WOOD EXTRACTIVES IN RADIATA PINE ARE THE SOURCE OF THE OBSERVED PITCH PROBLEMS IN THE PULP AND PAPER INDUSTRY. VARIOUS METHODOLOGIES HAVE BEEN STUDIED AND USED TO REDUCE OR ELIMINATE THEIR NEGATIVE EFFECTS. A BIOLOGICAL TREATMENT WITH ALBINO FUNGI OF THE OPHIOSTOMA GENUS, FUNGI THAT DEGRADE THE LIPIDIC COMPONENTS OF EXTRACTIVES, HAS BEEN PROPOSED AS A MORE ENVIRONMENTALLY FRIENDLY ALTERNATIVE FOR PITCH DEGRADATION. THE CURRENT METHODS USED TO SEARCH FOR OPHIOSTOMA ALBINO STRAINS WITH THE HIGHEST DEGRADATION RATES OF WOOD EXTRACTIVES ARE LABOR INTENSIVE AND REQUIRE A LARGE AMOUNT OF RESOURCES. THE TWEEN 80® OPACITY TEST, AN ASSAY DESIGNED TO MEASURE LIPOLYTIC ENZYME ACTIVITY IN FILAMENTOUS FUNGI, WAS STUDIED TO VERIFY THE FEASIBILITY OF ITS APPLICATION AS A METHODOLOGY TO RANK OPHIOSTOMA ALBINO STRAINS WITH DERESINATION CAPABILITIES. THE TWEEN 80® OPACITY TEST WAS FIRST CHARACTERIZED BY IMPLEMENTING A NON-REPLICATED 2K-P FRACTIONAL FACTORIAL DESIGN OF RESOLUTION V FOR A 5 FACTORS WITH 16 TREATMENTS AND THEN TO STUDY THE EFFECT OF THE FUNGUS SPECIES ON THE LIPOLYTIC ENZYME ACTIVITY; A RANDOMIZED ONE FACTOR GENERAL FACTORIAL DESIGN WAS CONDUCTED. THE INCUBATION TEMPERATURE; ANTIBIOTICS PRESENCE; AND TWEEN 80®, CACL2 , AND PEPTONE CONCENTRATIONS WERE INVESTIGATED IN THE FIRST EXPERIMENT. THE OPHIOSTOMA SPECIES EFFECT WAS STUDIED IN THE SECOND EXPERIMENT. IN BOTH EXPERIMENTS, THE HALO AREA SIZE, WHICH WAS FORMED BY THE FATTY ACID-CALCIUM COMPLEX PRECIPITATE, WAS THE RESPONSE VARIABLE. THE RESULTS DEMONSTRATED THE EFFECTIVENESS OF THE TWEEN 80® OPACITY TEST TO MEASURE THE LIPOLYTIC ENZYME ACTIVITY OF OPHIOSTOMA ALBINO STRAINS. SIMILARLY, THE INCUBATION TEMPERATURE AND THE CONCENTRATIONS OF TWEEN 80®, CACL2 , AND BACTERIOLOGICAL PEPTONE HAD THE HIGHEST STATISTICALLY SIGNIFICANT EFFECT ON THE RESPONSE VARIABLE. IN ADDITION, OUR DATA DEMONSTRATED THAT THE ALBINO STRAINS FROM THE SPECIE O. FLOCCOSUM EXHIBITED THE HIGHEST RATE OF LIPOLYTIC ENZYME PRODUCTION.

OOMYCETES SUCH AS SAPROLEGNIA SP. ARE RESPONSIBLE FOR SERIOUS ECONOMIC LOSSES IN AQUACULTURE, THE STRATEGIES FOR THEIR CONTROL LEAD TO CONCERNS ABOUT THEIR EFFICACY AND ENVIRONMENTAL REPERCUSSIONS, SO ALTERNATIVES FOR THEIR REGULATION ARE BEING SOUGHT. THE AIM OF THIS STUDY WAS TO EVALUATE THE IN VITRO SUSCEPTIBILITY OF 2 REPRESENTATIVE STRAINS OF SAPROLEGNIA SP. TOWARD 2,4-DIHYDROXY-5

