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Parthenolide

Parthenolide

IUPAC name	(1aR,7aS,10aS)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b- octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Other names	4xi-Germacra-1(10),11(13)-dien-12-oic acid, 4,5-epoxy-6.alpha.- hydroxy-, gamma-lactone
Molecular formula	C₁₅H₂₀O₃
Identifiers
CAS number	20554-84-1
PubChem	5353864
RTECS number	LY4220000
Properties
Molar mass	248.317 g/mol
Melting point	113-115
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Parthenolide is a sesquiterpene lactone which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it in named. It is found in highest concentration in the flowers and fruit.

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The plant is well known in natural medicine. Tablets and tinctures are used for the relief of migraine, to help prevent blood clots [1], as an anti-inflammatory providing relief in cases of arthritis, to relieve some types of menstrual problems, and as a digestive aid. Parthenolide is the main active ingredient. Many vendors of feverfew remedies specify the content of parthenolide in their products. Lack of solubility in water limits the benefits of parthenolide as a drug, and now motivates drug researchers to develop synthetic analogs that will be easier to absorb.

Biological activities

It is a potential anticancer drug. It destroys acute myelogenous leukemia (AML) cells by inducing apoptosis, leaving normal bone marrow cells relatively unscathed. Moreover, the compound may get at the root of the disease because it also kills stem cells that give rise to AML.^[1] Parthenolide is under consideration as a potential cancer drug in combination with sulindac.
Parthenolide is active against a parasite Leishmania amazonensis.^[2]
Microtubule-interfering activity of parthenolide.^[3]
Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones.^[4]
Parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-kappaB activity.^[5]

References

^ Guzman ML, Rossi RM, Karnischky L, Li X, Peterson DR, Howard DS, Jordan CT (2005). "The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells". Blood 105 (11): 4163–9. PMID 15687234. Free full text.
^ Tiuman TS, Ueda-Nakamura T, Garcia Cortez DA, Dias Filho BP, Morgado-Diaz JA, de Souza W, Nakamura CV (2005). "Antileishmanial activity of parthenolide, a sesquiterpene lactone isolated from Tanacetum parthenium." Antimicrob Agents Chemother 49 (1): 176–82. PMID 15616293. Full text at PMC: 538891.
^ Miglietta A, Bozzo F, Gabriel L, Bocca C (2004). "Microtubule-interfering activity of parthenolide". Chem Biol Interact 149 (2-3): 165–73. PMID 15501437.
^ Feltenstein MW, Schuhly W, Warnick JE, Fischer NH, Sufka KJ (2004). "Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones". Pharmacol Biochem Behav 79 (2): 299–302. PMID 15501305.
^ Yip KH, Zheng MH, Feng HT, Steer JH, Joyce DA, Xu J (2004). "Sesquiterpene lactone parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-kappaB activity". J Bone Miner Res 19 (11): 1905–16. PMID 15476591.

Categories: Terpenes and terpenoids | Lactones | Epoxides

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Parthenolide". A list of authors is available in Wikipedia.