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Planta Med 2022; 88(13): 1209-1222
DOI: 10.1055/a-1671-5525
Natural Product Chemistry and Analytical Studies
Original Papers

Cyanogenesis in Aralia spinosa (Araliaceae)[ # ]

Matthias Lechtenberg 
University of Münster, Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Münster, Germany
,
Jandirk Sendker
University of Münster, Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Münster, Germany
,
Lisa Kastner
University of Münster, Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Münster, Germany
,
Andreas Hensel 
University of Münster, Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Münster, Germany
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Abstract

A systematic survey of Aralia spinosa (Araliaceae), covering an entire growing season and including aboveground organs at various developmental stages, revealed that only about half of all samples collected showed cyanogenesis. Cyanogenesis was detected in inflorescences and leaves but is apparently restricted to certain harvest times or developmental stages. The structurally unusual triglochinin, characterized by a hex-2-enedioic acid partial structure, was the only cyanogenic glycoside detected. This is the first description of triglochinin in this species and in the family of Araliaceae. Triglochinin is biogenetically derived from tyrosine, which is in good agreement with the few cyanogenic glycosides previously detected in members of the Araliaceae family. Triglochinin was identified, characterized, and quantified by modern chromatographic methods, and the amount of enzymatically releasable hydrocyanic acid was determined qualitatively and quantitatively. Two isomers of triglochinin were detected chromatographically at minor levels. The isomeric pattern agreed well with literature data from other triglochinin-containing plants. This was confirmed in the two species, Triglochin maritima and Thalictrum aquilegiifolium, which were comparatively studied. In the case of A. spinosa, inflorescence buds harvested in July showed the highest content of triglochinin, just under 0.2% on a dry weight basis. The detection of triglochinin adds to the knowledge of toxicological properties and the dereplication of U(H)PLC/MS² data provides a comprehensive phytochemical profile of A. spinosa.

Key words

Aralia spinosa - Araliaceae - cyanogenesis - triglochinin

# Dedicated to Prof. Dr. A. Nahrstedt (*1940 †2016) on the 5th anniversary of his death. He made a major scientific contribution to the knowledge of cyanogenic glycosides in plants and insects.


Supporting Information

    Color photographs of A. spinosa (Fig. 1Sa/1Sb), Feigl-Anger tests of A. spinosa samples (Fig. 2S), TLC of CNglcs and A. spinosa, (Fig. 3S), UV chromatograms of all A. spinosa samples (Fig. 4S), UV and MS spectra of A. spinosa sample #10B (Fig. 5S), and a mass list of “dissect compounds” of sample #10B are available as Supporting Information.

  • Supporting Information


Publication History

Received: 03 May 2021

Accepted after revision: 11 October 2021

Article published online:
16 November 2021

© 2021. Thieme. All rights reserved.

Georg Thieme Verlag KG
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