CONTEXT: LAURELIA SEMPERVIRENS (R. ET P.) TUL., IS AN EVERGREEN TREE THAT GROWTHS IN SOUTHERN CHILE, ITS LEAVES AND BARK ARE USED IN FOLK MEDICINE AS AN INFUSION. OBJECTIVE: THE ANTIMICROBIAL ACTIVITIES OF THE ESSENTIAL OIL AND ETHYL ACETATE EXTRACT OBTAINED FROM THE BARK OF LAURELIA SEMPERVIRENS WERE INVESTIGATED. MATERIALS AND METHODS: ETHYL ACETATE EXTRACT AND ESSENTIAL OIL WERE ANALYZED BY GC- MASS AND THE ANTIMICROBIAL ACTIVITY WAS INVESTIGATED AGAINST GRAM POSITIVE AND GRAM NEGATIVE BACTERIA. RESULTS: THE EXTRACT AND ESSENTIAL OIL SHOWED A STRONG ANTIMICROBIAL ACTIVITY AGAINST BACTERIA SUCH AS ACINETOBACTER BAUMANII, A RELEVANT WORLD NOSOCOMIAL PATHOGEN DISCUSSION AND CONCLUSION: THESE FINDINGS DEMONSTRATE THAT THE ETHYL ACETATE EXTRACT AND ESSENTIAL OIL OF L.SEMPERVIRENS BARK HAVE EXCELLENT ANTIMICROBIAL ACTIVITIES AND THUS HAVE GREAT POTENTIAL AS A SOURCE FOR NATURAL HEALTH PRODUCTS.

BACKGROUND: ANTHOCYANINS, FLAVONOIDS AND ORGANIC ACIDS WIDELY OCCURRING IN EXTRACTS OF THE FRUITS OF ARISTOTELIA CHILENSIS (?MAQUI?), CONCERTEDLY ACTS ON THE EXPRESSION OF CYCLOOXYGENASE-2 (COX-2), NF-?B, HT-29 AND CACO-2 COLON CANCER CELL GROWTH INHIBITION AND ON THE PRODUCTION OF INFLAMMATORY MEDIATORS. OBJECTIVE: TO ASSESS THE ANTI-INFLAMMATORY EFFECTS OF EXTRACTS FROM FRUITS OF ?MAQUI BERRY?, ON THE HT-29 AND CACO-2 HUMAN COLORECTAL CANCER CELL LINES BY MEASURING COX-2 AND NF-?B AS WELL AS THEIR ANTIOXIDANT ACTIVITIES. MATERIAL AND METHODS: METHANOL/WATER EXTRACTS AND ITS PARTITIONS (ACETONE AND ETHYL ACETATE) FROM THREE VARIETIES OF ?MAQUI? WERE USED TO ACCESS THEIR EFFECTS ON GROWTH OF HT-29 AND CACO-2 COLON CANCER CELLS, COX-2, NF-?B, NO FORMATION, OXIDATIONS BY DPPH, TBARS, FRAP AND ORAC.

THE AIM OF THIS STUDY WAS TO DETERMINE, FIRST, THE CHEMICAL COMPOSITION OF ALOYSIA POLYSTACHYA (GRISEB) MOLDENKE ESSENTIAL OIL, FROM LEAVES HARVESTED IN CENTRAL CHILE; AND SECOND, ITS ANTIOXIDANT AND CYTOTOXIC ACTIVITY. EIGHT COMPOUNDS WERE IDENTIFIED VIA GAS CHROMATOGRAPHY?MASS SPECTROMETRY (GC?MS) ANALYSES, WITH THE MOST REPRESENTATIVE BEING R-CARVONE (91.03%), R-LIMONENE (4.10%), AND DIHYDROCARVONE (1.07%). FOR ALOYSIA POLYSTACHYA ESSENTIAL OIL, ANTIOXIDANT ASSAYS (2,2-DIPHENYL-1-PICRYLHYDRAZYL (DPPH), H2O2, FERRIC REDUCING ANTIOXIDANT POWER (FRAP), AND TOTAL REACTIVE ANTIOXIDANT POTENTIAL (TRAP)) SHOWED GOOD ANTIOXIDANT ACTIVITY COMPARED TO COMMERCIAL ANTIOXIDANT CONTROLS; AND ANTI-PROLIFERATIVE ASSAYS AGAINST THREE HUMAN CANCER CELL LINES (COLON, HT-29; PROSTATE, PC-3; AND BREAST, MCF-7) DETERMINED AN IC50 OF 5.85, 6.74, AND 9.53 ?G/ML, AND SELECTIVITY INDICES OF 4.75, 4.12, AND 2.92 FOR HT-29, PC-3, AND MCF-7, RESPECTIVELY. WE ALSO REPORT ON ASSAYS WITH CCD 841 CON (COLON EPITHELIAL). OVERALL, RESULTS FROM THIS STUDY MAY REPRESENT, IN THE NEAR FUTURE, DEVELOPMENTS FOR NATURAL-BASED CANCER TREATMENTS.

