Anthemis cotula L

Nota de alcance

PARTE UTILIZADA= Used part: Florales. 

ACCIÓN FARMACOLÓGICA= Pharmacological action: Antiflamatorio, espasmolítico, carminativo, emenagogo, sedante. 

COMPOSICIÓN QUÍMICA= Chemical composition: The investigation of roots of Anthemis cotula (Asteraceae) from eastern Serbia revealed that, in addn. to polyacetylenes previously isolated from the same species, three prenylated 4-hydroxyacetophenones, were detected for the first time in any Anthemis species. It is possible that they act as phytoalexins in the plant. From the aerial parts, six linear sesquiterpene lactones (four known and two new ones), as well as two known flavones, apigenin and hispidulin, were isolated. 

ZONA GEOGRÁFICA= Geografical zone: Uruguay.

Nota de alcance

DIVERSIDAD GENÉTICA Y MEJORAMIENTO DE PLANTAS MEDICINALES= Medicinal plants and improvement of medicinal herbs

1. Chromosome numbers resp. karyotypes are established and compared for 18 species of the Anthemideae genera Anthemis, Chamaemelum, Tripleurospermum, Matricaria, Sphaeroclinium, and Pentzia (Table 1, Figs. 1-2). 2. Selfing tests demonstrate that various perennial and annual species of these genera are predominantly selfsterile; only Matricaria discoidea is an obligate inbreeder (p. 162f.). 3. An experimental crossing programm involving 12 species from 5 genera has resulted in 22 successful F1-combinations which where analysed in regard to morphology, chromosome number, pollen meiotic behaviour, pollen (and partly seed) fertility (Fig. 3), and compared with their parents (Figs. 4-18, Tables 3-17). 4. Karyotype similarities, F1-chromosome pairing and F1-fertility together with morphological, embryological, biochemical and other data contribute to the controversial problem of relationships and systematics of Anthemideae (p. 183-188):Anthemis is rather heterogeneous, its subgen. Cota may deserve generic status, sect. Maruta approaches Chamaemelum; Tripleurospermum is coherent; the two latter genera link Anthemis with the more advanced Matricaria; they all form a related N. Hemisphere group. S. Hemisphere taxa are more remote: "Matricaria" nigellifolia is much closer to Cotula and should be placed in the genus Sphaeroclinium; the inclusion of other "Matricariae" into the S. African genus Pentzia is justified; some form the hitherto unrecognized annual P. globifera group. 5. Cytogenetic results illustrate mechanisms underlying evolutionary differentiation of Anthemideae (p. 188-194): genie and cytoplasmic factors determine color and shape of flowers, presence or absence of paleae, azulene content, etc.; small karyotype changes appear already within species and gradually reduce chromosome pairing affinities in species hybrids; gross translocations and loss of centromeres have led to species divergence and descending dysploidy (2 n=16→12) in the Pentzia globifera group; experimental allotetraploids have originated from intergeneric hybridization involving 2 x members of Anthemis, Tripleurospermum, and Matricaria; through unreduced gametes several 3 x progenies have been produced; reproductive barriers between species and genera are of very complex nature. Different recombination systems and evolutionary strategies within Anthemideae are discussed. 

Nota de alcance

ÚLTIMOS AVANCES EN LA QUÍMICA Y ACTIVIDADES BACTERIOLÓGICAS EN LAS PLANTAS MEDICINALES= Medicinal plants, last advances on chemistry and bacteria activities on the medicinal herbs

1) Although there are more than two hundred taxa in the pharmacol. important genus Anthemis, essential oil compn. is known only for a small no. of them.  This is the first report on the volatiles of A. segetalis Ten. GC and GC/MS analyses of the essential oil hydrodistd. from A. segetalis aerial parts enabled the identification of 155 constituents, representing 92.4% of the total oil.  Major constituents of the oil were sabinene (19.5%), germacrene D (12.6%), terpinen-4-ol (6.2%) and 1,8-cineole (6.1%).  Monoterpenoids (49.9%, esp. those of thujane and p-menthane skeletons) and sesquiterpenoids (39.4%, predominantly those of germacrane-, cadinane- and caryophyllane-types) were found to be the most abundant compd. classes.  The comparison of the essential oil compn. of other Anthemis species with the present one was used as an addnl. tool for the clarification of infrageneric relationships.  The results support the treatment of Anthemis subg. Cota as a sep. genus.

2) Retrobiosynthetic anal. of the allergenic sesquiterpene lactone, anthecotuloide, suggested that this natural product could be formed either by head to head condensation of geranyl diphosphate with dimethylallyl diphosphate, or from farnesyl diphosphate (FPP), the accepted regular sesquiterpene precursor via the rearrangement of a germacranolide precursor.  Isotopic labeling of anthecotuloide has now been achieved by feeding [1-13C]-glucose, [U-13C6]-glucose and [6,6-2H2]-glucose to aseptically grown plantlets of Anthemis cotula(family Asteraceae).  Anal. of labeling patterns and abs. 13C abundances using quant. 13C NMR spectroscopy showed that the isoprene building blocks of this sesquiterpene are formed exclusively via the MEP terpene biosynthetic pathway.  This was supported by results from an expt. using [U-13C6]-glucose.  A deuterium labeling expt. using [6,6-2H2]-glucose supported the original proposal and showed that anthecotuloide is formed from a non FPP precursor.  Isotope ratio mass spectrometry suggested that there were two pathways for sesquiterpene biosynthesis in A. cotula.

Nota bibliográfica

1) GONZALEZ, Matías ; LOMBARDO, Atilio ; VALLARINO, Aida. Plantas de la medicina vulgar del Uruguay. Montevideo : Talleres Gráficos, 1937, p.85.

2) VUCKOVIC, Ivan, et al. Phytochemical investigation of Anthemis cotula. Journal of the Serbian Chemical Society. 2006, vol.71, nº2, p.127-133.
3) MITSUOKA, S.; EHRENDORIER, F. Cytogenetics and evolution of Matricaria and related genera (asteraceae-anthemideae). Österreichische Botanische Zeitschrift. 1972, vol.120, nº1-2, p.155-200.
4) RADULOVIC, Niko S., et al. Chemotaxonomically important volatiles of the genus Anthemis L. - a detailed GC and GC/MS analyses of Anthemis segetalis Ten. from Montenegro. Journal of the Chinese Chemical Society (Taipei, Taiwan). 2009, vol.56, nº3, p.642-652.
5)  VAN KLINK, John, et al.. Biosynthesis of anthecotuloide, an irregular sesquiterpene lactone from Anthemis cotula L. (Asteraceae) via a non-farnesyl diphosphate route. Biomolecular Chemistry. 2003, vol.1, nº9, p.1503-1508.

Anthemis cotula L
Término aceptado: 28-Ago-2007