Lactucin

Last updated
Lactucin
Lactucin.png
Names
Preferred IUPAC name
(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12-,13+,14+/m1/s1 X mark.svgN
    Key: VJQAFLAZRVKAKM-QQUHWDOBSA-N X mark.svgN
  • InChI=1/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12-,13+,14+/m1/s1
    Key: VJQAFLAZRVKAKM-QQUHWDOBBA
  • CC1=C2[C@@H]([C@@H]3[C@@H]([C@@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)CO
Properties
C15H16O5
Molar mass 276.28 g/mol
AppearanceWhite crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lactucin is a bitter substance that forms a white crystalline solid and belongs to the group of sesquiterpene lactones. It is found in some varieties of lettuce and is an ingredient of lactucarium. It has been shown to have analgesic and sedative properties [1] which are speculated to occur via modulation of the GABAA receptor. [2] It has also shown some antimalarial effects. [3] It is also found in dandelion coffee.

See also

Related Research Articles

Lactucarium is the milky fluid secreted by several species of lettuce, especially Lactuca virosa, usually from the base of the stems. It is known as lettuce opium because of its sedative and analgesic properties. It has also been reported to promote a mild sensation of euphoria. Because it is a latex, lactucarium physically resembles opium, in that it is excreted as a white fluid and can be reduced to a thick smokable solid.

<i>Cannabis sativa</i> Plant species

Cannabis sativa is an annual herbaceous flowering plant. The species was first classified by Carl Linnaeus in 1753. The specific epithet sativa means 'cultivated'. Indigenous to Eastern Asia, the plant is now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history and used as a source of industrial fiber, seed oil, food, and medicine. It is also used as a recreation drug and for religious and spiritual purposes.

Sesquiterpene lactones (SLs) are a class of sesquiterpenoids that contain a lactone ring. They are most often found in plants of the family Asteraceae. Other plant families with SLs are Umbelliferae and Magnoliaceae (magnolias). A collection of colorless, lipophilic solids, SLs are a rich source of drugs. They can be allergenic and toxic in grazing livestock causing severe neurological problems in horses. Some are also found in corals of the order Alcyonacea.

<i>Lactuca virosa</i> Species of plant

Lactuca virosa is a plant in the Lactuca (lettuce) genus, often ingested for its mild analgesic and sedative effects. It is related to common lettuce, and is often called wild lettuce, bitter lettuce, laitue vireuse, opium lettuce, poisonous lettuce, tall lettuce, great lettuce or rakutu-karyumu-so.

<i>Quassia amara</i> Species of tree

Quassia amara, also known as amargo, bitter-ash, bitter-wood, or hombre grande is a species in the genus Quassia, with some botanists treating it as the sole species in the genus. The genus was named by Carl Linnaeus who named it after the first botanist to describe it: the Surinamese freedman Graman Quassi. Q. amara is used as insecticide, in traditional medicine and as additive in the food industry.

<span class="mw-page-title-main">Humulene</span> Chemical compound

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

<span class="mw-page-title-main">Lactucopicrin</span> Chemical compound

Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect, acting on the central nervous system. It is a sesquiterpene lactone, and is a component of lactucarium, derived from the plant Lactuca virosa, as well as being found in some related plants such as Cichorium intybus. It is also found in dandelion coffee.

<span class="mw-page-title-main">Helenalin</span> Chemical compound

Helenalin, or (-)-4-Hydroxy-4a,8-dimethyl-3,3a,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, is a toxic sesquiterpene lactone which can be found in several plants such as Arnica montana and Arnica chamissonis Helenalin is responsible for the toxicity of the Arnica spp. Although toxic, helenalin possesses some in vitro anti-inflammatory and anti-neoplastic effects. Helenalin can inhibit certain enzymes, such as 5-lipoxygenase and leukotriene C4 synthase. For this reason the compound or its derivatives may have potential medical applications.

<i>Abutilon indicum</i> Species of plant

Abutilon indicum is a small shrub in the family Malvaceae, native to tropical and subtropical regions. This plant is a valuable medicinal and ornamental plant, its roots and leaves being used for curing fevers. It has been widely introduced outside of its native range, and is considered invasive on certain tropical islands.