ANTIOXIDANTS ARE KNOWN TO BE BENEFICIAL TO HEALTH. THIS PAPER EVALUATES THE POTENTIAL CHEMOPREVENTIVE AND ANTICANCER PROPERTIES OF PHENOLIC COMPOUNDS PRESENT IN GRAPE JUICE EXTRACTS (GJE) FROM AUTUMN ROYAL AND RIBIER VARIETIES. THE EFFECTS OF THESE GJE ON VIABILITY (SRB DAY ASSAY) AND METASTATIC POTENTIAL (MIGRATION AND INVASION PARAMETERS) OF COLON CANCER CELL LINES HT-29 AND SW-480 WERE EVALUATED. THE EFFECTS OF GJE ON TWO MATRIX METALLOPROTEINASE GENE EXPRESSIONS (MMP2 AND MMP9) WERE ALSO EVALUATED VIA QRT-PCR. IN THE FORMER, GJE REDUCED CELL VIABILITY IN BOTH CELL LINES IN A DOSE-DEPENDENT MANNER. GJE TREATMENT ALSO REDUCED CELL MIGRATION AND INVASION. MOREOVER, MMP-2 AND MMP-9 GENE EXPRESSION DIMINISHED DEPENDING ON EXTRACT AND ON CELL TYPE. CONCLUSIONS. THESE RESULTS PROVIDE NOVEL INFORMATION CONCERNING ANTICANCER PROPERTIES OF SELECTED GJE BY REVEALING SELECTIVE CYTOTOXICITY AND THE ABILITY TO REDUCE INVASIVENESS OF COLON CANCER CELLS.

ACANTHOSCELIDES OBTECTUS SAY (COLEOPTERA:CHRYSOMELIDAE) AND EPILACHNA VARIVESTIS MULSANT (COLEOPTERA:COCCINELLIDAE) ARE IMPORTANT PREDATORS OF DRY BEANS. DUE TO INFESTATION DURING CROP AND STORAGE, THESE INSECTS AFFECTS THE QUALITY OF SEED AND CROP YIELDS. THIS STUDY AIMED TO INVESTIGATE THE EFFECTS OF SAMPLES ISOLATED FROM CALCEOLARIA INTEGRIFOLIA SENSU LATO COMPLEX AERIAL PARTS, ON A. OBTECTUS AND E. VARIVESTIS ADULTS AND LARVAL DEVELOPMENT, RESPECTIVELY. THE AERIAL PARTS OF SELECTED SPECIMENS OF C. INTEGRIFOLIA S.L. EHRHART COMPLEX (CALCEOLARIACEAE), C. INTEGRIFOLIA, C. TALCANA, C. ANDINA, AND THE HYBRID C. INTEGRIFOLIA X C. TALCANA WERE STUDIED AS INSECT GROWTH REGULATORS AGAINST DRY BEAN INSECT PESTS. IN ADDITION TO EXTRACTS AND FRACTIONS, SOME MIXTURES OF COMPOUNDS WERE EVALUATED AGAINST THE DRY BEAN WEEVIL (A. OBTECTUS), AND MEXICAN BEAN BEETLE (E. VARIVESTIS). NEEM EXTRACT (WITH AZADIRACHTIN), GEDUNIN, A KNOWN INSECT GROWTH REGULATOR ISOLATED FROM CEDRELA SPP., CEDRELA EXTRACT, SOME NAPHTHOQUINONES AND MALATHION WERE USED AS POSITIVE CONTROLS. WHEN TESTED FOR MORTALITY ON NEONATE LARVAE IN A CONTACT ARTIFICIAL DIET BIOASSAY, MANY SAMPLES, ESPECIALLY FRACTIONS OF DITERPENES, TRITERPENES AND PHENOLIC COMPOUNDS, TOGETHER WITH N-HEXANE AND ETHYL ACETATE EXTRACTS, AT 500 ?G/CM2 CAUSED SIGNIFICANT MORTALITY WITH 40?81% AGAINST A. OBTECTUS AND WITH 35.0?88.9% AGAINST E. VARIVESTIS, RESPECTIVELY. AT LOWER CONCENTRATIONS, THESE SUBSTANCES EXHIBITED GROWTH REDUCTION EFFECTS, SUCH AS STRONG REPELLENCY EFFECTS. THEY INCREASED THE DEVELOPMENT TIME OF SURVIVING LARVAE AND A SIGNIFICANT DELAY IN TIME TO PUPATION AND ADULT EMERGENCE. ACUTE TOXICITY AGAINST LARVAE OF E. VARIVESTIS WAS ALSO FOUND. IN ADDITION TO N-HEXANE EXTRACT OF C. ANDINA AND THE HYBRID (C. INTEGRIFOLIA X C. TALCANA), THOSE FRACTIONS RICH IN DITERPENES, QUINONES (MIXTURE M5), AZADIRACHTIN, GEDUNIN, CEDRELA-MEOH-EXTRACT, JUGLONE, PLUMBAGIN, 1,4-NAPHTHOQUINONE AND MALATHION HAD THE MOST POTENT LETHAL EFFECT

