Pterostilbene () (trans-3,5-dimethoxy-4-hydroxystilbene) is a

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with Chalconoid, chalcones. Most stilbenoids ...

chemically related to

resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, ba ...

. In plants, it serves a defensive

phytoalexin Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized ''de novo'' by plants ...

role.

Natural occurrence

Pterostilbene is found in

almonds The almond (''Prunus amygdalus'', syn. ''Prunus dulcis'') is a species of tree from the genus ''Prunus''. Along with the peach, it is classified in the subgenus ''Amygdalus'', distinguished from the other subgenera by corrugations on the sh ...

, various ''

Vaccinium ''Vaccinium'' is a common and widespread genus of shrubs or dwarf shrubs in the heath family (Ericaceae). The fruits of many species are eaten by humans and some are of commercial importance, including the cranberry, blueberry, bilberry (wh ...

'' berries (including

blueberries Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' with the genus ''Vaccinium''. Commercial blueberries—both wild (lowbush) ...

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,0 ...

leaves and

vine A vine is any plant with a growth habit of trailing or scandent (that is, climbing) stems, lianas, or runners. The word ''vine'' can also refer to such stems or runners themselves, for instance, when used in wicker work.Jackson; Benjamin; Da ...

s. It is also encountered in the

xylem Xylem is one of the two types of transport tissue (biology), tissue in vascular plants, the other being phloem; both of these are part of the vascular bundle. The basic function of the xylem is to transport water upward from the roots to parts o ...

, particularly in the heartwood of '' Pterocarpus marsupium'' as well as in other species of the ''Pterocarpus'' family, including Malay padauk, the Narra tree (''Pterocarpus indicus''), Muninga and African padauk (''Pterocarpus erinaceus''), thus contributing to the high natural durability as a known

Safety and regulation

Pterostilbene is considered to be a

corrosive substance Corrosion is a natural process that converts a refined metal into a more chemically stable oxide. It is the gradual deterioration of materials (usually a metal) by chemical or electrochemical reaction with their environment. Corrosion engine ...

, is dangerous upon exposure to the eyes, and is an environmental

toxin A toxin is a naturally occurring poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919), derived ...

, especially to aquatic life. A preliminary study of healthy human subjects given pterostilbene for 6–8 weeks, showed pterostilbene to be safe for human use at dosages up to 250 mg per day, although this study did not assess metabolic effects on the lipid profile. Other studies have reported dose-based elevations of low density lipoprotein cholesterol (LDL-C, " bad cholesterol") and decreased high density lipoprotein cholesterol (HDL-C, "

good cholesterol High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are t ...

") within 4 to 8 weeks of daily dosing. The elevation of LDL-C may move previously normal ranges into borderline high or high reference range and has raised questions about the longterm cardiovascular risk of pterostilbene supplementation in humans. Its chemical relative,

, received FDA GRAS status in 2007, and approval of

synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

resveratrol as a safe compound by the

European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002 ...

(EFSA) in 2016. Pterostilbene differs from resveratrol by exhibiting increased bioavailability (80% compared to 20% in resveratrol) due to the presence of two

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

s which cause it to exhibit increased

lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

and oral absorption.

Research

Pterostilbene is being studied in laboratory and preliminary

clinical research Clinical research is a branch of medical research that involves people and aims to determine the effectiveness (efficacy) and safety of medications, devices, diagnostic products, and treatment regimens intended for improving human health. The ...

References

{{Stilbenes Nutrients Stilbenoids Phytoalexins

Natural occurrence

Safety and regulation

Research

See also

References