Withanolide

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Withaferin A Withaferin A.svg
Withaferin A
Salpichrolid A Salpichrolide A.svg
Salpichrolid A
Nicandrenon-1 Nicandrenone-1.svg
Nicandrenon-1
Ixocarpalacton A Ixocarpalactone A.svg
Ixocarpalacton A

Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton. [1] [2] They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo.

Structurally, withanolides consist of a steroid backbone bound to a lactone or one of its derivatives; they are produced via oxidation of steroids. It remains unknown to what end withanolides are produced; they may act as a deterrent for feeding insect larvae and other herbivores.

Genera within the nightshade family that produce withanolides include: Datura , [3] Iochroma , [4] Lycium , [5] Nicandra , [6] Physalis , [7] Salpichroa , [8] Solanum , [9] Mandragora , [10] Withania , [11] and Jaborosa . [12] No withanolide has been discovered in Nicotiana to date.

Examples

Withaferin A, the first withanolide to be isolated, was found in winter cherry (Withania somnifera) [13] and Acnistus arborescens. [14]

Salpichrolides A, B and G (isolated from Salpichroa origanifolia ) exhibit an inhibitory effect on the growth of larva of the Mediterranean fruit fly (Ceratitis capitata). For this reason, potential pesticide uses for the compounds are being explored. [15]

Related Research Articles

<i>Datura</i> Genus of poisonous, potentially psychoactive plants

Datura is a genus of nine species of highly poisonous, vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and death if taken internally.

<span class="mw-page-title-main">Scopolamine</span> Tropane alkaloid & anticholinergic drug

Scopolamine, also known as hyoscine, or Devil's Breath, is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.

<i>Iochroma</i> Genus of shrubs

Iochroma is a genus of about 34 species of shrubs and small trees belonging to the nightshade family Solanaceae. Species are native from Mexico to south Brazil. They are found in the forests of Mexico and South America. Their hummingbird-pollinated flowers are tubular or trumpet-shaped, and may be blue, purple, red, yellow, or white, becoming pulpy berries. The cupular (cup-shaped) calyx is inflated in some species. The leaves are alternate, simple, and entire.

<i>Physalis</i> Genus of flowering plants

Physalis is a genus of approximately 75 to 90 flowering plants in the nightshade family (Solanaceae), which are native to the Americas and Australasia. At least 46 species are endemic to Mexico. Cultivated and weedy species have been introduced worldwide. A defining feature of Physalis is a large, papery husk derived from the calyx, which partly or fully encloses the fruit. Many species bear edible fruit, and some species are cultivated.

<i>Nicandra physalodes</i> Species of flowering plant in the tomato family Solanaceae

Nicandra physalodes is a species of flowering plant in subfamily Solanoideae of the nightshade family. It is known by the common names apple-of-Peru and shoo-fly plant. It is thought originally to have been native to western South America, including Peru, and is known elsewhere as an introduced and ruderal species – sometimes as a weed – in tropical, subtropical and, to a lesser extent, temperate areas all over the world. It has also long been cultivated as an ornamental plant for its attractive flowers and curious fruits and has been adopted into the traditional medicine of countries far-removed from its original home.

<i>Withania somnifera</i> Species of plant

Withania somnifera, known commonly as ashwagandha or winter cherry, is an evergreen shrub in the Solanaceae or nightshade family that grows in India, the Middle East, and parts of Africa. Several other species in the genus Withania are morphologically similar.

<i>beta</i>-Sitosterol Chemical compound

β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

<i>Alternaria</i> Genus of fungi

Alternaria is a genus of Deuteromycetes fungi. All species are known as major plant pathogens. They are also common allergens in humans, growing indoors and causing hay fever or hypersensitivity reactions that sometimes lead to asthma. They are present in the human mycobiome and readily cause opportunistic infections in immunocompromised people such as AIDS patients.

