Verbascoside is a caffeoyl phenylethanoid glycoside in which the

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

caffeic acid Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one ...

and the

phenylethanoid Phenylethanoids are a type of phenolic compounds characterized by a phenethyl alcohol structure. Tyrosol and hydroxytyrosol are examples of such compounds. Glycosides The red deadnettle (''Lamium purpureum'') contains phenylethanoid glycosides ...

hydroxytyrosol Hydroxytyrosol is an organic compound with the formula . Classified as a phenylethanoid, i.e. a relative of phenethyl alcohol, Its derivatives are found in a variety of natural sources, notably olive oils and wines. The compound is colorless solid ...

form an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

and an

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

bond respectively, to the

rhamnose Rhamnose (Rha, Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose predominantly occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most o ...

part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

Occurrences

Natural occurrences

Verbascoside can be found in species in all the families of the order

Lamiales The order Lamiales (also known as the mint order) are an order in the asterid group of dicotyledonous flowering plants. It includes about 23,810 species, 1,059 genera, and is divided into about 25 families. These families include Acanthaceae, Bi ...

(syn. Scrophulariales). Only two examples are known from outside the order, in the clade

Asterids In the APG IV system (2016) for the classification of flowering plants, the name asterids denotes a clade (a monophyletic group). Asterids is the largest group of flowering plants, with more than 80,000 species, about a third of the total floweri ...

. ; in the Lamiales In the family

Lamiaceae The Lamiaceae ( ) or Labiatae are a family of flowering plants commonly known as the mint, deadnettle or sage family. Many of the plants are aromatic in all parts and include widely used culinary herbs like basil, mint, rosemary, sage, savory ...

, it can be found in the medicinal plants in the genus ''

Phlomis ''Phlomis'' is a genus of over 100 species''Phlomis''.
Flora of China. of

'', in the

Scrophulariaceae The Scrophulariaceae are a family of flowering plants, commonly known as the figwort family. The plants are annual and perennial herbs, as well as shrubs. Flowers have bilateral (zygomorphic) or rarely radial (actinomorphic) symmetry. The Scr ...

, in '' Verbascum phlomoides'', ''

Verbascum mallophorum ''Verbascum'' is a genus of over 450 species of flowering plants, common name mullein (), in the figwort family Scrophulariaceae. They are native to Europe and Asia, with the highest species diversity in the Mediterranean. Mullein or "mullein le ...

'', or, in the family

Buddlejaceae Buddlejaceae is a family of flowering plants that is not currently recognized by the Angiosperm Phylogeny Group, but as of 2016 it is being used by many botanists as one of several small families that divide the Lamiales. Phylogenetic reconstruc ...

, in ''

Buddleja globosa ''Buddleja globosa'', also known as the orange-ball-tree, orange ball buddleja, and matico, is a species of flowering plant endemism, endemic to Chile and Argentina, where it grows in dry and moist forest, from sea level to 2,000 m.Norman, E ...

'' or ''

Buddleja cordata ''Buddleja cordata'' is endemic to Mexico, growing along forest edges and water courses at elevations of 1500–3000 m; it has also naturalized in parts of Ethiopia.Norman, E. M. (2000). Buddlejaceae. ''Flora Neotropica 81'', New York Bo ...

'', in the family

Bignoniaceae Bignoniaceae is a family of flowering plants in the order Lamiales commonly known as the bignonias or trumpetvines.Vernon H. Heywood, Richard K. Brummitt, Ole Seberg, and Alastair Culham. ''Flowering Plant Families of the World''. Firefly Books: ...

, in '' Pithecoctenium sp'' and '' Tynanthus panurensis'', in the family

Orobanchaceae Orobanchaceae, the broomrapes, is a family of mostly parasitic plants of the order Lamiales, with about 90 genera and more than 2000 species. Many of these genera (e.g., ''Pedicularis'', ''Rhinanthus'', ''Striga'') were formerly included in the ...

, in '' Cistanche sp'' and ''

Orobanche rapum-genistae ''Orobanche rapum-genistae'', the greater broomrape, is a plant species in the genus ''Orobanche''. It is a parasitic plant, native to Europe, growing on the roots of plants in the bean family, usually common broom or European gorse. Descriptio ...

'', in the

Plantaginaceae Plantaginaceae, the plantain family, is a large, diverse family of flowering plants in the order Lamiales that includes common flowers such as snapdragon and foxglove. It is unrelated to the banana-like fruit also called "plantain." In older cl ...

, in ''

Plantago lanceolata ''Plantago lanceolata'' is a species of flowering plant in the plantain family Plantaginaceae. It is known by the common names ribwort plantain, narrowleaf plantain, English plantain, ribleaf, lamb's tongue, and buckhorn. It is a common weed on c ...

'', in

Verbenaceae The Verbenaceae ( ), the verbena family or vervain family, is a family of mainly tropical flowering plants. It contains trees, shrubs, and herbs notable for heads, spikes, or clusters of small flowers, many of which have an aromatic smell. The ...

, in ''

Verbena officinalis ''Verbena officinalis'', the common vervain or common verbena, is a perennial herb native to Europe. It grows up to 70 cm high, with an upright habitus. The lobed leaves are toothed, and the delicate spikes hold clusters of two-lipped mauv ...

