Worldwide, there are plants known as psychoactive plants that naturally contain psychedelic active components. They have a high concentration of neuroprotective substances that can interact with the nervous system to produce psychedelic effects. Despite these plants' hazardous potential, recreational use of them is on the rise because of their psychoactive properties. Early neuroscience studies relied heavily on psychoactive plants and plant natural products (NPs), and both recreational and hazardous NPs have contributed significantly to the understanding of almost all neurotransmitter systems. Worldwide, there are many plants that contain psychoactive properties, and people have been using them for ages. Psychoactive plant compounds may significantly alter how people perceive the world.
1. Forensic Sci Int. 2015 Apr;249:281-93. doi: 10.1016/j.forsciint.2015.02.011. Epub 2015 Feb 19. Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Paulke A(1), Kremer C(2), Wunder C(2), Wurglics M(3), Schubert-Zsilavecz M(3), Toennes SW(2). Author information: (1)Institute of Legal Medicine, University of Frankfurt/Main, Kennedyallee 104, D-60596 Frankfurt/Main, Germany. Electronic address: paulke@em.uni-frankfurt.de. (2)Institute of Legal Medicine, University of Frankfurt/Main, Kennedyallee 104, D-60596 Frankfurt/Main, Germany. (3)Institute for Pharmaceutical Chemistry, University of Frankfurt/Main, Max-von-Laue-Str. 9, D-60438 Frankfurt/Main, Germany. Seeds from the Hawaiian Baby Woodrose Argyreia nervosa of different origin and labelling and with allegedly high levels of ergot alkaloids were analysed using high performance liquid chromatography-high resolution mass spectrometry (HPLC-HRMS/MS) technique. Lysergic acid amide (LSA), ergometrine, lysergol/elymoclavine/setoclavine, chanoclavine, lysergic acid and their respective stereoisomers were identified as well as penniclavine and lysergic acid α-hydroxyethylamide. In addition, methylergometrine, methysergide, and lysergylalanine were detected, some high molecular weight ergot alkaloid derivatives and hydroxyalanine derived ergopeptide fragments were detected indicating the presence of ergopeptides in the seeds. The results of the study demonstrate that the content of ergot alkaloids in Argyreia nervosa seeds depends on the quality of the material. For a consumer the quality of the seeds is unforeseeable. For the toxicological expert it is essential to investigate not only the identity of such a confiscated seed material, but also the various ergot alkaloid constituents to assess the hazardous nature and the toxic potential of the material. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved. DOI: 10.1016/j.forsciint.2015.02.011 PMID: 25747328 [Indexed for MEDLINE] 2. Forensic Sci Int. 2014 Sep;242:62-71. doi: 10.1016/j.forsciint.2014.06.025. Epub 2014 Jun 30. Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products. Paulke A(1), Kremer C(2), Wunder C(2), Wurglics M(3), Schubert-Zsilavecz M(3), Toennes SW(2). Author information: (1)Institute of Legal Medicine, University of Frankfurt/Main, Kennedyallee 104, D-60596 Frankfurt/Main, Germany. Electronic address: paulke@em.uni-frankfurt.de. (2)Institute of Legal Medicine, University of Frankfurt/Main, Kennedyallee 104, D-60596 Frankfurt/Main, Germany. (3)Institute for Pharmaceutical Chemistry, University of Frankfurt/Main, Max-von-Laue-Str. 9, D-60438 Frankfurt/Main, Germany. Nowadays psychoactive plants marketed as "legal highs" or "herbal highs" increase in popularity. One popular "legal high" are the seeds of the Hawaiian baby woodrose Argyreia nervosa (Synonym: Argyreia speciosa, Convolvolus speciosus). At present there exists no study on A. nervosa seeds or products, which are used by consumers. The quality of commercial available A. nervosa seeds or products is completely unknown. In the present study, a commercial available seed collection (five seeds labeled "flash of inspiration", FOI) was analyzed for ergot alkaloids together with an A. nervosa product (two preparations in capsule form, "druids fantasy", DF). For this purpose high performance liquid chromatography high resolution tandem mass spectrometry (HPLC-HRMS/MS) technique was employed. Besides the major ingredients such as lysergic acid amide (LSA) and ergometrine the well known A. nervosa compounds lysergol/elymoclavine/setoclavine, chanoclavine and the respective stereoisomers were detected in DF, while only LSA and ergometrine could be found in FOI. In addition, in DF lysergic acid was found, which has not been reported yet as ingredient of A. nervosa. In both products, DF as well as in FOI, LSA/LSA-isomers were dominant with 83-84% followed by ergometrine/ergometrinine with 10-17%. Therefore, LSA, followed by ergometrine/ergometrinine, could be confirmed to be the main ergot alkaloids present in A. nervosa seeds/products whereas the other ergot alkaloids seemed to be of minor importance (less than 6.1% in DF). The total ergot alkaloid amounts varied considerably between DF and FOI by a factor of 8.6 as well as the LSA concentration ranging from 3 μg (lowest amount in one FOI seed) to approximately 34 μg (highest amount in one DF capsule). Among the FOI seeds, the LSA concentration varied from approximately 3-15 μg per seed. Thus, the quality/potency of seeds/preparations depends on the amount of ergot alkaloids and the intensity of an expected trip is totally unpredictable. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved. DOI: 10.1016/j.forsciint.2014.06.025 PMID: 25036782 [Indexed for MEDLINE] 3. Appl Environ Microbiol. 2010 Jun;76(12):3898-903. doi: 10.1128/AEM.02914-09. Epub 2010 Apr 30. An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways. Coyle CM(1), Cheng JZ, O'Connor SE, Panaccione DG. Author information: (1)West Virginia University, Division of Plant & Soil Sciences, Genetics and Developmental Biology Program, Morgantown, West Virginia 26506-6108, USA. Ergot fungi in the genus Claviceps and several related fungal groups in the family Clavicipitaceae produce toxic ergot alkaloids. These fungi produce a variety of ergot alkaloids, including clavines as well as lysergic acid derivatives. Ergot alkaloids are also produced by the distantly related, opportunistic human pathogen Aspergillus fumigatus. However, this fungus produces festuclavine and fumigaclavines A, B, and C, which collectively differ from clavines of clavicipitaceous fungi in saturation of the last assembled of four rings in the ergoline ring structure. The two lineages are hypothesized to share early steps of the ergot alkaloid pathway before diverging at some point after the synthesis of the tricyclic intermediate chanoclavine-I. Disruption of easA, a gene predicted to encode a flavin-dependent oxidoreductase of the old yellow enzyme class, in A. fumigatus led to accumulation of chanoclavine-I and chanoclavine-I-aldehyde. Complementation of the A. fumigatus easA mutant with a wild-type allele from the same fungus restored the wild-type profile of ergot alkaloids. These data demonstrate that the product of A. fumigatus easA is required for incorporation of chanoclavine-I-aldehyde into more-complex ergot alkaloids, presumably by reducing the double bond conjugated to the aldehyde group, thus facilitating ring closure. Augmentation of the A. fumigatus easA mutant with a homologue of easA from Claviceps purpurea resulted in accumulation of ergot alkaloids typical of clavicipitaceous fungi (agroclavine, setoclavine, and its diastereoisomer isosetoclavine). These data indicate that functional differences in the easA-encoded old yellow enzymes of A. fumigatus and C. purpurea result in divergence of their respective ergot alkaloid pathways. DOI: 10.1128/AEM.02914-09 PMCID: PMC2893504 PMID: 20435769 [Indexed for MEDLINE] 4. J Am Chem Soc. 2001 Jun 27;123(25):5918-24. doi: 10.1021/ja010577w. Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine. Liras S(1), Lynch CL, Fryer AM, Vu BT, Martin SF. Author information: (1)Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712, USA. Concise syntheses of the Ergot alkaloids rugulovasine A (3a), rugulovasine B (3b), and setoclavine (2) have been completed by strategies that feature inter- and intramolecular vinylogous Mannich reactions as the key steps. Thus, the first synthesis of 3a,b commenced with the conversion of the known indole 17 into 24 via the addition of the furan 22 to the iminium ion 21, which was generated in situ from the aldehyde 19. Cyclization of 24 by a novel S(RN)1 reaction followed by removal of the N-benzyl group furnished a mixture (1:2) of 3a and 3b. In an alternative approach to these alkaloids, the biaryl 35 was reduced with DIBAL-H to give an intermediate imine that underwent spontaneous cyclization via an intramolecular vinylogous Mannich addition to provide 36a,b. N-Methylation of the derived benzyl carbamates 37a,b followed by global deprotection gave a mixture (2:1) of rugulovasines A and B (3a,b). Setoclavine (2) was then prepared from the biaryl 41 using a closely related intramolecular vinylogous Mannich reaction to furnish the spirocyclic lactones 42a,b. These lactones were subsequently transformed by hydride reduction and reductive methylation into the ergoline derivatives 43a,b, which were in turn converted into 2 by deprotection and solvolytic 1,3-rearrangement of the allylic hydroxyl group. DOI: 10.1021/ja010577w PMID: 11414824 [Indexed for MEDLINE] 5. J Pharm Sci. 1975 Feb;64(2):343-4. doi: 10.1002/jps.2600640237. Conversion of agroclavine to setoclavine and isosetoclavine in cell-free extracts from Claviceps sp. SD 58 and in a thioglycolate-iron (II) system. Bajwa RS, Anderson JA. Agroclavine was converted to setoclavine and isosetoclavine in crude extracts from Claviceps sp. SD 58. The ratio of setoclavine to isosetoclavine was 0.95. The conversion with boiled crude extract was 68% of the conversion with unboiled extract. In a thioglycolate-iron (II) system at 40 degrees for 5 hr, 45.5% of agroclavine was converted to setoclavine and isosetoclavine. At 70 degrees for 4 hr in the thioglycolate-iron (II) system, 4% of 4-dimethylallyltryptophan was converted to clavicipitic acid. DOI: 10.1002/jps.2600640237 PMID: 236378 [Indexed for MEDLINE]