CANDIDA IS A GENUS OF YEASTS AND IS THE MOST COMMON CAUSE OF FUNGAL INFECTIONS WORLDWIDE. HOWEVER, ONLY A FEW ANTIFUNGAL DRUGS ARE CURRENTLY AVAILABLE FOR THE TREATMENT OF CANDIDA INFECTIONS. IN THE LAST DECADE, TERPENOPHENOLS HAVE ATTRACTED MUCH ATTENTION BECAUSE THEY OFTEN POSSESS A VARIETY OF BIOLOGICAL ACTIVITIES. IN THE SEARCH FOR NEW ANTIFUNGALS, EIGHT CARVEOYLPHENOLS WERE SYNTHESIZED AND CHARACTERIZED BY SPECTROSCOPIC ANALYSIS. BY USING THE BROTH MICRODILUTION ASSAY, THE COMPOUNDS WERE EVALUATED FOR ANTIFUNGAL ACTIVITIES IN VITRO AGAINST FOUR HUMAN PATHOGENIC YEAST, AND STRUCTURE-ACTIVITY RELATIONSHIPS (SAR) WERE DERIVED. NOTEWORTHY, IN THIS PRELIMINARY STUDY, COMPOUNDS 5 AND 6, HAVE SHOWN A SIGNIFICANT REDUCTION IN THE GROWTH OF ALL CANDIDA STRAINS TESTED. STARTING FROM THESE PRELIMINARY RESULTS, WE HAVE DESIGNED THE SECOND GENERATION OF ANALOGOUS IN THIS CLASS, AND FURTHER STUDIES ARE IN PROGRESS IN OUR LABORATORIES.

