Verbascoside is a

polyphenol Polyphenols () are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as ...

glycoside in which the

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

caffeic acid Caffeic acid is an organic compound with the formula . It is a polyphenol with a key role in scavenging reactive oxygen species (ROS) generated in energy metabolism. Caffeic acid is also one major polyphenol responsible for maintaining normal le ...

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 . It is a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, ...

form an

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

and an

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

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 mo ...

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 Lamiales (also known as the mint order) are an order of flowering plants in the asterids clade of the Eudicots. Under the APG IV system of flowering plant classification the order consists of 24 families, and includes about 23,810 species ...

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

Asterids Asterids are a large clade (monophyly, monophyletic group) of flowering plants, composed of 17 Order_(biology), orders and more than 80,000 species, about a third of the total flowering plant species. The asterids are divided into the unranked cl ...

. ; in the Lamiales In the family

Lamiaceae The Lamiaceae ( ) or Labiatae are a family (biology), 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 (herb), ba ...

, 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'', 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 reconstru ...

, in '' Buddleja globosa'' or '' Buddleja cordata'', in the family

Bignoniaceae Bignoniaceae () is a Family (biology), family of flowering plants in the Order (biology), order Lamiales commonly known as the bignonias or trumpet vines.Vernon H. Heywood, Richard K. Brummitt, Ole Seberg, and Alastair Culham. ''Flowering Plant ...

, in '' Pithecoctenium sp'' and ''

Tynanthus panurensis ''Tynanthus'' is a genus of woody plants that is part of the Bignoniaceae Bignoniaceae () is a Family (biology), family of flowering plants in the Order (biology), order Lamiales commonly known as the bignonias or trumpet vines.Vernon H. Hey ...

'', in the family

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

, in ''

Cistanche ''Cistanche'' is a worldwide genus of Parasitic plant, holoparasitic desert plants in the family Orobanchaceae. They lack chlorophyll and obtain nutrients and water from the host plants whose roots they parasitize. They are often known as desert ...

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. Descript ...

'', in the

Plantaginaceae Plantaginaceae, the plantain family or veronica family, is a large, diverse family (biology), family of flowering plants in the order Lamiales that includes common flowers such as Antirrhinum, snapdragon and Digitalis, foxglove. It is unrelated ...

, 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 ...

'', 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. T ...

, in ''

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

'' (common vervain), ''

Aloysia citrodora ''Aloysia citrodora'', lemon verbena, is a species of flowering plant in the verbena family (biology), family Verbenaceae, native plant, native to South America. Other common names include lemon beebrush. It was brought to Europe by the Spain, Sp ...

'' (lemon verbena) and ''

Lantana camara ''Lantana camara'' (common lantana) is a species of flowering plant in 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 introduced i ...

'', in the

Oleaceae Oleaceae, also known as the olive family or sometimes the lilac 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. Gree ...

, in ''Olea europaea'' (

olive The olive, botanical name ''Olea europaea'' ("European olive"), is a species of Subtropics, subtropical evergreen tree in the Family (biology), family Oleaceae. Originating in Anatolia, Asia Minor, it is abundant throughout the Mediterranean ...

), 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'', commonly known as butterworts, is a genus of carnivorous flowering plants in the family Lentibulariaceae. They use sticky, glandular leaves to lure, trap, and digest insects in order to supplement the poor mineral nutrition they ...

'', and, in the Byblidaceae, in ''

Byblis liniflora ''Byblis liniflora'' is a species of carnivorous plant in the family Byblidaceae. It is found in Australia, Indonesia, and Papua New Guinea. ''Byblis liniflora'' contains acteoside (verbascoside Verbascoside is a polyphenol glycoside in which ...

''.

Derivatives

Verbascoside derivatives can be found in the '' Verbascum undulatum'' 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 culture Cell culture or tissue culture is the process by which cells are grown under controlled conditions, generally outside of their natural environment. After cells of interest have been isolated from living tissue, they can subsequently be maint ...

s of ''

Leucosceptrum ''Leucosceptrum'' is a genus of flowering plant in the family Lamiaceae, first described in 1806. It contains only one known species, ''Leucosceptrum canum'', native to south-western China (Sichuan, Tibet, Yunnan),the eastern Himalayas (Nepal, Bh ...

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 roots 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 eastern China and the Korean Peninsula. It is an extremely fast-growing tree wit ...

'' (empress tree,

Paulowniaceae Paulowniaceae are a Family (biology), 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 ...

Biological activity

Verbascoside has an

antimicrobial An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth (bacteriostatic agent). Antimicrobial medicines can be grouped according to the microorganisms they are used to treat. For example, antibiotics are used aga ...

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 posi ...

''. It can also have

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation, fever or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs reduce pain by inhibiting mechan ...

properties. Although some ''

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

genotoxicity Genotoxicity is the chemical property, 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, bu ...

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 T cells (for cell-mediated and cytotoxic adaptive immunity), B cells (for humoral, antibody-driven adaptive immunity), an ...

s with an involvement of PARP-1 and

p53 protein p53, also known as tumor protein p53, cellular tumor antigen p53 (UniProt name), or transformation-related protein 53 (TRP53) is a regulatory transcription factor protein that is often mutated in human cancers. The p53 proteins (originally thou ...

s, 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, an ...

'' 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 Esters Rhamnosides Polyols

Occurrences

Natural occurrences

Derivatives

In ''in vitro'' cultures

Biological activity

See also

References