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Carpaine[1]
Skeletal formula of carpaine
Ball-and-stick model of the carpaine molecule
Names
IUPAC name
(1S,11R,13S,14S,24R,26S)-13,26-Dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione
Other names
(+)-Carpaine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.378 Edit this at Wikidata
UNII
  • InChI=1S/C28H50N2O4/c1-21-25-19-17-23(29-21)13-9-5-3-8-12-16-28(32)34-26-20-18-24(30-22(26)2)14-10-6-4-7-11-15-27(31)33-25/h21-26,29-30H,3-20H2,1-2H3/t21-,22-,23+,24+,25-,26-/m0/s1 checkY
    Key: AMSCMASJCYVAIF-QCVMBYIASA-N checkY
  • InChI=1/C28H50N2O4/c1-21-25-19-17-23(29-21)13-9-5-3-8-12-16-28(32)34-26-20-18-24(30-22(26)2)14-10-6-4-7-11-15-27(31)33-25/h21-26,29-30H,3-20H2,1-2H3/t21-,22-,23+,24+,25-,26-/m0/s1
    Key: AMSCMASJCYVAIF-QCVMBYIABP
  • O=C3O[C@H]1CC[C@H](N[C@H]1C)CCCCCCCC(=O)O[C@@H]2[C@@H](N[C@@H](CC2)CCCCCCC3)C
Properties
C28H50N2O4
Molar mass 478.70 g/mol
Melting point 121 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Carpaine is one of the major alkaloid components of papaya leaves which has been studied for its cardiovascular effects.[2] Circulatory effects of carpaine were studied in Wistar male rats weighing 314 +/- 13 g, under pentobarbital (30 mg/kg) anesthesia.[3] Increasing dosages of carpaine from 0.5 mg/kg to 2.0 mg/kg resulted in progressive decrease in systolic, diastolic, and mean arterial blood pressure. Selective autonomic nervous blockade with atropine sulfate (1 mg/kg) or propranolol hydrochloride (8 mg/kg) did not alter the circulatory response to carpaine. Carpaine, 2 mg/kg, reduced cardiac output, stroke volume, stroke work, and cardiac power, but the calculated total peripheral resistance remained unchanged. It is concluded from these results that carpaine affects the myocardium directly. The effects of carpaine may be related to its macrocyclic dilactone structure, a possible cation chelating structure.

Isolation of carpaine[edit]

The characterization of the powdered Carica papaya leaves, which the main active constituent is the macrocyclic lactone carpaine. Carpaine occurs in papaya leaves in concentrations as high as 0.4%, which is enough to make it available commercially at very reasonable costs.[4] In order to isolate carpaine by HPLC method, the plant leaves were first dried in an electric blast drying oven until constant mass, then the dried leaves were milled to fine powder. The powdered plant material were macerated with a mixed solution of ethanol/water/HCl for 24 hr at room temperature. The extract was then removed, stored, and desiccated, and this process was repeated five times. The whole extracts were pooled, and evaporated. The extract was then dissolved in water/HCl mixture, filtered, and extracted with petroleum ether to remove fat materials. The acid fraction was adjusted to pH 8.0 ~ 9.0 using [[NH4OH]] solution and extracted with chloroform. The chloroform fractions were pooled and evaporated. The whole operation was repeated again and the crude alkaloid carpaine was obtained.[5]

Mechanism of action[edit]

Pharmacology[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 1866.
  2. ^ Burdick, Everette M. "Carpaine. An alkaloid of Carica papaya. Chemistry and pharmacology." Economic Botany (1971), 25(4), 363-365.
  3. ^ Hornick, C. A.; Sanders, L. I.; Lin, Y. C. "Effect of carpaine, a papaya alkaloid, on the circulatory function in the rat." Research Communications in Chemical Pathology and Pharmacology (1978), 22(2), 277-289.
  4. ^ Burdick, Everette. "Carpaine: An Alkaloid of Carica Papaya: Its Chemistry and Pharmacology". JSTOR.
  5. ^ "Isolation and Identification Carpaine in Carica papaya L. Leaf by HPLC-UV Method". International Journal of Food Properties.
source: https://en.wikipedia.org/wiki/Carpaine

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