This newsletter is a special report on a compound known as Piperlongumine, a compound that is manufactured and sold by Indofine Chemical Company ( www.indofinechemical.com). Please follow the links below this article for purchasing information.
Piperlongumine is a natural alkaloid amide found in long peppers (Piper Longum, Family Piperaceae). It is a small shrub with large woody root and numerous creeping, jointed stem with thick node. The fruit contains a volatile oil known as resin in a 1% concentration. This waxy alkaloid has several medicinal properties. The primary compounds isolated from various parts of Piper longum are piperine, piperlongumine, sylvatin, sesamin, diaeudesmin piperlonguminine, pipermonaline, and piperundecalidine (Kumar S et al., 2011).
These compounds show various pharmacological properties including anti-fungal, anti-inflammatory, antioxidant and anti-cancer properties (Atal CK et al., 1985). When applied topically, they soothe and relieve muscular pains and inflammation. In addition, Piper Longum helps stimulate the appetite.
Anti Cancer Properties
Research involving piperlongumine has shown the compound’s significance as an anti-cancer agent; it kills cancer cells without affecting the normal cells. Cancer cells grow very fast due to their overactive metabolism. This growth also results in an increase of reactive oxygen species (ROS), which leads to a state of oxidative stress inside the cells. Piperlongumine inhibits ROS generation, reducing the oxidative stress without affecting the normal cells. Normal cells have a balanced level of ROS as a result of their low metabolism rate. The key point of Piperlongumine’s action may be its differentiation between normal cells and cancer cells (Nature, 2011).
Another study was conducted to explore the inhibitory effect of piperlongumine and dihydropiperlonguminine on the production of amyloid beta (Abeta) in human neuroblastoma cells (SK-N-SH) and to examine the underlying mechanism of this effect. Their data suggested that piperlonguminine and dihydropiperlonguminine could significantly inhibit the level of APP, Abeta 42 and Abeta 40 peptide without affecting the activity of beta-secretase and gamma-secretase in SK-N-SH cells (Qi HS et al., 2009). This study also attested the anticancer activity of piperlongumine.
In addition, some studies carried out on piperlongumine have suggested that this compound inhibits the biosynthesis of Aflatoxin B1 in Aspergillus Flavus (Lee SE et. al.,2002). Aflatoxins are secondary metabolites produced by many species of fungi known as Aspergillus: more specifically, Aspergillus flavus and Aspergillus parasiticus (Hudler G.,1998). Aflatoxin B1 and related compounds are thought to be the potential carcinogenic mycotoxin.The study carried out by Lee SE et. al. in 2002 has shown the antiaflatoxigenic mode of action of piperlongumine.This study may find significance in agriculture industries.
Melanin Modifier
Piperlongumine has also been studied for its significant effect on melanin production. Hyperpigmentation disorders results from the abnormal accumulation of melanin pigments. These disorders can usually be treated by using depigmenting agents. Melanocyte proliferation stimulants are of interest as potential treatments for the depigmentation skin disorder, vitiligo. A study carried out on piperlongumine has shown that this compound inhibits melanin production and is an efficient depigmenting agent with a novel mechanism of action (Kim KS et al., 2006). Another study carried out on this compound showed its inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells (Min KR et al., 2004).
Peripheral Blood Disorders
Piper longum L. has been used as a crude drug for the treatment of peripheral poor blood circulation in Asia. One study examined the effects of piperlongumine on rabbit platelet aggregation. Those conducting the study concluded that piperlongumine’s platelet aggregation effect was dependent on its concentration. It inhibits this aggregation as a thromboxane A(2) receptor antagonist (Iwashita M et al., 2007). The antiplatelet activity of Piperlongumine could be very beneficial for the synthesis of new antiplatelet agents (Iwashita M et al., 2007).
References:
Kumar S et al., J Acupunct Meridian Stud. 2011 Jun;4(2):134-40.
Qi HS et al., Chin J Physiol. 2009 Jun 30;52(3):160-8.
Kim KS et al., Pigment Cell Res. 2006 Feb;19(1):90-8.
Min KR et al., Planta Med. 2004 Dec; 70(12):1115-8.
Iwashita M et al., 2007 Eur J Pharmacol. 2007 Sep 10; 570(1-3):38-42.
Atal CK et al., (1985), J. Exp. Ther., 232: 258-262.
Nature Volume: 475, Pages: 231–234 (14 July 2011).
Lee SE et al., J. Microbiol. Biotechnol.2002; 12(4):679-682.
Hudler G.1998. Magical Mushrooms, Mischievous Molds. Princeton, NJ: Princeton University Press.
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Piperlongumine
Catalog Number: P-004
CAS: 20069-09-4
Formula: C17H19NO5
MW: 317.31 MP: 123-124°C
Appearance: White crystals
Soluble in Methanol
Purity: 98%+
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