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1.
Clin Dermatol ; 36(3): 399-419, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29908582

RESUMO

The plant and mushroom kingdoms have species used for intoxication, inebriation, or recreation. Some of these species are toxic. Given that many of these plants or substances are illegal and have histories of abuse, much of the research regarding therapeutic application is based on basic science, animal studies, and traditional use. This review examines Cannabis, Euphorbia, Ricinus, Podophyllum, Veratrum, mushrooms, and nightshades, along with resveratrol and cocaine as they relate to dermatology.


Assuntos
Agaricales , Cannabis , Fitoterapia , Preparações de Plantas/uso terapêutico , Dermatopatias/tratamento farmacológico , Pele/patologia , Solanum , Animais , Canabinoides/uso terapêutico , Dermatologia , Dermatomicoses/tratamento farmacológico , Dronabinol/uso terapêutico , Etanolaminas/uso terapêutico , Euphorbia , Fibrose , Humanos , Inflamação/tratamento farmacológico , Ácidos Palmíticos/uso terapêutico , Preparações de Plantas/farmacologia , Podophyllum peltatum , Resveratrol , Ricinus , Envelhecimento da Pele/efeitos dos fármacos , Neoplasias Cutâneas/tratamento farmacológico , Neoplasias Cutâneas/prevenção & controle , Estilbenos/uso terapêutico , Veratrum
2.
J Cutan Med Surg ; 21(4): 299-307, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28300437

RESUMO

INTRODUCTION: Plants and algae have played a central role in the treatment of skin conditions in both traditional First Nations healing and in modern dermatology. The objective of this study was to examine the evidence supporting the dermatological use of seaweed, witch hazel, bearberry, and mayapple. METHODS: Four plants and algae used in traditional First Nations treatments of skin disease were selected based on expert recommendations. Several databases were searched to identify relevant citations without language restrictions. RESULTS: Seaweed has potential clinical use in the treatment of acne and wrinkles and may be incorporated into biofunctional textiles. Witch hazel is an effective and well-tolerated treatment of inflammation and diaper dermatitis. Bearberry leaves contain arbutin, a skin-lightening agent that is an alternative for the treatment of hyperpigmentation. Mayapple contains podophyllotoxin, a treatment for condyloma accuminata, molluscum contagiosum, and recalcitrant palmoplantar warts. DISCUSSION: Common plants and algae are replete with bioactive agents that may have beneficial effects on the skin. Further research will open the door to new and innovative products in the future. Limitations of this study include that the scope of our study is limited to 4 plants and algae, a small sample of the breadth of plants used by First Nations for dermatological treatments.


Assuntos
Cosmecêuticos , Fármacos Dermatológicos , Medicina Tradicional , Preparações de Plantas , Arctostaphylos/química , Hamamelis/química , Humanos , Podophyllum peltatum/química , Alga Marinha/química
4.
Science ; 349(6253): 1224-8, 2015 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-26359402

RESUMO

Podophyllotoxin is the natural product precursor of the chemotherapeutic etoposide, yet only part of its biosynthetic pathway is known. We used transcriptome mining in Podophyllum hexandrum (mayapple) to identify biosynthetic genes in the podophyllotoxin pathway. We selected 29 candidate genes to combinatorially express in Nicotiana benthamiana (tobacco) and identified six pathway enzymes, including an oxoglutarate-dependent dioxygenase that closes the core cyclohexane ring of the aryltetralin scaffold. By coexpressing 10 genes in tobacco-these 6 plus 4 previously discovered-we reconstitute the pathway to (-)-4'-desmethylepipodophyllotoxin (the etoposide aglycone), a naturally occurring lignan that is the immediate precursor of etoposide and, unlike podophyllotoxin, a potent topoisomerase inhibitor. Our results enable production of the etoposide aglycone in tobacco and circumvent the need for cultivation of mayapple and semisynthetic epimerization and demethylation of podophyllotoxin.