IN THIS STUDY, THE ESSENTIAL OIL (EO) FROM LAURELIA SEMPERVIRENS WAS ANALYZED BY GC/MS AND SAFROLE (1) WAS IDENTIFIED AS THE MAJOR METABOLITE 1, WAS SUBJECTED TO DIRECT REACTIONS ON THE OXYGENATED GROUPS IN THE AROMATIC RING AND IN THE SIDE CHAIN, AND EIGHT COMPOUNDS (4 TO 12) WERE OBTAINED BY THE PROCESS. EO AND COMPOUNDS 4-12 WERE SUBJECTED TO BIOLOGICAL ASSAYS ON 24 STRAINS OF THE GENUS SAPROLEGNIA, SPECIFICALLY OF THE SPECIES 12 S. PARASITICA AND 12 S. AUSTRALIS. EO SHOWED A SIGNIFICANT EFFECT AGAINST SAPROLEGNIA STRAINS. COMPOUND 6 PRESENTS THE HIGHEST ACTIVITY AGAINST TWO RESISTANT STRAINS, WITH MINIMUM INHIBITORY CONCENTRATION (MIC) AND MINIMUM OOMYCETICIDAL CONCENTRATION (MOC) VALUES OF 25 TO 100 AND 75 TO 125 ?G/ML, RESPECTIVELY. THE RESULTS SHOW THAT COMPOUND 6 EXHIBITED SUPERIOR ACTIVITIES COMPARED TO THE COMMERCIAL CONTROLS BRONOPOL AND AZOXYSTROBIN USED TO COMBAT THESE PATHOGENS.

LAURELIOPSIS PHILIPPIANA (LOOSER) R. SCHODDE (MONIMIACEAE) IS A NATIVE TREE WIDESPREAD IN THE FOREST AREAS IN THE SOUTH OF CHILE AND ARGENTINA, KNOWN FOR ITS MEDICINAL PROPERTIES AND EXCELLENT WOOD. THE AIM OF THIS STUDY WAS TO EVALUATE THE CHEMICAL COMPOSITION OF L. PHILIPPIANA LEAF AND BARK ESSENTIAL OILS (EOS) USING GAS CHROMATOGRAPHY-MASS SPECTROMETRY (GC-MS), AND TO QUANTIFY ITS ANTI-OOMYCETE ACTIVITY, SPECIFICALLY AGAINST SAPROLEGNIA PARASITICA AND S. AUSTRALIS. ONLY SIX COMPONENTS WERE IDENTIFIED IN LEAF EO, 96.92% OF WHICH ARE PHENYLPROPANOIDS AND 3.08% ARE TERPENES. AS FOR BARK EO, 29 COMPONENTS WERE IDENTIFIED, REPRESENTING 67.61% FOR PHENYLPROPANOIDS AND 32.39% FOR TERPENES. LEAF EO WAS CHARACTERIZED MAINLY BY SAFROLE (96.92%) AND ?-PHELLANDRENE (1.80%). BARK EO WAS CHARACTERIZED MAINLY BY ISOSAFROLE (30.07%), SAFROLE (24.41%), EUCALYPTOL (13.89%), METHYLEUGENOL (7.12%), AND EUGENOL (6.01%). BARK EO HAS THE MOST PROMISING ANTI-SAPROLEGNIA ACTIVITY, WITH A MINIMUM INHIBITION CONCENTRATION (MIC) VALUE OF 30.0 ?G/ML AGAINST MYCELIA GROWTH AND A MINIMUM FUNGICIDAL CONCENTRATION (MFC) VALUE OF 50.0 ?G/ML AGAINST SPORES; FOR LEAF EO, THE MIC AND MFC VALUES ARE 100 AND 125 ?G/ML, RESPECTIVELY. THESE FINDINGS DEMONSTRATE THAT BARK EO HAS POTENTIAL TO BE DEVELOPED AS A REMEDY FOR THE CONTROL OF SAPROLEGNIA SPP. IN AQUACULTURE.

