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Piperine

 

 
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Piperine
 
 
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Piperine is the alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
 responsible for the pungency
Pungency

Pungency is a sharp and biting sense impression. Food that causes this sensation is often called "spicy". Regarding chili peppers, it refers to a scientific equivalent of the Scoville scale of measuring spicyness....
 of black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 and long pepper
Long pepper

Long pepper , sometimes called Javanese Long Pepper, Indian Long Pepper or Indonesian Long Pepper, is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
, along with chavicine
Chavicine

Chavicine is an alkaloid found in Black pepper. It is one of the four diastereomeric geometric isomers of piperine....
 (an isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 of piperine). It has also been used in some forms of traditional medicine
Traditional medicine

The term traditional medicine describes medical knowledge systems, which developed over centuries within various societies before the era of modern medicine; traditional medicines include practices such as herbal medicine, Ayurvedic medicine, Unani medicine, acupuncture, spinal manipulation, Siddha Medicine, traditional Chinese medicine, S...
 and as an insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
.

rine is commercially available. If desired, it may be extracted from black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 using dichloromethane
Dichloromethane

Dichloromethane or methylene chloride is the chemical compound with the chemical formula CarbonHydrogen2Chlorine2....
.

pungency caused by capsaicin
Capsaicin

Capsaicin is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an Irritation for mammals, including humans, and produces a sensation of burning in any Biological tissue with which it comes into contact....
 and piperine
Piperine

Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide....
 is caused by activation of the heat and acidity sensing TRPV
TRPV

TRPV is a family of transient receptor potential ion channels. These channels are selective for calcium and magnesium over sodium ions. Like other member of the TRP superfamily, TRPV channels can be activated through seemingly disparate mechanisms....
 ion channel
Ion channel

Ion channels are pore-forming proteins that help establish and control the small voltage gradient across the plasma membrane of all living cell s by allowing the flow of ions down their electrochemical gradient....
 TRPV1
TRPV1

The transient receptor potential cation channel, subfamily V, member 1 also known as TRPV1 is a protein which in humans is encoded by the TRPV1 gene....
 on nociceptors (pain sensing nerve cells
Neuron

Neurons are responsive cell in the nervous system that process and transmit information by electrochemical Signal . They are the core components of the brain, the vertebrate spinal cord, the invertebrate ventral nerve cord, and the peripheral nerves....
).

Piperine has also been found to inhibit human CYP3A4
CYP3A4

Cytochrome P450 3A4 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body....
 and P-glycoprotein
P-glycoprotein

P-glycoprotein is a well-characterized ABC-transporter of the Multidrug_resistance/Transporter_associated_with_antigen_processing subfamily. P-gp is also called ABCB1, ATP-binding cassette sub-family B member 1, MDR1, and PGY1....
, enzyme
Enzyme

Enzymes are biomolecules that catalysis chemical reactions. Almost all enzymes are proteins. In enzymatic reactions, the molecules at the beginning of the process are called Substrate , and the enzyme converts them into different molecules, the products....
s important for the metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
 and transport of xenobiotic
Xenobiotic

A xenobiotic is a chemical which is found in an organism but which is not normally produced or expected to be present in it. It can also cover substances which are present in much higher concentrations than are usual....
s and metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
s.






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Encyclopedia


Piperine is the alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
 responsible for the pungency
Pungency

Pungency is a sharp and biting sense impression. Food that causes this sensation is often called "spicy". Regarding chili peppers, it refers to a scientific equivalent of the Scoville scale of measuring spicyness....
 of black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 and long pepper
Long pepper

Long pepper , sometimes called Javanese Long Pepper, Indian Long Pepper or Indonesian Long Pepper, is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
, along with chavicine
Chavicine

Chavicine is an alkaloid found in Black pepper. It is one of the four diastereomeric geometric isomers of piperine....
 (an isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 of piperine). It has also been used in some forms of traditional medicine
Traditional medicine

The term traditional medicine describes medical knowledge systems, which developed over centuries within various societies before the era of modern medicine; traditional medicines include practices such as herbal medicine, Ayurvedic medicine, Unani medicine, acupuncture, spinal manipulation, Siddha Medicine, traditional Chinese medicine, S...
 and as an insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
.

Preparation

Piperine is commercially available. If desired, it may be extracted from black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 using dichloromethane
Dichloromethane

Dichloromethane or methylene chloride is the chemical compound with the chemical formula CarbonHydrogen2Chlorine2....
.

