• Drug Delivery Systems: Terpenes enhance drug solubility and bioavailability, making them useful in developing advanced delivery systems.
• Synthetic Biology: Terpenes serve as model molecules for designing synthetic pathways and engineering metabolic systems for sustainable production.

Figure 7: Potential industrial applications of terpenoids. (Câmara et al., 2024)

Our Product Portfolio

Steroids and terpenes exemplify the remarkable ingenuity of nature's molecular architecture. From mediating critical physiological processes to offering therapeutic and industrial applications, these compounds continue to inspire scientific exploration and innovation. Creative Enzymes offers steroids and terpenes portfolio, which is designed to meet your needs. Contact us today to learn more about our offerings and how we can support your projects.