Assuntos
Etoposídeo/metabolismo , Engenharia Genética , Oxigenases de Função Mista/metabolismo , Podofilotoxina/análogos & derivados , Podofilotoxina/metabolismo , Podophyllum peltatum/enzimologia , Tabaco/metabolismo , Inibidores da Topoisomerase/metabolismo , Sequência de Aminoácidos , Vias Biossintéticas/genética , Regulação Enzimológica da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Metilação , Oxigenases de Função Mista/genética , Dados de Sequência Molecular , Podofilotoxina/biossíntese , Podophyllum peltatum/genética , Tabaco/genética , Transcriptoma
5.
Mol Biotechnol ; 57(11-12): 961-73, 2015 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-26289300

RESUMO

Podophyllotoxin (PPT) is a plant natural product that serves as a precursor for the synthesis of many well-known chemotherapeutic drugs. The limited availability and high demand for the source plants of PPT have led to the exploration of alternative sources for this compound. In this study, we utilized the endophytic fungus Phialocephala podophylli (strain PPE7) that we isolated from the rhizomes of Podophyllum peltatum and is known to produce detectable amounts of PPT in broth culture. To date, the complete PPT biosynthetic pathway has yet to be determined in any species. Since fungi are well known for clustering genes that belong to secondary metabolite pathways, use of a fungal system for investigation of the PPT biosynthesis genes may ultimately lead to elucidation of the entire pathway. In this study, we investigated the secoisolariciresinol dehydrogenase (SD) gene that facilitates the dehydrogenation of secoisolariciresinol to form matairesinol, a mid-pathway intermediate product in PPT biosynthesis. We utilized PCR amplification to acquire the complete SD gene sequence in PPE7 and opted to synthesize the P. peltatum SD sequence for expression. Through western blotting, we confirmed the expression of the recombinant SD (PpSD) and verified protein functionality with a bioconversion assay followed by HPLC and LC-MS analyses. Here, we report the identification of the SD gene in PPE7; this is the first report of the SD gene in an endophytic fungus. Additionally, we established the groundwork for the future expression of the complete PPT biosynthetic pathway in the heterologous host Pichia pastoris.


Assuntos
Ascomicetos/enzimologia , Proteínas Fúngicas/metabolismo , Álcool Oxidorredutases Dependentes de NAD(+) e NADP(+)/metabolismo , Podofilotoxina/biossíntese , Sequência de Aminoácidos , Ascomicetos/genética , Ascomicetos/isolamento & purificação , Sequência de Bases , Vias Biossintéticas , Clonagem Molecular , Meios de Cultura , DNA Fúngico/genética , Proteínas Fúngicas/genética , Dados de Sequência Molecular , Álcool Oxidorredutases Dependentes de NAD(+) e NADP(+)/genética , Podophyllum peltatum/microbiologia , Conformação Proteica , Análise de Sequência de DNA
6.
Bioorg Med Chem ; 22(21): 6183-92, 2014 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-25282651

RESUMO

A series of C4-N-substituted podophyllum derivatives were synthesized and tested for cytotoxicity in HeLa, BGC-823, A549, Huh7 and MCF-7 cells by MTT assay. Pharmacologically, most derivatives displayed potent cytotoxicity against at least one of the tested tumor cell lines. Structure activity relationship (SAR) analysis suggests that compounds with imidogen exposed on the pyridine, rather than pyrimidine, exhibited significantly elevated potency. Moreover, the presence of a chlorine atom in the heterocyclic ring enhanced cytotoxicity, with the order 3-position>4-position>5-position>6-position. Specifically, two compounds, 3g and 3h, with 2-amino-3-chloropyridine substituted into the podophyllotoxin (PPT) and 4'-O-demethylepipodophyllotoxin (DMEP) scaffolds were shown to have the most potent HeLa cells cytotoxicity compared to other synthesized derivatives or reference compounds PPT, DMEP and etoposide (VP-16). The compound 3g was shown to inhibit microtubule polymerization and compound 3h affected topoisomerase II catalytic activity. Both compounds resulted in G2/M phase arrest and apoptosis, purportedly by increasing the expression of P53, followed by Bax up-regulation, Bcl-2 down-regulation, and caspase-3 activation. As a result of this work, we conclude that compounds 3g and 3h are more potent anticancer agents than VP-16, and that they work by different antitumor mechanisms.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Podofilotoxina/química , Podofilotoxina/farmacologia , Podophyllum peltatum/química , Antineoplásicos Fitogênicos/síntese química , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Humanos , Pontos de Checagem da Fase M do Ciclo Celular/efeitos dos fármacos , Neoplasias/tratamento farmacológico , Podofilotoxina/síntese química , Relação Estrutura-Atividade , Moduladores de Tubulina/síntese química , Moduladores de Tubulina/química , Moduladores de Tubulina/farmacologia
7.
Mycologia ; 104(4): 942-50, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-22495446

