€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****DISS ABSTR INT (SCI)***** Seida AA ISOLATION, IDENTIFICATION AND STRUCTURE ELUCIDATION OF CYTOTOXIC AND ANTITUMOR PRINCIPLES FROM AILANTHUS INTEGRIFOLIA, AMYRIS PINNATA AND BALANITES AEGYPTIACA In: Diss Abstr Int (Sci) (1979) 39(10):4843 Chromatography of the chloroform fraction of the root bark of Ailanthus integrifolia species calycina, resulted in the isolation of two compounds with cytotoxic activity, chaparrinone and the novel 6 alpha-tigloyloxy-chaparrinone. Structures for both compounds were established by spectral and chemical means. 6Alpha-tigloyloxy- chaparrinone is the first example of a simaroubolide esterified at the 6 position which has been shown to exhibit antileukemic activity. A noncytotoxic novel simaroubolide, K234, was obtained from the aqueous extract of the root bark of A integrifolia species calycina. A chloroform extract of stem bark yielded glaucarubol tiglate, beta- sitosterol and beta-sitosterol glucoside, three known compounds. Only glaucarubol tiglate exhibited cytotoxic activity. A chloroform fraction of the leaves and inflorescences of Amyris pinnata was chromatographed and yielded seselin, savinin, austrobailignan-1 and beta-sitosterol. Of these only the lignan austrobailignan-1 was found to be cytotoxic. A chloroform fraction of the stem bark of Balanites aegyptiaca was chromatographed over a column of silica gel and yielded beta-sitosterol, bergapten, marmesin and beta-sitosterol glucoside. None of these compounds were active in either 9KB5 (in vitro) or PO388 (in vivo) systems. (Author abstract) (no Refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****ARZNEIMITTEL-FORSCHUNG***** Vestweber AM Beuth J Ko HL Tunggal L Buss G Pulverer G [In vitro activity of Mercurius cyanatus complex against relevant pathogenic bacterial isolates] In-vitro-Aktivitat von Mercurius cyanatus-Komplex gegenuber relevanten pathogenen Bakterienisolaten. In: Arzneimittelforschung (1995 Sep) 45(9):1018-20 ISSN: 0004-4172 (Published in German) The antimicrobial activity of mercurius cyanatus complex (Oligoplex) and its components Mercurius cyanatus D5, Echinacea angustifolia D1, Ailanthus glandulosa D3, Ammonium bromatum D3, Baptisia tinctoria D3, Euspongia officinalis D2, alcohol 5% (dilution: D1 = 1: 10, D2 = 1 : 100 etc.) was tested in vitro by serial dilution tests against 105 clinical isolates (grampositive/negative, aerobes and anaerobes with relevance for pharyngitis). The bactericidal activity was compared with that of vancomycin when appropriate. One component of the composition (Mercurius cyanatus) exerted a considerable bactericidal activity against S. pyogenes, S. agalactiae, S. pneumoniae, S. aureus, E. faecalis in serial dilutions of the clinical relevant concentration D5. However, growth of H. influenzae, Bacteriodes sp. and Actinobacillus actinomycetemcomitans was not inhibited by Mercurius cyanatus and any other component of the composition. The composition, however, exerted a bactericidal range similar to that of Mercurius cyanatus, but less efficient. Analysis of the bactericidal effect of Mercurius cyanatus and vancomycin revealed comparability for S. pyogenes, S. agalactiae, S. pneumoniae, S. aureus and E. faecalis for vancomycin concentrations of 0.063-2 mg/l, which are clinically relevant. Registry Numbers: 1404-90-6 (Vancomycin) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****CANCER LETTERS***** Kubota K Fukamiya N Tokuda H Nishino H Tagahara K Lee KH Okano M Quassinoids as inhibitors of Epstein-Barr virus early antigen activation. In: Cancer Lett (1997 Feb 26) 113(1-2):165-8 ISSN: 0304-3835 Short-term in vitro assays for tumor promoters and antitumor promoters (Epstein-Barr virus activation test) were carried out for 14 quassinoids isolated from Ailanthus altissima. Some quassinoids, including ailantinol B, ailantinol C, ailanthone, and shinjulactone A, showed moderate activity at a molar ratio of 1:100 (TPA/quassinoids), and the results led to the elucidation of structure-activity relationships. Registry Numbers: 1448-23-3 (Glaucarubin) 16561-29-8 (Tetradecanoylphorbol Acetate) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****CHEMICAL AND PHARMACEUTICAL BULLETIN***** Kosuge K Mitsunaga K Koike K Ohmoto T Studies on the constituents of Ailanthus integrifolia. In: Chem Pharm Bull (Tokyo) (1994 Aug) 42(8):1669-71 ISSN: 0009-2363 A new phenolic glycoside, 3,4,5-trimethoxyphenol-1-(6- xylopyranosyl)glucopyranoside, was isolated together with twenty known compounds identified as koaburaside, 3,4,5-trimethoxyphenol, 5,7-dihydroxychromone-7-neohesperidoside, naringin, neoeriocitrin, p- coumaric acid, vanillin, vanillic acid, coniferyl aldehyde, ferulic acid, trans-triacontyl-4-hydroxy-3-methoxycinnamate, p- methoxycinnamic acid, 2,6-dimethoxybenzoquinone, 2-(1- hydroxyethyl)naphtho[2,3-b]furan-4,9-dione, 2-acetylnaphtho[2,3- b]furan-4,9-dione, 2-(1-hydroxyethyl)-6-methoxynaphtho[2,3-b]furan- 4,9-dione, 2-acetyl-6-methoxynaphtho[2,3-b]furan-4,9-dione, specioside, jioglutin C and rehmaglutin D from the bark of Ailanthus integrifolia Lamk (Simaroubaceae). €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****INDIAN JOURNAL OF EXPERIMENTAL BIOLOGY***** Dhanasekaran S Suresh B Sethuraman M Rajan S Dubey R Antifertility activity of Ailanthus excelsa Linn. in female albino rats. In: Indian J Exp Biol (1993 Apr) 31(4):384-5 ISSN: 0019-5189 Alcoholic extract of leaf and stem bark of A. excelsa at a dose of 250 mg equivalent of plant material/kg body weight, exhibited remarkably high anti-implantation and early abortifacient activities. The results are in agreement with the traditional use of this plant as a abortifacient by the Irula women of the Nilgiri district. