Withanolide
Encyclopedia
Withanolides are a group of at least 300 naturally occurring chemical compound
s. They occur as secondary metabolite
s 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 deterrent for feeding insect larva and other herbivores. In the laboratory, many withanolides exhibited medicinally interesting properties. Genera within the nightshade family that have been found to produce withanolides include: Datura
, Dunalia, Iochroma
, Lycium, Nicandra, Physalis
, Salpichroa, Solanum
, Withania
, and Jaborosa.
, the first withanolide to be isolated, was found in Winter Cherry (Withania somnifera), also known as Ashwaganda in ayurvedic medicine
. The anti-inflammatory effects of a few dozen known withanolides were demonstrated in animal experiments.
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.
The nicandrenones of Nicandra physalodes are another group of withanolides with insecticidal effects. 30 years after their discovery, the first total synthesis of nicandrenones was carried out in the year 2000.
Ixocarpalactone A, isolated from the tomatillo
(Physalis philadelphica), shows promise as an anti-tumor agent.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
s. They occur as secondary metabolite
Secondary metabolite
Secondary metabolites are organic compounds that are not directly involved in the normal growth, development, or reproduction of an organism. Unlike primary metabolites, absence of secondary metabolities does not result in immediate death, but rather in long-term impairment of the organism's...
s primarily in genera
Genus
In biology, a genus is a low-level taxonomic rank used in the biological classification of living and fossil organisms, which is an example of definition by genus and differentia...
of the Nightshade family
Solanaceae
Solanaceae are a family of flowering plants that include a number of important agricultural crops as well as many toxic plants. The name of the family comes from the Latin Solanum "the nightshade plant", but the further etymology of that word is unclear...
, for example in the tomatillo
Tomatillo
The tomatillo is a plant of the nightshade family, related to the cape gooseberry, bearing small, spherical and green or green-purple fruit of the same name. Tomatillos are a staple in Mexican cuisine. Tomatillos are grown as annuals throughout the Western Hemisphere...
. Structurally, withanolides consist of a steroid backbone
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
bound to a lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
or one of its derivatives
Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by some chemical or physical process. In the past it was also used to mean a compound that can be imagined to arise from another compound, if one atom is replaced with another atom or group of atoms, but modern...
; they are produced via oxidation of steroids. It remains unknown to what end withanolides are produced; they may act as deterrent for feeding insect larva and other herbivores. In the laboratory, many withanolides exhibited medicinally interesting properties. Genera within the nightshade family that have been found to produce withanolides include: Datura
Datura
Datura is a genus of nine species of vespertine flowering plants belonging to the family Solanaceae. Its precise and natural distribution is uncertain, owing to its extensive cultivation and naturalization throughout the temperate and tropical regions of the globe...
, Dunalia, Iochroma
Iochroma
Iochroma is a genus of about 34 species of shrubs and small trees found in the forests of South America. They range from Colombia to Argentina or when certain species are excluded from Colombia to Peru. Their hummingbird pollinated flowers are tubular or trumpet-shaped, and may be blue, purple,...
, Lycium, Nicandra, Physalis
Physalis
Physalis is a genus of plants in the nightshade family , native to warm temperate and subtropical regions throughout the world. The genus is characterised by the small orange fruit similar in size, shape and structure to a small tomato, but partly or fully enclosed in a large papery husk derived...
, Salpichroa, Solanum
Solanum
Solanum, the nightshades, horsenettles and relatives, is a large and diverse genus of annual and perennial plants. They grow as forbs, vines, subshrubs, shrubs, and small trees, and often have attractive fruit and flowers. Many formerly independent genera like Lycopersicon or Cyphomandra are...
, Withania
Withania
Withania is a genus of flowering plants in the nightshade family, Solanaceae.-Etymology:Withania Pauquy, Diss. Bellad. 14 Withania is a genus of flowering plants in the nightshade family, Solanaceae.-Etymology:Withania Pauquy, Diss. Bellad. 14 (1825) Withania is a genus of flowering plants in the...
, and Jaborosa.
Examples
Withaferin AWithaferin A
Withaferin A is a chemical compound which was the first member of the withanolides to be discovered. It was first isolated from Winter cherry ....
, the first withanolide to be isolated, was found in Winter Cherry (Withania somnifera), also known as Ashwaganda in ayurvedic medicine
Ayurveda
Ayurveda or ayurvedic medicine is a system of traditional medicine native to India and a form of alternative medicine. In Sanskrit, words , meaning "longevity", and , meaning "knowledge" or "science". The earliest literature on Indian medical practice appeared during the Vedic period in India,...
. The anti-inflammatory effects of a few dozen known withanolides were demonstrated in animal experiments.
Salpichrolides A, B and G (isolated from Salpichroa origanifolia
Salpichroa origanifolia
Salpichroa origanifolia is a species of flowering plant in the nightshade family known by the common name Pampas lily of the valley. It is native to South America...
) exhibit an inhibitory effect on the growth of larva of the Mediterranean Fruit Fly
Ceratitis capitata
Ceratitis capitata, the Mediterranean fruit fly, or medfly for short, is a species of fruit fly capable of causing extensive damage to a wide range of fruit crops...
(Ceratitis capitata). For this reason, potential pesticide uses for the compounds are being explored.
The nicandrenones of Nicandra physalodes are another group of withanolides with insecticidal effects. 30 years after their discovery, the first total synthesis of nicandrenones was carried out in the year 2000.
Ixocarpalactone A, isolated from the tomatillo
Tomatillo
The tomatillo is a plant of the nightshade family, related to the cape gooseberry, bearing small, spherical and green or green-purple fruit of the same name. Tomatillos are a staple in Mexican cuisine. Tomatillos are grown as annuals throughout the Western Hemisphere...
(Physalis philadelphica), shows promise as an anti-tumor agent.