RESUMO

Mayapple rust is a common, disfiguring disease that is widespread in temperate eastern North America wherever the host, Podophyllum peltatum, occurs. Puccinia podophylli, the etiological agent of this rust, has been shown to be distantly related to both Puccinia and Uromyces as exemplified by their types. A systematic study was made to determine the generic classification of P. podophylli. Phylogenetic analyses of two rDNA loci from multiple specimens support the recognition of this taxon as a separate genus of Pucciniaceae. Based on historical literature and type material, P. podophylli was found to represent the type of the forgotten genus Allodus and it is correctly named Allodus podophylli. A neotype is designated for Puccinia podophylli Schwein. (≡ Allodus podophylli) and a lectotype is designated for Aecidium podophylli.


Assuntos
Basidiomycota/classificação , DNA Fúngico/genética , Podophyllum peltatum/microbiologia , Basidiomycota/citologia , Basidiomycota/genética , Basidiomycota/patogenicidade , DNA Ribossômico/genética , Loci Gênicos , Técnicas de Tipagem Micológica , Filogenia , Doenças das Plantas/microbiologia , Folhas de Planta/microbiologia , Alinhamento de Sequência , Análise de Sequência de DNA , Esporos Fúngicos/citologia
8.
Ultrason Sonochem ; 19(1): 22-31, 2012 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-21664168

RESUMO

The effect of high-power ultrasound pretreatment on the extraction of podophyllotoxin from Podophyllum peltatum was investigated. Direct sonication by an ultrasound probe horn was applied at 24 kHz and a number of factors were investigated: particle size (0.18-0.6 mm), type of solvent (0-100% aqueous ethanol), ultrasonic treatment time (2-40 min), and power of ultrasound (0-100% power intensity, maximum power: 78 W). The optimal condition of ultrasound was achieved with 0.425-0.6 mm particle size, 10 min sonication time, 35 W ultrasound power, and water as the medium. There was no obvious degradation of podophyllotoxin with ultrasound under the applied conditions, and an improvement in extractability was observed. The SEM microscopic structure change of treated samples disclosed the effect of ultrasound on the tissue cells. The increased pore volume and surface area after ultrasonic treatment also confirmed the positive effect of ultrasound pretreatment on the extraction yield of podophyllotoxin from the plant cells.


Assuntos
Podofilotoxina/isolamento & purificação , Podophyllum peltatum/química , Rizoma/química , Ultrassom , Tamanho da Partícula , Propriedades de Superfície , Ultrassom/instrumentação
9.
Biomed Chromatogr ; 25(11): 1230-6, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-21374649

