Faculty of Pharmacy, Pharmacognosy Department

Beta-and gamma-eudesmols mixture was microbiologically transformed by Gibberella suabinetti ATCC 20193. Seven different eudesmanoidal metabolites (3Ð9) were isolated and their structures were elucidated by the different spectroscopic techniques. These metabolites are: eudesma-4-en-11-ol-3-one (carissone), eudesma-3-en-2 , 11-diol, eudesma-4-en-3 ,11diol, eudesma-4(15)-en-8,11-diol, eudesma-4(15)-en-2α,11-diol (pterocarpol), 1(3)cyclo-eudesma-4(15)-en-11,12-diol and eudesma-4-en-11,15-diol.

The wetland Juncus plants (e.g., Juncus acutus, Juncus roemerianus and Juncus effusus) are considered a rich source of nitrogen-free alkylated phenanthrenoids. 1-11) Juncusol, 1,6-dimethyl-5-vinyl-9,10-dihydrophenanthrene-2,7-diol (2), isolated from J. roemerianus 1) is the first example of this class of natural products. A wide range of biological activities such as cytotoxicity, 1,2) antitumor, 3) antialgal, antimicrobial, and DNA-binding photosentizing antimicrobial 8) have been reported for Juncus phenanthrenoids. Although the phenanthrenoid-rich plant J. effusus is used traditionally in Japan, China, and Taiwan as an antipyretic and antiphlogistic agent, no antiinflammatory studies have been reported of its phenanthrenoids. Our chemical investigation of the rhizomes of J. acutus L. (Juncaceae) growing in Egypt has led to the isolation of a novel phenanthrenoid, juncutol (1), along with three related compounds (2-4). The structure of the novel metabolite was mainly determined on the basis of spectroscopic analyses, including 2D NMR ( 1 H-1 H COSY, HMQC, and HMBC) spectroscopy and by spectral comparison. The antiinflammatory effects of the isolated phenanthrenoids were evaluated in vitro by measuring the percent inhibition of proinflammatory inducible nitric oxide synthase (iNOS) protein expression in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.

Two new triglycosides, kaempferol-3-O-{(4-b-D-apiofuranosyl)-a-L-rhamnopyranoside}-7-O-a-L-rhamnopyranoside and kaempferol-3-O-{(4-b-D-xylopyranosyl)-a-L-rhamnopyranoside}-7-O-a-L-rhamnopyranoside were isolated from the methanol extract of Chenopodium murale, together with a known diglycoside, kaempferol-3-O-b-D-glucopyranoside-7-O-a-Lrhamnopyranoside. The characterization of the three compounds was achieved by various spectroscopic methods. #

Biotransformation of 18b-glycyrrhetinic acid, using Absidia pseudocylinderospora ATCC 24169, Gliocladium viride ATCC 10097 and Cunninghamella echinulata ATCC 8688a afforded seven metabolites, which were identified by different spectroscopic techniques ( 1 H, 13 C NMR, DEPT, 1 H-1 H COSY, HMBC and HMQC). Three of these metabolites, viz. 15a-hydroxy-18a-glycyrrhetinic acid, 13b-hydroxy-7a,27-oxy-12-dihydro-18b-glycyrrhetinic acid and 1a-hydroxy-18b-glycyrrhetinic acid are new. The 13 C NMR data and full assignment for the known metabolite 7b, 15a-dihydroxy-18b-glycyrrhetinic acid are described here for the first time. The major metabolites were evaluated for their hepatoprotective activity using different in vitro and in vivo models. These included protection against FeCl 3 /ascorbic acid-induced lipid peroxidation of normal mice liver homogenate, induction of nitric oxide (NO) production in rat macrophages and in vivo hepatoprotection against CCl 4 -induced hepatotoxicity in albino mice.

The phytoestrogen daidzein was metabolized by Nocardia species NRRL 5646 to give two metabolites obtained by hydroxylation and methylation. These metabolites were spectrally characterized as 7-methoxy-4 0 -hydroxyisoflavone (isoformononetin) and 7,8dimethoxy-4 0 -hydroxyisoflavone. Mortierella isabellina ATCC 38063 was able to metabolize daidzein to the unusual metabolite daidzein-4 0 -rhamnopyranoside.

