Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. [1] Many have insecticidal and piscicidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones.
Many plants in the subfamily Faboideae contain rotenoids. Rotenoids can be found in Lonchocarpus sp. Deguelin and tephrosin can be found in Tephrosia vogelii . [2] 6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of Amorpha fruticosa . [3] Elliptol, 12-deoxo-12alpha-methoxyelliptone, 6-methoxy-6a,12a-dehydrodeguelin, 6a,12a-dehydrodeguelin, 6-hydroxy-6a,12a-dehydrodeguelin, 6-oxo-6a,12a-dehydrodeguelin and 12a-hydroxyelliptone can be isolated from the twigs of Millettia duchesnei . [4] Deguelin, dehydrodeguelin, rotenol, rotenone, tephrosin and sumatrol can be found in Indigofera tinctoria . [5] 6aα,12aα-12a-hydroxyelliptone can be found in the stems of Derris trifoliata . [6] Amorphol, a rotenoid bioside, can be isolated from plants of the genus Amorpha . [7] Deguelin, rotenone, elliptone and α-toxicarol can be found in the seeds of Lonchocarpus salvadorensis . [8] Clitoriacetal, stemonacetal, 6-deoxyclitoriacetal, 11-deoxyclitoriacetal, 9-demethylclitoriacetal and stemonal can be isolated from Clitoria fairchildiana . [9]
Rotenoids can also be found in the plant family Nyctaginaceae. Mirabijalone A, B, C and D, 9-O-methyl-4-hydroxyboeravinone B, boeravinone C and F, and 1,2,3,4-tetrahydro-1-methylisoquinoline-7,8-diol) can be isolated from the roots of Mirabilis jalapa . [10] Boeravinones G and H are two rotenoids isolated from Boerhavia diffusa . [11] Abronione and boeravinone C can be found in the desert annual Abronia villosa . [12] In 2015, a new rotenoid called crocetenone was extracted from the rhizome of Iris crocea . [13]
The Faboideae are a subfamily of the flowering plant family Fabaceae or Leguminosae. An acceptable alternative name for the subfamily is Papilionoideae, or Papilionaceae when this group of plants is treated as a family.
Rotenone is an odorless, colorless, crystalline isoflavone used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids.
Amorpha is a genus of plants in the pea family, Fabaceae. All the species are native to North America, from southern Canada, most of the United States (US), and northern Mexico. They are commonly known as false indigo. The name Amorpha means "deformed" or "without form" in Greek and was given because flowers of this genus only have one petal, unlike the usual "pea-shaped" flowers of the Faboideae subfamily. Amorpha is missing the wing and keel petals.
Indigofera tinctoria, also called true indigo, is a species of plant from the bean family that was one of the original sources of indigo dye.
Deguelin is a derivative of rotenone. Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides. They can be produced by extraction from several plant species belonging to three genera of the legume family, Fabaceae: Lonchocarpus, Derris, or Tephrosia.
Lonchocarpus is a plant genus in the legume family (Fabaceae). It includes 166 species native to the tropical Americas, tropical Africa, and Madasgascar. The species are called lancepods due to their fruit resembling an ornate lance tip or a few beads on a string.
Abronia villosa is a species of sand-verbena known by the common names desert sand-verbena and chaparral sand-verbena. It is in the four o'clock plant family (Nyctaginaceae). It is native to sandy areas in the deserts of the southwestern United States and northern Mexico, associated with creosote-bush and coastal-sage scrub habitats.
Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of Tephrosia purpurea and T. vogelii.
Amorpha fruticosa is a species of flowering plant in the legume family Fabaceae, known by several common names, including desert false indigo, false indigo-bush, and bastard indigobush. It is native to North America.
Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.
Derris taiwaniana is a perennial climbing shrub belonging to the genus Derris. It is known by several synonyms, including Millettia pachycarpa and M. taiwaniana. It is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.
Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.
Sarcolobus globosus is a twining shrub native to tropical regions of Asia including India, China, Thailand, Malaysia, Myanmar-Burma, the Philippines and Indonesia.
The tribe Millettieae is one of the subdivisions of the plant family Fabaceae.
Millettia duchesnei is a large forest liana in the genus Millettia.
Derris trifoliata is a plant species in the genus Derris of the family Fabaceae. It common in India and in various Indian languages it is known as Angaar valli in Sanskrit; Karanjvel in Marathi; Firta in Konkani; Tigekranugu, Nauatige and Chirathelathige in Telugu; Ketia and Swanlata in Oria; Kammattivalli and Ponumvalli in Malayalam; Kaliya lata or Kalilata and Panlata in Bengali; Panlata also in Hindi. It is also common in various parts of South East Asia with names eg Filipino ; Indonesian ; Malay ; Thai ; Vietnamese etc.
Clitoria fairchildiana, the sombreiro, is a flowering plant species in the genus Clitoria found in Campina Grande, Brazil.
Lonchocarpus salvadorensis, the Sangre de Chucho, is a plant species in the genus Lonchocarpus.