RESUMO

A new rapid UPLC-UV-MS method has been developed that permits the analysis of four lignans (4'-O-demethylpodophyllotoxin, podophyllotoxin, α-peltatin and ß-peltatin) in P. peltatum L. Podophyllotoxin is a natural lignan that is being used as a precursor for the semi-synthetic anti-cancer drugs etoposide, teniposide and etopophos. The chromatographic separation was achieved using a reversed-phase C18 column with a mobile phase of water and acetonitrile, both containing 0.05% formic acid. Analyses of P. peltatum leaves collected from different colonies within a single site indicated a significant variation in 4'-O-demethylpodophyllotoxin, α-peltatin, podophyllotoxin and ß-peltatin content. Within 3.0 min four main lignans could be separated with detection limits of 0.1, 0.3, 0.3 and 0.2 µg/mL, respectively. 4'-O-demethylpodophyllotoxin and α-peltatin appeared most prominently among the lignans obtained. The podophyllotoxin content was found in the range of 0.004-0.77% from 16 samples collected from 6 colonies within the same site. The content of podophyllotoxin is directly proportional to the content of 4'-O-demethylpodophyllotoxin and inversely proportional to α-peltatin and ß-peltatin content. LC-mass spectrometry coupled with electrospray ionization (ESI) interface method is described for the identification of four lignans in various populations of plant samples. By applying principal component analysis and hierarchical cluster analysis, Podophyllum samples collected from various colonies within a location were distinguished.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Folhas de Planta/química , Podofilotoxina/análogos & derivados , Podofilotoxina/análise , Podophyllum peltatum/química , Análise por Conglomerados , Limite de Detecção , Modelos Lineares , Espectrometria de Massas/métodos , Extratos Vegetais/química , Podofilotoxina/química , Análise de Componente Principal , Reprodutibilidade dos Testes
10.
Yale J Biol Med ; 82(1): 25-36, 2009 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-19325943

RESUMO

Historians have examined the significant contributions John and William Bartram made to 18th- and 19th-century knowledge of indigenous North American flora. However, the Bartrams' contribution to medicinal botanical knowledge, particularly William Bartram's compilation of Indians' knowledge on the preparation and use of medicinal botanicals, is not well-known. In addition, while William Bartram's contemporaries relied on his accounts of medicinal botanicals, they rarely acknowledged Bartram or Indians in their own works. Contemporaries plagiarized Bartram's writings and used his exquisite illustrations to ornament their own publications. This paper reconstructs William Bartram's careful collection and recording of medicinal botanical knowledge that became part of late 18th- and early 19th-century American pharmacology, as well as provides evidence for 54 Bartram-identified indigenous species and the pirating of William Bartram's work by contemporaries.


Assuntos
Etnofarmacologia/história , Índios Norte-Americanos/história , Fitoterapia/história , Podophyllum peltatum , História do Século XVIII , História do Século XIX , Humanos , Estados Unidos
11.
Clin Toxicol (Phila) ; 46(2): 159-63, 2008 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-17852156

RESUMO

Bajiaolian (Dysosma pleianthum), a species in the Mayapple family (Podophyllum pelatum), has been widely used as a traditional Chinese herbal medication for the remedies of snake bite, tumor growth, post-partum recovery, and acne. It has also been used in western medicine, especially topically for various skin lesions. Both oral ingestion and dermal application may result in severe toxicity. The clinical presentations reported after Bajiaolian poisoning include nausea, vomiting, diarrhea, abdominal cramps, tachycardia, orthostatic hypotension, paralytic ileus, urinary retention, hepatorenal dysfunction, leukocytosis followed by leukopenia, thrombocytopenia, prolonged areflexia, prolonged paraethesia and sensory ataxia, dizziness, fever, memory impairment, hallucinations, paranoia, convulsion, fainting, and coma. There are no previous reports in the literature about the cessation of nail growth as a clinical presentation following Bajiaolian poisoning. We present a case of nail growth that was halted for more than seven years after a single case of Bajiaolian poisoning.


Assuntos
Medicamentos de Ervas Chinesas/envenenamento , Unhas/efeitos dos fármacos , Podophyllum peltatum/química , Adulto , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/uso terapêutico , Feminino , Cefaleia/tratamento farmacológico , Humanos , Doenças da Unha/induzido quimicamente , Doenças da Unha/patologia , Unhas/crescimento & desenvolvimento
12.
J Nat Prod ; 69(8): 1121-4, 2006 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-16933860

