
Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno
,4-bhromene nucleus. Many have
insecticidal activity, such as the prototypical member of the family,
rotenone. Rotenoids are related to the
isoflavone Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae ...
s.
Natural occurrences
Many plants in the subfamily
Faboideae contain rotenoids. Rotenoids can be found in ''
Lonchocarpus sp''.
Deguelin
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 leg ...
and
tephrosin
Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of ''Tephrosia purpurea'' and '' T. vogelii''.Production of rotenoids by heterotrophic and photomixotrophic cell cultures of tephrosia vogelii. Nadine Lambert, Marie- ...
can be found in ''
Tephrosia vogelii
''Tephrosia'' is a genus of flowering plants in the pea family, Fabaceae. It is widespread in both the Eastern and Western Hemisphere, where it is found in tropical and warm-temperate regions.
The generic name is derived from the Greek word Ï„ ...
''.
6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of ''
Amorpha fruticosa''.
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''. Deguelin,
dehydrodeguelin,
rotenol,
rotenone,
tephrosin
Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of ''Tephrosia purpurea'' and '' T. vogelii''.Production of rotenoids by heterotrophic and photomixotrophic cell cultures of tephrosia vogelii. Nadine Lambert, Marie- ...
and
sumatrol can be found in ''
Indigofera tinctoria''.
6aα,12aα-12a-hydroxyelliptone can be found in the stems of ''
Derris trifoliata
''Derris trifoliata'' is a plant species in the genus ''Derris'', Family - Leguminosae
It is known as "Karanjvel" in Marathi - local language of Maharashtra, India.
It is a large climber found commonly in coastal swamps of Konkan (India). It is ...
''.
Amorphol, a rotenoid
bioside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
, can be isolated from plants of the genus ''
Amorpha
''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'' ...
''. Deguelin, rotenone,
elliptone and
α-toxicarol can be found in the seeds of ''
Lonchocarpus salvadorensis
''Lonchocarpus salvadorensis'', the Sangre de Chucho, is a plant species in the genus ''Lonchocarpus''.
The rotenoids deguelin, rotenone
Rotenone is an odorless, colorless, crystalline isoflavone used as a broad-spectrum insecticide, piscicide ...
''.
Clitoriacetal,
stemonacetal,
6-deoxyclitoriacetal,
11-deoxyclitoriacetal,
9-demethylclitoriacetal and
stemonal can be isolated from ''
Clitoria fairchildiana''.
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''.
Boeravinones G and
H are two rotenoids isolated from ''
Boerhavia diffusa
''Boerhaavia diffusa'' is a species of flowering plant in the Nyctaginaceae, four o'clock family which is commonly known as punarnava (meaning that which rejuvenates or renews the body in Ayurveda), red spiderling, spreading hogweed, or tarvine. ...
''.
Abronione and
boeravinone C can be found in the desert annual ''
Abronia villosa
''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 U ...
''. In 2015, a new rotenoid called
crocetenone was extracted from the rhizome of ''
Iris crocea
''Iris crocea'' is a species in the genus ''Iris'', it is also in the subgenus '' Limniris'' and the series '' Spuriae''. It is a rhizomatous perennial plant, found in Kashmir. It is cultivated as an ornamental plant. It is also commonly known ...
''.
References
{{Rotenoid
Phenol ethers