Lysergyl-alanine
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| Other names | Lysergylalanine |
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| Formula | C19H21N3O3 |
| Molar mass | 339.395 g·mol−1 |
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Lysergyl-alanine, or lysergylalanine, is an ergot alkaloid and biosynthetic intermediate of other ergot alkaloids like ergine (lysergic acid amide; LSA), lysergic acid hydroxyethylamide (LSH), and ergometrine.[1][2][3][4] It has been reported to occur in concentrations 4-fold lower than those of ergine in Epichloë-infected ryegrass leaves.[5] The alkaloid has also been detected in Argyreia nervosa (Hawaiian baby woodrose) seeds.[6][7] Lysergyl-alanine was first described in the scientific literature by 1969.[4]
See also
[edit]References
[edit]- ↑ Keller U (8 April 1999). "Biosynthesis of Ergot Alkaloids" (PDF). Ergot: The Genus Claviceps. CRC Press. pp. 109–179. doi:10.1201/9780203304198-12. ISBN 978-0-429-21976-4.
- ↑ Panaccione DG (April 2023). "Derivation of the multiply-branched ergot alkaloid pathway of fungi". Microbial Biotechnology. 16 (4): 742–756. doi:10.1111/1751-7915.14214. PMC 10034635. PMID 36636806.
The lysergic acid amides ergonovine and LAH are derived from the intermediate lysergyl-alanine formed on a complex of nonribosomal peptide synthetases Lps2 and Lps3 (Figure 6). In addition to ergonovine and LAH, free lysergyl-alanine (liberated from the peptide synthetase without modification) and ergine (the simple amide of lysergic acid) accumulate in some fungi. Critical enzymes in the pathway from lysergic acid to lysergic acid amides include a combination of Lps2 and Lps3 for the synthesis of ergonovine from lysergic acid and alanine (Ortel & Keller, 2009) along with enzymes EasO and EasP to convert the lysergyl-alanine intermediate into LAH (Britton et al., 2022; Steen et al., 2021). All fungi that produce LAH have the capacity to produce ergonovine from the same lysergyl-alanine precursor; however, in all cases, the relative abundance of LAH compared to ergonovine is heavily shifted in favour of LAH (Table 2). Ergine can arise from spontaneous hydrolysis of LAH (Flieger et al., 1982; Kleinerova & Kybal, 1973; Leadmon et al., 2020; Figure 6) and other lysergic acid amides (Panaccione et al., 2003).
- ↑ Fabian SJ, Jones AM, Fuss JL, Panaccione DG (2026). "A single lysergyl peptide synthetase assembles lysergic acid amides in Aspergillus species". PLOS ONE. 21 (6) e0350650. doi:10.1371/journal.pone.0350650. PMC 13278392. PMID 42313736.
The agriculturally and pharmaceutically important lysergic acid amides ergonovine and lysergic acid α-hydroxyethylamide (LAH) are synthesized from a lysergyl-alanine precursor. In ergot-alkaloid producing fungi of the family Clavicipitaceae, lysergylalanine is assembled and then reduced to ergonovine by a complex of two monomodular nonribosomal peptide synthetases: lysergyl peptide synthetase 2 (Lps2) and Lps3.
- 1 2 Basmadjian G, Floss HG, Gröger D, Erge D (1969). "Biosynthesis of ergot alkaloids. Lysergylalanine as precursor of amide-type alkaloids". J. Chem. Soc. D. 0 (8): 418–419. doi:10.1039/C29690000418. ISSN 0577-6171.
- ↑ Panaccione DG (October 2005). "Origins and significance of ergot alkaloid diversity in fungi". FEMS Microbiology Letters. 251 (1): 9–17. Bibcode:2005FEMML.251....9P. doi:10.1016/j.femsle.2005.07.039. PMID 16112823.
- ↑ Chen W, De Wit-Bos L (2020). Risk assessment of Argyreia nervosa (PDF) (Report). doi:10.21945/rivm-2019-0210.
- ↑ Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW (April 2015). "Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high". Forensic Science International. 249: 281–293. doi:10.1016/j.forsciint.2015.02.011. PMID 25747328.
On the other hand, methylergometrine, methysergide, and lysergylalanine were detected, which have not yet been reported as compounds of Argyreia nervosa seeds. [...] The fragmentation pattern and the suggested fragment formation indicated lysergylalanine as precursor molecule. Until now, lysergylalanine has not been reported to be a component of Argyreia nervosa seeds. Nevertheless, the presence of lysergylalanine in Argyreia nervosa appears plausible as lysergylalanine is considered to be a precursor of amide-type alkaloids like, e.g. ergometrine during the ergot alkaloid biosynthesis [34–36].
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