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. J Org Chem. 2024 Jul 19;89(14):10388-10392. doi: 10.1021/acs.joc.4c01105. Epub 2024 Jul 2. Construction of the Akuammiline Alkaloid Core Structure via Stereoselective E-Ring Formation. Hashimoto N(1), Taguchi J(1), Kasagi T(1), Arichi N(1), Inuki S(1), Ohno H(1). Author information: (1)Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. Construction of the core structure of akuammiline alkaloids with three-dimensional cage-like structures for their diversity-oriented synthesis was investigated. Extensive exploration centered around the introduction of nitrogen functional groups and construction of the E-ring in an intramolecular or intermolecular manner revealed that a Claisen rearrangement approach involving intramolecular amination provided a common precursor, potentially facilitating divergent access to various types of akuammiline alkaloids. DOI: 10.1021/acs.joc.4c01105 PMID: 38952036 2. J Org Chem. 2024 Apr 5;89(7):4461-4466. doi: 10.1021/acs.joc.3c02619. Epub 2024 Mar 25. Regioselective Synthesis of the Tetrahydrocarbazole Core of Akuammiline Alkaloids via Palladium-Catalyzed Intramolecular Arylation Reaction. Vampugani NMR(1), Shelke AB(1), Singh PB(1), Ahmad A(1), Kapat A(1). Author information: (1)Department of Chemistry, School of Natural Sciences, Shiv Nadar (Institution of Eminence Deemed to be University) Delhi-NCR, Dadri, Chithera, Gautam Buddha Nagar, Greater Noida, Uttar Pradesh 201314, India. Tetrahydrocarbazole is the central core for several biologically active alkaloids, and regioselective synthesis of this core is a challenging task. Herein, we report an efficient strategy for the synthesis of this core involving palladium-catalyzed intramolecular arylation reaction with excellent regioselectivity (>99%) starting from N-phenyl-bromoalkene without having any relocation of double bonds via competitive palladium-catalyzed isomerization reaction. Broad functional group tolerance and exclusive regioselectivity have been observed for meta-substituted halide substrates. Furthermore, this reaction can be scalable on the gram scale. DOI: 10.1021/acs.joc.3c02619 PMID: 38527008 3. Fitoterapia. 2024 Apr;174:105873. doi: 10.1016/j.fitote.2024.105873. Epub 2024 Feb 28. Chemodiverse monoterpene indole alkaloids from Kopsia teoi, inhibitory potential against α-amylase, and their molecular docking studies. Muhammad MT(1), Beniddir MA(2), Phongphane L(3), Abu Bakar MH(4), Hussin MH(5), Awang K(6), Litaudon M(7), Supratman U(8), Azmi MN(9). Author information: (1)Natural Products and Synthesis Organic Research Laboratory (NPSO), School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia; Nursing department, Darbandikhan Technical Institute (DATI), Sulaimani Polytechnic University, Kurdistan Region, Sulaimani 46001, Iraq. (2)Équipe Chimie des Substances Naturelles, BioCIS, Centre National de la Recherche Scientifique (CNRS), Université Paris-Saclay, Orsay, France. (3)Natural Products and Synthesis Organic Research Laboratory (NPSO), School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia. (4)Bioprocess Technology Division, School of Industrial Technology, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia. (5)Materials Technology Research Group (MaTReC), School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia. (6)Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. (7)Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR 01, Univ. Paris-Sud 11, Av. de la Terrasse, 91198 Gif-sur-Yvette, France. (8)Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, 45363 Jatinangor, Indonesia. (9)Natural Products and Synthesis Organic Research Laboratory (NPSO), School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia. Electronic address: mnazmi@usm.my. Diabetes mellitus stands as a metabolic ailment marked by heightened blood glucose levels due to inadequate insulin secretion. The primary aims of this investigative inquiry encompassed the isolation of phytochemical components from the bark of Kopsia teoi, followed by the assessment of their α-amylase inhibition. The phytochemical composition of the K. teoi culminated in the discovery of a pair of new indole alkaloids; which are 16-epi-deacetylakuammiline N(4)-methylene chloride (akuammiline) (1), and N(1)-methoxycarbonyl-11-methoxy-12-hydroxy-Δ14-17-kopsinine (aspidofractinine) (2), together with five known compounds i.e. kopsiloscine G (aspidofractinine) (3), akuammidine (sarpagine) (4), leuconolam (aspidosperma) (5), N-methoxycarbonyl-12-methoxy-Δ16, 17-kopsinine (aspidofractinine) (6), and kopsininate (aspidofractinine) (7). All compounds were determined via spectroscopic analyses. The in vitro evaluation against α-amylase showed good inhibitory activities for compounds 5-7 with the inhibitory concentration (IC50) values of 21.7 ± 1.2, 34.1 ± 0.1, and 30.0 ± 0.8 μM, respectively compared with the reference acarbose (IC50 = 34.4 ± 0.1 μM). The molecular docking outputs underscored the binding interactions of compounds 5-7 ranging from -8.1 to -8.8 kcal/mol with the binding sites of α-amylase. Consequently, the outcomes highlighted the anti-hyperglycemic attributes of isolates from K. teoi. Copyright © 2024 Elsevier B.V. All rights reserved. DOI: 10.1016/j.fitote.2024.105873 PMID: 38417682 [Indexed for MEDLINE] Conflict of interest statement: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. 4. J Org Chem. 2023 Dec 15;88(24):17306-17321. doi: 10.1021/acs.joc.3c02142. Epub 2023 Dec 5. Gold(I)-Catalyzed Cascade Cyclization of Alkynyl Indoles for the Stereoselective Construction of the Quaternary Carbon Center of Akuammiline Alkaloids. Hashimoto N(1), Taguchi J(1), Arichi N(1), Inuki S(1), Ohno H(1). Author information: (1)Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. A gold-catalyzed cyclization reaction of alkynyl-indoles has been developed for the stereoselective construction of the quaternary carbon center of fused indolines. This reaction efficiently produces fused indolines via diastereoselective 6-endo-dig cyclization controlled by a bulky TIPS group, followed by nucleophilic attack of the carboxy group on the resulting imine. The lactone moiety of the fused indoline can be reductively cleaved to produce a tricyclic indoline, which could be useful for the synthesis of akuammiline alkaloids. DOI: 10.1021/acs.joc.3c02142 PMID: 38051730 5. Org Lett. 2023 Oct 6;25(39):7252-7257. doi: 10.1021/acs.orglett.3c02882. Epub 2023 Sep 27. Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles. Li Z(1), Zhang XM(1), Zhang FM(1), Tu YQ(1). Author information: (1)State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China. An asymmetric conjugate addition of aldehydes with o-azaxylylene intermediates (indol-2-ones) from 3-bromooxindoles has been developed. The use of a novel spiro-pyrrolidine (SPD)-derived bifunctional N-sulfonylated amide catalyst is essential for a highly diastereo- and enantioselective transformation to provide a wide array of enantioenriched C3 quaternary oxindoles with structurally diverse β-aldehyde appendages. Further application of this synthetic methodology enables the construction of the tricyclic cores of akuammiline-type alkaloids. DOI: 10.1021/acs.orglett.3c02882 PMID: 37754207