Carpaine

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] Carpaine extracted from Carica papaya trees has been reported to have diverse biological properties, such as anti-malarial, anti-inflammatory, anti-oxidant, and vasodilatory effects.[3] Especially, Carpaine possessed significant anti-plasmodial activity in vitro (IC50 of 0.2 μM) and high selectivity towards the parasites.[4]

Circulatory effects of carpaine were studied in Wistar male rats weighing 314 +/- 13 g, under pentobarbital (30 mg/kg) anesthesia.[5] 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.

  1. ^ Merck Index, 11th Edition, 1866.
  2. ^ Burdick, Everette M. (December 1971). "Carpaine: An alkaloid of Carica papaya—its chemistry and pharmacology". Economic Botany. 25 (4): 363–365. doi:10.1007/BF02985202.
  3. ^ Sudi, Suhaini; Chin, Yee-Zheng; Wasli, Nur Syafinaz; Fong, Siat-Yee; Shimmi, Sadia Choudhury; How, Siew-Eng; Sunggip, Caroline (15 February 2022). "Carpaine Promotes Proliferation and Repair of H9c2 Cardiomyocytes after Oxidative Insults". Pharmaceuticals. 15 (2): 230. doi:10.3390/ph15020230. PMC 8880139. PMID 35215343. This article incorporates text from this source, which is available under the CC BY 4.0 license.
  4. ^ Julianti, Tasqiah; Oufir, Mouhssin; Hamburger, Matthias (25 August 2014). "Quantification of the Antiplasmodial Alkaloid Carpaine in Papaya (Carica papaya) Leaves". Planta Medica. 80 (13): 1138–1142. doi:10.1055/s-0034-1382948. PMID 25153096.
  5. ^ 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.