Cell-suspension cultures of pyrrolizidinealkaloid-producing species selectively take up and accumulate senecionine (sen) and its N-oxide (sen-Nox). Cultures established from non-alkaloid-producing species are unable to accumulate the alkaloids. The uptake and accumulation of 14C-labelled alkaloids w
Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides inSenecio vulgarisL.
β Scribed by Thomas Hartmann; Adelheid Ehmke; Udo Eilert; Kirsten Borstel; Claudine Theuring
- Book ID
- 104752897
- Publisher
- Springer-Verlag
- Year
- 1989
- Tongue
- English
- Weight
- 1006 KB
- Volume
- 177
- Category
- Article
- ISSN
- 0032-0935
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β¦ Synopsis
14C-Labelled alkaloid precursors (arginine, putrescine, spermidine) fed to Senecio vulgaris plants via the root system were rapidly taken up and efficiently incorporated into the pyrrolizidine alkaloid senecionine N-oxide (sen-Nox) with total incorporations of 3-6%. Considerable amounts of labelled sen-Nox were translocated into the shoot and were directed mainly into the inflorescences, the major sites of pyrrolizidine-alkaloid accumulation. Detached shoots of S. vulgaris were unable to synthesize pyrrolizidine alkaloids, indicating that the roots are the site of their biosynthesis. Further evidence was obtained from studies with in-vitro systems established from S. vulgaris: root cultures were found to synthesize pyrrolizidine alkaloids but not cell-suspension cultures, tumor cultures or shoot-like teratomas obtained by transformation with Agrobacterium tumefaciens. Studies on transport of [14C]sen-Nox, which was fed either to detached shoots or to the root system of intact plants, indicate that the alkaloid N-oxide does not simply follow the transpiration stream but is specifically channelled to the target tissues such as epidermal stem tissue and flower heads. Exogenously applied [14C]senecionine is rapidly N-oxidized. If the phloem path along the stem is blocked by a "steam girdle" translocation of labelled sen-Nox is blocked as well. Root-derived sen-Nox accumulated below the girdle and only trace amounts were found in the tissues above. It is most likely that the root-toshoot transport of sen-Nox occurs mainly if not exclusively via the phloem. In accordance with previous studies the polar, salt-like N-oxides, which are often considered to be artifacts, were found
π SIMILAR VOLUMES
Sceleratine [l] and its N-oxide [Z] have been isolated from Senecio ZatifoZius DC and their structures determined by spectroscopic and chemical methods and X-ray crystal= lography. Recently we isolated the N-oxide of merenskine [3],' a new pyrrolizidine alkaloid N-oxide from Senecio Zatifolius DC.'
Pyrrolizidine alkaloid (PA)-containing plants are widely distributed in the world. PAs are hepatotoxic, affecting livestock and humans. PA N-oxides are often present together with PAs in plants and also exhibit hepatotoxicity but with less potency. HPLC-MS is generally used to analyze PA-containing