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Pterostilbene Monograph

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Pterostilbene Monograph Monograph amr Pterostilbene Monograph OH H3CO Introduction Pterostilbene is a chemical classified as a benzylidene compound (more specifically a stilbene) and is biologically classified as a Pterostilbene phytoalexin, which are antimicrobial sub- OCH stances that are part of the plant’s defense 3 system and are synthesized in response to pathogen infection. This monograph focuses coronary heart disease, as it can increase the HDL/ on trans-pterostilbene. LDL cholesterol ratio.20 Stilbenes are low molecular weight (approxi- Colon cancer is one of the leading causes of mately 200-300 g/mol), naturally occurring cancer mortality in men and women in Western polyphenol compounds produced by a variety of countries. Epidemiological studies have linked the plants that secrete them in response to environ- consumption of fruits and vegetables to a reduced mental challenges such as viral, microbial, and risk of colon cancer, in particular small fruits that fungal infection or excessive ultraviolet exposure.1 are particularly rich sources of pterostilbene and Stilbenes are found in a wide range of plant other pharmacologically active stilbenes.14 Recent families, including Vitis and Vaccinium.2,3 These advances in the study of colon cancer have stimu- molecules are synthesized via the phenylpropanoid lated an interest in diet and lifestyle as an effective pathway and are structurally similar to estrogen.4 means of prevention. As constituents of small Natural sources of pterostilbene include Vitis fruits such as grapes and berries and their products, vinifera, Vaccinium spp., and Pterocarpus spp. stilbenes are under intense investigation as cancer Ayurvedic medicine cites Darakchasava as a chemopreventive agents.21 One of the best charac- well-known Indian herbal preparation of Vitis terized stilbenes, resveratrol, is known to be an vinifera that contains pterostilbene and is pre- antioxidant and an anti-aging compound, as well as scribed as a cardiotonic.5 In addition, Pterocarpus an anti-inflammatory agent.22 Pterostilbene is marsupium has been used for many years in the closely related structurally to resveratrol and shows treatment of diabetes mellitus. Pterostilbene was many of the same characteristics, as well as its own found to be one of the active constituents in the unique therapeutic potential.21 extracts (known as Vijyasar) of the Pterocarpus marsupium heartwood. It is suggested that ptero- Pharmacokinetics stilbene might be one of the principal antidiabetic Pterostilbene might show higher biological constituents in these extracts.6-9 activity based on relatively higher bioavailability Pterostilbene is known to have diverse pharma- compared to resveratrol, since substitution of a cological benefits for the prevention and treatment hydroxy with a methoxy group increases the of a wide variety of diseases, including cancer,10-15 transport into cells and increases the metabolic dyslipidemia,16 diabetes,8,17,18 cardiovascular stability of the molecule. Thus, pterostilbene is not degeneration,17 and pain.19 As a potent chemo- as quickly glucuronidated and sulfated as resvera- preventative, antioxidant, and anti-inflammatory trol. In a recent study evaluating the pharmacoki- agent, pterostilbene has the potential to ameliorate netics and pharmacodynamics of trans-pterostil- the effects of aging when used by healthy individu- bene by intravenous administration of 20 mg/kg of als.7 Pterostilbene may be effective in correcting pterostilbene into rats,23 a glucuronidated ptero- the dyslipidemia that leads to atherosclerosis and stilbene metabolite was detected in serum and 159 Alternative Medicine Review Volume 15, Number 2 Copyright © 2010 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. amr Monograph urine. Another pharmacokinetic study carried out intracellular ROS; pterostilbene (with two methoxy in rats showed the terminal elimination half-life and one hydroxyl group) reduces extracellular and clearance of pterostilbene were 96.6 ± 23.7 ROS.30 This localization of antioxidative effect minutes and 37.0 ± 2.5 mL/min/kg, respectively, allows the use of pterostilbene to target extracel- while its absolute oral bioavailability was 12.5 ± 4.7 lular reactive oxygen species that are, among other percent; in this study, pterostilbene demonstrated things, responsible for tissue damage during improved pharmacokinetic characteristics over its chronic inflammation. naturally occurring analog, resveratrol.24 Pterostilbene’s peroxyl radical scavenging activity appears to be similar to resveratrol. Mechanisms of Action Pterostilbene exhibited moderate inhibition (IC50 = Pterostilbene owes its potential to diverse 19.8 μM) of cyclooxygenase (COX)-1 