AN EVALUATION OF ANTIOXIDANT AND ANTICANCER ACTIVITY WAS SCREENED IN LEPTOCARPHA RIVULARIS DC FLOWER EXTRACTS USING FOUR SOLVENTS (N-HEXANE (HEX), DICHLOROMETHANE (DCM), ETHYL ACETATE (ACOET), AND ETHANOL (ETOH)). EXTRACTS WERE COMPARED FOR TOTAL EXTRACT FLAVONOIDS AND PHENOL CONTENTS, ANTIOXIDANT ACTIVITY (2,2-DIPHENYL-1-PICRYL-HYDRAZYL-HYDRATE (DPPH), FERRIC REDUCING ANTIOXIDANT POTENTIAL (FRAP), TOTAL REACTIVE ANTIOXIDANT PROPERTIES (TRAP) AND OXYGEN RADICAL ABSORBANCE CAPACITY (ORAC)) ACROSS A DETERMINED VALUE OF REDUCED/OXIDIZED GLUTATHIONE (GSH/GSSG), AND CELL VIABILITY (THE SULFORHODAMINE B (SRB) ASSAY). THE MOST ACTIVE EXTRACTS WERE ANALYZED BY CHROMATOGRAPHIC ANALYSIS (GC/MS) AND TESTED FOR APOPTOTIC PATHWAYS. EXTRACTS FROM HEX, DCM AND ACOET REDUCED CELL VIABILITY, CAUSED CHANGES IN CELL MORPHOLOGY, AFFECTED MITOCHONDRIAL MEMBRANE PERMEABILITY, AND INDUCED CASPASE ACTIVATION IN TUMOR CELL LINES HT-29, PC-3, AND MCF-7. THESE EFFECTS WERE GENERALLY LESS PRONOUNCED IN THE HEK-293 CELL LINE (NONTUMOR CELLS), INDICATING CLEAR SELECTIVITY TOWARDS TUMOR CELL LINES. WE ATTRIBUTE LIKELY EXTRACT ACTIVITY TO THE PRESENCE OF SESQUITERPENE LACTONES, IN COMBINATION WITH OTHER COMPONENTS LIKE STEROIDS AND FLAVONOIDS.

NATURAL COMPOUNDS FROM DRIMYS WINTERI FORST AND DERIVATIVES EXHIBITED LARVICIDAL EFFECTS AGAINST DROSOPHILA MELANOGASTER TIL-TIL. THE MOST ACTIVE COMPOUND WAS ISODRIMENIN (4). THE HIGHEST LETHAL CONCENTRATION TO THE LARVAE OF D. MELANOGASTER WAS 4.5 ± 0.8 MG/L. AT VERY LOW CONCENTRATIONS DRIMENOL (1), CONFERTIFOLIN (3), AND DRIMANOL (5) DISPLAYED ANTIFEEDANT AND LARVAE GROWTH REGULATORY ACTIVITY. THE ANTIFEEDANT RESULTS OF NORDRIMANIC AND DRIMANIC COMPOUNDS WERE BETTER IN FIRST INSTAR LARVAE. THE EC?? VALUE OF POLYGODIAL (2) WAS 60.0 ± 4.2 MG/L; OF DIOL 15 45.0 ± 2.8 MG/L, AND OF DIOL 17 36.9 ± 3.7 MG/L, WHILE THE NEW NORDRIMANE COMPOUND 12 PRESENTED A VALUE OF 83.2 ± 3.5 MG/L.

FRUIT ROTS CAUSED BY FILAMENTOUS FUNGI SUCH AS MONILINIA FRUCTICOLA AND MONILINIA LAXA HAVE A STRONG IMPACT ON CROP YIELD AND FRUIT COMMERCIALIZATION, ESPECIALLY AS THEY AFFECT A WIDE VARIETY OF STONE FRUITS. THE ANTIFUNGAL EFFICACY OF BENZYLIDENE-CYCLOALKANONES HAS BEEN PREVIOUSLY DESCRIBED IN IN VITRO ASSAYS AGAINST M. FRUCTICOLA; SO, THIS STUDY AIMS TO EVALUATE THE IN VIVO INHIBITORY POTENTIAL OF THESE HYBRIDS ON FRUITS THAT HAVE BEEN INOCULATED WITH M. FRUCTICOLA, AND USE MOLECULAR DOCKING TO VISUALIZE THE MAIN INTERACTIONS OF THESE MOLECULES IN THE ACTIVE SITE OF THE ENZYME SUCCINATE DEHYDROGENASE (SDH). THE RESULTS INDICATE THAT COMPOUND C ACHIEVES THE HIGHEST INHIBITION OF BOTH MONILINIA SPECIES (15.7-31.4 MU G/ML), SPORE GERMINATION IN VITRO (

