Solasodine
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Solasodine
Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. Literature survey reveals that solasodine has diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and various effects on central nervous system. Uses It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate. See also * ''Solanum mauritianum ''Solanum mauritianum'' is a small tree or shrub native to South America, including Northern Argentina, Southern Brazil, Paraguay and Uruguay. Its common names include earleaf nightshade (or "ear-leaved nightshade"), woolly nightshade, flannel we ...'' References Steroidal alkaloids Plant toxins Steroi ...
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Steroidal Alkaloids
Steroidal alkaloids have organic ring backbones which feature nitrogen-based functional groups. More specifically, they are distinguished by their tetracyclic cyclopentanophenanthrene backbone that marks their close relationship with sterols. They fall in two major categories: Solanum alkaloids and Veratrum alkaloids. A Steroidal alkaloid has also been found in ''Chonemorpha fragrans'' (Frangipani vine), 'chonemorphine' was used to treat intestinal infections in Wistar rats. (Chatterjee DK et al (1987) Parasitol Res 74, 1, 30-33). ''Solanum'' alkaloids These compounds generally appear as their corresponding glycoside in plants of the genus ''Solanum''. ''Solanum'' includes plants like potatoes, tomatoes, and various nightshades Starting with cholesterol, the biosynthesis of these compounds follow a similar general mechanism including hydroxylation, oxidation, and transamination before differentiating. Alkaloids found in these plants include chaconine, solanine, solasodine, tomat ...
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Poisonous
Poison is a chemical substance that has a detrimental effect to life. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figuratively, with a broad sense. Whether something is considered a poison may change depending on the amount, the circumstances, and what living things are present. Poisoning could be accidental or deliberate, and if the cause can be identified there may be ways to neutralise the effects or minimise the symptoms. In biology, a poison is a chemical substance causing death, injury or harm to organisms or their parts. In medicine, poisons are a kind of toxin that are delivered passively, not actively. In industry the term may be negative, something to be removed to make a thing safe, or positive, an agent to limit unwanted pests. In ecological terms, poisons introduced into the environment can later cause unwanted effects elsewhere, or in other parts of the food ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken and/or new bonds formed. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, using the s ...
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Solanaceae
The Solanaceae , or nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida ( dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology. The name Solanaceae derives from the genus ''Solanum''. The etymology of the Latin word is unclear. The name may come from a perceived resemblance of certain solanaceous flowers to the sun and its rays. At least one species of ''Solanum'' is known as the "sunberry". Alternatively, the name could originate from the Latin verb ''sol ...
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Solasonine
Solasonine is a glycoalkaloid that is found in Solanum plants of the family Solanaceae. Solasonine is a poisonous chemical compound when used at high levels. It is a glycoside of solasodine Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetus .... Glycoalkaloids such as Solasonine have various applications including pharmacology, cancer treatments and even a role as a pesticide. High levels of glycoalkaloids are toxic to humans due to their ability to disrupt cell-membrane function. There is a loss of membrane integrity which puts the cell at risk for apoptosis (cell death) due to the ability of any chemical coming into contact with the cell. Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine. Side Effects Although, solasonine has anti-in ...
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Solamargine
Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from '' Solanum nigrum'' fungal endophyte ''Aspergillus flavus''. It is a glycoalkaloid derived from the steroidal alkaloid solasodine. Solamargine was one component of the unsuccessful experimental cancer drug candidate Coramsine. See also * ''Solanum americanum ''Solanum americanum'', commonly known as American black nightshade, small-flowered nightshade or glossy nightshade, is a herbaceous flowering plant of wide though uncertain native range. The certain native range encompasses the tropics and subtr ...'' References External links *{{Commonscatinline Steroidal alkaloids Alkaloid glycosides Plant toxins Steroidal alkaloids found in Solanaceae ...
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Glycoalkaloid
Glycoalkaloids are a family of chemical compounds derived from alkaloids to which sugar groups are appended. Several are potentially toxic, most notably the poisons commonly found in the plant species ''Solanum dulcamara'' (bittersweet nightshade) and other plants in the genus ''Solanum'', including potato. A prototypical glycoalkaloid is solanine (composed of the sugar solanose and the alkaloid solanidine), which is found in the potato. The alkaloidal portion of the glycoalkaloid is also generically referred to as an aglycone. The intact glycoalkaloid is poorly absorbed from the human gastrointestinal tract, gastrointestinal tract but causes gastrointestinal irritation. The aglycone is absorbed and is believed to be responsible for observed nervous system signs. Glycoalkaloids are typically bitter (taste), bitter tasting, and produce a burning irritation in the back of the mouth and side of the tongue. The Aymara people of Bolivia use taste to detect the levels of glycoalkaloids ...
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Teratogenic
Teratology is the study of abnormalities of physiological development in organisms during their life span. It is a sub-discipline in medical genetics which focuses on the classification of congenital abnormalities in dysmorphology. The related term developmental toxicity includes all manifestations of abnormal development that are caused by environmental insult. These may include growth retardation, delayed mental development or other congenital disorders without any structural malformations. Teratogens are substances that may cause birth defects via a toxic effect on an embryo or fetus. Known teratogens include: retinol, thalidomide, Mercury (element), mercury, Alcohol (drug), alcohol, lead, polychlorinated biphenyls (PCBs), and 2,3,7,8-tetrachlorodibenzodioxin. Etymology The term was borrowed in 1842 from the French , where it was formed in 1830 from the Greek language, Greek (word stem ), meaning "sign sent by the gods, portent, marvel, monster", and (''-ology''), used ...
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Steroidal
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. ''Also ...
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Contraceptive Pill
Oral contraceptives, abbreviated OCPs, also known as birth control pills, are medications taken by mouth for the purpose of birth control. Female Two types of female oral contraceptive pill, taken once per day, are widely available: * The combined oral contraceptive pill contains estrogen and a progestin. Colloquially known as "The Pill". * The progestogen-only pill, colloquially known as "minipill". * Ormeloxifene is a selective estrogen receptor modulator which offers the benefit of only having to be taken once a week. Emergency contraception pills ("morning after pills") are taken at the time of intercourse, or within a few days afterwards: * Levonorgestrel, sold under the brand name Plan B * Ulipristal acetate * Mifepristone and misoprostol, when used in combination, are more than 95% effective during the first 50 days of pregnancy. Male * Male oral contraceptive Male contraceptives, also known as male birth control, are methods of preventing pregnancy that solely invol ...
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16-DPA
16-Dehydropregnenolone acetate (16-DPA) is a chemical compound used as an intermediate or synthon in the production of many semisynthetic steroids. As 7-ACA is for cephalosporins and 6-APA is for penicillins, 16-DPA is for steroids. While it is not easy to synthesize, it is a convenient intermediate which can be made from other more available materials, and which can then be modified to produce the desired target compound. Upstream sources 16-DPA can be produced from a variety of steroidal sapogenins. Industrially useful sources are diosgenin in mexican yams and solasodine from certain nightshades. These two sapogenins can be used in a one-pot synthesis. Solanidine in potato greens, an alkaloid sapogenin, is also a key source material. Downstream products Compounds derived from 16-DPA include: * Corticosteroids (mainly of a C22 pregnane backbone): hydrocortisone*, betamethasone*, dexamethasone*, beclometasone*, fluticasone, and prednicarbate; * Progestogen (mainly of a C22 p ...
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