piperidines and pipernonaline

Piper chaba Hunter, called Chui Jhal or Choi Jhal, is commonly used as a culinary (spice) herb in India and Bangladesh. It exhibits numerous important biological activities and has been widely used in traditional medicine.. This review focuses on the chemical and pharmacological activities of a culinary ingredient P. chaba based on information extracted from the literature to highlight its use in traditional medicine.. A literature search in known databases was conducted (till September 2019) for published articles using the relevant keywords.. Findings suggest that, to date, a number of important phytoconstituents such as dimeric alkaloids, and alkamides have been isolated from various parts of P. chaba. Extracts from P. chaba or derived compounds exhibit diverse biological activities, such as anti-microbial, anti-leishmanial, anti-malarial, anti-parasitic, cytotoxic/anticancer, adipogenic, hepato- and gastro-protective, anti-diabetic, analgesic, anti-diarrheal, depressive, anti-inflammatory, diuretic, anti-hypertensive, antipyretic, anti-ulcer, and immunomodulatory effect. Among the isolated compounds, chabamides, piperine, piplartine, retrofractamides A/B, methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid, n-butyl or n-pentyl amine, piperlonguminine, pipernonaline, dehydropipernonaline, N-isobutyl-(2E,4E)-octadecadienamide, and N-isobutyl-(2E,4E,14Z)-eicosatrienamide have documented important biological effects in various test systems.. Taken together, P. chaba may be a potential source of plant-based therapeutic lead compounds, which justify its uses in traditional medicine.

Topics: Adipogenesis; Alkaloids; Animals; Antifungal Agents; Antimalarials; Antiparasitic Agents; Bangladesh; Benzodioxoles; Dioxolanes; Humans; Hypoglycemic Agents; India; Medicine, Traditional; Phytotherapy; Piper; Piperidines; Plant Extracts; Polyunsaturated Alkamides

Pipernonaline (1), one of the components of the spice pepper, preferentially reduced the survival of human pancreatic cancer PANC-1 cells under nutrient-deprived conditions witha PC

Topics: Alkaloids; Antineoplastic Agents; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Drug Screening Assays, Antitumor; Humans; Pancreatic Neoplasms; Piperidines

Six amides, piperbonamides A-F, three neolignans piperbonins A-C, and 11 known compounds were isolated from the aerial parts of Piper bonii (Piperaceae). The structures of piperbonamides A-F and piperbonins A-C were elucidated based on the analysis of 1D and 2D NMR and MS data. Piperbonin A, (+)-trans-acuminatin, (+)-cis-acuminatin, (+)-kadsurenone, and pipernonaline showed weak activity against platelet aggregation with IC50 values of 118.2, 108.5, 90.02, 107.3, and 116.3 μM, respectively, as compared with the positive control, tirofiban, with an IC50 value of 5.24 μM. Piperbonamides A-F were inactive against five tumor cell lines at concentrations up to 40 μM.

Topics: Alkaloids; Amides; Benzofurans; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Flavonoids; Glycosides; Humans; Inhibitory Concentration 50; Lignans; Molecular Structure; Piper; Piperidines; Plant Components, Aerial; Platelet Aggregation; Platelet Aggregation Inhibitors; Structure-Activity Relationship; Tirofiban; Tyrosine

The antiproliferation effects of pipernonaline, a piperine derivative, were investigated on human prostate cancer PC-3 cells. It inhibited growth of androgen independent PC-3 and androgen dependent LNCaP prostate cells in a dose-dependent (30-90 μM) and time-dependent (24-48 h) manner. The growth inhibition of PC-3 cells was associated with sub-G(1) and G(0)/G(1) accumulation, confirmed by the down-regulation of CDK2, CDK4, cyclin D1 and cyclin E, which are correlated with G(1) phase of cell cycle. Pipernonaline up-regulated cleavage of procaspase-3/PARP, but did not change expression of proapoptotic bax and antiapoptotic bcl-2 proteins. Its caspase-3 activation was confirmed by the caspase-3 assay kit. In addition, pipernonaline caused the production of reactive oxygen species (ROS), increase of intracellular Ca(2+), and mitochondrial membrane depolarization, which these phenomena were reversed by N-acetylcysteine, a ROS scavenger. The results suggest that pipernonaline exhibits apoptotic properties through ROS production, which causes disruption of mitochondrial function and Ca(2+) homeostasis and leads to its downstream events including activation of caspase-3 and cleavage of PARP in PC-3 cells. This is the first report of pipernonaline toward the anticancer activity of prostate cancer cells, which provides a role for candidate agent as well as the molecular basis for human prostate cancer.

Topics: Alkaloids; Antineoplastic Agents; Apoptosis; Caspase 3; Cell Line, Tumor; Cell Proliferation; G1 Phase Cell Cycle Checkpoints; Humans; Male; Piper; Piperidines; Poly(ADP-ribose) Polymerases; Prostatic Neoplasms; Proto-Oncogene Proteins c-bcl-2; Reactive Oxygen Species; Resting Phase, Cell Cycle

A bioassay-guided isolation of an ethanol extract of the fruit of Piper longum L. yielded piperlonguminine, piperine and pipernonaline, as the main antihyperlipidemic constituents. They exhibit appreciable antihyperlipidemic activity in vivo, which is comparable to that of the commercial antihyperlipidemic drug, simvastatin.

Topics: Alkaloids; Animals; Benzodioxoles; Dioxolanes; Fruit; Hypolipidemic Agents; Male; Molecular Structure; Piper; Piperidines; Polyunsaturated Alkamides; Rats; Rats, Wistar; Simvastatin

Mosquito larvicidal activity of Piper longum fruit-derived materials against the fourth-instar larvae of Aedes aegypti was examined. A crude methanol extract of P. longum fruits was found to be active against the larvae, and the hexane fraction of the methanol extract showed a strong larvicidal activity of 100% mortality. The biologically active component of P. longum fruits was characterized as pipernonaline by spectroscopic analyses. The LC(50) value of pipernonaline was 0.25 mg/L. The toxicity of pipernonaline is comparable to that of pirimiphos-methyl as a mosquito larvicide. In tests with available components derived from P. longum, no activity was observed with piperettine, piperine, or piperlongumine.

Topics: Aedes; Alkaloids; Animals; Fruit; Insecticides; Larva; Methanol; Piperaceae; Piperidines; Plant Extracts

A methanol extract of Piper longum fruit was found to be active against mosquito larvae of Culex pipiens pallens at 10 microg/ml after 24 h. A piperidine alkaloid, pipernonaline, was found to be responsible for this activity, with the 24-h median lethal dose (LD50) value for this compound being 0.21 mg/liter. The LD50 value of pipernonaline was not much higher than those for the 3 organophosphorous insecticides malathion, chlorpyrifos-methyl, and pirimiphos-methyl, used for comparative purpose in this study. Structural elucidation of pipernonaline was by means of mass spectrometry (1H and 13C nuclear magnetic resonance imaging).

Topics: Alkaloids; Animals; Capsicum; Chlorpyrifos; Cholinesterase Reactivators; Culex; Insecticides; Larva; Lethal Dose 50; Malathion; Organothiophosphorus Compounds; Piperidines; Plants, Medicinal