Pyrrolizidine alkaloids from Heliotropium transoxanum Bunge

Document Type : Original paper


1 Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

2 Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.


Background and objectives: The plants belonging to the genus Heliotropium L. (Boraginaceae) are the main sources of toxic pyrrolizidine alkaloids (PAs). In the present study, we have investigated the PAs of the aerial parts of Heliotropium transoxanum Bunge, a perennial species native to Iran. Methods: Silica gel column chromatography and silica gel PTLC were applied for the isolation of PAs present in the total methanol extract of H. transoxanum. The structures of the isolated compounds were identified using 1H-NMR, 13C-NMR and EIMS spectral analyses. Results: Three PAs, heliotrine (1), lasiocarpine (2) and heliotrine N-oxide (3),with known mutagenic and genotoxic properties, were isolated from the aerial parts of H. transoxanum. Conclusion: The results of this study on the presence of toxic PAs in H. transoxanum introduce this herb as a poisonous species and also suggest it as an appropriate source for the isolation of heliotrine and lasiocarpine for further toxicological and pharmacological studies.


[1] Goyal N, Sharma SK. Bioactive phytoconstituents and plant extracts from genus Heliotropium. Int J Green Pharm. 2014; 8(4): 217-225.
[2] El-Shazly A, Wink M. Diversity of pyrrolizidine alkaloids in the Boraginaceae structures, distribution, and biological properties. Diversity. 2014; 6(2): 188-282.
[3] Fu PP, Xia Q, Lin G, Chou MW. Genotoxic pyrrolizidine alkaloids-mechanisms leading to DNA adduct formation and tumorigenicity. Int J Mol Sci. 2002; 3(9): 948-964.
[4] Wiedenfeld H, Edgar J. Toxicity of pyrrolizidine alkaloids to humans and ruminants. Phytochem Rev. 2011; 10(1): 137-151.
[5] Chen T, Mei N, Fu PP. Genotoxicity of pyrrolizidine alkaloids. J Appl Toxicol. 2010; 30(3): 183-196.
[6] Ober D, Kaltenegger E. Pyrrolizidine alkaloid biosynthesis, evolution of a pathway in plant secondary metabolism. Phytochemistry. 2009; 70(15): 1687-1695.
[7] Khatamsaz M. Flora of Iran: Boraginaceae. Tehran: Research Institute of Forests and Rangelands, 2002.
[8] Akramov S, Shadmanov Z, Samatov A, Yunusov SY. Alkaloids of Senecio jacobea, Heliotropium acutiflorum, and H. transoxanum. Chem Nat Compd. 1968; 4(4): 221-222.
[9] Yassa N, Farsam H, Shafiee A, Rustaiyan A. Pyrrolizidine alkaloids form Heliotropium esfandiarii. Planta Med. 1996; 62(6): 583-584.
[10] Farsam H, Yassa N, Sarkhail P, Shafiee A. New pyrrolizidine alkaloids from Heliotropium crassifolium. Planta Med. 2000; 66(4): 389-391.
[11] Shafiee A, Salimi M, Farsam H, Yassa N. Pyrrolizidine alkaloids from Heliotropium dissitiflorum Boiss. DARU. 2002; 10(4): 168-170.
[12] Asibal CF, Gelbaum LT, Zalkow LH. Pyrrolizidine alkaloids from Heliotropium rotundifolium. J Nat Prod. 1989; 52(4): 726-731.
[13] Singh B, Sahu P, Singh S. Antimicrobial activity of pyrrolizidine alkaloids from Heliotropium subulatum. Fitoterapia. 2002; 73(2): 153-155.
[14] Jain SC, Sharma R. Antimicrobial activity of pyrrolizidine alkaloids from Heliotropium ellipticum. Chem Pharm Bull. 1987; 35(8): 3487-3489.
[15] Singh B, Sahu P, Jain S, Singh S. Antineoplastic and antiviral screening of pyrrolizidine alkaloids from Heliotropium subulatum. Pharm Biol. 2002; 40(8): 581-586.