Lunamarine

Last updated
Lunamarine
Lunamarine.png
Names
Preferred IUPAC name
2-(2H-1,3-Benzodioxol-5-yl)-7-methoxy-1-methylquinolin-4(1H)-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H15NO4/c1-19-14(11-3-6-17-18(7-11)23-10-22-17)9-16(20)13-5-4-12(21-2)8-15(13)19/h3-9H,10H2,1-2H3 Yes check.svgY
    Key: GOMVNCXQVLUIGA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C18H15NO4/c1-19-14(11-3-6-17-18(7-11)23-10-22-17)9-16(20)13-5-4-12(21-2)8-15(13)19/h3-9H,10H2,1-2H3
    Key: GOMVNCXQVLUIGA-UHFFFAOYSA-N
  • Cn1c2cc(ccc2c(=O)cc1c3ccc4c(c3)OCO4)OC
Properties
C18H15NO14
Molar mass 469.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lunamarine (punarnavine) is a quinolone alkaloid present in Boerhavia diffusa (punarnava).

The compound has shown some in vitro anticancer, [1] antiestrogenic, [2] immunomodulatory, [3] and anti-amoebic activity (particularly against Entamoeba histolytica ). [4]

Related Research Articles

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<i>Entamoeba histolytica</i> Anaerobic parasitic protist

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Borage Species of flowering plant in the family Boraginaceae

Borage, also known as starflower, is an annual herb in the flowering plant family Boraginaceae. It is native to the Mediterranean region, and has naturalized in many other locales.

<i>Turnera diffusa</i> Species of shrub

Turnera diffusa, known as damiana, is a shrub native to southern Texas in the United States, Central America, Mexico, South America, and the Caribbean. It belongs to the family Passifloraceae.

Tetrahydroharmine

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Lactucopicrin 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.

<i>Sceletium tortuosum</i> Species of succulent

Sceletium tortuosum is a succulent plant commonly found in South Africa, which is also known as Kanna, Channa, Kougoed —which literally means, 'chew(able) things' or 'something to chew'.

Auranofin

Auranofin is a gold salt classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura.

Mesembrine 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). Still more recently, in an in vitro study published in 2015, scientist concluded that "a high-mesembrine Sceletium extract exerts its anti-depressant effect by acting primarily as monoamine releasing agent, rather than as selective serotonin-reuptake inhibitor." As such, mesembrine likely plays a dominant role in the antidepressant effects of kanna. The levorotatory isomer, (−)-mesembrine, is the natural form.

Mitraphylline Chemical compound

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom. As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa along with a number of isomeric alkaloids.

<i>Alstonia scholaris</i> Species of tree

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Rhynchophylline Chemical compound

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla and Uncaria tomentosa. It also occurs in the leaves of Mitragyna speciosa (kratom), a tree native to Thailand. Chemically, it is related to the alkaloid mitragynine.

<i>Boerhavia diffusa</i> Species of flowering plant

Boerhaavia diffusa is a species of flowering plant in the four o'clock family which is commonly known as punarnava, red spiderling, spreading hogweed, or tarvine. It is taken in herbal medicine for pain relief and other uses. The leaves of Boerhaavia diffusa are often used as a green vegetable in many parts of India.

Galangin Chemical compound

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

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Coronaridine Chemical compound

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species, including Tabernaemontana divaricata for which it was named.

Palmatine Chemical compound

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<i>Rhus chinensis</i> Species of tree

Rhus chinensis, the Chinese sumac or nutgall tree, is a deciduous shrub or small tree in the genus Rhus. Growing to 6 m (20 ft) tall, it has downy shoots and leaves comprising several leaflets. These turn red in autumn before falling.

Bakuchiol Chemical compound

Bakuchiol is a meroterpene in the class terpenophenol.

Entamoeba invadens is an amoebozoa parasite of reptiles, within the genus Entamoeba. It is closely related to the human parasite Entamoeba histolytica, causing similar invasive disease in reptiles, in addition to a similar morphology and lifecycle.

References

  1. Manu K.A.; Kuttan G. (2009). "Punarnavine induces apoptosis in B16F-10 melanoma cells by inhibiting NF-kappaB signaling". Asian Pacific Journal of Cancer Prevention. 10 (6): 1031–1037. PMID   20192578.
  2. Sreeja S.; Sreeja S. (2009). "An in vitro study on antiproliferative and antiestrogenic effects of Boerhaavia diffusa L. extracts". Journal of Ethnopharmacology. 126 (2): 221–225. doi:10.1016/j.jep.2009.08.041. PMID   19723573.
  3. Manu K.A.; Kuttan G. (2009). "Immunomodulatory activities of Punarnavine, an alkaloid from Boerhaavia diffusa". Immunopharmacology and Immunotoxicology. 31 (3): 377–387. doi:10.1080/08923970802702036. PMID   19555203. S2CID   2066582.
  4. Sohni YR.; Kaimal P.; Bhatt RM. (Jan 1995). "The antiamoebic effect of a crude drug formulation of herbal extracts against Entamoeba histolytica in vitro and in vivo". Journal of Ethnopharmacology . 45 (1): 43–52. doi:10.1016/0378-8741(94)01194-5. PMID   7739226.