Lignans of Piper clusii☆

Koul, Surrinder; Taneja, Subhash C.; Dhar, K.L.; Atal, C.K.

doi:10.1016/0031-9422(83)85040-7

Cited by 58 publications

(33 citation statements)

References 4 publications

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“…Thus, we assumed that 3 belongs to a class of dibenzylbutyrolactol lignan. C-NMR spectral data of 3 with those of 1 and 2, in addition to comparison with the reported data for 1, 13,14) cubebinin (4), 15) and clusin (5). 13) The stereochemistry at the C-8, C-8Ј, C-9 and C-9Ј positions of 3 was also deduced from 1 H-and 13 C-NMR spectral comparisons.…”

Section: Structural Elucidation Ofmentioning

confidence: 80%

“…C-NMR spectral data of 3 with those of 1 and 2, in addition to comparison with the reported data for 1, 13,14) cubebinin (4), 15) and clusin (5). 13) The stereochemistry at the C-8, C-8Ј, C-9 and C-9Ј positions of 3 was also deduced from 1 H-and 13 C-NMR spectral comparisons. As shown in Tables 1 and 2, chemical shifts and coupling constants of signals of 3 attributable to the tetrahydrofuranol moiety (C-8, C-8Ј, C-9, C-9Ј carbons and 8-H, 8Ј-H, 9-Ha, 9-Hb, 9Ј-H protons) were very similar to those of 1 and 2.…”

Section: Structural Elucidation Ofmentioning

confidence: 80%

“…On the basis of comparison of the physicochemical data of 1 and 2 with those of the reported data, [7][8][9][10][11][12][13][14] 1 and 2 were identified as (Ϫ)-cubebin and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin, respectively. The comparisons of 1 H-and 13 C-NMR spectral data of 1 with the reported data 11,13,14) are shown in Tables 1 and 2, respectively. From analysis of the 1 H-and 13 C-NMR spectral data (Tables 1, 2) for 1 and 2, it was found that these lignans were obtained as a mixture of a-isomer and b-isomer, as previously reported for the dibenzylbutyrolactol class of lignans.…”

Section: Measurement Of Produced Melanin In Cultured B16 Melanoma Cellsmentioning

confidence: 99%

“…11) Compound 3 gave the characteristic 1 H-, 13 C-NMR and C-H COSY spectra, indicating that 3 was a mixture of a-isomer and b-isomer as well as 1 and 2. The ratio of a-isomer and b-isomer of 3 based on the signal integral value of the 9b-H proton was 60 : 40, as shown in Table 1.…”

Section: Structural Elucidation Ofmentioning

confidence: 99%

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Melanogenesis Stimulation in Murine B16 Melanoma Cells by Piper nigrum Leaf Extract and Its Lignan Constituents

Matsuda

Kawaguchi

Yamazaki

et al. 2004

Biological & Pharmaceutical Bulletin

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A methanolic extract from the leaves of Piper nigrum L. showed a significant stimulatory effect on melanogenesis in cultured murine B16 melanoma cells. Activity-guided fractionation of the methanolic extract led to the isolation of two known lignans, (؊)-cubebin (1) and (؊)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2), together with a new lignan, (؊)-3-desmethoxycubebinin (3). Among these lignans, 1 and 2 showed a significant stimulatory activity of melanogenesis without any significant effects on cell proliferation.

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Section: Structural Elucidation Ofmentioning

confidence: 80%

Section: Structural Elucidation Ofmentioning

confidence: 80%

Section: Measurement Of Produced Melanin In Cultured B16 Melanoma Cellsmentioning

confidence: 99%

Section: Structural Elucidation Ofmentioning

confidence: 99%

See 2 more Smart Citations

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Piper nigrum Leaf Extract and Its Lignan Constituents

Matsuda

Kawaguchi

Yamazaki

et al. 2004

Biological & Pharmaceutical Bulletin

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“…Although aliphatic nitro compounds are unusual in nature 7 , the occurrence of nitrophenanthrene alkaloids is widespread in the Aristolochiaceae 8,9 . In addition, loliolide (18), trans-and cis-N-feruloyltyramine (19,22), trans-and cis-N-p-coumaroyltyramine (20,23) and trans-N-feruloyl-3-O-methyldopamine (21) were isolated. Structural elucidation of the new alkaloid cis-N-feruloyl-3-O-methyldopamine (24), isolated for the first time from a natural source, is discussed.…”

Section: Introductionmentioning

confidence: 99%

Alkamides and phenethyl derivatives from Aristolochia gehrtii

Navickiene¹,

Lopes²

2001

J. Braz. Chem. Soc.

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Foram isolados de galhos de Aristolochia gehrtii a cis-N-feruloil-3-O-metildopamina, um derivado hemiacetálico do 5-hidroximetilfurfural, e vinte e dois compostos conhecidos. Entre estes compostos estão cinco lignanas, três terpenos, seis alcalóides dos quais cinco são alcamidas, dois derivados do ácido benzóico e seis derivados constituídos pelo grupo feniletil. As estruturas dos compostos isolados foram determinadas por métodos espectroscópicos e comparação de dados físicos e espectroscópicos dos compostos com aqueles disponíveis na literatura.From the stems of Aristolochia gehrtii, the cis-N-feruloyl-3-O-methyldopamine and a hemiacetal derivative of 5-hydroxymethylfurfural were isolated, together with twenty-two known compounds. These compounds include five lignans, three terpenes, six alkaloids (five alkamides), two benzoic acid derivatives, and six phenethyl derivatives. The structures of the isolated compounds were determined by means of spectroscopic methods and comparison with literature data.

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Stereochemistry of diastereomeric neolignans fromPiper hookeri by nuclear magnetic resonance spectroscopy

Pradhan

Banerji

1998

Phytochem. Anal.

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A new 8.1′ type neolignan, (8R,1′S or 8S,1′R)‐4‐[2‐(1,3‐benzodioxolo‐5‐yl)‐1‐methylethyl]‐2,5‐dimethoxy‐1‐propenyl‐2,5‐cyclohexadienone, hookerinone B a diastereomer of hookerinone A, and a pair of 8.3′ type diastereomeric neolignans, lancifolin C and lancifolin D, were isolated from the alchoholic extracts of the medicinal plant Piper hookeri. The absolute configurations of these neolignans and of a third diastereomeric pair, dihydroisofutoquinol A and dihydroisofutoquinol B, were established by nuclear magnetic resonance spectroscopic methods. © 1998 John Wiley & Sons, Ltd.

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Lignans of Piper clusii☆

Cited by 58 publications

References 4 publications

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Piper nigrum Leaf Extract and Its Lignan Constituents

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Piper nigrum Leaf Extract and Its Lignan Constituents

Alkamides and phenethyl derivatives from Aristolochia gehrtii

Stereochemistry of diastereomeric neolignans fromPiper hookeri by nuclear magnetic resonance spectroscopy

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