IN THIS STUDY, WE EXAMINED THE CYTOTOXIC EFFECTS OF SEVEN ENT-LABDANE DERIVATIVES 1-7 (0-100 ?M) IN DIFFERENT HUMAN CANCER CELL LINES. OUR RESULTS SHOWED THAT COMPOUNDS 1-3 EXHIBITED SIGNIFICANT DOSE-DEPENDENT INHIBITION ON THE GROWTH OF THE THREE DIFFERENT HUMAN CELL LINES, ACCORDING TO THE SULPHORHODAMINE B ASSAY AND PRODUCED MORPHOLOGICAL CHANGES CONSISTENT WITH APOPTOSIS, AS CONFIRMED BY HOESTCH 3342 STAINING ANALYSIS. THEY INDUCED APOPTOSIS IN VARIOUS CANCER CELL LINES, AS SHOWN BY NUCLEAR CONDENSATION AND FRAGMENTATION AND CASPASE 3 ACTIVATION. SUCH INDUCTION WAS ASSOCIATED WITH THE DEPLETION OF MITOCHONDRIAL MEMBRANE POTENTIAL. THESE ACTIVITIES LED TO THE CLEAVAGE OF CASPASES AND THE TRIGGER OF CELL DEATH PROCESS. OVERALL, THE COMPOUNDS SHOWED POTENT PROAPOPTOTIC EFFECTS ON THE TWO DIFFERENT CANCER CELL LINES, SUGGESTING THAT THE COMPOUNDS DESERVE MORE EXTENSIVE INVESTIGATION OF THEIR POTENTIAL MEDICINAL APPLICATIONS.

METHANOL EXTRACT OBTAINED FROM AERIAL PARTS OF 24 SELECTED PLANTS FROM CENTRAL VALLEY AND PRE-ANDEAN FOOTHILL FROM ÑUBLE PROVINCE OF CHILE WERE TESTED FOR ITS INHIBITORY GERMINATION ACTIVITY AGAINST TRIFOLIUM REPENS AND RAPHANUS SATIVUS. MANY EXTRACTS (13/24 = 54%) SHOWED INHIBITION OF T. REPENS GERMINATION WITH IG% > 50%, BUT NONE ON R. SATIVUS.

AN EFFICIENT SYNTHESIS OF A SERIES OF 4-OXYALKYL-ISOCORDOIN ANALOGUES (2-8) IS REPORTED FOR THE FIRST TIME. THEIR STRUCTURES WERE CONFIRMED BY ¹H-NMR, 13C-NMR, AND HRMS. THEIR ANTI-OOMYCETE ACTIVITY WAS EVALUATED BY MYCELIUM AND SPORES INHIBITION ASSAY AGAINST TWO SELECTED PATHOGENIC OOMYCETES STRAINS: SAPROLEGNIA PARASITICA AND SAPROLEGNIA AUSTRALIS. THE ENTIRE SERIES OF ISOCORDOIN DERIVATIVES (EXCEPT COMPOUND 7) SHOWED HIGH INHIBITORY ACTIVITY AGAINST THESE OOMYCETE STRAINS. AMONG THEM, COMPOUND 2 EXHIBITED STRONG ACTIVITY, WITH MINIMUM INHIBITORY CONCENTRATION (MIC) AND MINIMUM OOMYCETICIDAL CONCENTRATION (MOC) VALUES OF 50 µG/ML AND 75 µG/ML, RESPECTIVELY. THE RESULTS SHOWED THAT 4-OXYALKYLATED ANALOGUES OF ISOCORDOIN COULD BE POTENTIAL ANTI-OOMYCETE AGENTS.

