LC-MS analysis of tropane alkaloids from datura innoxia

Foreword

Probably the first interest in alkaloids was medical because many plants were used as drugs for thousands of years owing their effects to the presence of alkaloids.

The tropane alkaloids are secondary plant metabolites found in Solanaceae, Convolvulaceaea, Erhythroxylaceae, and some other plant families. More than 200 tropane alkaloids were isolated from plants up to date. The core structural element of the tropane alkaloids is azabicyclo [3.2.1] octane skeleton.

The effects of tropane alkaloids heavily depend upon dosage and method of application. A mild dosage produces medicinal and healing effects, a moderate dosage can act as an aphrodisiac and high dosages cause hallucinations. Overdoses usually result in a delirious state that can last for days after which little or nothing can be recalled. The last feature of tropane alkaloids is sometimes employed by criminals. Tropane alkaloids containing plants have long been employed by witches and shamans to induce perceptions of altered reality however attempts by ordinary people to achieve a similar state usually end up in very unpleasant experiences accompanied by frightening visions.

Datura species have long been employed as medicinal plants and sacred hallucinogens in Central and Southern America, China, and India. American Indians used fresh datura plant parts and ointment preparations to treat wounds, muscle and joint pain,  rattlesnake and tarantula bites, root was used as an anesthetic, and dried leaves were used to treat asthma, and bronchitis.

Yellow Henbane grows in southern Europe and the Middle East. The medical properties of henbane were praised by Hippocrates. It was one of the most important analgesics of the antiquity. As with all plants containing tropane alkaloids overdoses result in undesired effects.

Mandrake (Mandragora officinarum) can be found in the Eastern Mediterranean region. This plant is surrounded by mystery and is one of the most famous magical plants in history; it is mentioned in the Old Testament. In ancient times, the mandrake was a very important ritual, inebriating, and medical plant. Few plants in ancient times had such a wide spectrum of uses as the mandrake. It was used as a sleeping agent, analgesic, anesthetic, antidote, aphrodisiac, and inebriant. A list of medical indications for which it was used is too long to mention here.

Three plants occurring in Israel, namely, thorn apple, yellow henbane, and mandrake were collected for analysis. 

Instrumental: Orbitrap Discovery hybrid FT mass spectrometer coupled with Accela UPLC (Thermo Scientific). The mass spectrometer was operated in positive ESI mode using scan and MSn (MS2 and MS3) options. Chromatographic separations were carried out using Gemini Hexyl-Phenyl column (2×150 mm, 3µ particle size, Phenomenex) using linear gradients of acetonitrile/water (with 0.1% AcOH). 

References

M. Lounasmaa, T. Tamminen, “The Tropane Alkaloids”, The Alkaloids, Vol. 44, Academic Press. Inc. 1993.