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. ACS Omega. 2023 Jul 18;8(30):27190-27205. doi: 10.1021/acsomega.3c02464. eCollection 2023 Aug 1. Investigation of Small-Molecule Constituents in Voacanga africana Seeds and Mapping of Their Spatial Distributions Using Laser Ablation Direct Analysis in Real-Time Imaging-Mass Spectrometry (LADI-MS). Coon AM(1), Musah RA(1). Author information: (1)Department of Chemistry, University at Albany, State University of New York, 1400 Washington Ave, Albany, New York 12222, United States. Plant seeds are a renewable resource that can furnish access to medicinal natural products that can only otherwise be isolated from aerial or root parts, the harvest of which may be destructive to the plant or threaten its viability. However, optimization of the isolation of such compounds from seeds would be greatly assisted if the spatial distribution of the molecules of interest within the plant tissue were known. For example, iboga alkaloids that hold promise for the treatment of opioid use disorder are typically isolated from the leaves, bark, or roots of Tabernanthe or Voacanga spp. trees, but it would be more environmentally sustainable to isolate such compounds from their seeds. Here, we leveraged the unique capabilities of the ambient mass spectral imaging technique termed laser ablation direct analysis in real-time imaging-mass spectrometry (LADI-MS) to reveal the spatial distributions of a range of molecules, including alkaloids within V. africana seeds. In addition to six compounds previously reported in these seeds, namely, tetradecanoic acid, n-hexadecanoic acid, (Z,Z)-9,12-octadecadienoic acid, (Z)-9-octadecenoic acid, octadecanoic acid, and Δ14-vincamine, an additional 31 compounds were newly identified in V. africana seeds. The compound classes included alkaloids, terpenes, and fatty acids. The ion images showed that the fatty acids were localized in the embryo of the seed. The alkaloids, which were mainly localized in the seed endosperm, included strictamine, akuammidine, polyneruidine, vobasine, and Δ14-vincamine. This information can be exploited to enhance the efficiency of secondary metabolite isolation from V. africana seeds while eliminating the destruction of other plant parts. © 2023 The Authors. Published by American Chemical Society. DOI: 10.1021/acsomega.3c02464 PMCID: PMC10399170 PMID: 37546641 Conflict of interest statement: The authors declare no competing financial interest. 2. Angew Chem Int Ed Engl. 2021 May 3;60(19):10603-10607. doi: 10.1002/anie.202101752. Epub 2021 Apr 6. Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach. Gao B(1), Yao F(1), Zhang Z(1), Ding H(1)(2). Author information: (1)Department of Chemistry, Zhejiang University, Hangzhou, 310058, China. (2)State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China. A bioinspired photo-Fries/imine capture cascade reaction was developed in continuous-flow mode, which facilitated the rapid construction of a series of diversely functionalized 2,7-heterocycle-fused tetrahydrocarbazoles, the ubiquitous core structures embedded in strychnos and akuammiline-type monoterpene indole alkaloids. The synthetic utility of this novel method has been preliminarily explored by the first total synthesis of (+)-alsmaphorazine C and formal synthesis of (+)-strictamine in a concise and efficient manner. © 2021 Wiley-VCH GmbH. DOI: 10.1002/anie.202101752 PMID: 33660898 3. Org Lett. 2021 Feb 19;23(4):1355-1360. doi: 10.1021/acs.orglett.1c00018. Epub 2021 Feb 1. Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine. Jarret M(1), Abou-Hamdan H(1), Kouklovsky C(1), Poupon E(2), Evanno L(2), Vincent G(1). Author information: (1)Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Saclay, CNRS, 91405 Orsay, France. (2)Biomolécules: Conception, Isolement et Synthèse (BioCIS), Université Paris-Saclay, CNRS, 92296 Châtenay-Malabry, France. Toward the mavacurane and akuammilane monoterpene indole alkaloids, we developed divergent oxidative couplings between the indole nucleus (at N1 or C7) and the C16-malonate of a common tricyclic model related to strictosidine according to a biosynthetic hypothesis postulated by Hesse and Schmid. These oxidative cyclizations led selectively to the formation of the N1-C16 bond of pleiocarpamine or to the C7-C16 bond of strictamine. We were then able to obtain the scaffold of talbotine. DOI: 10.1021/acs.orglett.1c00018 PMID: 33522824 [Indexed for MEDLINE] 4. Angew Chem Int Ed Engl. 2019 Apr 23;58(18):6059-6063. doi: 10.1002/anie.201901074. Epub 2019 Mar 5. Asymmetric Total Syntheses of the Akuammiline Alkaloids (-)-Strictamine and (-)-Rhazinoline. Li W(1), Chen Z(2), Yu D(1), Peng X(1), Wen G(1), Wang S(1), Xue F(1), Liu XY(1), Qin Y(1). Author information: (1)Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China. (2)School of Pharmaceutic Science, Chongqing University, Chongqing, 401331, P. R. China. Strictamine and rhazinoline are representative methanoquinolizidine-containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji-Trost allylation, a palladium- or nickel-mediated cyclization, and a late-stage intramolecular N-alkylation reaction. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. DOI: 10.1002/anie.201901074 PMID: 30775833 [Indexed for MEDLINE] 5. J Am Chem Soc. 2018 May 23;140(20):6483-6492. doi: 10.1021/jacs.8b03404. Epub 2018 May 15. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies. Picazo E(1), Morrill LA(1), Susick RB(1), Moreno J(1), Smith JM(1), Garg NK(1). Author information: (1)Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States. The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2( S)-cathafoline, (+)-akuammiline, and (-)-Ψ-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-Ψ-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof. DOI: 10.1021/jacs.8b03404 PMCID: PMC6085837 PMID: 29694031 [Indexed for MEDLINE] Conflict of interest statement: The authors declare no competing financial interest.