• Journal of Applied Biological Chemistry
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• 제48권2호
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• pp.65-74
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• 2005

Fungicidal, insecticidal, and mosquito larvicidal activities of piperidine alkaloids, pipernonaline and piperoctadecalidine, and isobutylamide alkaloids, pellitorine, guineensine, pipercide, and retrofractaminde A, derived from Piperaceae fruits were studied. Pipernonaline and piperoctadecalidine showed potent fungicidal activities against Puccinia recondita with 91 and 80% control values at 500 ppm. Against Phytophthora infestans, pipernonaline showed strong fungicidal activity with 91 and 80% control values at 1,000 and 500 ppm. $LD_{50}$ values of pipernonaline and piperoctadecalidine against Plutella xylostella were 125 and 95.5 ppm, respectively, and that of piperoctadecalidine against Tetranychus urticae was 246 ppm. Against larvae of Aedes aegypti and Culex pipiens pallens, $LD_{50}$ values of pipernonaline were 0.35 and 0.21 ppm, respectively. Highest larvicidal activities of pipercide and retrofractamide A were found against A. aegypti, A. togoi, and C. pipiens pallens. $LD_{50}$ values of pipercide and retrofractamide A were 0.10 and 0.039 ppm against A. aegypti, 0.26 and 0.01 ppm against A. togoi, and 0.004 and 0.028 ppm against C. pipiens pallens, respectively. Based upon these results and earlier findings, bioactive components derived from Piperaceae fruits may be valuable for development of useful lead product of possibly safer fungicidal, insecticidal, and mosquito larvicidal agents.

• 생명과학회지
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• 제22권11호
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• pp.1552-1557
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• 2012

Pipernonaline은 후추나무과에 속하는 필발(Piper longum Linn.)의 유도체로서 전립선 암세포에 대한 항암활성이 보고되고 있다. 하지만 실제 암세포 내에서 생물학적 정보를 가진 수 많은 유전자들에 대한 발현이 어떻게 이루어지고 있는지 알려진 바가 없다. 본 연구에 사용된 microarray 분석은 동시에 수 만개 이상의 유전자 발현양상을 한번에 관찰할 수 있는 기술로서 특정 질병의 유전학적 특성과 기전 연구를 더 광범위하게 연구 할 수 있는 기술이다. 본 연구에서는 전립선 암세포인 PC-3 세포에 pipernonaline을 처리하여 cDNA microarray를 실시하였다. 이후, DAVID database를 이용하여 gene ontology의 Biological Process를 분석하여 세포사멸과 세포주기, 세포성장 및 증식에 관련된 유전자들을 우선적으로 분석하였다. 그 결과, 세포주기관련 256개, 세포사멸관련 197개, 세포성장 및 증식관련에 154개의 유전자가 확인 되었다. 이러한 결과는 pipernonaline은 전립선 암세포 내에 존재하는 생물학적 신호전달체계에 관련된 유전자 발현을 조절함으로써 항암활성을 나타내 것을 알 수 있었고, 이후 이러한 microarray의 추가적인 분석은 암세포 내 새로운 유전자의 탐색 및 메커니즘을 규명하는데 유용하게 사용할 수 있을 것으로 사료된다.

• 생명과학회지
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• 제19권5호
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• pp.671-675
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• 2009

Prostate cancer has been a critical health problem due to an increase of prostate cancer-related deaths worldwide. Also, a frequent treatment option for prostate cancer is androgen ablation, but this treatment has a limited scope, especially for hormone-refractory cancer. There is an urgent need for the identification of alternative therapeutic strategies for prostate cancer. Previously, over one hundred species of dried-plant methanol extracts were tested for inhibitory effects on proliferation. One of them, Piper longum Linn. was selected based on its potent anti-proliferation effect. The dried root of P. longum Linn. was extracted with 100% methanol for 2-3 days and its extract was fractionated using chloroform. The chloroform layer was then subjected to column chromatography on silica gel, reverse phase-18 (RP-18) and Sephadex LH-20, in turn. Finally, the pure compound was obtained and identified as pipernonaline by NMR spectroscopic and physico-chemical analysis. In this study, anti-proliferation and cell cycle arrest effects of pipernonaline on human prostate cancer PC-3 cells were investigated using the MTT and PI staining, respectively. Our findings suggest that pipernonaline represents a dose-dependent growth inhibition pattern on PC-3 cells and, moreover, its growth inhibition is associated with sub-G1 and G0/G1 cell cycle accumulation in PC-3 cells. Also, these results provide an anticancer candidate for human prostate cancer.

• Journal of Microbiology and Biotechnology
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• 제12권4호
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• pp.679-682
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• 2002

The alkaloids, piperlongumine, piperine, pipernonaline, and piperoctadecalidine, isolated from Piper longum L., were found to inhibit the biosynthesis of aflatoxin $B_1$ (AF$B_1$) in Aspergillus flavus WRRC 3-90-42-12. Piperlongumine was the most active among the compounds tested, with a 96% inhibition of AF$B_1$biosynthesis at 0.2% (w/v) supplement in a potato dextrose agar (PDA) medium. The three other piperidine alkaloids, pipeline, pipernonaline, and piperoctadecalidine, also inhibited the biosynthesis of AF$B_1$. Of these three alkaloids, piperoctadecalidine exhibited a potent inhibitory activity with a 100% inhibition of AF$B_1$ production at 0.7% (w/v) supplement in a PDA medium. Therefore, piperlongumine and piperoctadecalidine could be used as antiaflatoxigenic agents in agricultural industries. To determine the antiaflatoxigenic mode of action of piperlongumine, further studies are needed.

• Bulletin of the Korean Chemical Society
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• 제13권4호
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• pp.388-391
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• 1992

A chemical investigation of the fruits of Piper retrofractum (Piperaceae) has led to the isolation and characterization of a novel piperidine alkaloid, piperoctadecalidine together with three known alkaloids piperine, pipernonaline and guineensine. The structure of the new compound was detemined to be (2E,4E,14Z)-N-(2,4,14-Octadecatrienoyl) piperidine by spectral and synthetic methods.