Echinops

Echinopsine. From Echinops Ritro (seeds) and other Echinops spp. Greshoff isolated this alkaloid, which Spath and Kolbe have shown is l-methyl-4-quinolone. Greshoff also obtained from the same source fi-echinopsine, m.p. 135°, and echinopseine. 

From Bidens species 5-metbyl 5 -butadienyl-2 -bithienyl (245) has been isolated, the constitution of which was eonfirmed synthetically. Another 2,2 -bithienyl derivative has been isolated as an additional nematodicidal principal of the roots of Tagetes, for which strueture (246) has been suggested. On the other hand Sorensen et aL have isolated from the thistles, Berkheya macrocepkala and Echinops spareocephalm, a compound with very similar UV and IR spectra as (246) for which they suggested structure (247), based on... 

Thiophene-containing molecules can be found in both natural products and synthetic chemotherapeutics. Bithiophene 1, a naturally occurring nematocide, is isolated from the roots of Echinops spaerocephalus, whereas tiaprofenic acid, an anti-inflammatory agent, is a synthetic thiophene derivative. Moreover, thiophene is a useful template for four-carbon homologation via reduction [1], as well as a bioisostere of the benzene ring and other heterocycles in medicinal chemistry. 

In letzter Zeit sind eine Reihe von 1,3-disubstituierten Ci4-Verbin-dungen isoliert worden, die vermuten lassen, daB es sich um Vorstufen einer Reihe andercr Polyine handclt. Aus Matricaria oreades Boiss. isoliert man das optisch aktive Diacetat LXXIX (28), wiilirend in Echinops-Avten das entsprechende Diol LXXX vorkommt (7). 

In verschiedenen Echinops-Artcn findet man die Thiophen-Derivate CLXI—CLXVII (7), die offenbar alle iiber CLV aus LIX gebildet werden, wic Versuche mit H—LIX zeigen (27) ... 

Auch die Derivatc von CLXX, die vor aUem aus Echinops-Kxiea isoliert wurden (7), werden in der Pflanze aus LIX gebildet (27). 

Fokialakis N, Cantrell CL, Duke SO, Skaltsounis AL, Wedge DE, Antifungal activity of thiophenes from Echinops ritro. UJAgric Food Chem 54 1651—1655, 2006. 

The structure of a novel benzothiophene glycoside, echinothiophene 132, isolated from the roots of Echinops grijissii was elucidated by a combination of spectroscopic methods (MS and NMR) <990L197>. Interestingly, 132 undergoes a facile epimerization to 134, perhaps through enol intermediate 133. 

Echinops dahuricus Fisch. E. gmelini Ledeb. E. grijsii Hance E. latifollus Tausch. E. sphacrocephalus Miq. Lou Lu (Globe thistle) (root, flower stalk) Echinopsine.48 Anthelmintic, galactagogue, depurative, treat tumors, swellings, leucorrhea, and gout. 

Echinops grijsii Hance, E. gmelini Ledeb., E. dahuricus Fisch., E. sphacrocephalus Miq. 

Echinopsine Echinops dahuricus, E. gmelini, E. grijsii, E. sphacrocephalus, E. latifollus... 

Van den Ende, W., Clerens, S., Vergauwen, R., Boogaerts, D., Le Roy, K., Arckens, L., and Van Laere, A., Cloning and functional analysis of a high DP fructan fructan 1-fructosyl transferase from Echinops ritro (Asteraceae) comparison of the native and recombinant enzymes, Exp. Bot., 57, 775-789, 2006. 

Vergauwen, R., Van Laere, A., and Van den Ende, W., Properties of fructan fructan 1-fructosyltransferase (1-FFT) from Cichorium intybus L. and Echinops ritro L., two Asteraseae plants storing greatly different types of inulin, Plant Physiol., 133, 391 401, 2003. 

Four new natural products, namely 5,5"-dichloro-a-terthiophene, 5-chloro-a-terthiophene, 5-acetyl-a-terthio-phene, and 5-carboxyl bithiophene, together with seven known thiophenes were isolated and purified from ethanol extract of roots of Echinops grijisii Hance <2002M1175>. 

Echinacea (purple coneflower) Echinops (globe thistle)... 

Echinops commutatiis Juuratska (Compositae) (XII, 475) Echinorine was isolated 87). 

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