Piper nigrum alkaloids

Alkaloids with the piperidine nucleus, such as pelletierine (Punica grana-tum), lobelanine Lobelia inflata) and piperine Piper nigrum), have a typical biosynthesis pathway. It starts with L-lysine and continues via cadaverine (biogenic amine), A -piperideine and A -piperidinium cations and lobelanine, to be synthesized as lobeline. Piperine is synthesized from A -piperideine via piperidine (Figure 49). For the transformation from A -piperideine to A -piperideine cation, the residue from acetyl-CoA is needed, together with SAM activity in the transformation to lobelanine. Piperine is synthesized from piperidine through the formation of amide. 

The pungency of the fruits of black pepper (Piper nigrum Piperaceae), a widely used condiment, is mainly due to the piperidine alkaloid piperine (Figure 6.24). In this structure, the piperidine ring forms part of a tertiary amide structure, and is incorporated via piperidine itself, the reduction product of A1 -pipcridcine (Figure 6.22). 

The fruit of the plant Piper nigrum is the common black pepper of the household. This fruit yields an alkaloid known as pipeline present to about 4 to 9 per cent in commercial pepper. On hydrolysis the alkaloid yields piperidine or hexa-hydro pyridine and an acid known as piperic acid. Piperine is thus considered as a piperidine amide of piperic acid. Physiologically this alkaloid acts like quinine but is less active and is uncertain. It is only rarely used in medicine. 

Piperine (1-piperoylpiperidine), alkaloid from piper nigrum L., belonged to the group of... 

Two cinnamoylpyrrolidine alkaloids (6 R1 = R2 = H, n = 1) and (6 R1 = OMe, R2 = H, n = 1) have been isolated from Piper methysticum (kava roots) for the first time.12 A detailed re-investigation of the constituents in black pepper (Piper nigrum) has been published.13 Aside from several piperidine alkaloids, piperyline (6 R1 + R2 = 0CH20, n = 2) was isolated and fully characterized by spectral and chemical means and by synthesis, utilizing a Wittig reaction as the key step. 

Ethnopharmacological research on natural products can contribute to the discovery of new active compounds with novel structures which may serve as leads to the development of new antiepileptic drugs. An example is the isolation of the active alkaloid piperine from Piper nigrum L. which is one of the component herbs of an ancient Chinese medicine used for the treatment of epilepsy. Its structural modifications resulted in the synthesis of seven derivatives including antiepilepserine which was found to be more potent than the parent compound with fewer side effects and it has been used as an antiepileptic drug [10-12]. 

Piperidine alkaloids occur in only a few species of higher plants. However, (S)-pipecolic acid 3 [121] is widely distributed in higher plants, microorganisms and animals. Lobeline 4 is the main constituent of lobelia alkaloids (Lobelia inflata, Campanulaceae). It is a respiratory stimulant in mammals. Pi-perine 5 is the active ingredient in black pepper (Piper nigrum). On hydrolysis it furnishes piperic acid 6 and piperidine (hence its name) [122] ... 

Piperine is an alkaloid found in black pepper (Piper nigrum), long pepper (Piper longuni), cubeb (Piper cubebd) and grains-of-paradise (Aframomum melegueta), and is responsible in... 

Several representatives of the genus Piper (Piperaceae) are of economic importance. Some of these plants [e.g.. Piper nigrum (black pepper)] include alkaloids that are partially responsible for the desirable pungent and preservative properties of the plant. Other species are P. hetle (widely used as a masticatory), P. methysticum (widely used in the South Pacific as a soporific drug), and P. guineense (ashanti pepper). Most of these plants contain compounds that combine phenylpropanoid compounds see Chapter 8) and pyr-... 

Piper alkaloids a group of alkaloids occurring in various species of Piper, especially black pepper Piper nigrum). Structurally, P.a. consist of an aromatic carboxylic acid with an unsaturated side chain (e.g. piperic acid, sinapic acid) in amide linkage with a basic component, usually piperidine. The chief representative is Piperine (see). 

Piperine piperic acid piperidide, a Piper alkaloid (see), the chief alkaloid of black pepper Piper nigrum) and responsible for its sharp taste. Af, 285.35, m.p. 16°C. Both double bonds are irons (Fig.). The cis-cis isomer, earlier called chavicine, does not occur naturally. 

Biological activities biosynthesis of piperidine alkaloids HPLC and LC-MS/MS Lobelia inflata lobeline and their derivates pelletierine Piper nigrum piperine Punic a granatum... 

While for developing of simple piperidine alkaloids, e.g., pelletierine (Punica granatum), piperine (Piper nigrum et longum), and lobeline (Lobelia inflata), only one molecule of lysine is necessary, for quinolizidine alkaloids - e.g., lupinine (Lupinus luteus), sparteine of antiarrhythmic activity (Sarothamnus scoparius), and cytisine of respiratory stimulant effect (Laburnum species) - two molecules of lysines are indispensable. It was also proved that lycopodine (Lycopodium tristachyum, clubmoss) of quinolizidine structure has no polyketide origin, but it is a modified dimer of pelletierine, which, in turn, is derivable from lysine and acetate. 

Li S, Lei Y, Jia Y, Li N, Wink M, Ma Y (2011) Piperine, a piperidine alkaloid from Piper nigrum re-sensitizes P-gp, MRPl and BCRP dependent multidrug resistant cancer cells. Phytomedicme 19 83-87... 

Koul IB, Kapil A (1993) Evaluation of the liver protective potential of piperine, an active principle of black and long peppers. Planta Med 59 413 17 81. Lin Z, Hoult JR, Bennett DC, Raman A (1999) Stimulation of mouse melanocyte proliferation by Piper nigrum fruit extract and its main alkaloid - piperine. Planta Med 65 600-603... 

The most important alkaloids derived from piperidine (10-6) are alkaloids of black pepper Piper nigrum, Piperaceae). 

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