€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****DISS ABSTR INT (SCI)***** Comezoglu SN ISOLATION AND CHARACTERIZATION OF NEW TRICHOTHECENES FROM BACCHARIS MEGAPOTAMICA; CHEMICAL MODIFICATIONS OF BACCHARINOID B5 In: Diss Abstr Int (Sci) (1987) 47(9):3768 ISSN: 0419-4217 A large scale extract (approx 1800 Kg) of the Brazilian plant Baccharis megapotamica has yielded a large number of trichothecenes called baccharinoids. These compounds are highly toxic and many exhibit excellent in vivo and in vitro anticancer activity. From this plant extract, over 20 baccharinoid and roridin type macrocyclic trichothecenes have been isolated. The isolation and characterization of a series of new baccharinoids (B1, B2, B9, B12, B13, B14, B16, B17, B20, B21, B23, B24, B25, and B27) are described. These compounds possess either an 8beta-hydroxy group or 9beta,10beta-epoxy group, with the exception of B12 which has a 3alpha-hydroxy group, and B23 and B24 which have a 16-hydroxy group. They also differ from each other by a number of variations in their macrocyclic ring. In addition, they exist as diastereomers, epimeric at C13', such as (B1,B2),(B9,B10),(B13,B14), and (B23,B24). All the new baccharinoids were found to be cytotoxic against L1210 antileukemic cells. This suggests that they may be promising anticancer agents. Several synthetic derivatives were prepared of baccharinoid B5 which is one of the major trichothecenes found in B megapotamica. B5 was converted to a verrucarin-type compound with tetrabutylammonium chromate in 35% yield. Oxidation of B5 to the verrucarin-type derivative with chromium reagents proved to be difficult because of the presence of the 4'-hydroxy group. When the 4'-hydroxy group was blocked, the oxidative conversion to the verrucarin-type compound proceeded smoothly. 4',13'-Dioctanoyl B5, 4'-monooctanoyl B5, 7',8'-epoxy B5, 4',13'-diphosphorylated B5 and 4',13'-di(4-methyl-1-piperazine)acetyl B5 were prepared. Their in vitro activities against L1210 leukemic cells were tested. A decrease in the toxicity of 4',13'-dioctanoyl B5 was observed and it also was found to be inactive in vivo against P388 mouse leukemia. (Full text available from University Microfilms International, Ann Arbor, MI, as Order No: AAD86-28972) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****APPLIED AND ENVIRONMENTAL MICROBIOLOGY***** Mirocha CJ Abbas HK Treeful L Bean G T-2 toxin and diacetoxyscirpenol metabolism by Baccharis spp. In: Appl Environ Microbiol (1988 Sep) 54(9):2277-80 ISSN: 0099-2240 Hybrids resulting from crosses between Baccharis sarothroides and B. pilularis (FS1), B. sarothroides (FS2) and B. megapotamica (FS3) were tested for their tolerance to trichothecenes as well as their ability to metabolize the toxins. B. sarothroides (desert broom) was placed in an aqueous solution containing 500 ppm of T-2 toxin and showed visible signs of toxicity on the twigs at 21 h after exposure but not at 6 h, indicating some resistance. Samples of the twigs harvested 6 and 21 h after treatment contained, respectively, T-2 (0.03 and 2.2 micrograms/g), HT-2 (0.09 and 7.6 micrograms/g), and T-2-tetraol (2.1 and 2.6 micrograms/g). The hybrid FS1 showed no signs of toxicity 6 h after treatment, and its twigs contained T-2 (0.8 micrograms/g), HT-2 (10.2 micrograms/g), and T-2-tetraol (10.8 micrograms/g). The leaves at 6 h contained 0.5 micrograms of T-2, 1.7 micrograms of HT-2, 0.01 microgram of 3'-hydroxy-HT-2, and 41 micrograms of T-2-tetraol per g. At 21 h, toxic signs were apparent and the twigs contained T-2 (39 micrograms/g), HT-2 (62 micrograms/g), 3'-hydroxy-HT-2 (0.8 microgram/g), and T-2-tetraol (22 micrograms/g).