RESUMO

The lignan podophyllotoxin (1) is highly valued as the precursor to clinically useful anticancer drugs. Substantial drug development of this compound class continues, including potential new use for inflammatory disease. We have isolated two endophyte fungi, both strains of Phialocephala fortinii, from rhizomes of the plant Podophyllum peltatum. The fungi were identified through DNA sequencing and morphology. Both strains of fungi are slow-growing and produce 1 at low but measurable amounts in broth culture. The compound was confirmed through matching HPLC retention times, absorption spectra, and MS data to authentic 1. The yield of 1 has ranged from 0.5 to 189 microg/L in 4 weeks of culture. These fungi have implications for the sustained production of 1 independent of wild populations of the source plants.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Ascomicetos/química , Podofilotoxina/isolamento & purificação , Podophyllum peltatum/química , Pró-Fármacos/isolamento & purificação , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Artemia/efeitos dos fármacos , Ascomicetos/metabolismo , DNA Fúngico/química , DNA Fúngico/genética , DNA Fúngico/isolamento & purificação , Estrutura Molecular , Podofilotoxina/química , Podofilotoxina/farmacologia , Pró-Fármacos/química , Pró-Fármacos/farmacologia , Rizoma/química
13.
Planta Med ; 72(9): 824-9, 2006 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-16791769

RESUMO

Podophyllotoxin is a pharmaceutical compound found in leaves and rhizomes of American mayapple (P. peltatum L.), a species being investigated as an alternative to that of the Indian mayapple (P. emodi). Leaves alone can serve as a renewable source of podophyllotoxin (and other lignans) leaving rhizomes undisturbed to produce leaf biomass in subsequent years. It is not known, however, how frequently or severely plants can be defoliated without adversely affecting future plant growth, lignan content, or podophyllotoxin yield (g.m(-2)). This study compared harvest strategies that were mild to severe in frequency and timing of leaf removal. A wild population in full sun was subjected to leaf removal treatments of varying frequency (every year, every 2nd or 3rd year) and timing (early or late). Control plots not previously harvested were included every year. Plots were 1.0 m2 and established during spring of 2001. Duration of the study was four years. P. peltatum plants did not tolerate the most severe harvest treatment: annual harvest frequency in combination with early harvest time. Early annual harvests reduced total leaf dry mass and total leaf area in a consistent and linear manner. In contrast, plants tolerated annual harvests when conducted late in the growing season and tolerated early harvests when conducted every 2nd or 3rd year. The number of sexual shoots was reduced to zero by early annual harvests. Podophyllotoxin content was 2.7 to 6.5 times greater in leaves harvested early compared to those harvested late, though content was significantly greater in only two out of four years. In conclusion, we can recommend leaf removal every year from well-established P. peltatum populations grown in full sun if harvests are conducted late in the growing season. This harvest strategy ensures maximum podophyllotoxin yield without jeopardizing future leaf biomass yield. Leaves harvested early appear to have greater podophyllotoxin content, but we discourage early harvest every year. Instead, our results indicate that leaves can be harvested early every other year without reducing long-term performance of P. peltatum populations.


Assuntos
Luz , Podofilotoxina/análise , Podophyllum peltatum/química , Podophyllum peltatum/crescimento & desenvolvimento , Agricultura/métodos , Biomassa , Folhas de Planta/química , Folhas de Planta/crescimento & desenvolvimento , Folhas de Planta/metabolismo , Podophyllum peltatum/metabolismo , Fatores de Tempo
14.
Org Biomol Chem ; 4(5): 808-16, 2006 Mar 07.
Artigo em Inglês | MEDLINE | ID: mdl-16493463

