Piper Piperine

Anderson first hydrolysed piperine by alkalis into a base and an acid, which were named by Babo and Keller piperidine and piperic acid respectively. The chemistry of these products is so well known that it need not be discussed here. The alkaloid was synthesised by Rugheimer by the action of piperoyl chloride on pijieridine. 

The chemistry of pepper has long been studied and the pungent principle of black pepper—a piperidine alkaloid, piperine 134—was isolated as early as 1877 (201). Its synthesis from the acid and piperidine was accomplished in 1882. (202). The corresponding pyrrolidine alkaloid trichostachyne (135) was isolated some 100 years later from several Piper species (see below). The cooccurence of piperidine and pyrrolidine alkaloids is a common feature of the chemistry of pepper. In many cases, the crude alkaloid extract is first cleaved with acids or bases and then each alkaloid is reconstituted by selective amidation. For the sake of unity, this chapter will be limited to comments on pyrrolidines, even in cases where they are minor alkaloids. 

Piper guineense Schum. and Thonn is a creeper found in humid and shady forests from Guinea to Uganda and Angola it is known as the source of the Ashanti pepper. Its fruit and roots contain the above-mentioned piperine 134 and trichostachyne (135) (203, 204). In the root was also found wisanidine (136) named after the Nigerian vernacular name of the species, wisa osoro (205). The... 

The Aedes aegypti (Diptera Culicidae) mosquito is the primary vector in transmitting dengue and yellow fever. Insecticide use has been the primary method of control of this and other mosquitoe species. Piperine [(T,. S )- -piperoyl-piperidine], is the major constituent in Piper nigrum... 

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. 

Spices pepper piperine, clavicine, piperidine alkal., also bearing a cyclobutane ring, such as pipercyclobutanamide A Fujiwara 2001 black pepper Piper spp., including Piper nigrum h., Piperaceae, Ang. from India, Indonesia, and the Philippines... 

Piperine Piperine, molecular formula C17H19NO3, a component of black pepper (Piper nigrum), has been used in various traditional medicine preparations, and also as an insecticide. Piperine has various effects on human drug metabolizing enzymes, and is marketed under the brand name, Bioperine , as an adjunct for increasing bioavailability of various dietary supplements, especially curcumin, one of the active ingredients of turmeric (Curcuma longa). 

Piper longum L. Bi Ba (Indian long pepper) (fruit) Volatile oil, piperine, Antipyretic, carminative, aromatic stomachic, analgesic in gastralgia, flatulence, headache. 

Piper nigrum L. Hu Jiao (Black pepper) (fruit) Piperine, chavicine, piperamine, piperonal, dihydrocarveol, cryptone, caryophyllene. This herb may cause irritation to the system.33-45 Anticonvulsive, sedative. 

Commercially available black pepper comes from the entire unripe fruit of a Piper nigrum L. plant and is valued for its pungent taste and aroma. Besides its hot flavor, there are many folk medicine remedies using black pepper. It has antiallergic activity. Piperine strongly inhibits hepatic arylhydrocarbonhydroxylase and UDP-glucuronyl transferase activities. Some proven uses for black pepper extracts are as an insecticide and as a tumor inhibitor. To research claims such as these, it is necessary to isolate the components of pepper. 

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 chemistry of the pungent compounds of pepper has been under study since the isolation of piperine in 1820. Piperine was shown to be a piperidide of piperic acid, and had the trans. trans configuration. The three other possible isomers were soon postulated, and they were named isopiperine (cis.trans). isochavicine (trans. cis) and chavicine (cis.cis) even before they were synthesized. The assignment of the isomeric configuration starts from the amide end. 

Certain analogs and homologs of piperine have been reported in pepper as minor constituents. The earliest of this was piper— ettine, the heptenoic analog of piperine with three double bonds, giving it the characteristic absorption maximum at 360 rim. This compound shows substantial absorption at 342 nm, the absorption maximum of piperine, and thus, would enhance the piperine value. 