(ABSTRACT TRUNCATED AT 250 WORDS) Registry Numbers: 21259-20-1 (T-2 Toxin) 2270-40-8 (diacetoxyscirpenol) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF THE AMERICAN CHEMICAL SOCIETY***** Kupchan SM Jarvis BB Dailey RG Bright W Bryan RF Shizuri Y BACCHARIN, A NOVEL POTENT ANTILEUKEMIC TRICHOTHECENE TRIEPOXIDE FROM BACCHARIS MEGAPOTACEMICA (LETTER). In: J Am Chem Soc (1976) 98(22):7092-7093 ISSN: 0002-7863 The isolation and structural elucidation of an active antileukemic agent from ethanol extracts of Baccharis megapotamica Spreng are reported. These extracts and the isolated compound, baccharin, show inhibitory activity towards human KB cells in vitro and against P-388 leukemia in mice. Baccharin appears to be the first reported trichothecene triepoxide isolated from natural sources. The chemical structure and molecular stereochemistry of baccharin were determined by a direct single-crystal x-ray analysis. (11 refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF ETHNOPHARMACOLOGY***** Verastegui MA Sanchez CA Heredia NL Garcia-Alvarado JS Antimicrobial activity of extracts of three major plants from the Chihuahuan desert. In: J Ethnopharmacol (1996 Jul 5) 52(3):175-7 ISSN: 0378-8741 Dilution methods were employed to determine the effect of ethanolic extracts of Agave lecheguilla Torr. (Agavaceae), Baccharis glutinosa Pers. (Compositae) and Larrea tridentata (DC.) Cov. (Zygophyllaceae) on growth of yeasts, molds and bacteria. The three extracts analyzed showed good antimicrobial activity against more than one organism. The minimal inhibitory concentration of the extracts was also determined. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Tortoriello J Aguilar-Santamaria L Evaluation of the calcium-antagonist, antidiarrhoeic and central nervous system activities of Baccharis serraefolia. In: J Ethnopharmacol (1996 Sep) 53(3):157-63 ISSN: 0378-8741 Baccharis serraefolia is a widely used plant to treat diarrhoea in Mexican traditional medicine. Although the methanolic extract of this plant has shown an important dose-dependent spasmolytic activity, its underlying mechanism has not been studied. In the present work, the methanolic extract of B. serraefolia significantly delayed the onset of tonic seizures induced by strychnine and pentylenetetrazol; besides, it diminished the death rate and number of animals that exhibited convulsions. It produced potentiation of the hypnotic effect of pentobarbital. Oral administration produced an inhibition of gastrointestinal transit in mice as effective as that produced by loperamide. As to the effect on smooth muscles, the active extract produced an inhibition of contraction induced electrically, which could not be reversed by naloxone. The calcium concentration- contraction curve showed a rightward displacement when the extract was added to isolated guinea pig ileum depolarized with high K+ and cumulative concentrations of Ca2+. The results suggest that the methanolic extract does not interact with classical opiate receptors and its effects, at least that produced on smooth muscle, may be due to a probable interference with calcium influx and/or calcium release from an intra-cellular store. Registry Numbers: 53179-11-6 (Loperamide) 54-95-5 (Pentylenetetrazole) 57-24-9 (Strychnine) 67-56-1 (Alcohol, Methyl) 7440-70-2 (Calcium) 76-74-4 (Pentobarbital) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF NATURAL PRODUCTS***** Jarvis BB Midiwo JO Bean GA Aboul-Nasr MB Barros CS The mystery of trichothecene antibiotics in Baccharis species. In: J Nat Prod (1988 Jul-Aug) 51(4):736-44 ISSN: 0163-3864 The Brazilian higher plant Baccharis coridifolia has been shown to synthesize de novo a series of highly toxic macrocyclic trichothecene antibiotics heretofore found to be produced only by fungi. These compounds are produced only by female plants that have undergone pollination. Neither the male nor female plant is sensitive to the toxic effects of trichothecenes, whereas North American Baccharis species are. The macrocyclic trichothecenes found in B. coridifolia are the same as those produced by Myrothecium fungi, and it is suggested that the plant has acquired the toxin-producing genes from this fungus. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Fullas F Hussain RA Chai HB Pezzuto JM Soejarto DD Kinghorn AD Cytotoxic constituents of Baccharis gaudichaudiana. In: J Nat Prod (1994 Jun) 57(6):801-7 ISSN: 0163-3864 Three new labdane diterpenes, gaudichaudols A-C [1-3], a new clerodane diterpenoid, gaudichaudone [4], and the known clerodane, articulin acetate [5] have been isolated from the aerial parts of Baccharis gaudichaudiana, together with the known compounds, apigenin, hispidulin, spathulenol, and ursolic acid. Through the application of 1D- and 2D nmr spectroscopy, the structures of the new diterpenoids [1-4] were, in turn; elucidated as 15,16,18,19- tetrahydroxylabd-5-ene, 15-O-acetyl-16,18,19-trihydroxylabd-5-ene, 16- O-p-trans-coumaroyl-15,18,19-trihydroxylabd-5-ene, and 2 beta-hydroxy- 15,16-epoxycleroda-1(10),15,16-trien-18,19-olide++ +. The isolated compounds were evaluated in P-388 lymphocytic leukemia cells as well as a battery of human cancer cell lines. Among the diterpenoids, gaudichaudol C [3], gaudichaudone [4], and articulin acetate [5] exhibited significant cytotoxic activity against certain cancer cells. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Jarvis BB Comezoglu SN Ammon HL Breedlove CK Miller RW Woode MK Streelman DR Sneden AT Dailey RG Jr Kupchan SM New macrocyclic trichothecenes from Baccharis megapotamica. In: J Nat Prod (1987 Sep-Oct) 50(5):815-28 ISSN: 0163-3864 The isolation and structural elucidation of biologically active baccharinoids B1 [11a], B2 [12a], B3 [5a], and B7 [6a] are reported with crystal structure determinations of baccharinoid B7 and of the triacetate of baccharinoid B2. All four compounds are isomeric with 11a/12a and 5a/6a being epimeric at C13'. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF ORGANIC CHEMISTRY***** Wagner H Seitz R Lotter H Herz W NEW FURANOID ENT-CLERODANES FROM BACCHARIS TRICUNEATA In: J Org Chem (1978) 43(17):3339-3345 ISSN: 0022-3263 An ethanol extract of Baccharis tricuneata (L. f.) Pers. var. tricuneata, which is widely used in Colombian folk medicine, showed significant antitumor and antiviral activity (no further details). The hexane extract of this plant yielded four closely related ent- clerodane diterpenoids (bacchotricuneatins A-D). Two flavonoids (cirsimaritin and cirsiliol) and a coumarin (scopoletin) were also isolated. The structures of the ent-clerodanes were elucidated. Biological activities of these compounds are not described. (34 Refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Kupchan SM Streelman DR Jarvis BB Daily RG Sneden AT ISOLATION OF POTENT NEW ANTILEUKEMIC TRICHOTHECENES FROM BACCHARIS MEGAPOTAMICA In: J Org Chem (1977) 42(26):4221-4225 ISSN: 0022-3263 The isolation and structural elucidation of the new potent antileukemic trichothecenes baccharin, baccharinol, isobaccharinol, and isobaccharin are reported. Baccharinol and isobaccharinol were shown by hydrolysis to be esters of 8-beta-hydroxyverrucarol. Conversion of baccharinol and isobaccharinol to a common intermediate demonstrated that isobaccharin and isobaccharinol were the C-13' epimers of baccharin and baccharinol, respectively. (16 Refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****MEMORIAS DO INSTITUTO OSWALDO CRUZ***** Vargas VM Guidobono RR Henriques JA Genotoxicity of plant extracts. In: Mem Inst Oswaldo Cruz (1991) 86 Suppl 2:67-70 ISSN: 0074-0276 Aqueous extracts of seven species used in Brazilian popular medicine (Achyrocline satureoides, Iodina rhombifolia, Desmodium incanum, Baccharis anomala, Tibouchina asperior, Luehea divaricata, Maytenus ilicifolia) were screened to the presence of mutagenic activity in the Ames test (Salmonella/microsome). Positive results were obtained for A. satureoides, B. anomala and L. divaricata with microsomal activation. As shown elsewhere (Vargas et al., 1990) the metabolites of A. satureoides extract also show the capacity to induce prophage and/or SOS response in microscreen phage induction assay and SOS spot chromotest. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Gamberini MT Skorupa LA Souccar C Lapa AJ Inhibition of gastric secretion by a water extract from Baccharis triptera, Mart. In: Mem Inst Oswaldo Cruz (1991) 86 Suppl 2:137-9 ISSN: 0074-0276 Baccharis triptera Mart, is a widespread Compositae used in Brazilian folk medicine to treat gastrointestinal disturbances, rheumatic disease, mild fever, diabetes and as an anti-helminthic. Water extract of small branches of the plant (WE) administered to mice and rats (0.1 to 2 g/kg, p.o.) did not alter spontaneous motor activity, sleeping time induced by barbiturates or the tail-flick response in mice. The extract decreased by 40% the number of writhings induced by 0.8% acetic acid, i.p., but did not influence paw edema induced by carrageenan or dextran in rats. WE (2 g/kg, p.o.) decreased the intestinal transit of charcoal in mice by 20%. Gastric secretion in pylorus ligated rats was reduced after treatment with WE (1 and 2 g/kg, i.p. or intraduodenal) and the gastric pH was raised. The extract (1 g/kg, p.o.) prevented gastric ulcers induced in rats by immobilization at 4 degrees C, but not those induced by indomethacin (10 mg/kg, s.c.). The results indicate that WE may relieve gastrointestinal disorders by reducing acid secretion and gastrointestinal hiperactivity. Neither analgesic nor anti- inflammatory activities were detectable. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PHYTOCHEMISTRY***** Zdero C Bohlmann F Niemeyer HM ent-labdane glycosides from Baccharis pingraea. In: Phytochemistry (1990) 29(8):2611-6 ISSN: 0031-9422 The aerial parts of Baccharis pingraea, collected in Chile, afforded, in addition to two diterpene glycosides isolated previously, 14 new ones and two of the corresponding desacyl aglycones. The structures were elucidated by high field 1H NMR spectroscopy. The differences between the collections from Argentina and Chile are discussed. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PLANTA MEDICA***** Gene RM Cartana C Adzet T Marin E Parella T Canigueral S Anti-inflammatory and analgesic activity of Baccharis trimera: identification of its active constituents. In: Planta Med (1996 Jun) 62(3):232-5 ISSN: 0032-0943 The butanolic fraction (BT-II) derived from the aqueous crude extract was prepared from aerial parts of Baccharis trimera and assessed in anti-inflammatory, analgesia, and ulcerogenesis models. Intraperitoneal pretreatment with lyophilized BT-II, at doses ranging from 40 to 100 mg/kg, markedly inhibited carrageenan- and dextran- induced inflammation (70.4-90.8% and 25.7-71.3%, respectively) and weakly decreased C16-paf- and arachidonic acid-induced swelling (24.9- 36.7% and 0-30.6%, respectively). No effect was observed, at the same doses, on zymosan-induced edema. The intraperitoneal examination indicates that the anti-phlogistic action of BT-II was not due to an irritating effect at the injection site. Besides, BT-II reduced abdominal constrictions in mice following injection of acetic acid: at 50 mg/kg, it gave 67.4% inhibition and, at 100 mg/kg, 95.1%. The ulcerogenic assay showed that the incidence of ulcers after BT-II i.p. treatment was 2/6 at 50 mg/kg and 6/6 at 100 mg/kg. Ulcerogenic indices were 1.3 +/- 0.5 and 2.7 +/- 0.8, respectively. These results indicate that B.trimera shows strong anti-inflammatory and analgesic properties which seem to be due, at least partly, to the inhibition of prostaglandin biosynthesis. The chromatographic separation of BT- II monitored by bio-assay (carrageenan-induced edema test in mice) was carried out. The active constituents were found to be mainly saponins in which echinocystic acid (or its enantiomer) is the major aglycone, and also rutin. Registry Numbers: 53-86-1 (Indomethacin) 64-19-7 (acetic acid glacial) 9000-07-1 (Carrageenan) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Rahalison L Benathan M Monod M Frenk E Gupta MP Solis PN Fuzzati N Hostettmann K Antifungal principles of Baccharis pedunculata [letter] In: Planta Med (1995 Aug) 61(4):360-2 ISSN: 0032-0943 Four compounds including a flavone, an acetylenic lactone, a prenylated coumarin, and a 3-methyl ether flavone were isolated from the dichloromethane leaf extract of Baccharis pedunculata (Mill.) Cabr. (Asteraceae). The latter three compounds were identified to be responsible for the antifungal activity against some human pathogenic and phytopathogenic fungi. The most active compound, lachnophyllum lactone, an acetylenic lactone, showed a very high toxicity (LD50 2 micrograms/ml) against human keratinocytes. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€