Stéroïdes

Applications 11,12-Dehydroxy-Betamethasone is an impurity of the steroid Betamethasone (B327000) which is a glucocorticoid used as an anti-inflammatory agent.
References Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977), Li, A., et al.: Chem. Biol. Interact., 142, 7 (2002), Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (2005), Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (2006),

Applications 3β-Hydroxy Progesterone is a biotransformation product of Progesterone (P755900), by Chlorella spp. Progesterone is a steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer
References Pollio, A., et al.: Phytochem., 42, 685 (1996); Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002); Lanari, C., et al.: Breast Cancer Res., 4, 240 (2002); Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2003); Qiu, M., et al.: J. Steroid Biochem. Mol. Biol., 85, 147 (2003);

Applications 10β-Hydroperoxy Norethindrone Acetate is a derivative of Norethindrone (N676000), a progesterone in combination with acetate used as an oral contraceptive (1,2). It is reasonably anticipated to be a human carcinogen.
References 1. Shroff, A. et al.: Anal. Profiles Drug Subst. 1975 ; 4;268-293;

Applications Cholesta-3,5-diene-7-one-25,26,26,26,27,27,27-d7 is a compound useful in organic synthesis.

Otophylloside B is a naturally occurring triterpenoid saponin, which is a secondary metabolite derived from the roots of the plant **Ophiorrhiza pumila**. This compound is characterized by its complex glycosidic structure, featuring a unique arrangement of sugar moieties attached to its aglycone core. The mode of action of Otophylloside B involves modulation of cellular pathways, particularly influencing apoptosis and cell cycle regulation. Its structure allows interaction with specific cellular receptors, leading to potential inhibition of tumor growth and metastasis.

Formononetin-7-acetate is a naturally-derived isoflavonoid, which is a product of acetylation of formononetin, predominantly sourced from red clover and other leguminous plants. Its mode of action involves mimicking the effects of estrogens by binding to estrogen receptors, though with less potency than endogenous estrogens. This interaction may lead to modulation of various estrogen-mediated physiological processes.

Estetrol (E4) is a naturally occurring estrogen, which is synthesized by the human fetal liver. It acts as a selective estrogen receptor modulator with a unique mode of action differentially impacting various tissues. Estetrol selectively binds to estrogen receptors, thereby facilitating a range of estrogenic activities. Interestingly, it exhibits modest estrogenic effects on both the endometrium and breast tissue, reducing potential risks typically associated with hormone therapies.

Isodeoxycholic Acid, an epimer of deoxycholic acid by gut bacteria, has lower detergent activity and inhibits C. difficile germination and toxicity.

Applications epi-Glycochenodeoxycholic Acid Sodium Salt-d7 is a labelled epimer analogue of Glycochenodeoxycholic Acid Sodium Salt (G641255), which is a bile salt formed in the liver from chenodeoxycholate and glycine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.
References Ollila, F., et al.: Langmuir, 17, 7107 (2001); Uekama, K., et al.: Chem. Pharm. Bull., 52, 900 (2004); Tongiani, S., et al.: J. Pharm. Sci., 94, 2380 (2005);

Asparanin B is a natural compound, which is a specialized saponin derived from the roots of asparagus plants, specifically from Asparagus officinalis. It exerts its effects through the modulation of cellular pathways, including the inhibition of cell proliferation, induction of apoptosis, and disruption of key signaling mechanisms involved in cancer development and progression. As a result, Asparanin B is being studied for its potential anticancer properties.

Used to produce peptide modified lipid nanoparticles.

Pregnanediol 3α-O-β-D-glucuronide is a steroid conjugate, which is primarily a urinary metabolite derived from the catabolism of progesterone. It represents an important biomarker in endocrinological studies with direct relevance to reproductive biology. The compound originates in the body during the breakdown of progesterone, where it is conjugated with glucuronic acid to increase its solubility for renal excretion. This transformation allows for convenient and non-invasive monitoring of progesterone levels in clinical and research settings.

Phytosterol with anti-osteoarthritic activity; inhibits cholesterol biosynthesis

Androsta-1,4,6-triene-3,17-dione is a steroidal aromatase inhibitor, which is a synthetic compound derived from modifications of naturally occurring steroid structures. Its mode of action involves the inhibition of the aromatase enzyme. Aromatase catalyzes the conversion of androgens into estrogens, a critical step in the biosynthesis of estrogens. By inhibiting this enzyme, Androsta-1,4,6-triene-3,17-dione effectively reduces estrogen levels, which can be of particular interest in research environments exploring the role of estrogens in various biological processes.

**Azedarachol** is a botanical compound, which is a natural product derived from the neem tree (Azadirachta indica). This compound is known for its role as a bioactive agent, working through mechanisms that involve disrupting insect endocrine systems and acting as an antifeedant. Azedarachol's mode of action is primarily through its interference with hormonal balance within target organisms, which can lead to decreased feeding, stunted growth, and interrupted reproduction, making it an area of interest for pest control research.

Saponins are naturally occurring glycosides, which are compounds sourced primarily from various plant species, including legumes, herbs, and certain vegetables. These compounds are characterized by their unique structure, comprising a hydrophobic aglycone linked to hydrophilic sugar moieties. This dual nature endows saponins with surfactant-like properties, allowing them to interact with both hydrophilic and hydrophobic molecules.