THE AIM OF THIS STUDY WAS TO SYNTHESIZE A SERIES OF NOVEL AND KNOWN DIHYDROCARVONE-HYBRID DERIVATIVES (2-9) AND TO EVALUATE MYCELIAL GROWTH ACTIVITY OF HYBRID MOLECULES AGAINST TWO STRAINS OF MONILINIA FRUCTICOLA, AS WELL AS THEIR TOXICITY. DIHYDROCARVONE-HYBRID DERIVATIVES HAVE BEEN SYNTHESIZED UNDER SONICATION CONDITIONS AND CHARACTERIZED BY FTIR, NMR, AND HRMS. ANTIFUNGAL EFFICACY AGAINST BOTH STRAINS OF M. FRUCTICOLA WAS DETERMINED BY HALF MAXIMAL EFFECTIVE CONCENTRATION (EC50) AND TOXICITY USING THE BRINE SHRIMP LETHALITY TEST (BSLT). AMONG THE SYNTHESIZED COMPOUNDS, 7 AND 8 SHOWED THE BEST ACTIVITY AGAINST BOTH STRAINS OF M. FRUCTICOLA WITH EC50 VALUES OF 148.1 AND 145.9 ?G/ML FOR STRAIN 1 AND 18.1 AND 15.7 ?G/ML FOR STRAIN 2, RESPECTIVELY, COMPARED TO BC 1000® (COMMERCIAL ORGANIC FUNGICIDE) BUT LOWER THAN MYSTIC® 520 SC. HOWEVER, THESE COMPOUNDS SHOWED LOW TOXICITY VALUES, 910 AND 890 ?G/ML, RESPECTIVELY, COMPARED TO MYSTIC® 520 SC, WHICH WAS HIGHLY TOXIC. BASED ON THE RESULTS, THESE HYBRID COMPOUNDS COULD BE CONSIDERED FOR THE DEVELOPMENT OF MORE ACTIVE, LESS TOXIC, AND ENVIRONMENTALLY FRIENDLY ANTIFUNGAL AGENTS AGAINST PHYTOPATHOGENIC FUNGI.

BACKGROUND: EPHEDRA CHILENSIS K PRESL, KNOWN LOCALLY AS PINGO-PINGO, IS A CHILEAN ENDEMIC PLANT USED IN TRADITIONAL MEDICINE AS AN ANTI-INFLAMMATORY AND USED IN OTHER TREATMENTS. HOWEVER, UNLIKE FOR THE OTHER EPHEDRA SPECIES, THERE HAVE BEEN NO REPORTS ON THE ANTIOXIDANT AND CYTOTOXIC EFFECTS OF THIS PLANT. THE PRESENT STUDY AIMS TO EXPLORE THE POTENTIAL APPLICATIONS OF E. CHILENSIS EXTRACT AS A CYTOTOXIC AGENT AGAINST IN VITRO CANCER CELL LINES AND TO EXPLORE THE RELATIONSHIP BETWEEN THIS EXTRACT AND ANTIOXIDANT ACTIVITY. METHODS: TOTAL ANTHRAQUINONE, FLAVONOID, AND PHENOLIC CONTENTS, AS WELL AS ANTIOXIDANT ACTIVITY (DPPH, FRAP, AND TRAP ASSAYS) AND CYTOTOXIC EFFECT ON SEVERAL CANCER CELL LINES (MCF-7, PC-3, DU-145, AND HT-29) WERE MEASURED FOR THE HEXANE, DICHLOROMETHANE AND ETHANOL EXTRACTS OF E. CHILENSIS. IN ADDITION, SEVERAL CORRELATIONS AMONG THE PHYTOCHEMICAL CONTENT, ANTIOXIDANT ACTIVITY, AND CYTOTOXIC EFFECT WERE EVALUATED. FINALLY, GC-MS ANALYSES OF THE MOST ACTIVE EXTRACTS WERE CARRIED OUT TO IDENTIFY THEIR MAJOR COMPONENTS AND TO RELATE THESE COMPONENTS TO THE CYTOTOXIC EFFECT. RESULTS: ANTIOXIDANT ACTIVITY WAS FOUND IN THE ETOH EXTRACTS OF EPHEDRA, AND THE RESULTS WERE CORRELATED WITH THE PHENOLIC CONTENT. FOR THE CYTOTOXIC ACTIVITY, THE NON-POLAR EXTRACTS OF E. CHILENSIS HAD THE HIGHEST ANTIPROLIFERATIVE EFFECT FOR THE MCF-7 AND PC-3 CANCER LINES; THE EXTRACT WAS SHOWN TO BE UP TO THREE TIMES MORE SELECTIVE THAN DOXORUBICIN. HOWEVER, THE CYTOTOXIC EFFECT WAS NOT CORRELATED WITH THE ANTIOXIDANT ACTIVITY. LASTLY, THE GC-MS ANALYSIS SHOWED A HIGH CONCENTRATION OF SATURATED FATTY ACIDS (MAINLY N-HEXADECANOIC ACID) AND TERPENOIDS (MAINLY 4-(HYDROXY-ETHYL)-?-BUTANOLACTONE).