'' (common vervain), ''

Aloysia citrodora ''Aloysia citrodora'', lemon verbena, is a species of flowering plant in the verbena family Verbenaceae, native to South America. Other common names include lemon beebrush. It was brought to Europe by the Spanish and the Portuguese in the 17th ce ...

'' (lemon verbena) and ''

Lantana camara ''Lantana camara'' (common lantana) is a species of flowering plant within the verbena family (Verbenaceae), native to the American tropics. It is a very adaptable species, which can inhabit a wide variety of ecosystems; once it has been introduc ...

'', in the

Oleaceae Oleaceae, also known as the olive family, is a taxonomic family of flowering shrubs, trees, and a few lianas in the order Lamiales, It presently comprises 28 genera, one of which is recently extinct.Peter S. Green. 2004. "Oleaceae". pages 296-30 ...

, in ''Olea europaea'' (

olive The olive, botanical name ''Olea europaea'', meaning 'European olive' in Latin, is a species of small tree or shrub in the family Oleaceae, found traditionally in the Mediterranean Basin. When in shrub form, it is known as ''Olea europaea'' ...

), in the

Lentibulariaceae Lentibulariaceae is a family of carnivorous plants containing three genera: ''Genlisea'', the corkscrew plants; ''Pinguicula'', the butterworts; and ''Utricularia'', the bladderworts. The genera ''Polypompholyx'' (two species of pink petticoats ...

, in the carnivorous plant ''

Pinguicula lusitanica ''Pinguicula lusitanica'', commonly known as the pale butterwort, is a small butterwort that grows wild in acidic peat bog areas along coastal atlantic western Europe from western Scotland and Ireland south through western England and western Fr ...

'', and, in the Byblidaceae, in '' Byblis liniflora''.

Derivatives

Verbascoside derivatives can be found in the ''

Verbascum undulatum ''Verbascum'' is a genus of over 450 species of flowering plants, common name mullein (), in the figwort family Scrophulariaceae. They are native to Europe and Asia, with the highest species diversity in the Mediterranean. Mullein or "mullein le ...

'' and notably apiosides in ''

Verbascum ''Verbascum'' is a genus of over 450 species of flowering plants, common name mullein (), in the figwort family Scrophulariaceae. They are native to Europe and Asia, with the highest species diversity in the Mediterranean. Mullein or "mullein le ...

sp''.

In ''in vitro'' cultures

It can also be produced in plant cell cultures of '' Leucosceptrum sp'' (

) and ''

Syringa ''Syringa'' is a genus of 12 currently recognized species of flowering plant, flowering woody plants in the olive family or Oleaceae called lilacs. These lilacs are native to woodland and scrub from southeastern Europe to eastern Asia, and wid ...

sp'' (

). It can also be produced in

hairy root Hairy root culture, also called transformed root culture, is a type of plant tissue culture that is used to study plant metabolic processes or to produce valuable secondary metabolites or recombinant proteins, often with plant genetic engineering. ...

s cultures of ''

Paulownia tomentosa ''Paulownia tomentosa'', common names princess tree, empress tree, or foxglove-tree, is a deciduous hardwood tree in the family Paulowniaceae, native to central and western China. It is an extremely fast-growing tree with seeds that disperse rea ...

'' (empress tree,

Paulowniaceae Paulowniaceae are a family of flowering plants within the Lamiales. They are a monophyletic and monogeneric family of trees with currently 7 confirmed species. They were formerly placed within Scrophulariaceae ''sensu lato'', or as a segregate of ...

Biological activity

Verbascoside has an

antimicrobial An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...

activity, notably against ''

Staphylococcus aureus ''Staphylococcus aureus'' is a Gram-positive spherically shaped bacterium, a member of the Bacillota, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive ...

''. It can also have

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as o ...

properties. Although some ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...

genotoxicity Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, but some genotoxic sub ...

of verbascoside has been reported on human

lymphocyte A lymphocyte is a type of white blood cell (leukocyte) in the immune system of most vertebrates. Lymphocytes include natural killer cells (which function in cell-mediated, cytotoxic innate immunity), T cells (for cell-mediated, cytotoxic ad ...

s with an involvement of

PARP-1 Poly DP-ribosepolymerase 1 (PARP-1) also known as NAD+ ADP-ribosyltransferase 1 or poly DP-ribosesynthase 1 is an enzyme that in humans is encoded by the ''PARP1'' gene. It is the most abundant of the PARP family of enzymes, accounting for 90% o ...

and p53 proteins, subsequent ''

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...

'' tests reported no genotoxicity for high dosage oral administration. It is a

protein kinase C In cell biology, Protein kinase C, commonly abbreviated to PKC (EC 2.7.11.13), is a family of protein kinase enzymes that are involved in controlling the function of other proteins through the phosphorylation of hydroxyl groups of serine and t ...

inhibitor.

References

{{Hydroxycinnamic acid Phenylpropanoid glycosides Phenylethanoids

Occurrences

Natural occurrences

Derivatives

In ''in vitro'' cultures

Biological activity

See also

References