Chemical epigenetic manipulation of Penicillium citreonigrum led to profound changes in the secondary metabolite profile of its guttate. While guttate from control cultures exhibited a relatively simple assemblage of secondary metabolites, the guttate collected from cultures treated with 50 μM 5-azacytidine (a DNA methyltransferase inhibitor) were highly enriched in compounds representing at least three distinct biosynthetic families. The metabolites obtained from the fungus included six azaphilones (sclerotiorin (1), sclerotioramine (6), ochrephilone (2), dechloroisochromophilone III (3), dechloroisochromophilone IV (4), and 6-((3E,5E)-5,7-dimethyl-2-methylenenona-3,5-dienyl)-2,4-dihydroxy-3-methylbenzaldehyde (5)), pencolide (7), and two new meroterpenes (atlantinones A and B (9 and 10, respectively)). While pencolide was detected in the exudates of both control and 5-azacytidine-treated cultures, all of the other natural products were found exclusively in the guttates of the epigenetically modified fungus. All of the metabolites from the P. citreonigrum guttate were tested for antimicrobial activity in a disk diffusion assay. Both sclerotiorin and sclerotioramine caused modest inhibition of Staphylococcus epidermidis growth; however, only sclerotioramine was active against a panel of Candida strains.Our research group has been actively pursuing the development of chemical epigenetic methods for procuring secondary metabolites from fungi. 1 We have demonstrated that this is an effective technique for promoting the transcription of silent biosynthetic pathways involved in the formation of polyketide, non-ribosomal peptide, and hybrid polyketide-non-ribosomalpeptide natural products. 2 Moreover, we have shown that a chemical epigenetics approach is well suited for the generation of structurally unique secondary metabolites with promising drug discovery applications. 3,4 In order to maximize the opportunity for detecting novel secondary metabolites, we have begun using chemical epigenetic induction as a routine part of our screening program involving the exploration of fungi obtained from minimally explored environments/ecological niches (e.g., insects and littoral zones4).* To whom correspondence should be addressed. Tel: (405) 325-6969. rhcichewicz@ou.edu.. † Natural Products Discovery Group, Department of Chemistry and Biochemistry. ‡ Current address: Empresa Brasileira de Pesquisa Agropecuária-EMBRAPA, Coastal Tablelands, Av. Beira Mar, 3250, 49025-040, Aracaju, SE, Brazil. § Department of Chemistry and Biochemistry. ⊥ Ecology and Evolutionary Biology Program.Supporting Information Available: NMR ( 1 H and 13 C NMR, HSQC, HMBC, COSY, and ROESY) data for compounds 6, 7, 9, and 10 and 1 H NMR and 1D difference NOE data for 8 are provided. This information is available free of charge via the Internet at http://pubs.acs.org. NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2011 May 28. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptOur investiga...

RESUMO: "Atividade antimicrobiana e perfi l fi toquímico das raízes de Lippia alba (Mill.) N.E. Brown". Lippia alba (Mill.) N.E. Brown (Verbenaceae) é geralmente usada na medicina popular brasileira para o tratamento de doenças gástricas, febre, asma e como tranqüilizante. Este trabalho avaliou a atividade antimicrobiana dos extratos acetato de etila, metanol e aquoso das raízes de L. alba usando métodos de difusão em poços e o perfi l fi toquímico. Os resultados obtidos mostraram que os extratos acetato de etila e metanol apresentaram atividade antimicrobiana contra Staphylococcus aureus (ATCC 6538P), Staphylococcus aureus (ATCC 6538) e Klebsiella pneumonia (ATCC 10031). Terpenóides, fenilpropanóides e açúcares foram detectados na análise fi toquímica.Unitermos: Lippia alba, Verbenaceae, atividade antimicrobiana, análise fi toquímica.ABSTRACT: Lippia alba (Mill.) N.E. Brown (Verbenaceae) is commonly used in the Brazilian folk medicine to the treatment of gastric illnesses, diarrhea, fever, asthma, and as a tranquilizer. This work evaluated the antimicrobial activity of ethyl acetate, methanol and aqueous extracts from the roots of the L. alba using plates-holes diffusion assay and the phytochemical profi le. The results obtained showed that the ethyl acetate and methanol extracts presented antimicrobial activity against Staphylococcus aureus (ATCC 6538P), Staphylococcus aureus (ATCC 6538) and Klebsiella pneumonia (ATCC 10031). Terpenoids, phenylpropanoids and sugars were detected in the phytochemical analysis.