<i>Withania</i> Genus of flowering plants

Withania is a genus of flowering plants in the nightshade family, Solanaceae, with 19 to 23 species that are native to parts of North Africa, western Asia, south Asia, southern Europe, the Mediterranean, and the Canary Islands. Withania was initially included within Physalis by Linnaeus in 1753 but has since become its own genus. This grouping was due to the shared feature of an inflated Calyx that surrounds and protects the fruit.

<i>Iochroma arborescens</i> Species of plant

Iochroma arborescens is a species of flowering plant in the genus Iochroma, belonging to the nightshade family Solanaceae. Formerly it was considered the single species in the monotypic genus Acnistus. Common names include gallinero, mata-gallina, fruta-de-sabiá, hollowheart, wild tobacco, siyou, bastard sirio, galán arbóreo, tabaco de monte, nigüito, marieneira, güitite, and tabak djab.

<span class="mw-page-title-main">Patuletin</span> Chemical compound

Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.

<span class="mw-page-title-main">Withaferin A</span> Chemical compound

Withaferin A is a steroidal lactone, derived from Acnistus arborescens, Withania somnifera and other members of family Solanaceae. It is the first member of the withanolide class of ergostane type product to be discovered.

<i>Jaborosa</i> Genus of flowering plants

Jaborosa is a genus of flowering plants in the family Solanaceae, the nightshades. There are about 23 species, all native to South America, where they are distributed from Peru to Patagonia. Most occur in the Andes. Most can be found in Argentina and ten are endemic to the country.

Biomimetic synthesis is an area of organic chemical synthesis that is specifically biologically inspired. The term encompasses both the testing of a "biogenetic hypothesis" through execution of a series of reactions designed to parallel the proposed biosynthesis, as well as programs of study where a synthetic reaction or reactions aimed at a desired synthetic goal are designed to mimic one or more known enzymic transformations of an established biosynthetic pathway. The earliest generally cited example of a biomimetic synthesis is Sir Robert Robinson's organic synthesis of the alkaloid tropinone.

<i>Physalis virginiana</i> Species of flowering plant

Physalis virginiana, the Virginia groundcherry, is a rhizomatous perennial with a deeply buried stem base. It is found mostly in eastern North America as far west as Wyoming.

<span class="mw-page-title-main">Ergostane</span> Chemical compound

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides. However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.

<i>Withania coagulans</i> Species of flowering plant

Withania coagulans is a plant in the Solanaceae or nightshade family, native to Afghanistan, Pakistan and the Indian subcontinent. Within the genus Withania, W. somnifera (Ashwagandha) and W. coagulans are economically significant, and are cultivated in several regions for their use in Ayurveda. It is claimed to help control diabetes. The berries contain a rennet-like protease that can be used to clot milk for cheese production. The plant is prone to leaf spot disease caused by Alternaria alternata.

<i>Mandragora</i> (genus) Genus of plants

Mandragora is a plant genus belonging to the nightshade family (Solanaceae). Members of the genus are known as mandrakes. Between three and five species are placed in the genus. The one or two species found around the Mediterranean constitute the mandrake of ancient writers such as Dioscorides. Two or three further species are found eastwards into China. All are perennial herbaceous plants, with large tap roots and leaves in the form of a rosette. Individual flowers are bell-shaped, whitish through to violet, and followed by yellow or orange berries.

<span class="mw-page-title-main">Solanaceae</span> Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or the 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.

<i>Alkekengi</i> Species of edible flowering plant native to Eurasia

Alkekengi officinarum, the bladder cherry, Chinese lantern, Japanese-lantern, strawberry groundcherry, winter cherry, alchechengi berry, or Klabuster cherry is a species of flowering plant in the nightshade family Solanaceae. It is a close relative of the new world Calliphysalis carpenteri and a somewhat more distant relative to the members of the Physalis genus. This species is native to the regions covering Southern Europe to South Asia and Northeast Asia.

References

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