Trypanocidal tetrahydrofuran lignans from inflorescences of Piper solmsianum

Martins, Roberto Carlos Campos; Lago, João Henrique G.; Albuquerque, Sérgio de; Kato, Massuo Jorge

doi:10.1016/s0031-9422(03)00356-x

Cited by 97 publications

(82 citation statements)

References 19 publications

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“…The relative configurations of C-3, -4, and -5 were presumed as S, S, and S, respectively, which was confirmed from the NOESY cross signals (Table 1) between H-2 and H-3, between H-3 and H-4, between H-4 and H-5, and between -NHand H-3 and by the coupling constants for those cis-protons (J < 7.2 Hz) at tetrahydrofuran (for trans-protons, J > 7.2 Hz) (26,27). The relative configuration of C-2′ was determined to be R by comparing the chemical shift and coupling constants of H-2′ with previously reported data (28)(29)(30).…”

Section: Resultssupporting

confidence: 53%

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

Lipids

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Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxy- (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [ 1 H NMR, 13 C NMR (distortionless enhancement by polarization transfer), 1 H-1 H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

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Section: Resultssupporting

confidence: 53%

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

Lipids

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“…13 Other bis-tetrahydrofuran lignans have also been described from Achillea lingulata (Asteraceae). 14 In previous reports, Martins et al 3 described the isolation of (-)-grandisin (6) from Piper solmsianum and Lopes and co-workers 4,15 from Virola surinamensis (Rol.) Warb, which belong to Piperaceae and Myristicaceae, respectively.…”

Section: Introductionmentioning

confidence: 98%

“…1 In particular, the optically active tetrahydrofuran lignans display a wide range of pharmacological activities, including anti-parasite, [2][3][4] antibacterial, 5 antifungal, 6 antitumoral, 7 anti-inflammatory 8,9 and platelet-activating factor (PAF) inhibition. [10][11][12] Several non-symmetrical 2,5-diaryltetrahydrofuran lignans, shown in Table 1, have been isolated from Piper species (Piperaceae) containing either piperonyl, veratryl or 3,4,5-trimethoxyphenyl substituent at 2 and 5 positions and methyl groups at 3 and 4 positions attached to the tetrahydrofuran ring, as illustrated by (+)-calopiptin (1, P. schmidtii), 5-[rel-(2S,3S,4S,5S)-5'-(3'',4''-dimethoxyphenyl)-3',4'-dimethyl-2'-tetrahydro-furanyl)]-1,3-benzodioxole (2, P. wightii), (2S,3R,4S,5R)-3,4-dimethyl-2,5-bis(3',4'-dimethoxyphenyl)-tetrahydrofuran (3, P. clarkii), (±)-galgravin (4, P. futokadsura, P. hancei, P. puberculum, P.wallichii), (-)-galbelgin (5, P. attenuatum, P. futokadsura, P. thomsoni, P. wightii), (+)-grandisin (6, P. polysyphorum), (+)-machilin G (7, P. schmidtii, P. wightii), (+)-veraguensin (8, P. cuneifolium, P. futokadsura, P. puberculum) and (-)-zuonin A (9, P. schmidtii).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis Sp.

