22.1 Introduction
Piperine contains numerous pharmacological activities and many health benefits,
particularly against chronic conditions such as insulin resistance reduction,
anti-inflammatory activity, and correction in hepatic steatosis (Derosa et al. 2016).
Piperine was first isolated in 1820 by the Danish chemist Hans Christian Orstedt; it
occurs as a yellow crystalline solid (MW = 285.33 g mol
−1 , m.p. = 128–130 ˚C)
poorly soluble in water and presents weak base properties (Chavarria et al. 2016;
Koleva et al. 2012).
22.2 Biosynthesis of Piperine
Piperine is a secondary metabolite biosynthetically derived from L-lysine and a
cinnamoyl-CoA precursor. Decarboxylation of L-lysine by lysine decarboxylase
(LDC) yields cadaverine, which undergoes oxidative deamination by copper amine
oxidase (CuAO,) originating 5- aminopentanal. This compound is rapidly cyclized
into D
1 -piperidine Schiff base and subsequently reduced to form piperidine. In
parallel, piperonyl-CoA is generated from a cinnamoyl –CoA precursor; this precursor undergoes chain elongation with malonylCoA in a Claisen-like reaction,
generating a keto-ester that is reduced by NADPH and then dehydrated to afford
piperonyl-CoA. The piperine unit reacts with piperonyl-CoA affording piperine
(Fig. 22.1).
22.3 Extraction Techniques
The extraction of piperine from the plants can be made with different techniques
and that are present in Fig. 22.2 (Raman and Gaikar 2002; Rathod 2014).
22.4 Effect on Heart
Piperine produced both positive chronotropic and inotropic responses in the isolated
rat atria but not in the ventricular muscles. A tachyphylaxis to piperine occurred
rapidly depending on the dose of preincubation. It has been revealed that piperine
diminishes the level of substance P in the rat spinal cord, possibly as a result of an
extensive discharge of this neuropeptide. In the heart, it has been shown that
capsaicin releases CGRP from NANC nerves and the released CGRP shows positive chronotropic and inotropic effects (Franco-Cereceda and Lundberg 1985;
Franco-Cereceda et al. 1988; Miyauchi et al. 1987, 1988). Therefore, the lack of
760
N. Sachan et al.
Piperine contains numerous pharmacological activities and many health benefits,
particularly against chronic conditions such as insulin resistance reduction,
anti-inflammatory activity, and correction in hepatic steatosis (Derosa et al. 2016).
Piperine was first isolated in 1820 by the Danish chemist Hans Christian Orstedt; it
occurs as a yellow crystalline solid (MW = 285.33 g mol
−1 , m.p. = 128–130 ˚C)
poorly soluble in water and presents weak base properties (Chavarria et al. 2016;
Koleva et al. 2012).
22.2 Biosynthesis of Piperine
Piperine is a secondary metabolite biosynthetically derived from L-lysine and a
cinnamoyl-CoA precursor. Decarboxylation of L-lysine by lysine decarboxylase
(LDC) yields cadaverine, which undergoes oxidative deamination by copper amine
oxidase (CuAO,) originating 5- aminopentanal. This compound is rapidly cyclized
into D
1 -piperidine Schiff base and subsequently reduced to form piperidine. In
parallel, piperonyl-CoA is generated from a cinnamoyl –CoA precursor; this precursor undergoes chain elongation with malonylCoA in a Claisen-like reaction,
generating a keto-ester that is reduced by NADPH and then dehydrated to afford
piperonyl-CoA. The piperine unit reacts with piperonyl-CoA affording piperine
(Fig. 22.1).
22.3 Extraction Techniques
The extraction of piperine from the plants can be made with different techniques
and that are present in Fig. 22.2 (Raman and Gaikar 2002; Rathod 2014).
22.4 Effect on Heart
Piperine produced both positive chronotropic and inotropic responses in the isolated
rat atria but not in the ventricular muscles. A tachyphylaxis to piperine occurred
rapidly depending on the dose of preincubation. It has been revealed that piperine
diminishes the level of substance P in the rat spinal cord, possibly as a result of an
extensive discharge of this neuropeptide. In the heart, it has been shown that
capsaicin releases CGRP from NANC nerves and the released CGRP shows positive chronotropic and inotropic effects (Franco-Cereceda and Lundberg 1985;
Franco-Cereceda et al. 1988; Miyauchi et al. 1987, 1988). Therefore, the lack of
760
N. Sachan et al.