Pregnenolone acetate is a synthetic compound classified as a steroidal hormone precursor. It is derived from pregnenolone, which is a naturally occurring steroid hormone in the body. Pregnenolone is primarily synthesized from cholesterol, a fundamental component upon which steroidogenesis is based. The acetate form is an ester derivative, which can enhance stability and bioavailability.

β-Sitosterol β-D-glucoside is a phytosterol glycoside, which is primarily derived from plant sources such as fruits, vegetables, nuts, and seeds. As a natural component of plant cell membranes, it exhibits bioactive properties. The compound functions by modulating cholesterol metabolism and has anti-inflammatory, immunomodulatory, and antioxidant effects. It achieves this by interfering with the absorption of cholesterol in the intestines and modulating the activity of enzymes involved in its metabolism.

Formononetin-7-O-gentiobioside is an isoflavonoid glycoside, which is a type of naturally occurring compound often found in plants, specifically in the Fabaceae family. This compound is primarily sourced from various legumes and has been studied for its potential bioactive properties due to its unique chemical structure. The mode of action of formononetin-7-O-gentiobioside involves its interaction with biological pathways, where it may exhibit antioxidant, anti-inflammatory, or estrogen-like activities, similar to other isoflavonoids. These interactions are significant in modulating cellular pathways that can contribute to various physiological effects.

Phytoestrogen with anti-cancer properties

Periplogenin is a compound classified as a cardiac glycoside, which is typically derived from certain plant species such as those in the Apocynaceae family. These compounds are known for affecting the heart by influencing cellular ion transport mechanisms. The primary mode of action of periplogenin involves inhibition of the Na⁺/K⁺-ATPase pump. This inhibition leads to an increased intracellular concentration of sodium ions, which indirectly increases intracellular calcium levels via the sodium-calcium exchanger. The elevated calcium concentration enhances cardiac muscle contractility, a mechanism often leveraged in treating certain heart conditions.

Withaferin A is a bioactive compound, which is a steroidal lactone with antiproliferative properties. It is derived from the medicinal plant *Withania somnifera*, commonly known as Ashwagandha. Withaferin A exerts its effects by modulating various signaling pathways, including the inhibition of NF-kB and induction of oxidative stress, which lead to apoptotic cell death in cancer cells and reduced inflammation.

Prednisolone is a synthetic corticosteroid, which is a derivative of the natural hormone cortisol. It is derived from the modification of the corticosteroid structure to enhance its anti-inflammatory and immunosuppressive properties. The mode of action of prednisolone involves binding to glucocorticoid receptors, leading to the modulation of gene expression. This results in the suppression of pro-inflammatory cytokines and the inhibition of various immune responses.

DHED is a neuroactive steroid precursor, specifically a bioprecursor prodrug of estradiol, which is derived from chemical synthesis pathways. It is unique in its targeted mode of action, as it selectively converts to the active hormone estradiol within the brain via enzymatic processes that occur in situ. This specificity is facilitated by 17β-hydroxysteroid dehydrogenase type 1, which catalyzes the conversion of DHED to estradiol exclusively in the brain, minimizing peripheral estrogenic effects.

1-Dehydroepiandrosterone is a steroid hormone and a metabolic intermediate in the biosynthesis of androgen and estrogen sex steroids, which is derived from cholesterol in the adrenal glands, gonads, and brain. Acting primarily as a prohormone, it facilitates the synthesis of active steroid hormones by serving as a precursor molecule that undergoes enzymatic conversion into potent androgens like testosterone and dihydrotestosterone, as well as estrogens such as estradiol within peripheral tissues.

Pregna-4,8-diene-3,20-dione is a synthetic corticosteroid, which is an analog of naturally occurring hormones produced by the adrenal cortex. This compound is synthesized through complex chemical pathways utilizing steroidal intermediates to produce a substance with potent biological activity. The mode of action of Pregna-4,8-diene-3,20-dione involves its ability to alter the transcription of certain genes by binding to glucocorticoid receptors. This interaction induces the synthesis of proteins that inhibit the inflammatory response and suppress the immune system.

Ophiopogonin D is a steroidal glycoside, which is a secondary metabolite sourced from the plant Ophiopogon japonicus. This compound is characterized by its presence in the roots, commonly referred to as radix Ophiopogonis, and is part of the broader group of ophiopogonins. Its mode of action primarily involves exerting anti-inflammatory and antioxidant effects. Ophiopogonin D has been shown to modulate signaling pathways that influence cellular oxidative stress and inflammatory responses, which are key in various pathological conditions.

3,9-Di-O-methylcoumestrol is a synthetic coumestan derivative, which is primarily derived or synthesized from various plant sources that produce isoflavonoids and related compounds. As a type of phytoestrogen, it exhibits selective estrogen receptor modulating activity, interacting with estrogen receptors in a manner similar to endogenous hormones but with distinctive affinity and specificity. This mode of action suggests it could influence estrogen-responsive pathways, making it of particular interest in fields like endocrinology and pharmacology.