Iridoids and ecdysteroids are found in some genera of the family Verbenaceae. In such cases, they are used as chemotaxonomic markers for the difficult task of taxonomic identification by using morphological characteristics of plants belonging to this family. The present work describes the distribution of ecdysteroids in plants from the genus Vitex from a review of previous work on seventeen Vitex species. In addition, (13)C-NMR data of the main ecdysteroids found in this genus are described. This study attempted to summarize previous research on ecdysteroids distribution in Vitex species with the addition of (13)C-NMR analysis to further refine the characterization of these compounds in the Verbenaceae family.

Many references to the use of Lantana spp. can be found in the ethnopharmacological literature from locations around the globe. This study was focused on examining constituents from the polar extracts of Lantana radula Sw. and Lantana canescens Kunth, for which no prior chemical investigations had been reported. A new phenylethanoid glycoside, raduloside, and lignan glycoside, radulignan, were identified along with the known compounds alyssonoside, arenarioside, calceolarioside E, isonuomioside, samioside, and verbascoside.

Spectral Data -[31 refs.]. -(SENA FILHO*, J. G.; DURINGER, J.; MAIA, G. L. A.; TAVARES, J. F.; XAVIER, H. S.; SOBRAL DA SILVA, M.; DA-CUNHA, E. V. L.; BARBOSA-FILHO, J. M.; Chem. Biodiversity 5 (2008) 5, 707-728; Lab. Tecnol. Farm., Univ. Fed. Paraiba, Joao Pessoa, 58051-970 Paraiba, Brazil; Eng.) -Lindner 32-235

RESUMO:Crotalaria retusa é uma planta encontrada no Nordeste brasileiro, pertence ao gênero Crotalaria e à família Leguminosae, e possuem mais de seissentas espécies no mundo e mais de quarenta no Brasil. As variedades tóxicas mais conhecidas são C. spectabilis, C. crispata, C. retusa, C. dura e C. globifera. Plantas do gênero Crotalaria são de interesse porque são usadas na medicina popular. Esses gêneros são ricos em alcaloides pirrolizidínicos (AP), que são as principais toxinas e apresentam efeitos pneumotóxicos, nefrotóxicos, cardiotóxicos, fetotóxicos, carcinogênicos, inflamação, hemorragia e fibrose. A monocrotalina é o principal alcaloide pirrolizidínico encontrado nessas plantas e é ativamente oxidada in vivo pelo citocromo P450 no fígado, formando intermediários altamente reativos tipo pirrólicos que são responsáveis pela ligação cruzada do DNA-DNA e DNAproteína. O presente trabalho teve como objetivo fazer um levantamento bibliográfico via internet, utilizando bancos de dados, programas de pesquisa científica e pesquisa em livros relacionados, acerca da atividade farmacológica e do mecanismo de ação da monocrotalina extraída de plantas do gênero Crotalaria, ressaltando desde os aspectos botânicos da planta, estrutura química dos alcaloides pirrolizidínicos, exemplos experimentais de toxicidade e provável mecanismo de ação.Unitermos: Monocrotalia, hepatotóxico, Crotalaria, dehidromonocrotalina. ABSTRACT: "Pharmacological activity of monocrotalina isolated from plants of the genusCrotalaria." Crotalia retusa is a plant found in Brazilian Northeast and belongs to the genus Crotalaria and the family Leguminosae, which comprises more than 600 species throughout the world and more than forty in Brazil. The most known toxic species are C. spectabilis, C. crispata, C. retusa, C. dura and C. globifera. Plants of the Crotalaria genus are of great interest because they are used by humans for folk medicine. These plants are rich in pyrrolizidine alkaloids (PA), which are the main toxins that cause effects such as pneumotoxic, nefrotoxic, cardiotoxic, fetotoxic, carcinogenic, inflammation, hemorrhage and fibrosis. Monocrotaline is the main pirrolizidinic alkaloid found in plants and is actively oxidated in vivo by the cytochrome P450 in the liver, yielding highly reactive pyrrolic type intermediates, which are responsible for DNA-DNA and DNA-protein cross-links reaction. The aim of this work is to make a bibliographic survey via internet, using databases, scientific research programs and related books, about pharmacological activity and mechanism of action of monocrotaline extracted from plants of Crotalaria genus, emphasizing plant botanical aspects, chemical structure of pirrolizidinic alkaloid, experimental examples of toxicity and probable action mechanism.

The distribution of iridoid glucosides in plants from the genus Lippia (Verbenaceae) is described. In the present work, three known iridoids (theviridoside, mussaenoside and gardoside) were isolated from the roots of L. alba and were confirmed by NMR (1H and 13C) spectroscopic data. This information was combined with previous work on seven other Lippia species (obtained through a literature review) to give a thorough account of the iridoid glucosides currently found in this genus.

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