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. Angew Chem Int Ed Engl. 2023 Sep 11;62(37):e202307286. doi: 10.1002/anie.202307286. Epub 2023 Aug 4. A Homo-Mannich Reaction Strategy Enables Collective Access to Ibophyllidine, Aspidosperma, Kopsia, and Melodinus Alkaloids. Jiang D(1), Tang P(1), Xiong H(1), Lei S(1), Zhang Y(1), Zhang C(1), He L(1), Qiu H(1), Zhang M(1). Author information: (1)Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing 401331, China. We report here a homo-Mannich reaction of cyclopropanol with an iminium ion, generated by an asymmetric allylic dearomatization of indole, to construct a tricyclic hydrocarbazole core, which is shared by a variety of monoterpenoid indole alkaloids across families. Through this approach, an all-carbon quaternary stereogenic center as well as an allyl and a ketone group were installed. Using this functionalized hydrocarbazole as the structural platform, D ring and E rings of different sizes (i.e., five-, six-, and seven-membered) were successively or simultaneously assembled, leading to a collective asymmetric synthesis of seven alkaloids belonging to the ibophyllidine, Aspidosperma, Kopsia, and Melodinus alkaloid families. © 2023 Wiley-VCH GmbH. DOI: 10.1002/anie.202307286 PMID: 37490018 [Indexed for MEDLINE] 2. J Ethnopharmacol. 2022 Mar 1;285:114848. doi: 10.1016/j.jep.2021.114848. Epub 2021 Nov 17. Anti-inflammatory and analgesic monoterpenoid indole alkaloids of Kopsia officinalis. Jin Q(1), Zhao YL(2), Liu YP(3), Zhang RS(1), Zhu PF(1), Zhao LQ(1), Qin XJ(4), Luo XD(5). Author information: (1)State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China. (2)Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China. (3)State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China. (4)State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China. Electronic address: qinxujie@mail.kib.ac.cn. (5)State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China; Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China. Electronic address: xdluo@mail.kib.ac.cn. ETHNOPHARMACOLOGICAL RELEVANCE: "Ya gai", an important part of Dai medical theory, is traditionally recognized as an antidote. Kopsia officinalis Tsiang et P. T. Li is a "Ya gai" related medicine and has been widely used by Dai people for the treatment of pain and inflammation. Previous literature on title species suggested that monoterpenoid indole alkaloids (MIAs) could be its main bioactive components. However, the specific bioactive ingredients for inflammation-related treatment are still unrevealed, which inspired us to conduct a phytochemical and pharmacological investigation related to its traditional use. AIM OF THE STUDY: To support the traditional use of K. officinalis by assessing the anti-inflammatory and analgesic effects of its purified MIAs. MATERIAL AND METHODS: Compounds were isolated and purified from the barks and leaves of K. officinalis using diverse chromatographic methods. The structures were established by means of extensive spectroscopic analyses and quantum computational technique. The anti-inflammatory activities of the purified MIAs were evaluated in vitro based on the suppression of lipopolysaccharide-activated inflammatory mediators (COX-2, IL-1β, and TNF-α) in RAW 264.7 macrophage cells. Anti-inflammatory and analgesic activities in vivo were assessed with carrageenan-induced paw edema and acetic acid-stimulated writhing in mice models. RESULTS: 23 MIAs including four new compounds were obtained and structurally established. Most of isolates showed significant anti-inflammatory effects in vitro by inhibiting inflammatory mediators (COX-2, IL-1β, and TNF-α). Further pharmacological evaluation in vivo revealed that 12-hydroxy-19(R)-hydroxy-ibophyllidine (1) and 11,12-methylenedioxykopsinaline N4-oxide (5) remarkably decreased the number of writhing, while kopsinic acid (8), (-)-kopsinilam (12), and normavacurine-21-one (20) significantly relieved paw edema, respectively, even better than the positive control aspirin. CONCLUSIONS: The in vitro and in vivo findings supported the traditional use of K. officinalis with respect to its anti-inflammatory and analgesic effect, as well as provided potent bioactive MIAs for further chemical modification and pharmacological investigation. Copyright © 2021. Published by Elsevier B.V. DOI: 10.1016/j.jep.2021.114848 PMID: 34798159 [Indexed for MEDLINE] 3. Nat Prod Rep. 2021 Apr 1;38(4):693-701. doi: 10.1039/d0np00036a. Epub 2020 Oct 19. Synthetic strategies for the ibophyllidine alkaloids. Reuß F(1), Heretsch P. Author information: (1)Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany. philipp.heretsch@fu-berlin.de. Covering: 1975-2020The ibophyllidine alkaloids are unique pyrroloindole alkaloids exhibiting a five-membered D-ring in contrast to the six-membered D-ring of the more common Aspidosperma and Strychnos alkaloids. This structural feature has made them sought-after targets for organic chemists as well as for the elucidation of their biosynthesis. Beginning with the first and eponymous member ibophyllidine, isolation and structure determination is discussed. The main focus of this review are the diverse chemical approaches towards the ibophyllidines in context with their respective biosynthesis. The often employed Diels-Alder reaction strategy, two other named reaction-based strategies and the most recent enantioselective strategies are presented and compared. DOI: 10.1039/d0np00036a PMID: 33074277 [Indexed for MEDLINE] 4. Org Lett. 2020 May 15;22(10):3956-3959. doi: 10.1021/acs.orglett.0c01242. Epub 2020 May 5. Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction. Reuß F(1), Heretsch P(1). Author information: (1)Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany. A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises a [2 + 2]-photocycloaddition, a Ramberg-Bäcklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids. DOI: 10.1021/acs.orglett.0c01242 PMID: 32368923 5. Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13436-13440. doi: 10.1002/anie.201605503. Epub 2016 Sep 23. Expeditious and Divergent Total Syntheses of Aspidosperma Alkaloids Exploiting Iridium(I)-Catalyzed Generation of Reactive Enamine Intermediates. Tan PW(1)(2), Seayad J(3), Dixon DJ(4). Author information: (1)Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. (2)Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical Grove, Neuros, #07-01, Singapore, 138665, Singapore. (3)Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical Grove, Neuros, #07-01, Singapore, 138665, Singapore. jayasree_seayad@ices.a-star.edu.sg. (4)Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. darren.dixon@chem.ox.ac.uk. A new approach for the divergent total syntheses of (±)-vincaminorine, (±)-N-methylquebrachamine, (±)-quebrachamine, (±)-minovine and (±)-vincadifformine, each in less than 10 linear steps starting from a single δ-lactam building block, is reported. Key to our route design is the late-stage generation of reactive enamine functionality from stable indole-linked δ-lactams via a highly chemoselective iridium(I)-catalyzed reduction. The efficiently formed secodine intermediates subsequently undergo either a formal Diels-Alder cycloaddition or a competitive Michael addition/reduction to access aspidosperma-type alkaloids in excellent diastereoselectivities. Product selectivity could be controlled by changing the indole N-protecting group in the reductive cyclization precursors. An asymmetric variant of this synthetic strategy for the synthesis of (+)-20-epi-ibophyllidine is also described. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. DOI: 10.1002/anie.201605503 PMID: 27659476 [Indexed for MEDLINE]