Piper species

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. 

The Indian Piper species have been the subject of a review article describing their chemistry and biological activities (221). 

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). 

Chazdon R. L. and Field C. B. (1987) Determinants of photosynthetic capacity in six rainforest Piper species. Oecologia 73, 222—230. 

Mundina, M. Vila, R. Tomi, F. Gupta, M.P. Adzet, T. Casanova, J. Canigueral, S. Leaf essential oils of three Panamanian piper species. Phytochemistry 1998, 47, 1277-1282. 

Bhat, S.R., Chandel, K.P.S. and MaUk, S.K. (1995) Plant regeneration from various explants of cultivated Piper species. Plant Cell Reports, 14, 398-A02. 

Thus the kava alkaloids contain either a cinnamoyl or phenylpropionyl moiety. One would expect that a homologous series of such alkaloids may exist in the P. methysticum plant, since Achenbach and Karl (1971) isolated a series of substituted cinnamic, benzoic and phenyl propionic acids. These acids would be expected to react readily with amines to form the amide alkaloids. However, such a series of alkaloids does not appear to occur in the P. methysticum plant, although several similar alkaloids have been isolated from other Piper species, such as P. longum which yields piplactine, piperlongumine and piperlongiuninine (Chatterjee and Dutta, 1967). 

Desai, S.J., Chaturvedi, R.N., Badheka, L.P. and Mulchandani, N.B. (1989) Aristolactams and 4,5-dioxoaporphines from Indian Piper species. Indian Journal of Chemistry, Section B, 28B, 775—777. 

Pipeline (121), a biologically active component of black pepper (Piper nigrum), long pepper (P. longum) and other Piper species, has been isolated from additional sources, including Anelhum sowa [360], Vicoa indica [361], and an Unocladium sp [362]. 

Sengupta, S. andA.B. RayigSy. Theche-mistty of Piper species A review Fito-terapia 58 147-166. 

APPENDIX A-V AMP4-PYroNES AND PSYCHOACTIVE PIPER SPECIES... 

UNSATURATED AMTOES FROM PIPER SPECIES (PIPERACEAE) ... 

ABSTRACT An extensive compilation of structures of unsaturated amide products from Piper species (Piperaceae) with relevant literature references, and including a few representative examples of related compounds from other families, is presented. The biological activity attributed to Piper species, and many of the unsaturated amides they produce, includes organoleptic, medicinal and insecticidal effects and some of the more interesting biological properties are discussed in this chapter. Numerous synthetic approaches to the unsaturated amides have been developed, and a representative sampling of these strategies is presented. 

Plants of the genus Piper, in particular P. nigrum, have been valued from antiquity to the present day for their organoleptic and medicinal properties. Indeed, black pepper, from the dried fruit of the latter species, remains the most widely consumed and important spice in the modern world [1,2] and is still used in traditional medicine [3]. In recent years, attention has also focused on the insecticidal properties of some Piper species [4]. Interest in insecticides of natural origin has been heightened by environmental and other problems associated with widespread use of broad spectrum synthetic pesticides. Two earlier reviews [4,5], of somewhat limited scope, focus specifically on a few unsaturated Piper amides in the context of their insecticidal potential. 

This chapter aims to provide a relatively comprehensive, yet inevitably not exhaustive, compilation of structures of amides isolated from Piper species (Tables 1 and 2). The chemistry and biological activity of some of these compounds as well as new developments in their synthesis are reviewed.2... 

The amides are characteristically straight-chain, usually unsaturated compounds, and many incorporate an aromatic group (frequently 3, 4 -methylenedioxyphenyl) at the terminus remote from the amide function. Amides with and without a distal aromatic group are frequently produced by the same plant. Isobutylamine, pyrrolidine and piperidine predominate as the amine components of the Piper amides, although other amide classes, e.g., -pentyl or isopentylamides may be occasionally encountered [6]. In the case of at least one Piper species, P. guineense, attention has been drawn to the existence, which is intuitively predictable, of geographic variations in the relative proportions of amide constituents found in a species [7]. 

Table 1. Aliphatic Unsaturated Amides from Piper Species...

Although the range of medical conditions where Piper species have been claimed to be effective may appear somewhat extravagant (cf. Table 4), significant antimicrobial, anthelminthic, vasodilating and local anaesthetic properties, as well as modest cytotoxicity have indeed been documented for a number of the amides or crude Piper extracts. These findings are consistent with the efficacy of Piper species in many of the traditional remedies. 

A. St. Hil. of two further alkaloids, i -pilocarpine and i -jaborine both were amorphous, optically inactive bases which were not completely characterized. D. Parodi (22) described the isolation of a weak base, jaborandine, C20H12O6N2 ( ), melting point 110°, from a sample of Paraguay jaborandi derived from a Piper species, and E. Harnack and... 

Biological Activity of Tropane Alkaloids Distribution of Tropane Alkaloids Piperidine Alkaloids Alkaloids from Piper Species Piperine Alkaloids Involving Condensation with Acetate/Malonate Sedum Alkaloids Lobelia Alkaloids Lycopodium Alkaloids Piperidine Alkaloids in Insects Polyketide-Derived Alkaloids Coniine... 

A number of Piper species, e.g., Piper longum, have been used in Ayurvedic medicine in India. This drug seems to increase the bioavailability of other drugs. Piperine (31) is similar in action to many central nervous system depressants (Fodor and Colosanti, 1985). 

The biosynthesis, occurrence, and biological activities of piperidine alkaloids arising from lysine have been studied Punica granatum. Piper species, and Lobelia inflata). The isolation process, chromatographic purification/analysis, and structure elucidation of the significant alkaloids are discussed. 

Allameh A, Saxena M, Biswas G et al (1992) Piperine, a plant alkaloid of the Piper species, enhances the bioavailability of aflatoxin B1 in rat tissues. Cancer Lett 61 195-199... 

Piperine (54) and antiepilepsirine (55), piperidine alkaloids that occur in Piper species (Piperaceae), are MAOIs with greater selectivity for MAO-B [173], yet they have not been studied extensively for therapeutic potential in PD. Some Vinca alkaloids, including vincristine, vinblastine, leurosine, and vindoline from Catharanthus roseus (L.) G.Don (Apocynaceae), are reported as selective MAO-B inhibitors, but cytotoxicity limits their development as potential drug candidates for PD [174, 175] (see Sect. 6) (Scheme 42.14). 

Reen RK, Singh J (1991) In vitro and in vivo inhibition of pulmonary cytochrome P450 activities by piperine, a major ingredient of piper species. Indian J Exp Biol 29 568-573... 

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