Effect of diarylheptanoids

Prasain, J.K. et al.. Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages, Biol. Pharm. Bull, 21, 371, 1998. 

Araujo, C.A.C., Alegrio, L.V., Castro, D., Lima, M.E.F., Comescardoso, L. and Leon, L.L. (1 999) Studies on the effectiveness of diarylheptanoid derivatives against Leishmania amazonensis. Memdrias do Instituto Oswaldo Cruz 94, 791-794. 

ZO079 Yamahara, ]., S. Hatakeyama, K. Taniguchi, M. Kawamura, and M. Yoshikawa. Stomachic principles in ginger. II. Pungent and anti-ulcer effects of low polar constituents isolated from ginger, the dried rhizoma of Zingiber officinale Roscoe, cultivated in Taiwan. The absolute stereostructure of a new diarylheptanoid. Yakugaku Zasshi 1992 112(9) 645-655. 

Table 3. Effect of some diarylheptanoids on the cytotoxic effect of CCI4 and galactosanune (GalN) in rat hepatocites at 1 mg/ml concentration...

No studies on biological effects of Type IV diarylheptanoids have been reported, but antibacterial activities of the garuganins from Garuga species have been predicted based molecular mechanics and molecular orbital calculations [47]. 

The major pigment in Curcuma species (Zingiberaceae family) is the yellow phenolic diarylheptanoid curcumin (Jl). Curcumin and its analogs have potent antioxidant and antiinflammatory effects, cytotoxicity against tumor cells, and antitumor-promoting activity (96). The biologic effects and targets of curcumin, as well as its possible roles in cancer prevention and therapy, have been reviewed recently (97, 98). 

As seen in the sections above, several of the diarylheptanoids of Types I, n, and V have been reported to exhibit various types of biological activities. Most of these studies have been performed on biomedically relevant targets in vitro (e.g. protein kinase C [14], LPS-activated macrophages [22], CC14-challenged hepatocytes [10], but in vivo anti-inflammatory effects have also been demonstrated for some compounds [3, 17]. Toxic effects on parasites, such as nematodes [6,27] and trypanosomatids [8] have also been recorded for the first time. 

Four diarylheptanoids were isolated from the methanol ic extract of the rhizomes of 4. officinarum and identified on the basis of their spectral data and by chemical correlations as l,7-diphenylhept-4-en-3-one (40), 7-(4"-hydroxy-3"-methoxyphenyl)-l-phenylhept-4-en-3-one (41), 1,7-dipheny 1-5-hydroxy-3-heptanone (43) and 5-hydroxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (44) [38]. From the chloroform-soluble fraction of the methanolic extract of the rhizomes of A. officinarum, three new diarylheptanoids, 5-methoxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (46), 5-hydroxy-7-(4"-hydroxyphenyl)- -phenyl-3-heptanone (45) and 7-(4"-hydroxy-3"-methoxyphenyl)- -phenyl-3,5-heptanedione (49) were isolated together with 41, 43 and 44 [39]. Compound 44 was the major constituent of the chloroform-soluble fraction. Compounds 41, 43-46 and 49 showed inhibitory effect against PG synthetase and IC50 values of the compounds were reported [39]. In addition to compounds 43, 44 and 52, three new diarylheptanoids, 42,47 and 48 were isolated from the rhizomes of A. officinarum and the structures were elucidated on the basis of the spectroscopic data [40]. The configuration of C-5 of 43 and 52 was determined to be R and that of hexahydrocurcumin was S [40]. 

Im et al. formulated monoolein-based cubic crystalline phase and its nanoparticle system of oregonin and hirsutanonol (both diarylheptanoid derivatives) to treat atopic dermatitis [91]. Diarylheptanoids have a therapeutic effect on the dermal inflammation as selective 5-hpoxygenase inhibitor and thus are expected to be applicable for atopic dermatitis [91]. For the effective treatment of atopic dermatitis with topical administration of therapeutics, penetration and accumulation of the agent into the relevant layers of the skin is required. Therefore, Im et al. explored the localization factors for local skin delivery of oregonin and... 

Diarylheptanoids and related compounds exhibit antibiotic effects (11) and appear to be part of the defense system of the plants. It is also ndtable that the... 

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