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 chalcones. Most stilbenoids are prod ...

chemically related to

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

. 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 t ...

role.

Natural occurrence

Pterostilbene is found in

almonds The almond (''Prunus amygdalus'', Synonym (taxonomy)#Botany, syn. ''Prunus dulcis'') is a species of tree native to Iran and surrounding countries, including the Levant. The almond is also the name of the edible and widely cultivated seed of th ...

, 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 (whort ...

'' 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'' within the genus ''Vaccinium''. ''Vaccinium'' also includes cranberries, bi ...

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 perhaps 8,000 years ago, ...

leaves and

vine A vine (Latin ''vīnea'' "grapevine", "vineyard", from ''vīnum'' "wine") 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 themselv ...

s, and ''

Pterocarpus marsupium ''Pterocarpus marsupium'', also known as Malabar kino, Indian kino, Vijayasar, or Venkai is a medium to large, deciduous tree that can grow up to tall. It is native to India (where it occurs in parts of the Western Ghats in the Karnataka-Kerala ...

'' heartwood.

Safety and regulation

Pterostilbene is considered to be a

corrosive substance A corrosive substance is one that will damage or destroy other substances with which it comes into contact by means of a chemical reaction. Etymology The word ''corrosive'' is derived from the Latin verb ''corrodere'', which means ''to gnaw'', ...

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

toxin A toxin is a naturally occurring organic poison produced by metabolic activities of living cells or organisms. Toxins occur especially as a protein or conjugated protein. The term toxin was first used by organic chemist Ludwig Brieger (1849– ...

, especially to

aquatic life An aquatic ecosystem is an ecosystem formed by surrounding a body of water, in contrast to land-based terrestrial ecosystems. Aquatic ecosystems contain communities of organisms that are dependent on each other and on their environment. The tw ...

. A

randomized In common usage, randomness is the apparent or actual lack of pattern or predictability in events. A random sequence of events, symbols or steps often has no order and does not follow an intelligible pattern or combination. Individual rand ...

double-blind In a blind or blinded experiment, information which may influence the participants of the experiment is withheld until after the experiment is complete. Good blinding can reduce or eliminate experimental biases that arise from a participants' expec ...

placebo-controlled Placebo-controlled studies are a way of testing a medical therapy in which, in addition to a group of subjects that receives the treatment to be evaluated, a separate control group receives a sham "placebo" treatment which is specifically designed ...

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. Its chemical relative,

, received FDA GRAS status in 2007, and approval of synthetic 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 as ...

s which cause it to exhibit increased

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

and oral absorption.

Research

Pterostilbene is being studied in laboratory and preliminary

clinical research Clinical research is a branch of healthcare science that determines the safety and effectiveness ( efficacy) of medications, devices, diagnostic products and treatment regimens intended for human use. These may be used for prevention, treatm ...

References

{{Stilbenes Nutrients Stilbenoids Phytoalexins

Natural occurrence

Safety and regulation

Research

See also

References