Phenolic sesquiterpene

The total synthesis of the phenolic sesquiterpene (+)-parviflorine was accomplished by L.A. Maldonado and co-workers. The key step in the synthetic sequence was the reaction of an enamine with acrolein to form a bicyclic intermediate, which was subjected to a Grob fragmentation to afford the eight-membered ring of the natural product. The bicyclic ketone substrate was refluxed in benzene using a Dean-Stark trap and the resulting enamine was taken to the next step as crude material. 

Main components 1.5-4% essential oil, which contains linalool, bomeol, terpinene -ol, a-terpineol, the methyl ethers of thymol, carvacrol and eugenol, cuparophenol (a phenolic sesquiterpene), sesquiterpene hydrocarbons, cascarilladiene, cascarillone [45, 46] and cascarillic acid ]47], Moreover, cascarilline (bitter constituent), cascaril-line A, vanillic aldehyde, resin, tannins, fat and starch are present. 

The phenolic sesquiterpene xanthorrhizol is found as a blue-violet zone at R, — 0.55, directly above the reference compound thymol (Tl). 

Piper camphor. 0 9465 + 19 21 Camphor, borneol, terpenes, free acids, phenols, sesquiterpene alcohol. 

Semmler has detected a small qnaotitv of a sesquiterpene alcohol, and a phenol ether to which he assigned the name elemicin. This body h 3 a specific grariiy 1-063 at 30, refractive index 1 3365, aud boils at 144 to 147 - at lO mm. 

L and Pyoian found Ihe oil lo conta.iri a phenol having the ugL Dol, free tatty acids, aud a sesquiterpene having the follnw-... 

Isolation of Sesquiterpene Lactones. The ether extract was evaporated and dissolved in 952 ethanol. Then an equal volume of 42 aqueous lead acetate was added. After 1 hour the mixture was filtered to remove precipitated chlorophyll and phenolic products and the ethanol removed under vacuum. The aqueous layer was extracted with chloroform giving a dark colored oil from which the sesquiterpenes were isolated by a combination of chromatographic procedures, i.e., LH-20 gel permeation, silica gel using both packed columns and thin layer plates. A variety of solvents were also used to purify the individual sesquiterpene lactones, e.g., benzene-acetone (1 1), ethyl acetate, chloroform-methanol (9 1). On thin layer chromatographic plates, spots were visualized by spraying with 22 aqueous KMn04 solution. 

Kampa et al. made the interesting observation that protocatechuic acid, which is found in grapes and red wine from Vitis vimfera (Vitaceae), showed a time- and dose-dependent inhibitory effect on cell growth of T47D human breast cancer cells at low concentrations (108). The phenolic compound is a potent inhibitor of topoisomerase I (109). The plant likely contains some germanacrolides because these sesquiterpenes are known... 

Resins older than 40 000 years are considered to be fossil resins. The fossilization of resins begins with polymerisation and forms ambers and copals. Most of the ambers are derived from components of diterpenoid resins with a labdanoid structure other ambers are based on polymers of sesquiterpene hydrocarbons such as cadinene, and may include triterpenoids less common ambers from phenolic resins derive from polymers of styrene. Figure 1.4 shows the skeletal structures of the components which make up the polymers occurring in fossil resins [141]. 

Pollen allelopathy is phenomenon when pollen chemicals (e.g., phenols, terpenoids, sesquiterpene lactones, etc.) inhibit sexual reproduction in heterospecific individuals due to influencing of fertilization (Murphy 1992). The phenomenon includes excretion of signaling compounds from the donor cell (pollens, pistil stigma), recognition of a specific signal, transmission of information (pollen), and the development of a characteristic response in the acceptor cell. The possible mechanism of the effect was described in Roshchina (2001). 

Other phenolic compounds of commercial importance include the terpenoids, including mono, di, tri, and sesquiterpenes. While most of these are used as essential oils, fragrances, and flavors in various products, they are toxins in certain species. For example the sesquiterpene lactones of the Centaurea species cause an irreversible Parkinson s-like condition in horses called nigro-pallidal encephalomalacia. This is a lethal condition and the prognosis for recovery is grave in most cases, affected horses should be euthanized before reaching the terminal stages. 

In the Andes, nearly all of the about 160 varieties of wild potatoes, and two of the eight cultivated species are toxic. Some frost-resistant species that grow above 3600 m have high levels of alkaloids, which are bitter and potentially toxic. These are hybrids between Solanum stenotonum and wild potatoes such as Solanum megistacrolohum and Solanum acaulc. Other secondary plant compounds in potatoes are saponins, phytohemagglutinin, proteinase inhibitors, sesquiterpene phytoalexins, and phenols. 

Fujimoto, Y., K. Maruno, and S. Made. Antitumor sesquiterpene extraction from ginger roots. Patent-Japan Kokai Tokkyo Koho-01 221,344 1989 6 pp. Yabe, T., K. Toriizuka, and H. Yamada. Kami-untan-to (Kut) improves cholinergic deficits in aged rats. Phytomedicine 1996 2(3) 253-258. Nishimura, K., Y. Kitada, and T. Fukuda. Phenols for moisture-increas-... 

Wright, A.E. Pomponi, S.A. McConnell, O.J. Kohmoto, S. McCarthy, P.J. (1987) (+)-Curcuphenol and (+)-curcudiol, sesquiterpene phenols from shallow and deep wata collections of the marine sponge Didiscus Jlavus. J. Nat. Prod., 50, 976-8. 

In addition to vitamins and minerals, tubers contain a complex assortment of other small molecules, many of which are phytonutrients. These include polyphenols, flavonols, antho-cyanins, phenolic acids, carotenoids, polyamines, glycoalkaloids, tocopherols, calystegines, and sesquiterpenes. 

A wide variety of EOs are known to possess antimicrobial properties and in many cases this activity is due to the presence of active constituents, mainly attributable to isoprenes such as monoterpenes, sesquiterpenes and related alcohols, other hydrocarbons and phenols [8, 9]. 

Hedychium coronarium Koen. Shan Ren (Ginger lily) (flower, rhizome) Sesquiterpenes, phenols, aldehyde, ketone, 1,8-cineole, camphene, beta-pinene.60-195 Stimulant. 

N.A. Phenolic glycosides, eugenol, tannins, sesquiterpene lactone." Treat fever, stomach and intestinal complaints, diarrhea, and reduce bleeding, inflammation, and hemorrhoids. 

N.A. Geum urbanum L. Phenolic glycosides (eugenol), tannins, volatile oil, sesquiterpene lactone, cnicin." Treat mouth, throat, and gastrointestinal tract disorders. For peptic ulcers, irritable bowel syndromes. 

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