Enantioselective conversion of p-hydroxypropenylbenzene to (+)-conocarpan in Piper regnellii

Sartorelli, Patrı́cia; Benevides, Paulo José Coelho; Ellensohn, Ricardo Machado; Rocha, Mônica V.A.F; Moreno, Paulo Roberto Hrihorowitsch; Kato, Massuo Jorge

doi:10.1016/s0168-9452(01)00512-x

Cited by 31 publications

(26 citation statements)

References 29 publications

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“…In previous studies, the biosynthetic pathway of the (+)-conocarpan P. decurrens was determined by using insecticide bioassay-guided fractionation (Chauret et al1996, Sartorelli et al 2001. Conocarpan represents a class of the benzofuran neolignans with a variety of biological activities, including anti-PAF, antifungical, and insecticide activity.…”

Section: Resultsmentioning

confidence: 99%

“…Chauret et al (1996) have reported for the first time in a species of the Piperaceae three known neolignans (conocarpan, eupomatenoid-5, and eupomatenoid-6) isolated from Piper decurrens via insecticidal bioassayguided fractionation. In another phytochemical study accomplished with P. regnellii leaves, the biosynthetic pathway was established which leads to the dihydrobenzofuran neolignan (+)-conocarpan by means of in vivo administration of labeled l-phenylalanine [U- 14 C] and enantioselective conversion of p-hydroxypropenylbenzene to (+)-conocarpan (85%) by an enzyme fraction from the leaves (Sartorelli et al 2001).…”

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confidence: 99%

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Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck

Pessini¹,

Filho²,

Nakamura³

et al. 2003

Mem. Inst. Oswaldo Cruz

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck

Pessini¹,

Filho²,

Nakamura³

et al. 2003

Mem. Inst. Oswaldo Cruz

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“…The search of new drugs against leishmaniasis, potentially compounds and their derivatives have been described in the literature. [14][15][16] Neolignans are groups of compounds that show a wide range of biological effects including antifungal, [17][18][19] anti-schistosomal, [20][21][22][23] antiplasmodial, 24 trypanocidal, [25][26][27] antibacterial, 28 anti-PAF, 29,30 antipsychotic, 31 antioxidant, 32,33 activities, and biological activity against Escherichia coli,…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Nascimento¹,

Santos²,

Santos³

et al. 2010

J. Braz. Chem. Soc.

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A síntese e a estrutura cristalina por difração de raios-X de dois análogos de neolignanas, 2-(4-clorofenil)-1-feniletanona (20) e 2-[tio(4-clorofenil)]-1-(3,4-dimetoxifenil)propan-1-ona (12) são descritas. O composto 12 apresenta atividade intracelular contra Leishmania donovani e Leishmania amazonensis de amastigotas que causam a leishmaniose tegumentar e visceral. Além disso, a teoria do funcional de densidade (DFT) com o funcional híbrido B3LYP foi empregado para calcular um conjunto de descritores moleculares para dezenove análogos sintéticos de neolignanas com atividades antileishmaniose. Posteriormente, a análise discriminante stepwise foi realizada para investigar possíveis relações entre a estrutura molecular e atividades biológicas. Por meio dessa análise os compostos foram classificados em dois grupos ativos e inativos de acordo com seu grau de atividade biológica, e as propriedades mais importantes foram as cargas de alguns átomos, a afinidade eletrônica e o ClogP.The synthesis and X-ray crystal diffraction structure of two analogues of neolignans, 2-(4-chlorophenyl)-1-phenylethanone (20) and 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl) propan-1-one (12) is described. The compound 12 presents activity against intracellular Leishmania donovani and Leishmania amazonensis amastigotes that cause cutaneous and visceral leishmaniasis. In addition, the density functional theory (DFT) with the B3LYP hybrid functional was employed to calculate a set of molecular descriptors for nineteen synthetic analogues of neolignans with antileishmanial activities. Afterwards, the stepwise discriminant analysis was performed to investigate possible relationship between the molecular descriptors and biological activities. Through this analysis the compounds were classified into two groups active and inactive according to their degree of biological activities, and the more important properties were charges on some key atoms, electronic affinity and ClogP.

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“…14) Several compounds of this class (benzofuran neolignans) have been isolated from species of Piperaceae, and show a variety of biological activity including anti-PAF, antifungical, and insecticidal. 15) In the present study, we describe the anti-Trypanosoma cruzi activity of extracts and neolignans isolated from P. regnellii var. pallescens.…”

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confidence: 97%

Activity of Neolignans Isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi

Luize

Ueda-Nakamura²,

Filho³

et al. 2006

Biological & Pharmaceutical Bulletin

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The in vitro antiproliferative effects of 4 neolignans purified from the ethyl-acetate extract from leaves of Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi were investigated. These isolated compounds were identified through spectral analyses of UV, EI-MS, 1 H-, 13 C-NMR, H-H COSY, gNOE, HETCOR, and HMBC. The compounds eupomatenoid-5, eupomatenoid-6, and conocarpan showed considerable activity against epimastigote forms of T. cruzi, with 50% inhibition concentrations (IC 50 ) of 7.0, 7.5, and 8.0 m mg/ml respectively. After methylation, these compounds showed a lessened inhibitory activity to the growth of the protozoan, suggesting that loss of the hydroxyl group from their molecules reduces the activity. The compound eupomatenoid-3 showed lower activity than the hexane fraction. Eupomatenoid-5 was significantly more active than benznidazole, the antiparasitic drug of choice for treatment of Chagas' disease. The crude extract, hexane fraction, and eupomatenoid-5 caused no lysis in sheep blood at concentrations which inhibit the growth of epimastigote forms. The compound eupomatenoid-5 showed low cytotoxic effects against Vero cells. These results provide new perspectives on the development of novel drugs obtained from natural products with trypanocidal activity. However, the extracts and active compound isolated from P. regnellii var. pallescens should be further studied in animal models for in vivo efficacy.

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Enantioselective conversion of p-hydroxypropenylbenzene to (+)-conocarpan in Piper regnellii

Cited by 31 publications

References 29 publications

Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck

Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Activity of Neolignans Isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi

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