The wetland Juncus plants (e.g., Juncus acutus, Juncus roemerianus and Juncus effusus) are considered a rich source of nitrogen-free alkylated phenanthrenoids. 1-11) Juncusol, 1,6-dimethyl-5-vinyl-9,10-dihydrophenanthrene-2,7-diol (2), isolated from J. roemerianus 1) is the first example of this class of natural products. A wide range of biological activities such as cytotoxicity, 1,2) antitumor, 3) antialgal, antimicrobial, and DNA-binding photosentizing antimicrobial 8) have been reported for Juncus phenanthrenoids. Although the phenanthrenoid-rich plant J. effusus is used traditionally in Japan, China, and Taiwan as an antipyretic and antiphlogistic agent, no antiinflammatory studies have been reported of its phenanthrenoids. Our chemical investigation of the rhizomes of J. acutus L. (Juncaceae) growing in Egypt has led to the isolation of a novel phenanthrenoid, juncutol (1), along with three related compounds (2-4). The structure of the novel metabolite was mainly determined on the basis of spectroscopic analyses, including 2D NMR ( 1 H-1 H COSY, HMQC, and HMBC) spectroscopy and by spectral comparison. The antiinflammatory effects of the isolated phenanthrenoids were evaluated in vitro by measuring the percent inhibition of proinflammatory inducible nitric oxide synthase (iNOS) protein expression in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.

The immunomodulatory bioassay-guided fractionation of the oleogum resin of frankincense (Boswellia carterii Birdwood) resulted in the isolation and identification of 9 compounds; palmitic acid and eight triterpenoids belonging to lupane, ursane, oleanane, and tirucallane skeleta were isolated form the resin. These triterpenoids are lupeol, beta-boswellic acid, 11-keto-beta-boswellic acid, acetyl beta-boswellic acid, acetyl 11-keto-beta-boswellic acid, acetyl-alpha-boswellic acid, 3-oxo-tirucallic acid, and 3-hydroxy-tirucallic acid. The structures of the isolated compounds were deduced based on spectroscopic evidences. The lymphocyte transformation assay of the isolated compounds proved that the total extract retained more activity than that of any of the purified compounds.

The yield of steam distillation of frankincense essential oil (3%); and its physicochemical constants were determined. Capillary GC/MS technique was used for the analysis of the oil. Several oil components were identified based upon comparison of their mass spectral data with those of reference compounds published in literature or stored in a computer library. The oil was found to contain monoterpenes (13.1%), sesquiterpenes (1%), and diterpenes (42.5%). The major components of the oil were duva-3,9,13-trien-1,5alpha-diol-1-acetate (21.4%), octyl acetate (13.4%), o-methyl anisole (7.6%), naphthalene decahydro-1,1,4a-trimethyl-6-methylene-5-(3-methyl-2-pentenyl) (5.7%), thunbergol (4.1%), phenanthrene-7-ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydro-1,1,4a,7-tetramethyl (4.1%), alpha-pinene (3.1%), sclarene (2.9%), 9-cis-retinal (2.8%), octyl formate (1.4%), verticiol (1.2%) decyl acetate (1.2%), n-octanol (1.1%). The chemical profile of the oil is considered as a chemotaxonomical m...

The composition of the essential oil of the fruits, leaves and stems of Daucus glaber Forssk has been studied by GC/MS. It was found that, the essential oil of the fruits consists of monoterpene hydrocarbons (limonene and sylvestrene are the majors) and phenylpropanoids (elemicin is the major). Sylvestrene has never been reported before in the essential oil of any Daucus species. The study of the essential oil of the leaves revealed the presence of monoterpene hydrocarbons; limonene and γ-terpinene are the majors and a small amount of sylvestrene. The essential oil of stems consists of monoterpene hydrocarbons (γ-terpinene is the major), terpene alcohols (mainly 4-terpineol) and phenylpropanoids (myristicin and elemicin are the majors). It is interesting that, the essential oil of the fruits is free from any oxygenated terpenes while that of the stems is free from limonene and sylvestrene which are present in the essential oil of the fruits and leaves in fairly large amounts. The essential oil of the fruits, leaves and stems shows broad antimicrobial activities against both gram positive and gram negative bacteria. In addition, the volatile oil of the stem, particularly, show activities against Candida albicans (yeast). Also, the prepared oils have variable cytotoxic activities with LC 50 21.52, 36.01 and 42.34 µg/ml, respectively.

The seeds of Citrus reticulata afforded the new limonoid derivative, isolimonexic acid methyl ether, in addition to the the previously isolated limonin, deacetylnomilin, obacunone and ichangin. The structure elucidation was achieved primarily through 1D and 2-D-NMR analyses. The marginal antimalarial activity of isolimonexic acid methyl ether is reported.

