Verbenalin

Last updated
Verbenalin
Verbenalin.svg
Names
IUPAC name
Methyl (1S,4aS,7S,7aR)-1-(β-D-glucopyranosyloxy)-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Preferred IUPAC name
Methyl (1S,4aS,7S,7aR)-5-oxo-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Other names
Verbenalol β-D-glucopyranoside; Verbenalol glucoside; Cornin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1 Yes check.svgY
    Key: HLXRWTJXGMHOFN-XJSNKYLASA-N Yes check.svgY
  • InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
    Key: HLXRWTJXGMHOFN-XJSNKYLASA-N
  • C[C@H]1CC(=O)[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Properties
C17H24O10
Molar mass 388.369 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in Verbena officinalis . [1] It is one of the sleep-promoting (soporific) components in Verbena officinalis. [2]

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Lemon balm Lemon balm, a species of plant

Lemon balm, balm, common balm, or balm mint, is a perennial herbaceous plant in the mint family and native to south-central Europe, the Mediterranean Basin, Iran, and Central Asia, but now naturalized elsewhere.

Valerian (herb) species of flowering plant in the honeysuckle family Caprifoliaceae

Valerian is a perennial flowering plant native to Europe and Asia. In the summer when the mature plant may have a height of 1.5 metres (5 ft), it bears sweetly scented pink or white flowers that attract many fly species, especially hoverflies of the genus Eristalis. It is consumed as food by the larvae of some Lepidoptera species, including the grey pug.

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Thujone Group of four possible stereoisomers found in various plants: a.o., absinthe and mint

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<i>Aloysia citrodora</i> Species of plant

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<i>Verbena</i> Genus of plants

Verbena is a genus in the family Verbenaceae. It contains about 250 species of annual and perennial herbaceous or semi-woody flowering plants. The majority of the species are native to the Americas and Asia. Verbena officinalis, the common vervain or common verbena, is the type species and native to Europe.

<i>Althaea officinalis</i> Species of plant

Althaea officinalis, or marsh-mallow, is a perennial species indigenous to Europe, Western Asia, and North Africa, which is used in herbalism and as an ornamental plant. A confection made from the root since ancient Egyptian times evolved into today's marshmallow treat, but most modern marshmallow treats no longer contain any marsh-mallow root.

Valeric acid Carboxylic acid with chemical formula CH3CH2CH2CH2CO2H

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH
3
(CH
2
)
3
COOH
. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

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<i>Verbena officinalis</i> Species of flowering plant

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 mauve flowers.

3-Methylbutanoic acid Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

Pyrrolizidine alkaloid

Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than 660 PAs and PA N-oxides have been identified in over 6,000 plants, and about half of them exhibit hepatotoxicity. They are found frequently in plants in the Boraginaceae, Asteraceae, Orchidaceae and Fabaceae families; less frequently in the Convolvulaceae and Poaceae, and in at least one species in the Lamiaceae. It has been estimated that 3% of the world’s flowering plants contain pyrrolizidine alkaloids. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines.

Rosmarinic acid Chemical compound

Rosmarinic acid is a chemical compound found in a variety of plants. It was found to exhibit photoprotective effect against ultraviolet C (UVC) damage when examined in vitro.

Valerenic acid Chemical compound

Valerenic acid is a sesquiterpenoid constituent of the essential oil of the valerian plant.

<i>Verbena urticifolia</i> Species of flowering plant

Verbena urticifolia, known as nettle-leaved vervain or white vervain, is a herbaceous plant in the vervain family (Verbenaceae). It belongs to the "true" vervains of genus Verbena.

<i>Cornus officinalis</i> Species of flowering plant

Cornus officinalis, the Japanese cornel or Japanese cornelian cherry, is a species of flowering plant in the dogwood family Cornaceae. Despite its name it is native to China and Korea as well as Japan. It is not to be confused with C. mas, which is also known as the Cornelian cherry. It is not closely related to the true cherries of the genus Prunus.

<i>Hyssopus officinalis</i> Species of plant

Hyssopus officinalis or hyssop is a shrub in the Lamiaceae or mint family native to Southern Europe, the Middle East, and the region surrounding the Caspian Sea. Due to its purported properties as an antiseptic, cough reliever, and expectorant, it has been used in traditional herbal medicine.

Cuttlefish Order of molluscs

Cuttlefish or cuttles are marine molluscs of the order Sepiida. They belong to the class Cephalopoda, which also includes squid, octopuses, and nautiluses. Cuttlefish have a unique internal shell, the cuttlebone, which is used for control of buoyancy.

Verbascoside Chemical compound

Verbascoside is a caffeoyl phenylethanoid glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

References

  1. Deepak, M.; Handa, S. S. (2000). "Antiinflammatory activity and chemical composition of extracts of Verbena officinalis". Phytotherapy Research. 14 (6): 463–465. doi:10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G. PMID   10960904.
  2. Makino, Y.; Kondo, S.; Nishimura, Y.; Tsukamoto, Y.; Huang, Z. L.; Urade, Y. (2009). "Hastatoside and verbenalin are sleep-promoting components in Verbena officinalis". Sleep and Biological Rhythms. 7 (3): 211–217. doi:10.1111/j.1479-8425.2009.00405.x.