Verza¹,

Arakawa²,

Lopes³

et al. 2009

J. Braz. Chem. Soc.

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A biotransformação da lignana tetraidrofurânica, (-)-grandisina, pelo fungo endofítico Phomopsis sp, obtido de Viguiera arenaria, conduziu à formação de um novo metabólito caracterizado como 3,4-dimetil-2-(4'-hidróxi-3',5'-dimetóxifenil)-5-metóxi-tetraidrofurano. O metabólito foi analisado contra o parasita Trypanosoma cruzi, o agente causador da doença de Chagas, e mostrou uma atividade tripanocida (IC 50 9,8 µmol L -1 ) similar ao precursor natural (IC 50 3,7 µmol L -1 ).The biotrasformation of the tetrahydrofuran lignan, (-)-grandisin, by the endophitic fungus Phomopsis sp, obtained from Viguiera arenaria, led to the formation of a new compound determined as 3,4-dimethyl-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-5-methoxy-tetrahydrofuran. The metabolite was evaluated against the parasite Trypanosoma cruzi, the causative agent of Chagas's disease, and showed a trypanocidal activity (IC 50 9.8 µmol L -1 ) similar to the natural precursor (IC 50 3.7 µmol L -1 ).Keywords: biotransformation, 2,5-diaryltetrahydrofuran, endophytic fungus, (-)-grandisin, trypanocidal activity IntroductionThe lignan family is a large group of natural products with noteworthy therapeutic activity as illustrated by podophyllotoxin derivatives (e. g. etoposide) with antitumoral activity. 1 In particular, the optically active tetrahydrofuran lignans display a wide range of pharmacological activities, including anti-parasite, 2-4 antibacterial, 5 antifungal, 6 antitumoral, 7 anti-inflammatory 8,9 and platelet-activating factor (PAF) inhibition. [10][11][12] Several non-symmetrical 2,5-diaryltetrahydrofuran lignans, shown in Table 1, have been isolated from Piper species (Piperaceae) containing either piperonyl, veratryl or 3,4,5-trimethoxyphenyl substituent at 2 and 5 positions and methyl groups at 3 and 4 positions attached to the tetrahydrofuran ring, as illustrated by (+)-calopiptin P. futokadsura, P. hancei, P. puberculum, P.wallichii), (-)-galbelgin (5, P. attenuatum, P. futokadsura, P. thomsoni, P. wightii), (+)-grandisin (6, P. polysyphorum), (+)-machilin G (7, P. schmidtii, P. wightii), (+)-veraguensin (8, P. cuneifolium, P. futokadsura, P. puberculum) and (-)-zuonin A (9, P. schmidtii). 13 Other bis-tetrahydrofuran lignans have also been described from Achillea lingulata (Asteraceae). 14 In previous reports, Martins et al. 3 described the isolation of (-)-grandisin (6) from Piper solmsianum and Lopes and co-workers 4,15 from Virola surinamensis (Rol.) Warb, which belong to Piperaceae and Myristicaceae, respectively. The tetrahydrofuran lignan (-)-grandisin (6) showed a potent trypanocidal activity against the trypomastigote form of Trypanosoma cruzi, responsible for Chagas´s disease in Latin America, at 5 µg mL -1 leading to a total parasite lysis after 24 h, without hematiae damage. 4 Furthermore, veraguensin (8) also isolated from Virola surinamensis 4 preserved this anti-parasite pattern along with a potent platelet-activating factor (PAF) inhibitory activity that may be involved in the mechanisms of the parasite growing and diffe...

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“…[1][2][3][4] The genus Peperomia has over 1000 species occurring in the tropics, its leaves have a variety of size and shape and are adapted to moist habitat and dry highlands as well. In despite of the large number of Peperomia species, only a few species have been chemically analyzed and, as a result, amides, chromenes, benzoic acids, lignoids and poliketide derivatives were isolated.…”

Section: Introductionmentioning

confidence: 99%

3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

Lago¹,

Oliveira

Guimarães³

et al. 2007

J. Braz. Chem. Soc.

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O óleo essencial obtido das folhas de Peperomia oreophila (Piperaceae) foi submetido a fracionamento em gel de sílica. Esse processo de separação resultou em uma fração composta por uma mistura de hidrocarbonetos sesquiterpênicos que foram identificados como β-elemeno, α-ilangeno, α-guaieno e β-selineno. Além desses, também foram identificados o espatulenol e dois sesquiterpenos com raro esqueleto ishwarano: o 3-ishwarol e a 3-ishwarona, sendo esta última, o componente majoritário do óleo bruto (78% em massa). Uma vez que o álcool foi obtido em quantidade insuficiente para caracterização estrutural, maiores quantidades foram obtidas por meio da redução da cetona original. Os dois sesquiterpenos foram purificados e depois caracterizados por meio de técnicas espectrométricas ( 1 H-1 H COSY, HMQC, HMBC e NOESY).The essential oil from Peperomia oreophila leaves (Piperaceae) was submitted to fractionation in silica gel column. This separation procedure yielded a fraction composed of a hydrocarbon sesquiterpene mixture which was identified as β-elemene, α-ylangene, α-guaiene and β-selinene. Besides, spathulenol and two sesquiterpenes with the rare ishwarane skeleton: 3-ishwarol and 3-ishwarone were also identified. 3-ishwarone was the major component of the crude oil (78% weight). Since the alcohol obtained was not sufficient to allow a complete structural determination, the original ketone was reduced to 3-ishwarol in order to give additional quantities. After the two sesquiterpenes purification, they were characterized by spectrometric techniques ( 1 H-1 H COSY, HMQC, HMBC and NOESY).

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Trypanocidal tetrahydrofuran lignans from inflorescences of Piper solmsianum

Cited by 97 publications

References 19 publications

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis Sp.

3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

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