409
have been reported such as epsilon viniferin and delta viniferin for dimeric resveratrol (Vitrac et al. 2005) and alpha viniferin for trimeric resveratrol. Stilbenoids such
as ampelopsin A and hopeaphenol have also been identified (Jeandet et al. 2000;
Guebaila et al. 2006).
17.3 Srilbene Derivatives
Many stilbene derivatives (stilbenoids) are naturally present in plants. These agents
are derived from micro-organisms, terrestrial plants, marine organisms and animals
(Newman and Cragg 2004; Schwartsmann et al. 2003). Diethylstilbestrol is a stilbene derivative, which is mainly used for the treatment of prostate and breast cancer
and to prevent threatened abortions (Metzler 1984). Trans-astringin and its aglycon
are active anti-leukemic agents (Mannila and Talvitie 1992; Mannila et al. 1993).
Trans-piceatannol is an inhibitor of protein tyrosine kinase (Geahlen and McLaughlin
1989; Oliver et al. 1994). The most widely distributed and biologically active stilbenoids are resveratrol, combretastatins and pterostilbene. These compounds and
their analogues possess a wide variety of biological activities.
Resveratrol (3, 4′, 5-trihydroxy trans-stilbene) is the major stilbene present in
grape wines. It is a naturally occurring phytoalexin and found in more than 70 plant
species including grapes, peanuts and pines. It can exist in two isomeric forms and
both these forms are found in grape wines (Sun et al. 2003) due to photochemical
isomerization of trans-form into cis-form (Jeandet et al. 1995; Roggero and Garcia
1995). Resveratrol was first described in 1940 as a phenolic component of the
medicinal herb hellebore Veratrum grandiflorum. Little attention was given to this
compound until its role in inhibiting growth of cancer cells in culture was discovered (Baur and Sinclair 2006). The most important source of resveratrol in wine is
the berry skin. It is absent or low in the fruit flesh (Creasy and Coffee 1988). It has
been assumed that in ripe berries, skin can be elicited to synthesize resveratrol
(Jeandet et al. 1995) as a free compound or as a glucoside. These compounds are
supposed to be extracted during alcoholic fermentation and degraded during malolactic fermentation by enzymatic activity of malolactic bacteria (Pezet and Cuenat
1996). Cis-resveratrol is a byproduct of fermentation and is rarely found in grapes
(Jeandet et al. 1995 and Mattavi et al. 1995). It is getting worldwide attention from
the scientific community because of its variety of biological activities such as antioxidant, radio-protective, phytoestrogen, anti-bacterial and anti-fungal (Aggarwal
and Shishodia 2006; Kumar 2007; Rocha et al. 2008; Alonso et al. 2009). Its therapeutic potential includes the chemo-prevention of cancer, inflammation, ageing,
obesity, cardiovascular diseases and neurodegeneration (Kovacic and Somanathan
2010).
Pterostilbene (3, 5-dimethoxy-4′-hydroxy trans-stilbene) is chemically related
to resveratrol. It is mainly found in blueberries and grapes that exhibit anti-cancer,
anti-hypercholesterolemia and anti-hypertriglyceridemia properties. It is more stable in vivo than resveratrol. It was also suggested that this compound has
17 Stilbenes and Their Derivatives in Traditional Medicine
have been reported such as epsilon viniferin and delta viniferin for dimeric resveratrol (Vitrac et al. 2005) and alpha viniferin for trimeric resveratrol. Stilbenoids such
as ampelopsin A and hopeaphenol have also been identified (Jeandet et al. 2000;
Guebaila et al. 2006).
17.3 Srilbene Derivatives
Many stilbene derivatives (stilbenoids) are naturally present in plants. These agents
are derived from micro-organisms, terrestrial plants, marine organisms and animals
(Newman and Cragg 2004; Schwartsmann et al. 2003). Diethylstilbestrol is a stilbene derivative, which is mainly used for the treatment of prostate and breast cancer
and to prevent threatened abortions (Metzler 1984). Trans-astringin and its aglycon
are active anti-leukemic agents (Mannila and Talvitie 1992; Mannila et al. 1993).
Trans-piceatannol is an inhibitor of protein tyrosine kinase (Geahlen and McLaughlin
1989; Oliver et al. 1994). The most widely distributed and biologically active stilbenoids are resveratrol, combretastatins and pterostilbene. These compounds and
their analogues possess a wide variety of biological activities.
Resveratrol (3, 4′, 5-trihydroxy trans-stilbene) is the major stilbene present in
grape wines. It is a naturally occurring phytoalexin and found in more than 70 plant
species including grapes, peanuts and pines. It can exist in two isomeric forms and
both these forms are found in grape wines (Sun et al. 2003) due to photochemical
isomerization of trans-form into cis-form (Jeandet et al. 1995; Roggero and Garcia
1995). Resveratrol was first described in 1940 as a phenolic component of the
medicinal herb hellebore Veratrum grandiflorum. Little attention was given to this
compound until its role in inhibiting growth of cancer cells in culture was discovered (Baur and Sinclair 2006). The most important source of resveratrol in wine is
the berry skin. It is absent or low in the fruit flesh (Creasy and Coffee 1988). It has
been assumed that in ripe berries, skin can be elicited to synthesize resveratrol
(Jeandet et al. 1995) as a free compound or as a glucoside. These compounds are
supposed to be extracted during alcoholic fermentation and degraded during malolactic fermentation by enzymatic activity of malolactic bacteria (Pezet and Cuenat
1996). Cis-resveratrol is a byproduct of fermentation and is rarely found in grapes
(Jeandet et al. 1995 and Mattavi et al. 1995). It is getting worldwide attention from
the scientific community because of its variety of biological activities such as antioxidant, radio-protective, phytoestrogen, anti-bacterial and anti-fungal (Aggarwal
and Shishodia 2006; Kumar 2007; Rocha et al. 2008; Alonso et al. 2009). Its therapeutic potential includes the chemo-prevention of cancer, inflammation, ageing,
obesity, cardiovascular diseases and neurodegeneration (Kovacic and Somanathan
2010).
Pterostilbene (3, 5-dimethoxy-4′-hydroxy trans-stilbene) is chemically related
to resveratrol. It is mainly found in blueberries and grapes that exhibit anti-cancer,
anti-hypercholesterolemia and anti-hypertriglyceridemia properties. It is more stable in vivo than resveratrol. It was also suggested that this compound has
17 Stilbenes and Their Derivatives in Traditional Medicine