Skip to main content
Log in

Identification of higenamine and its metabolites in rat by gas chromatography/mass spectrometry

  • Research Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

(±)-Higenamine is known as a cardiotonic principle of aconite root (root ofAconitum spp., Ranunculaceae). A simple and sensitive detection method for higenamine was developed by using gas chromatography-mass spectrometry (GC/MS). The recovery of higenamine after extraction and concentration with XAD-2 resin column was around 95% from rat biological fluids such as bile, plasma and urine. The limits of detection of higenamine in these biological fluids were approximately 0.1 ng/ml each. It has well been suggested that tetrahydroisoquinolines possessing catechol moiety such as higenamine should be subjected to the catechol-O-methyl transferase (COMT) activityin vivo. We detected two major peaks of presumed metabolites of higenamine in the total ion chromatogram obtained from the rat urine sample after the oral administration of (±)-higenamine. The scan mass spectrum of one of the metabolites coincided with those obtained from coclaurine (C6-O-methyl higenamine) and those of the other metabolite are suggestive of isococlaurine (C7-O-methyl higenamine).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References Cited

  • Cashaw, J. L., Geraghty, C. A., McLaughlin, B. R. and Davis, V. E., A Method for determination of subpicomole concentration of tetrahydropapaveroline in rat brain by high performance liquid chromatography with electrochemical detection.Anal. Biochem., 162, 274–282 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Chang, K. C., Lim, J. K., Park, C. W. and Kim, M. S., Studies on the mechanism of positive iontropic action of higenamine.Kor. J. Pharmacol., 17, 7–15 (1981).

    CAS  Google Scholar 

  • Chang, K. C., Yun-Choi, H. S., Lim, J. K. and Park, C. W., Synthesis of higenamine, A cardiotonic principle of aconite root.Arch. Pharm. Res., 7, 133–136 (1984).

    Article  CAS  Google Scholar 

  • Huang, L. Z., Zhang, D. Y. and Wang, C. Y., Synthesis of higenamine.Acta Pharmaceutica Sinica, 16, 931–933 (1981).

    PubMed  CAS  Google Scholar 

  • Kim, N. S., Hong, C. Y., Park, C. W. and Lim, J. K., An experimental study on the adrenergic effect of higenamine in rabbit cardiovascular system.Kor. Circ. J., 16, 1–18 (1986).

    Article  Google Scholar 

  • Kosuge, T., Yokota, M. and Nagasawa, M., Studies on cardiac principle in aconite roots I. Isolation and structural determination of higenamine.Yakugaku Zasshi., 98, 1370–1375 (1978).

    PubMed  CAS  Google Scholar 

  • Leboeuf, M. and Cave, A., Isolement de L’Higenamine a Partir de L’Annona Squamosa; Interet des resines adsorbantes macromoleculaires en chimie vegetale extractive.J. Nat. Prod., 44, 53–60 (1981).

    Article  CAS  Google Scholar 

  • Park, C. W., Chang, K. C. and Lim, J. K., Effects of higenamine on isolated heart adrenoceptor of rabbit.Arch. Int. Pharmacodyn, 267, 279–288 (1984).

    PubMed  CAS  Google Scholar 

  • Park, S. O., Hong, C. Y., Park, S. W. and Yun-Choi, H. S., Determination of blood concentration of higenamine by high pressure liquid chromatography.Arch. Pharm. Res., 10, 60–66 (1987).

    Article  CAS  Google Scholar 

  • Rozwadowska, M. D., Chrzanowska, M., Brossi, A., Creveling, C. R., Bembenek, M. E. and Abell, C. W., Mammalian alkaloids: O-methylation of (S)- and (R)-dideoxynorlandanosoline-1-carboxylic acid by catechol O-methyl-transferase and identification of a yellow pigment obtained at physiological pH.Helvetica Chimica Acta., 71, 1598–1607 (1988).

    Article  CAS  Google Scholar 

  • Sekine, Y., Creveling, C., Bell, M. and Brossi, M., 46. Mammalian alkaloids: O-methylation of (±)-norcoclaurine-1-carboxylic acid and related isoquionlines including (S)- and (R)-norcoclaurine with14C-labeled S-adenoxyl-L-methionine in presence of mammalian catechol O-methyltransferase.Hervetica Chimica Acta., 73, 426–432 (1990).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ryu, JC., Song, YS., Kim, M. et al. Identification of higenamine and its metabolites in rat by gas chromatography/mass spectrometry. Arch. Pharm. Res. 16, 213–218 (1993). https://doi.org/10.1007/BF02974485

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02974485

Key words

Navigation