The immunomodulatory bioassay-guided fractionation of the methanolic extract of henna (Lawsonia inermis L.; syn. Lawsonia alba L.) leaves resulted in the isolation of seven compounds; three have been isolated for the first time from the genus, namely p-coumaric acid, 2-methoxy-3-methyl-1,4-naphthoquinone and apiin, along with the previously isolated compounds: lawsone, apigenin, luteolin, and cosmosiin. Structural elucidation of the isolated compounds was based upon their physical, chemical as well as spectroscopic characters. Their immuomodulatory profile was studied using an in vitro immunoassay, the lymphocyte transformation assay. The ABTS [2,2Ј-azino-bis (3-ethyl benzthiazoline-6-sulfonic acid)], free radical scavenging assay depicted that all isolated compounds exhibited antioxidant activity comparable to that of ascorbic acid.

Four tetracyclic triterpenoids and lupeol were isolated from the hybrid Parthenium argentatum x P. tomentosa. The new triterpenoids were identified as 16, 24-epoxy-3a-hydroxylanost-8-ene (argentatin E); 16, 24-epoxy-25-hydroxycycloart-1, 11, 22-trien-3-one (argentatin F); 16,24-dihydroxycycloart-20, 25-dien-3-one (argentatin G) and 16, 24-dihydroxycycloart-25-en-3-one (argentatin H). The chemical identities of these compounds were confirmed by the different spectrometric measurements. #

Argentatin B is a naturally occurring tetracyclic triterpene isolated from Parthenium argentatum x P. tomentosa. It was microbiologically transformed to 16, 24-epoxycycloartan-3alpha, 25-diol, (isoargentatin D), by Nocardia corallina var. taoka ATCC 31338, Mycobacterium species NRRL B3683 and Septomyxa affinis ATCC 6737. The later microbe also produced 16, 24-epoxycycloartan-3beta, 25-diol (argentatin D) and 1, 2-didehydroargentatin B, (isoargentatin D). Sodium hydroxide converted argentatin B to argentatin D and isoargentatin D. Hydrochloric acid treatment gave cycloartan-25-ol-3, 24-dione. Cerium sulfate/sulfuric acid/aqueous methanol induced scission of the isopropanol moiety and provided an isomeric mixture of 24-methoxy-25-27-trinorargentatin B. Oxidation of this isomeric mixture with pyridinium chlorochromate, selectively, attacked the isomer with the equatorial proton at position-24 to give the corresponding lactone, 24-oxo-25-27-trinorargentatin B. The produced compounds wer...

Two pyridine alkaloids were isolated from the derubberized resin of the hybrid Parthenium argentatum ¥ P. tomentosa. These alkaloids are (ð)-N-[4-(1-aminoethyl) phenyl]-4-[3-methylbutenylidine]-1, 4-dihydropyridine (guayulamine A) and (ð)-N-[4-(1-aminoethyl) phenyl]-4-[4-methylpentenylidine]-1, 4-dihydropyridine (guayulamine B). The structures were established by one-and two-dimensional NMR spectroscopy and mass spectrometry.

The biotransformation of partheniol by the fungus Calonectria decora ATCC 14767, produced six metabolites. These metabolites are; aromadendr-1(10)-en-8α -ol; 5(9),6-tricyclohumul-1(10)-en-8α-ol; 4,15-didehydro-6-bicyclohumulan-8α,10α-diol; 5(9),6-tricyclohumulan-4α,8α-diol; maalian-1α,8α-diol and 14-epi-1(4)-epoxymaalian-8α-ol. The identities of these metabolites were established by different spectroscopic measurements. ture, University of Arizona, USA, for his support and ancouragement.

The biotransformation of a mixture of argentatin A (20%) 1 and incanilin (80%) 2 by Gibberella suabinetti ATCC 20193 and Septomyxa affinis ATCC 6737 demonstrated the conversion of incanilin to 16 -hydroxylanosta-2, 8, 23-triene, while argentatin A did not react. The acetate of this triterpenoid mixture was biotransformed by Septomyxa affinis ATCC 6737 to give five metabolites. Argentatin A acetate was transformed to 3 , 16 ,30-trihydroxycycloart-20, 24-diene, 20R, 24R-epoxy-16 , 25-dihydroxy-3, 4-seco-cycloart-4(28)-en-3-oic acid acetate and 20R, 24R-epoxy-16 , 25-dihydroxy-3, 4-seco-cycloart-4(28)-en-3-oic acid. Incanilin acetate was converted to 16 -hydroxylanosta-2, 8, 23-triene and 20R, 24R-epoxy-16 , 25-dihydroxy-3, 4-seco-lanost-1, 4(28), 8-trien-3-oic acid acetate. The structural elucidations of these metabolites were achieved by different spectroscopic methods.