<span class="mw-page-title-main">Mesembrine</span> Chemical compound

Mesembrine is an alkaloid present in Sceletium tortuosum (kanna). It has been shown to act as a serotonin reuptake inhibitor (Ki = 1.4 nM), and more recently, has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4) (Ki = 7,800 nM). In an in vitro study published in 2015, researchers concluded that "a high-mesembrine Sceletium extract" may exert anti-depressant effects by acting as a monoamine releasing agent." As such, mesembrine likely plays a dominant role in the antidepressant effects of kanna. The levorotatory isomer, (−)-mesembrine, is the natural form.

<span class="mw-page-title-main">Dihydroartemisinin</span> Drug used to treat malaria

Dihydroartemisinin is a drug used to treat malaria. Dihydroartemisinin is the active metabolite of all artemisinin compounds and is also available as a drug in itself. It is a semi-synthetic derivative of artemisinin and is widely used as an intermediate in the preparation of other artemisinin-derived antimalarial drugs. It is sold commercially in combination with piperaquine and has been shown to be equivalent to artemether/lumefantrine.

<i>Kaempferia galanga</i> Species of flowering plant

Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry, is a monocotyledonous plant in the ginger family, and one of four plants called galangal. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia, and India, but is also widely cultivated throughout Southeast Asia.

<span class="mw-page-title-main">Absinthin</span> Chemical compound

Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.

<span class="mw-page-title-main">Galangin</span> Chemical compound

Galangin is a flavonol, a type of flavonoid.

<i>Cissus quadrangularis</i> Species of grapevine

Cissus quadrangularis is a perennial plant of the grape family. It is commonly known as veldt grape, winged treebine or adamant creeper. The species is native to tropical Asia, the Arabian Peninsula and much of Africa.

<i>Artemisia herba-alba</i> Species of plant

Artemisia herba-alba, the white wormwood, is a perennial shrub in the genus Artemisia that grows commonly on the dry steppes of the Mediterranean regions in Northern Africa, Western Asia and Southwestern Europe. It is used as an antiseptic and antispasmodic in herbal medicine.

<i>Scorzoneroides</i> Genus of plants

Scorzoneroides or hawkbits is a genus of plants of the tribe Cichorieae within the family Asteraceae.

<span class="mw-page-title-main">Paeonol</span> Chemical compound

Paeonol is a phenolic compound found in peonies such as Paeonia suffruticosa, in Arisaema erubescens, and in Dioscorea japonica. It is a chemical compound found in some traditional Chinese medicines.

<span class="mw-page-title-main">Harpagoside</span> Chemical compound

Harpagoside is a natural product found in the plant Harpagophytum procumbens, also known as devil's claw. It is the active chemical constituent responsible for the medicinal properties of the plant, which have been used for centuries by the Khoisan people of southern Africa to treat diverse health disorders, including fever, diabetes, hypertension, and various blood related diseases.

<span class="mw-page-title-main">Xanthatin</span> Chemical compound

Xanthatin, or (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one (C15H18O3) is a major bioactive compound found in the leaves of the Xanthium strumarium (Asteracae) plant. It is classified as a natural sesquiterpene lactone. Xanthatin is believed to have anti-inflammatory, anti-tumour, anti-microbial, and anti-parasitic properties hence it is being researched for potential use in treatment of cancer and autoimmune diseases. While it has been used in traditional medicine for decades, its mechanisms and modern use haven’t been fully understood yet.

References

  1. Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E (2006). "Analgesic and Sedative Activities of Lactucin and some Lactucin-Like Guaianolides in Mice". Journal of Ethnopharmacology. 107 (2): 254–258. doi:10.1016/j.jep.2006.03.003. PMID   16621374.
  2. Kim H, Suh H, Choi H, Hong K, Jo K (2019). "Effectiveness of the Sleep Enhancement by Green Romaine Lettuce (Lactuca sativa) in a Rodent Model". Biol Pharm Bull. 42 (10): 1726–1732. doi:10.1248/bpb.b19-00454. PMID   31582660.
  3. Bischoff TA, Kelley CJ, Karchesy Y, Laurantos M, Nguyen-Dinh P, Arefi AG (2004). "Antimalarial Activity of Lactucin and Lactucopicrin: Sesquiterpene Lactones Isolated from Cichorium intybus L.". Journal of Ethnopharmacology. 95 (2–3): 455–457. doi:10.1016/j.jep.2004.06.031. PMID   15507374.