Chrysanthemum cinerariaefolium

Chrysanthemum cinerariaefolium (1) is a species of white flower and contains more insecticidal ingredients than other species. This pyrethrum species originated from Dalmatia and has been used for cultivation. On the other hand, the origin of Roseum (2) is Persia and the Caucasus. It has beautiful red flowers but its pyrethrin content is extremely low compared to (1). Known as red-flowered pyrethrum, it is used merely as an ornamental plant. Marshalli (3) originated from Persia and contains pyrethrins in negligible amounts therefore, the pyrethrum referred to in this text is from C. cinerariaefolium (1). 

Yamamoto R (1923) The insecticidal principle in Chrysanthemum cinerariaefolium. Parts II and III. On the constitution of pyrethronic acid. J Chem Soc Jpn 44 311-330... 

Gordin PJ, Sleeman RJ, Snarey M, Thain EM (1966) The jasmolins, new insecticidally active constituents of Chrysanthemum cinerariaefolium Vis. J Chem Soc C 332-334... 

Keywords Biosynthesis Chrysanthemum cinerariaefolium Natural pyrethrins Tanacetum cinerariifolium... 

Rivera SB, Swedlund BD, King GJ et al (2001) Chrysanthemyl diphosphate synthase isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium. Proc Natl Acad Sci USA 98 4373 -378... 

Crowley MP, Godin PJ, Inglis HS et al (1962) The biosynthesis of the pyrethrins . I. The incorporation of 14C-labelled compounds into the flowers of Chrysanthemum cinerariaefolium and the biosynthesis of chrysanthemum monocarboxylic acid. Biochim Biophys Acta 60 312-319... 

Ueda H, Matsuda K (2011) VOC-mediated within-plant communications and nonvolatile systemic signals upregulate pyrethrin biosynthesis in wounded seedlings of Chrysanthemum cinerariaefolium. J Plant Interact 6 89-91... 

Kikuta Y, Ueda H, Nakayama K et al (2011) Specific regulation of pyrethrin biosynthesis in Chrysanthemum cinerariaefolium by a blend of volatiles emitted from artificially damaged conspecific plants. Plant Cell Physiol 52 588-596... 

Natural pyrethrins, insecticidal ingredients occurring in the flowers of Tanacetum cinerariaefolium (also known as Chrysanthemum cinerariaefolium or Pyrethrum cinerariaefolium), have been modified for higher stability in the environment as well as better biological performance for more than 40 years, and consequently more than 30 synthetic pyrethroids have been marketed and used worldwide for controlling indoor and agricultural pest insects [1,2]. 

Figure 1. Structures of Six Insecticidal Esters Extracted from Pyrethrum (Chrysanthemum cinerariaefolium)...

The pyrethrins are valuable insecticidal components of pyrethrum flowers, Chrysanthemum cinerariaefolium (= Tanacetum cinerariifolium) (Compositae/Asteraceae). The flowers are harvested just before they are fully expanded, and usually processed to an extract. Pyrethrum cultivation is conducted in East Africa, especially Kenya, and more recently in Ecuador and Australia. The natural pyrethrins are used as a constituent of insect sprays for household use and as post-harvest insecticides, having a rapid action on the nervous system of insects, whilst being biodegradable and non-toxic to mammals, though they are toxic to fish and amphibians. This biodegradation, initiated by air and light, means few insects develop resistance to the pyrethrins, but it does limit the lifetime of the insecticide under normal conditions to just a few hours. 

The suggestion of an alternative non-mevalonoid route in monoterpenoid biosynthesis77 has received some support in the efficient incorporation of L-[l/- 4C]valine into the DMAPP moiety of linalool 78 a pathway via deamination to dimethylacrylic acid is proposed. L-Leucine and l-valine are also incorporated, at least in part, into the DMAPP moiety of geraniol (8) and citronellol.79 (lf ,3/ )-Chrysanthemic acid (25) is biosynthesized80 in Chrysanthemum cinerariaefolium from ( R,3R) chrysanthemyl alcohol (26) but not from precursors with the lavandulyl (27) or artemisyl (28) skeletons (Scheme 4) (li ,3R)-chrysanthemyl alcohol (26) has been... 

C,3H]Chrysanthemyl alcohol (17) was incorporated in relatively large amounts (0.7—2.0%) into chrysanthemic acid and pyrethrins by flowers of Chrysanthemum cinerariaefolium,61 and the 14C 3H ratio of the substrate was preserved in the product. In contrast, [14C]lavandulol, [3H]artemisyl alcohol (18), and the [14C]-diol (19) were not incorporated under similar conditions. Although probably correct, the... 

PYRETHRUM FLOWERS Pyrethri flos The drug consists of the dried flowerheads of Chrysanthemum cinerariaefolium (Trev.) Vis., family Asteraceae. 

Permethrin is a synthetic derivative of the insecticide pyrethrum, which was obtained originally from Chrysanthemum cinerariaefolium. Neurotoxicity associated with this compound is extremely rare. A 5% cream (Acticin, Elimite, others) is available in the treatment of scabies. This is used as an 8- to 12-hour or overnight application. A 1% permethrin cream rinse (NIX) also is available for the treatment of lice. 

Chrysanthemol from the leaves of Artemisia ludiviciana (Asteraceae) belongs to the cyclopropane monoterpenes Cinerins, jasmolins and pyrethrins (all including derivatives 1 and 11) are esters of /rara-chrysanthemic and pyrethric acid with terpenoid hydroxypentenones such as cinerolone, jasmolone and pyrethrolone. These are the active insecticidal constituents of pyrethrum recovered from dried flowers of several Chrysanthemum species (e.g. Chrysanthemum cinerariaefolium, Asteraceae). Some synthetic esters of chrysanthemic acid are also applied as insecticides. 

Pyrethrins diterpene insecticides present in the flowers of Chrysanthemum cinerariaefolium (syn. Pyr-ethrum cinerariaefolium). The dried flowers, known as pyrethrum", also have insecticidal activity and serve as starting material for the preparation of P. P. are esters of chrysanthemic acid (giving series I compounds)... 

Pyrethrum is comprised of the dried flowers of Chrysanthemum cinerariaefolium containing not less than 1% pyrethrins. Pyrethrin esters constitute a powerful degradable contact insecticide. They have a low order of systemic toxicity to man and produce no harmful residues on food crops. The flowers and extracts for pyrethrum are imported from Kenya and... 

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