Biological activity

The pungency caused by capsaicin
Capsaicin

Capsaicin is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an Irritation for mammals, including humans, and produces a sensation of burning in any Biological tissue with which it comes into contact....
 and piperine
Piperine

Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide....
 is caused by activation of the heat and acidity sensing TRPV
TRPV

TRPV is a family of transient receptor potential ion channels. These channels are selective for calcium and magnesium over sodium ions. Like other member of the TRP superfamily, TRPV channels can be activated through seemingly disparate mechanisms....
 ion channel
Ion channel

Ion channels are pore-forming proteins that help establish and control the small voltage gradient across the plasma membrane of all living cell s by allowing the flow of ions down their electrochemical gradient....
 TRPV1
TRPV1

The transient receptor potential cation channel, subfamily V, member 1 also known as TRPV1 is a protein which in humans is encoded by the TRPV1 gene....
 on nociceptors (pain sensing nerve cells
Neuron

Neurons are responsive cell in the nervous system that process and transmit information by electrochemical Signal . They are the core components of the brain, the vertebrate spinal cord, the invertebrate ventral nerve cord, and the peripheral nerves....
).

Piperine has also been found to inhibit human CYP3A4
CYP3A4

Cytochrome P450 3A4 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body....
 and P-glycoprotein
P-glycoprotein

P-glycoprotein is a well-characterized ABC-transporter of the Multidrug_resistance/Transporter_associated_with_antigen_processing subfamily. P-gp is also called ABCB1, ATP-binding cassette sub-family B member 1, MDR1, and PGY1....
, enzyme
Enzyme

Enzymes are biomolecules that catalysis chemical reactions. Almost all enzymes are proteins. In enzymatic reactions, the molecules at the beginning of the process are called Substrate , and the enzyme converts them into different molecules, the products....
s important for the metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
 and transport of xenobiotic
Xenobiotic

A xenobiotic is a chemical which is found in an organism but which is not normally produced or expected to be present in it. It can also cover substances which are present in much higher concentrations than are usual....
s and metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
s. In animal studies, piperine also inhibited other enzymes important in drug metabolism. By inhibiting drug metabolism, piperine may increase the bioavailability
Bioavailability

In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetics properties of medication....
 of various compounds. Notably, piperine may enhance bioavailability of curcumin
Curcumin

Curcumin is the principal curcuminoid of the popular Indian curry spice turmeric, which is a member of the ginger family . The other two curcuminoids are desmethoxycurcumin and bis-desmethoxycurcumin....
 by 2000% in humans.

In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin.

Due to its effects on drug metabolism, piperine should be taken cautiously (if at all) by individuals taking some other medication
Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
s.

Piperine was first discovered by Hans Christian Ørsted
Hans Christian Ørsted

Hans Christian ?rsted was a Denmark physicist and chemist. He shaped Kantianism and advances in science throughout the late nineteenth century....
 in 1819.

See also

  • Piperidine
    Piperidine

    Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic compound amine consists of a six-membered ring containing five methylene units and one nitrogen atom....
    , a cyclic six-membered amine
    Amine

    Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
     that results from hydrolysis
    Hydrolysis

    Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
     of piperine
  • Capsaicin
    Capsaicin

    Capsaicin is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an Irritation for mammals, including humans, and produces a sensation of burning in any Biological tissue with which it comes into contact....
    , the active piquant chemical in chili pepper
    Chili pepper

    Chili pepper is the fruit of the plants from the genus Capsicum, members of the Solanaceae, Solanaceae. Botany considers the plant a berry bush....
    s
  • Allyl isothiocyanate
    Allyl isothiocyanate

    Allyl isothiocyanate is the organosulfur compound with the formula CH2CHCH2NCS. This colourless oil is responsible for the pungent taste of Mustard , horseradish, and wasabi....
    , the active piquant chemical in mustard
    Mustard plant

    Mustards are several plant species in the genera Brassica and Sinapis whose small mustard seeds are used as a spice and, by grinding and mixing them with water, vinegar or other liquids, are turned into the condiment known as Mustard ....
    , radish
    Radish

    The radish is an Eating root vegetable of the Brassicaceae family that was domesticated in Europe in pre-Roman Empire times. They are grown and consumed throughout the world....
    es, horseradish
    Horseradish

    Horseradish is a perennial plant of the Brassicaceae family, which also includes Mustard plant, wasabi, and cabbages. The plant is probably native to southeastern Europe and western Asia, but is popular around the world today....
     and wasabi
    Wasabi

    Wasabi is a member of the Brassicaceae family, which includes cabbages, horseradish and Mustard plant. Known as "Japanese horseradish", its root is used as a spice and has an extremely strong flavour....
  • Allicin
    Allicin

    Allicin is an organic compound obtained from garlic. It is also obtainable from onions, and other species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J....
    , the active piquant flavor chemical in uncooked garlic
    Garlic

    Allium sativum L., commonly known as garlic, is a species in the onion family Alliaceae. Its close relatives include the onion, shallot, leek, and chive....
     and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)


External links

  • - Piperine