Sesquiterpenes ginger

This sesquiterpene was isolated from oil of ginger by Von Soden and Rojahn 1 and has been examined by them and by Schreiner and Kremers.2 It is obtained by fractional distillation under reduced pressure and is a colourless and nearly odourless oil. Its characters are as follows —... 

Brooks has isolated from the fraction of oil of ginger boiling at 151° to 157° at 15 mm. an alcohol which he finds to be a sesquiterpene alcohol, CjsH gO, corresponding to the sesquiterpene zingiberene. It has the fragrant odour of ginger, and probably possesses one of the following constitutions —... 

ZO088 Bednarczyk, A. A., W. G. Galetto, and A. Kramer. Cis- and trans-beta-sesquiphellandrol. Two new sesquiterpene alcohols from oil of ginger Zingiber officinale. J Agr Food Chem 1975 23(3) 499-501. 

Young. Isolation of antirhinoviral sesquiterpenes from ginger (Zingiber officinale). J Nat Prod 1994 57(5) ... 

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-... 

Isolation and identification of five major sesquiterpene hydrocarbons of ginger. Phytochem Anal 1991 2 (1) 26-3 4. 

Brooks, B. T. Zingiberol-a new sesquiterpene alcohol occurring in the essen- 20318 tial oil of ginger. J Amer Chem Soc 1916 38 430-432. 

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

Ginger owes its characteristic organoleptic properties to two classes of constituents the odour and the flavour of ginger are determined by the constituents of its steam-volatile oil, while the pungency is determined by non-steam-volatile components, known as the gingerols. The steam-volatile oil comprises mainly of sesquiterpene hydrocarbons, monoterpene... 

The aroma and flavour of ginger are determined by the composition of its steam-volatile oil, which is comprised mainly of sesquiterpene hydrocarbons, monoterpene hydrocarbons and oxygenated monoter-penes. The monoterpene constituents are believed to be the most important contributors to the aroma of ginger and they tend to be relatively more abundant in the natural oil of the fresh ( green ) rhizome than in the essential oil distilled from dried ginger. Oxygenated sesquiterpenes are relatively minor constituents of the volatile oil but appear to be significant contributors to its flavour properties. 

Ginger oil displays considerable compositional diversity but is typically characterized by a high content of sesquiterpene hydrocarbons, including zingiberene, ar-curcumene, (3-bisabolene and (S-sesquiphellandrene. 

Yu et al. (1998) reported the presence of monoterpenes and sesquiterpenes as the main components in three samples of steam-distilled oil. They could not find pungent components in oil. Besides sesquiterpenes, the supercritical C02-extracted ginger oils contained 18.61—23.09% pungent components. These oils preserve the typical spicy odour and pungency of ginger. 

The major sesquiterpene hydrocarbon constituent of ginger oil, (-)-a-zingiberene,... 

Composition of ginger oil prepared from fresh ginger rhizomes was determined by gas chromatography (GC) and GC-MS techniques. The main sesquiterpene hydrocarbons identified were a-zingiberene (27-30%), a-curcumene... 

Ginger oleoresin was extracted from rhizomes with ethanol, isopropanol or liquid carbon dioxide. All oleoresin samples had monoter-penes and sesquiterpenes. Carboxylic acids were found in organic solvent extracts for an extraction time of 2h. The components responsible for the pungent characteristic of the oleoresin gingerols were detected in... 

Ginger is one of the most extensively used spices because of its wide range of application. It is used fresh and in the preserved or dried form. The potential of ginger in the culinary, non-culinary and medicinal fields is based on the chemistry of volatile oil and non-volatile pungent principles. The oil yield is about 2-3% and the oil consists of 64% sesquiterpene hydrocarbons, 6% carbonyl compounds,... 

Composition Main constituent is zingiberene (>30%) followed by P-sesquiphelland-rene. (-H)-ar-curcumene, (E,E)-a-famesene and (-)-P-bisabolene are further important sesquiterpene hydrocarbons. a-Terpineol and citral (up to 9% in Australian ginger) result in the citrus note, whereas nerolidol is responsible for the woody-soapy taste [115]. Further constituents are camphene, limonene, phellandrene, bomeol, 1,8-cine-ole, linalool, a-bisabolene, oxygenated sesquiterpene hydrocarbons, etc. For recent analytical data see [116, 117, 118]. 

Figure 3. Ginger 1 - 1.8-cineole, 2 - oc-terpinolene, 3 - zingiberene, 4 - P-bisabolene, 5 - y-cadinene, 6 -P-sesquiterpene.

This intermediate essential oil/oleoresin character is apparent in R-134a ginger extracts. The product, obtained in around 4% yield from dried Nigerian root, is a clear, mobile golden-yellow oil. By preserving the citral content of the raw material as well as the major sesquiterpenic components, the R-134a extract has a warm, spicy ginger aroma with a distinctive fresh lemony undertone. 

Murakami, A. et al., Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis the alpha,beta-unsaturated carbonyl group is a prerequisite. 

A widely distributed group of sesquiterpenes in the plant kingdom, e.g., from Curcuma aromatica, a ginger plant, and Nectandra elaiophora (Lauraceae) (see table below). 

Sesquiterpene alcohols Sesquiterpene alcohols are not commonly found in essential oils but, like bis-abolol (found in the German chamomile) are antiallergen, anti-inflammatory, and can also act as liver and glandular stimulants. Other essential oils that contain sesquiterpene alcohols are sandalwood oil (the active alcohol being a-sanatol, the structure of which is included in F ure 4), oil of ginger, patchouH oil, vetiver oil, and carrot seed oil. 

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