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF NATURAL PRODUCTS***** Anderson LA Harris A Phillipson JD Production of cytotoxic canthin-6-one alkaloids by Ailanthus altissima plant cell cultures. In: J Nat Prod (1983 May-Jun) 46(3):374-8 ISSN: 0163-3864 Ailanthus altissima (Mill.) Swingle was established as callus- and cell-suspension cultures. Canthin-6-one and 1-methoxycanthin-6-one were isolated by a combination of preparative tlc and preparative hplc. The two alkaloids were identified by their uv, ms, and 1H-nmr spectra. The combined yield of the two alkaloids was 1.38% of dry weight from callus and 1.27% of dry weight from cell suspensions. The cytotoxicities of canthin-6-one, 1-methoxycanthin-6-one, 5- methoxycanthin-6-one, and canthin-6-one-3-N-oxide to guinea pig ear keratinocytes have been compared, and the IC50 values range from 1.11 to 5.76 micrograms/ml. There is no significant difference in activity among these four cytotoxic alkaloids. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Polonsky J Varon Z Moretti C Pettit GR Herald CL Rideout JA Saha SB Khastgir HN The antineoplastic quassinoids of Simaba cuspidata spruce and Ailanthus grandis Prain. In: J Nat Prod (1980 Jul-Aug) 43(4):503-9 ISSN: 0163-3864 The South American Simaba cuspidata Spruce and North Indian Ailanthus grandis Prain were investigated as sources of potentially useful antineoplastic agents. Both of these Simaroubaceae plant species were found to produce 6 alpha-tigloyloxychaparrinone (4a) and the new quassinoid 6 alpha-tigloyloxychaparrin (3b). The latter structure was determined by interpretation of spectral data and oxidation to 6 alpha-tigloyloxychaparrinone (4a). While both glycol 3b and alpha- ketol 4a were found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell line, only the alpha-ketol (4a) inhibited growth of the corresponding in vivo system. Registry Numbers: 1448-23-3 (Glaucarubin) 69423-71-8 (6 alpha-tigloyloxychaparrinone) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****LLOYDIA***** Seida AA Kinghorn AD Cordell GA Farnsworth NR Potential anticancer agents IX. Isolation of a new simaroubolide, 6alpha-tigloyloxychaparrinone, from Ailanthus integrifolia ssp. calycina (Simaroubaceae). In: Lloydia (1978 Nov-Dec) 41(6):584-7 ISSN: 0024-5461 Chaparrinone (1) and 6alpha-tigloyoxychaparrinone (2) were shown to be responsible for the antitumor and cytotoxic activities of the root bark of Ailanthus integrifolia ssp. calycina. The structure of the latter compound was established by analysis of spectral data. Compound 2 exhibited a more pronounced biological activity than chaparrinone (1) and demonstrates, for the first time, anticancer activity of a simaroubolide ester substituted at only the 6-position. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Ogura M Cordell GA Kinghorn AD Farnsworth NR Potential anticancer agents vi. Constituents of Ailanthus excelsa (Simaroubaceae). In: Lloydia (1977 Nov-Dec) 40(6):579-84 ISSN: 0024-5461 Ailanthione (1), glaucarubinone (2) and a mixture of glaucarubol 15- isovalerate (3) and 13,18-dehydroglaucarubol 15-isovalerate (4) were found to be the compounds responsible for the antitumor and cytotoxic activities of extracts of the root bark of Ailanthus excelsa (Simaroubaceae). The latter compound, 4, is new. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PHYTOCHEMISTRY***** Phillipson JD A matter of some sensitivity. In: Phytochemistry (1995 Apr) 38(6):1319-43 ISSN: 0031-9422 The development of sensitive chromatographic and spectroscopic techniques for the isolation and structure determination of natural products has greatly facilitated phytochemical investigations. Chemical investigations of herbarium material have resulted in the isolation of indole, quinoline and isoquinoline alkaloids from a wide number of plants. Examples of novel natural products from higher plants are given and include alkaloids, terpenoids, phenolics and quinones. Some plants investigated have not yielded the types of constituents which would have been predicted from them. Plant tissue cultures provide alternative sources of biologically active compounds and examples investigated include Cinchona, Ailanthus, Brucea and Artemisia for antiprotozoal compounds and Datura for tropane alkaloids. Biological tests are useful for bioassay-guided fractionation of plant extracts and examples of the isolation of a series of natural products with antiprotozoal and cytotoxic activities are given. Chemical and biological investigations into the traditional medicine Dragon's blood (Croton lechleri) from S. America and a Chinese prescription for the treatment of atopic eczema are described. The use of radio-ligand binding assays for the detection of a wide range of biological activities is discussed. Sensitivity of chemical and biological techniques has greatly improved prospects for finding new drug entities from plants and for investigating traditional medicines. Basic phytochemical investigations should continue to be encouraged especially in view of the rapid loss of plant species. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€