Bisabolol oxides

Bisabolol oxide (h/ f 40-45) appeared as pink and bisabolol (tiRf 65-70) as mauve-colored chromatogram zones on a pale yellow background. The detection limits per chromatogram zone were 40 ng for bisabolol oxide and 250 ng for bisabolol. 

Fig 1 Chromatogram of a chamomile flower extract and of chamomile oil components (A) and reflectance scans (B) of reference tracks with 3.75 pg bisabolol oxide (1) and 9.5 pg bisabolol (2) and a chromatogram track with chamomile flower extract (3). 

The dried capitula of Matricaria chamomilla L. (Asteraceae), or German chamomile, have been used as anti-inflammatory and antispasmodic remedies since very early times on account of its contents in bisabolol oxides the activity of which has been experimentally substantiated. The plant is listed in several European pharmacopeias, and is used in the form of tinctures, extracts, lotions, ointments, shampoos, and sunscreen products. 

The synthesis of tetrahydrofurans through cyclization via epoxide ring opening has been well investigated and has been applied to the preparation of a-bisabolol oxides (69IJC1060) and linalool oxides (77H(6)1365) and by Kishi et al. in the synthesis of lasalocid A (195), where the epoxide pathway resulted in a stereospecific construction of six out of the ten chiral centers (Scheme 93) (78JA2933). 

Bisabolol oxide Bisabolone oxide Caryophyllene oxide... 

The oils S-10 have less concentrated zones in the R, range 0.2-0.5, but prominent zones of azulene and THC at the solvent front. Oils 5 and 13 show a high polyine (IV) content, while oils 8 and 9 have hardly any polyines, but a relatively high amount of azulene (V) and bisabolol oxides A/B (I). OU 12 has a higher amount of bisabolol. 

Their main occurrence is also in essential oils, usually in combination with monoterpenes, although they have higher melting points. Essential oil of Roman chamomile, Anthemis nobilis (Asteraceae), contains the blue-coloured sesquiterpene chamazulene, while German chamomile Chamomilla recutita) contains the anti-inflammatory sesquiterpenes bisabolol and bisabolol oxides. 

Monoterpene oxides are relatively reactive, unstable molecules in which an oxygen atom is situated between two carbons. In most cases the oxygen atom substitutes a carbon in the ring of a monoterpenoid—usually an alcohol. An example is bisabolol oxide from chamomile Matricaria chamomilla). However, in the two most significant oxides—1,8-dneole and ascaridole—found in essential oils, the oxygen atoms are attached outside the main hydrocarbon ring. 

Five sesquiterpenes (a-bisabolol, a-bisabolol oxide A and B, chamazulene, fi-famesene) and two polyacetylenes (( )- and (Z)-ene-yne-dicycloether) were extracted fiom Chamomilla recutita and separated on a C g column (A = 200 lAn) using a 15-min 19/80/1- 59/40.5/0.5 acetonitrile/water/phosphoric acid gradient [1131]. Peak shapes were excellent and baseline resolution was achieved. Standard concentrations from 50 to 200 pg/mL were used. 

Bisabolol type Bisabolol oxide A type Azulene type Bisabolol oxide B type Bisabolon oxide type... 

Definition Blue essential oil obtained by steam distillation of the fresh or dried ower heads or owering tops of Matricaria recutita L. Chamomilla recutita L. Rauschert). There are two types of matricaria oils, which are characterized as rich in bisabolol oxides or rich in (-)-a-bisabolol. 

Content 1. Matricaria oil rich in bisabolol oxides bisabolol oxides 29%-81% chamazulene > 1%. 2. Matricaria oil rich in (-)- a-bisabolol (-)-a-bisabolol 10%-65%, chamazulene > 1%, total of bisabolol oxides and (-)-a-bisabolol > 20%. 

Bisabolol oxide B type Bisabolon oxide type... 

The oxidized bisabolene derivative a-bisabolol with antiphlogistic properties is a main active compound in German chamomile (Matricaria recutita). Depending on the origin of the plants and the chemotype or variety, varying proportions of the oxides (bisabolol oxide A, bisabolol oxide B, or bisabolone oxide A) may be present in the respective oils [30]. a-Bisabolol can also be found in larger... 

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