Cucurbitacin - the bitter end – University of Copenhagen

NaToxAq > Toxin of the week > Cucurbitacin

19 November 2018

Cucurbitacin - the bitter end

Natural toxin

Despite toxic, cucurbitacin is being studied as a drug for its pharmacological potential, due to its antidiabetic and anticancer effects

Cucurbitacin is a term that gather many compounds mainly produced by members of the Cucurbitaceae family, such as cucumber and pumpkin. Compounds range from Cucurbitacin A to T - depending on when they were discovered - and are chemically classified as triterpenes [1].

Structure of cucurbitacin 

These compounds produce a bitter taste in different parts of the plants [2]. All parts of the plant are susceptible of carrying cucurbitacines, while some species typically present it only on the roots. In some parts of Asia, this bitterness is exploited in traditional dishes prepared with bitter gourd (Momordica charantia). 

There has been some cases of poisoning for cucurbitacin in France, where hair loss cases were reported [3]. Other symptoms of poisoning can encompass diarrhea, vomiting, gastrointestinal bleeding, and hypotension [4]. Fortunately, its poisoning rarely ends in a fatal outcome, for its bitterness serve as an alarm. Moreover, cucurbitacin is being studied as a drug for its pharmacological potential, due to its antidiabetic and anticancer effects [5], [6].

SMILES (Cucurbitacin B): CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O

Pictures:

References:

  1.  Gry, I. Søborg, and H. Christer Andersson, Cucurbitacins in plant food. Nordic Council of Ministers, 2006.
  2. E. Teuscher, und Lindequist, U.(eds): Biogene Gifte-Biologie, Chemie, Pharmakologie. Gustav Fischer Verlag, 1994.
  3. P. Assouly, “Hair Loss Associated With Cucurbit Poisoning,” JAMA Dermatol., vol. 154, no. 5, pp. 617–618, May 2018.
  4. C. H. Ho, M. G. Ho, S.-P. Ho, and H. H. Ho, “Bitter Bottle Gourd (Lagenaria siceraria) Toxicity,” J. Emerg. Med., vol. 46, no. 6, pp. 772–775, Jun. 2014.
  5. U. Kaushik, V. Aeri, and S. R. Mir, “Cucurbitacins – An insight into medicinal leads from nature,” Pharmacogn. Rev., vol. 9, no. 17, pp. 12–18, 2015.
  6. A. A. Alghasham, “Cucurbitacins – A Promising Target for Cancer Therapy,” Int. J. Health Sci., vol. 7, no. 1, pp. 77–89, Jan. 2013.