On tasting the narrow, horizontal segments of the area from the start to the solvent front in many thin—layer separations of pepper extracts, we have noticed that there is a component always coming above the piperine spot which has a tingling sensation on the tongue. This substance has not been identified, but could consist of isobutylamide-like compounds reported from other Piper species by Atal t al (38). 

Figure 6. Correlation of pipeline content and pungency. Curves (A) pure piper-ine (B) piperine by direct 342 nm absorption of pepper extracts (C) pipeline by Labruyere s hydrolysis-distillation method (39)...

Thus, the estimation of piperine (along with the minor amounts of piperettine and piperylin) obtained by a measure of the absorption at 342 nm of the extract has been shown to be reasonably accurate (Table VII), and predictiv/e of the real pungency of pepper samples for routine quality control. The estimation of the piper-ine by 342 nm absorption has been approv/ed by the Indian Standards Institution and by the American Spice Trade Association. The latter, however, still keep, as a recommended method, a colorimetric method which has been repeatedly shown to give very variable results. 

Black pepper (Piper nigrum L.) Piperine, /3-caryophyllene, chavicine ... 

Vijayakumar, R.S., Surya, D. and Nalini, N. (2004) Antioxidant efficacy of black pepper (Piper nigrum L.) and piperine in rats with high fat diet induced oxidative stress. Redox Reporter 9(2), 105-110. 

Wood, A.B., Barrow, M.L. and James, D.J. (1 988) Piperine determination in pepper (Piper nigrum L.) and its oleoresins a reversed phase high performance liquid chromatographic method. Flavour and Fragrance journal 3(2), 55-64. 

Piperine, a constituent of black pepper and other species (e.g. Piper nigrum),... 

Heliotropin, Piperonal.— Heliotropin receives its other name of piperonal from its relation to compounds occurring in pepper. In black pepper, Piperus nigra there is present an alkaloid known as piperine (p. 888). From this alkaloid an acid, piperic acid, is obtained. This acid is a methylene di-ether containing an alpha unsaturated side chain as in iso-eugenole, etc. On oxidation the side chain breaks at the double bond, as has been explained, and yields an aldehyde which is piperonal. 

Protocatechuic Acid.—One of the di-hydroxy benzoic acids is related to vanillin, which we have already studied. The acid is known as protocatechuic acid, and derives its name from the fact that it may be obtained from a gum or resin, known as gum catechin by fusion with potash, i.e. by heat and oxidation in presence of an alkali. A large variety of plant products including alkaloids essential oils, gums, resins and tannins yield this acid. The following may be mentioned gum catechin, gum benzoin, guaiac resin, myrrh, piperine or piperic acid, vanillin, cafe-tannic acid. These natural sources at once suggest a relationship to vanillin (p. 661) and heliotropin (p. 662). It is the acid corresponding to protocatechuic aldehyde, 3-4-di-hydroxy benzal-dehyde (p. 661), which explains the relationship just mentioned. Its constitution, is then ... 

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. 

Protocatechualdehyde (3,4-dihydroxybenzfildehyde). The preparation of this aldehyde from piperonal was accomplished for the first time in 1871 at Tiibingen by Rudolf Fittig, age 36, and his American co-worker Ira Remsen, age 25. In earlier work on the alkaloid piperine and its cleavage products piperic acid and piperidine, Fittig had isolated two products of oxidation of piperic acid, piperonal and piperonylic acid, now known to be constituted as formulated. The aldehyde bore... 

Herbal effects on absorption can affect the bioavailability of antibiotics and has been demonstrated for Khat (Catha endulis) users (Attef et al., 1997). Absorption and decreased metabolism of the asthma drug theophylline are also affected by piperine from black pepper (Piper nigrum, Piper longum). 

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

Peptidomimetic inhibitors Petunidin Phenobarbital Phenothiazines Phenylcinnamides Phenylsulfonylfuroxans Phenytoin Phloretin Phloxine Phytosterols Pimozide Piper cubeba Piper nigrum fruit Piperine (black pepper) Pirarubicin ... 

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