Antifungal sesquiterpene

The antifungal sesquiterpene dialdehydes polygodial and warburganal, from Polygonum hydropiper, were determined by HPLC on an ODS column using methanol-... 

Antifungal Sesquiterpene Dialdehydes from the Warbiirgia Plants and their Synergists... 

More specifically, antifungal sesquiterpene dialdehydes from the Warburgia trees are reviewed based on our own study. These sesquiterpene dialdehydes are the rare phytochemicals that exhibited potent antifungal activity against C. albicans. The aim of this review is to describe an example of what can be done after identification of biologically active principles. 

Polygodial was first isolated as a hot tasting substance from the sprout of Polygonum hydropiper (Polygonaceae) (24), which has been used in folk medicines and food spices in several Aslan countries including Japan and Vietnam. For example, the sprout of P. hydropiper is a well known relish for "sashimi" in Japan (25,26). Subsequently, warburganal was also isolated from the same source in minute amounts (27). In addition to these three antifungal sesquiterpene dialdehydes (1-3), a number of... 

M. Taniguchi, Y. Yano, E. Tada, K. Dcenishi, S. Oi, H. Haraguchi, K. Hashimoto and I. Kubo, Mode of action of polygodial, an antifungal sesquiterpene dialdehyde, Agric. Biol. Chem., 52 (1988) 1409-1414. 

It is an antifungal sesquiterpenes induced in leaves of Nicotiana glutinosa following infection with tobacco mosaic virus (TMV). The compound could not be detected in inoculated leaves. Its isolation2 was achieved by Burden and coworkers. Young plants (6-8 weeks old) of N-glutinosa with 4-5 fully expanded leaves in aqueous suspension were inoculated with... 

The antifungal sesquiterpene (-)7-hydroxycalamenene (142) was first isolated68 from the heartwood of ulmus thomasii and subsequently found69 in the heartwood of other healthy elm species. The (+)-enantiomer has been isolated from Eremophila drummondii and its structure was 90, 29, 3449-3451. 

We have described the chemistry of some selected sesquiterpenes which have been classified as phytoallexins. We would to apologize for unintentional omission of any important information in this review, which we tried to make as comprehensive as possible. A variety of synthetic reactions has been used to achieve the total synthesis of these phytoalexin sesquiterpenes. The isolation and biological activity of these sesquiterpenes have been discussed. It is necessary to mention that Takasugi et al.81 have reported for the first time costunolide is an antifungal sesquiterpene which inhibited spore germination of Ceratocystis fimbriata at concentration of 32 pg/ml. Many diterpenes and flavonoides have been also listed as phytoallexins. It is hoped that the research workers would find some useful information in this article. It is safe to predict from discussions in this article that many organic chemists would try to isolate antifungal sesquiterpenes. 

Dellar et al. (55) isolated the antifungal sesquiterpenes aristolen-2-one (Compound 9) and prostantherol (Compound 10) from two species of Prostanthera (Labiatae). Activity was assessed and tracked through the separation procedure by the use of direct bioautography with Cladosporium cucumerinum as the target fungus. 

R. S. Burden, J. A. Bailey and G. G. Vincent, "Glutinosone, A New Antifungal Sesquiterpene from Nicotlana glutlnosa Infected with Tobacco Mosaic Virus", Phytochemistry, lA, 221-223 (1975). 

Stachybotris cylindrospora often has been isolated from clean xylem tissue of P. tremuloides. The metabolites produced by S. cylindrospora cultured in liquid medium were subjected to bioassay guided separation on XAD-16 non-ionic resin, followed by Sephadex LH-20 and silica gel chromatography to afford two known antifungal sesquiterpenes, trichodermin (20) and trichodermol (21) (Chart 4). Both compounds... 

N.A. Acoric acid, asarone, linalool, palmitic acid, methylamine, saponin, mucilage, sesquiterpenes.99 100 103 105 Used as a panacea. It is antibacterial, antifungal, antiseptic, antiamebic, antiprotozoal, a vermifuge. Treat digestive upset, fevers. 

N.A. Alpinia galanga Miq. Volatile oil, alpha-pinene, cineole, linalool, sesquiterpene lactones, galangol, galangin." A stimulant, carminative, prevents vomiting, antifungal. 

More recently, two new isonakafiiran-type sesquiterpenes were isolated from this sponge species [74], These types of compounds possess interesting antitumor and antifungal activity, and attempts to synthesize them are being conducted [75], Other bioactive metabolites, such as antifouling sesquiterpenes, have also been recently isolated from Dysidea herbacea [76],... 

Bicyclic sesquiterpenes include a variety of bioactive compounds including the Solanaceae phytoalexins capsidiol (G61G6) from Capsicum frutescms (pepper) and the Solanum tuberosum (potato) antifungals rishitin (G61C6) and solavetivone (G6-G5) the Ipomoea batatus... 

There are many examples in the literature for applications of LC-NMR in the pharmaceutical industry. In the area of natural products, LC-NMR has been applied to screen plant constituents from crude extracts [54,57,67,68] and to analyze plant and marine alkaloids [69-72], flavonoids [73], sesquiterpene lactones [74,75], saponins [58,76], vitamin E homologues [77], and antifungal and bacterial constituents [56,78,79] as examples. In the field of drug metabolism, LC-NMR has been extensively applied for the identihcation of metabolites [42, 80-88] and even polar [89] or unstable metabolites [43]. And hnally, LC-NMR has been used for areas such degradation products [90-93], drug impurities [94-102], drug discovery [103,104], and food analysis [105-107]. 

H2O as a mobile phase. These sesquiterpene dialdehydes were accumulated in young leaves and shoots and possessed antifungal activity. 

I. Kubo and M. Himejima, Potentiation of antifungal activity of sesquiterpene dialdehydes against Candida albicans and two other microorganisms, Experientia, 48 (1992) 1162-1164. 

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