Jasmolone is an irregular

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

. Irregular monoterpenes are derived from two

isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...

C5 units, but do not follow the usual head-to-tail coupling mechanism. Jasmolins are found in

pyrethrum ''Pyrethrum'' was a genus of several Old World plants now classified as ''Chrysanthemum'' or ''Tanacetum'' which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly inclu ...

flowers. They can specifically be found in the flower heads of ''

Chrysanthemum cinerariaefolium ''Pyrethrum'' was a genus of several Old World plants now classified as ''Chrysanthemum'' or ''Tanacetum'' which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly inclu ...

''. Jasmolins act as an insecticide for the flower. It is found in the

cytoplasm In cell biology, the cytoplasm is all of the material within a eukaryotic cell, enclosed by the cell membrane, except for the cell nucleus. The material inside the nucleus and contained within the nuclear membrane is termed the nucleoplasm. The ...

of plants. Jasmolone is part of the secondary alcohol family. Jasmolone is found in the alcohol portion of pyrethrins. It is thought that jasmolone is a derivative of cyclized and altered fatty acids. The cyclization of the fatty acids is similar to the biosynthetic pathway cyclization of

prostaglandin The prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids having diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derive ...

s. A precursor of jasmolone could be

alpha-linolenic acid ''alpha''-Linolenic acid (ALA), also known as α-Linolenic acid (from Greek ''alpha'' meaning "first" and ''linon'' meaning flax), is an ''n''−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, waln ...

with a 12-oxophytodienoic acid intermediate. The chain shortening could be produced by a beta-oxidation then a decarboxylation. 12-Oxophytodienoic acid is also used in the production of

jasmonic acid Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. It was first isolat ...

. Jasmonic acid is used in the production of secondary metabolites in a plants signaling system. Jasmonic acid is used in a plant's response to a microbial infection or wound.

Natural production

Jasmolone is one of the three alcohols (along with pyrethrolone and cinerolone) needed in combination with two specific acids (

chrysanthemic acid Chrysanthemic acid is an organic compound that is related to a variety of natural and synthetic insecticides. It is related to the pyrethrin I and II, as well as the pyrethroids. One of the four stereoisomers, (1''R'',3''R'')- or (+)-''trans''-c ...

and pyrethric acid) to form insecticidal esters. These six insecticidal esters are part of the

pyrethrin The pyrethrins are a class of organic compounds normally derived from ''Chrysanthemum cinerariifolium'' that have potent Insecticide, insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum f ...

s family. So far, pyrethrins have been found in ''

'', ''

Tagetes erecta ''Tagetes erecta'', the Aztec marigold, Mexican marigold, big marigold, ''cempazúchitl'' or ''cempasúchil'', is a species of flowering plant in the genus ''Tagetes'' native to Mexico. Despite being native to the Americas, it is often called the ...

'', '' C. coccinum'', ''

Tagetes minuta ''Tagetes minuta'' is a tall upright marigold plant from the genus ''Tagetes'', with small flowers, native to the southern half of South America. Since Spanish colonization, it has been introduced around the world, and has become naturalized i ...

'', '' Z. linnearis'', ''

Calendula officinalis ''Calendula officinalis'', the pot marigold, common marigold, ruddles, Mary's gold or Scotch marigold, is a flowering plant in the daisy family Asteraceae. It is probably native to southern Europe, though its long history of cultivation makes its ...

'', '' Demorphotheca sinuate'' and '' Zinnia elegans''. Pyrethrins are found mostly in the head of the flowers, but have also been found in the

callus A callus is an area of thickened and sometimes hardened skin that forms as a response to repeated friction, pressure, or other irritation. Since repeated contact is required, calluses are most often found on the feet and hands, but they may o ...

tissue of the flowers.K.Ramawat, J.Merillon, “Biotechnology: Secondary Metabolites Plants and Microbes”, Boca Raton: CRC Press Taylor & Francis Group, 2007, 136.

Biosynthesis

α-Linolenic acid ''alpha''-Linolenic acid (ALA), also known as α-Linolenic acid (from Greek ''alpha'' meaning "first" and ''linon'' meaning flax), is an ''n''−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, waln ...

undergoes a radical oxidation with O₂ and

lipoxygenase Lipoxygenases () are a family of (non-heme) iron-containing enzymes most of which catalyze the dioxygenation of polyunsaturated fatty acids in lipids containing a cis,cis-1,4- pentadiene into cell signaling agents that serve diverse roles as auto ...

to form a peroxide. Lipoxygenase is an iron-containing enzyme that is used to catalyze dioxygenation of polyunsaturated fatty acids in this case, α-linolenic acid. Lipooxygenase specifically binds to polyunsaturated fatty acids that have a ''cis'',''cis''-1,4-pentadiene present. Next, an allene oxide synthase occurs followed by allene oxide cyclase. 12-Oxophytodienoic acid is formed. It is unknown how jasmolone is formed from 12-oxophytodienoic acid after this step. JasmoloneschemeGIF

Laboratory synthesis

(''Z'')-Jasmolone was synthesized by Jacqueline Ficini and Jean Pierre Genet in June 1975. JasSynMethod

References

{{reflist Monoterpenes