and was pharmacological actions that may alleviate diseases weakly active (IC50 = 83.9 μM) against COX-2; associated with oxidative damage and aging and whereas, resveratrol strongly inhibited both promotion of health and an extended lifespan isoforms of the enzyme with IC50 values of approxi- when used by healthy individuals. In general terms, mately 1 μM.21 the pharmacological actions of trans-pterostilbene are anti-inflammatory, antineoplastic and antioxi- Anti-inflammatory dant; these activities stem from biological interac- In an in vitro colitis model, pterostilbene tions at a fundamental level for both control of inhibited prostaglandin E2 production in human gene expression and enzyme activity modulation. colon adenocarcinoma cells. An anti-inflammatory analysis was conducted in which interleukin-1b Antimicrobial was introduced into canine chondrocytes followed Resveratrol and its derivatives, including by treatment with pterostilbene. Decreased levels pterostilbene, are thought to be the most impor- of MMP-3 gene expression (a structural gene for tant stilbenes in grapevines (Vitis vinifera). One of Stromelysin-1 protein thought to be active in the the mechanisms of these substances in the plant development of atherosclerosis, tumor initiation, appears to be their activity as an antimicrobial. and metastasis) and tumor necrosis factor-alpha Pterostilbene exhibits potent antifungal properties (TNF-a; a cytokine involved in systemic inflamma- that are 5-10 times stronger than resveratrol.2,25 tion) were noted, compared with control levels. Pterostilbene also exhibits antiviral effects.26 The Increased TNF-a production has been implicated protection of the plant from various pathogens in a variety of human diseases, including cardiovas- appears to be an important mechanism of stilbenes cular disease and cancer.28 such as pterostilbene, and these protections may extend to humans and animals as well.1,20 Miscellaneous Mechanisms Studies show pterostilbene, like its cousin Antineoplastic resveratrol, possesses hypolipidemic16 and antidia- Pterostilbene exhibits anticancer effects via betic properties,8,9,17,18,31 and may be efficacious in various molecular mechanisms.10-15 Studies show reversing the deleterious effects of aging such as the actions of pterostilbene include modulation of cognitive function and working memory.7 signal transduction pathways,1 cell cycle regulatory Pterostilbene has properties that make it a poten- genes,15 cell differentiation genes,27 oncogenes,10-12 tial chemopreventive agent. For example, it and tumor suppressor genes.13-15 inhibited the activity of CYP1A1, CYP1A2 and CYP1B1 in vitro. CYP1A1 and CYP1B1 are the Antioxidant Activities inducible forms of cytochrome P450 enzymes in Pterostilbene possesses potent, concentration- extrahepatic tissues responsible for the biochemi- dependent, antioxidant effects.9,21,28,29 It is becom- cal conversion of polycyclic aromatic hydrocarbons, ing increasingly clear that the specific pharmaco- heterocyclic amines, and estradiol to potentially logical activities attributable to individual natural carcinogenic intermediate metabolites. stilbenes are governed by the unique structural Pterostilbene inhibits human CYP1A1 catalytic differences that distinguish them. For example, activity with a Ki value of 0.57 μM, thus exhibiting resveratrol (with three hydroxyl groups) neutral- a stronger inhibitory effect on CYP1A1 in compari- izes reactive oxygen species (ROS) in whole blood son to resveratrol. Pterostilbene inhibits CYP1B1 and isolated lymphoblasts, whereas pinosylvin with a Ki value of 0.91 μM, comparable to that of (with two hydroxyl groups) influences mainly resveratrol.32 Its effect on CYP1A2 is the most Volume 15, Number 2 Alternative Medicine Review 160 Copyright © 2010 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. Monograph amr potent, with a Ki value of 0.39 μM.33 Pterostilbene Gastric cancer is the second most prevalent exhibited an analgesic effect in Sprague-Dawley cause of worldwide cancer-related deaths and is rats dosed intravenously with 20 mg/kg. The significantly correlated with dietary habits, includ- animals had an increased latency period to ing increased reliance on processed meats and response in both tail-flick and hot-plate analgesic decreased intake of polyphenol-containing fruits tests.23 and vegetables. In an in vitro study of human gastric adenocarcinoma cells, pterostilbene Clinical Indications inhibited cellular proliferation and induced Infection apoptosis via a number of mechanisms, including Pterostilbene shows potent antiviral activity activation of the caspase cascade, alteration of against hepatitis C virus (HCV) at 10 μM, with no cell-cycle regulating proteins, and damage to associated toxicity.26 Pterostilbene
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