RESUMO

Secoisolariciresinol dehydrogenase (SDH) catalyzes the NAD+ dependent enantiospecific conversion of secoisolariciresinol into matairesinol. In Podophyllum species, (-)-matairesinol is metabolized into the antiviral compound, podophyllotoxin, which can be semi-synthetically converted into the anticancer agents, etoposide, teniposide and Etopophos. Matairesinol is also a precursor of the cancer-preventative "mammalian" lignan, enterolactone, formed in the gut following ingestion of, for example, various high fiber dietary foods, as well as being an intermediate to numerous defense compounds in vascular plants. This study investigated the mode of enantiospecific Podophyllum SDH catalysis, the order of binding, and the stereospecificity of hydride abstraction/transfer from secoisolariciresinol to NAD+. SDH contains a highly conserved catalytic triad (Ser153, Tyr167 and Lys171), whose activity was abolished with site-directed mutagenesis of Tyr167Ala and Lys171Ala, whereas mutagenesis of Ser153Ala only resulted in a much reduced catalytic activity. Isothermal titration calorimetry measurements indicated that NAD+ binds first followed by the substrate, (-)-secoisolariciresinol. Additionally, for hydride transfer, the incoming hydride abstracted from the substrate takes up the pro-S position in the NADH formed. Taken together, a catalytic mechanism for the overall enantiospecific conversion of (-)-secoisolariciresinol into (-)-matairesinol is proposed.


Assuntos
Oxirredutases do Álcool/química , Oxirredutases do Álcool/metabolismo , Podophyllum peltatum/enzimologia , Oxirredutases do Álcool/genética , Calorimetria/métodos , Catálise , Domínio Catalítico/genética , Espectroscopia de Ressonância Magnética , Mecânica , Mutagênese Sítio-Dirigida , NAD/síntese química , NAD/química , NAD/metabolismo , Álcool Oxidorredutases Dependentes de NAD(+) e NADP(+) , Podophyllum peltatum/metabolismo , Estereoisomerismo , Titulometria
15.
Planta Med ; 71(12): 1157-64, 2005 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-16395654

RESUMO

The spatial distribution of wild germplasm of Podophyllum peltatum L. (American mayapple) has been analyzed using the Geographic Information System (GIS) with the objective to develop a method and a database for evaluation of biotic and abiotic factors influencing drug yield, and to map elite genotypes for propagation and improvement. The field assessment followed a standard procedure including geographical coordinates of each accession, leaf biomass randomly harvested, identification of associate species, collection of herbarium specimen, soil sample and digital pictures of the site. By overlaying morphological and chemical data with geomorphic information, a thematic map was created locating the podophyllotoxin-rich accessions and the uniqueness of each site was recorded for post-collection analysis. This work has enabled the establishment of a database of P. peltatum germplasm in Mississippi with drug yield linked to spatial locations for rational utilization of our natural resources. While this method integrates information of well-characterized diverse in situ P. peltatum germplasm, it might become a strategy for curators to reduce cost for establishing and maintaining ex situ collections since the genetic material is geo-referenced.


Assuntos
Sistemas de Informação Geográfica , Plantas Medicinais/química , Podophyllum peltatum/química , Bases de Dados Factuais , Mississippi , Folhas de Planta/química , Solo/análise
18.
Biochim Biophys Acta ; 1646(1-2): 157-63, 2003 Mar 21.
Artigo em Inglês | MEDLINE | ID: mdl-12637023

RESUMO

A beta-glucosidase with high specificity for podophyllotoxin-4-O-beta-D-glucopyranoside was purified from the leaves of Podophyllum peltatum. The 65-kDa polypeptide had optimum activity at pH 5.0 and was essentially inactive at pH 6.5 or above. Maximum catalytic activity of this glucosidase was obtained at 45 degrees C, but the enzyme was not heat stable. This beta-glucosidase displayed higher substrate specificity for podophyllotoxin-4-O-beta-D-glucopyranoside than for the other lignans tested, and for the (1-->3) linkage of laminaribiose than for other glucosidic linkages.


Assuntos
Glucosídeos/metabolismo , Podofilotoxina/análogos & derivados , Podofilotoxina/metabolismo , Podophyllum peltatum/enzimologia , beta-Glucosidase/metabolismo , Dissacarídeos/química , Dissacarídeos/metabolismo , Estabilidade Enzimática , Glucosídeos/química , Concentração de Íons de Hidrogênio , Estrutura Molecular , Folhas de Planta/enzimologia , Podofilotoxina/química , Especificidade por Substrato , Temperatura , beta-Glucosidase/química , beta-Glucosidase/isolamento & purificação
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