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 Am Chem Soc. 2022 Aug 24;144(33):15033-15037. doi: 10.1021/jacs.2c06981. Epub 2022 Aug 10. Total Synthesis of Mollanol A. Wang Y(1), Zhao R(1), Yang M(1). Author information: (1)State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province 730000, China. Mollanol A is the first isolated member of the mollane-type grayanoids which possesses an unprecedented C-nor-D-homograyanane carbon skeleton and an 5,8-epoxide. Due to its transcriptional activation effects on the Xbp1 upstream promoters in different cell types, it has a potential therapeutic effect on inflammatory bowel disease. Here we report the first total synthesis of mollanol A, which constitutes a 15-step synthesis from commercially available materials via a convergent strategy. The synthesis involves an InCl3-catalyzed Conia-ene cyclization reaction to construct the bicyclo[3.2.1]octane moiety and a vinylogous aldol reaction/intramolecular oxa-Michael addition sequence to rapidly assemble the oxa-bicyclo[3.2.1] core. DOI: 10.1021/jacs.2c06981 PMID: 35948064 [Indexed for MEDLINE] 2. Bioorg Chem. 2021 Jun;111:104870. doi: 10.1016/j.bioorg.2021.104870. Epub 2021 Mar 29. Structurally diverse diterpenoids with eight carbon skeletons from Rhododendron micranthum and their antinociceptive effects. Jin P(1), Zheng G(1), Yuan X(1), Ma X(1), Feng Y(1), Yao G(2). Author information: (1)Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. (2)Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: gyap@mail.hust.edu.cn. Seventeen diterpenoids (1-17), classified into eight diverse carbon skeleton types, grayanane (1, 2, and 12), micranthane (3, 4, and 13), mollane (5-7 and 14), 1,5-seco-grayanane (8), kalmane (9-11), 1,5-seco-kalmane (15), A-homo-B-nor-ent-kaurane (16), and leucothane (17), respectively, were isolated from the leaves extract of Rhododendron micranthum. Among them, diterpenoids 1-9 are new compounds and their structures were elucidated via extensive spectroscopic methods, quantum chemical calculations including the 13C NMR-DP4+ analysis and electronic circular dichroism (ECD) calculations, and the single-crystal X-ray diffraction analysis. Micranthanol A (1) represents the first example of a 5αH,9αH-grayanane diterpenoid and a 6-hydroxy-6,10-epoxygrayanane diterpenoid, and micranthanone B (3) is the first 6,10-epoxymicranthane and the 5α-hydroxy-micranthane diterpenoids. 14-epi-Mollanol A (5) and mollanol B (6) represent the first examples of 14β-hydroxymollane diterpenoids. It is the first time to report mollane, 1,5-seco-kalmane, and A-homo-B-nor-ent-kaurane type diterpenoids from Rhododendron micranthum. All the seventeen diterpenoids showed significant antinociceptive activities at a dose of 5.0 mg/kg, and it is the first time to evaluate the antinociceptive activity of 1,5-seco-kalmane diterpenoid. Among them, compounds 3, 11, 14, and 15 exhibited significant antinociceptive activities even at a lower dose of 1.0 mg/kg. A preliminary structure-activity relationship for the antinociceptive effects of diterpenoids 1-17 is discussed, which provided a new basis to develop novel potent analgesics. Copyright © 2021 Elsevier Inc. All rights reserved. DOI: 10.1016/j.bioorg.2021.104870 PMID: 33845382 [Indexed for MEDLINE] 3. Org Biomol Chem. 2020 Mar 14;18(10):1877-1880. doi: 10.1039/d0ob00160k. Epub 2020 Feb 26. Toward the total synthesis of grayanane diterpene mollanol A by a Prins [3 + 2] strategy. Miao J(1), Zheng YX(1), Wang L(2), Lu SC(1), Zhang SP(1), Gong YL(1), Xu S(1). Author information: (1)State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng District, Beijing 100050, China. xushu@imm.ac.cn. (2)State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng District, Beijing 100050, China. xushu@imm.ac.cn and School of Pharmacy, Harbin University of Commerce, Harbin 150076, China. Toward the total synthesis of a novel grayanoid, mollanol A, we developed a concise convergent strategy based on a formal [3 + 2] cyclization initiated by the Prins reaction. In this key intermolecular reaction between an unprotected hydroxyaldehyde and activating-group-free olefins, two chiral carbons and one densely substituted tetrahydrofuran ring were constructed stereoselectively. DOI: 10.1039/d0ob00160k PMID: 32100814 4. Org Lett. 2014 Aug 15;16(16):4320-3. doi: 10.1021/ol5020653. Epub 2014 Aug 4. Mollanol A, a diterpenoid with a new C-nor-D-homograyanane skeleton from the fruits of Rhododendron molle. Li Y(1), Liu YB, Liu YL, Wang C, Wu LQ, Li L, Ma SG, Qu J, Yu SS. Author information: (1)State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. Two new grayanoids, mollanol A (1) and rhodomollein XXV (2), were isolated from the fruits of Rhododendron molle. Their structures were elucidated by spectroscopic methods and X-ray diffraction analyses. Mollanol A (1) possesses a new C-nor-D-homograyanane carbon skeleton, while rhodomollein XXV (2) is the first example of an 11,16-epoxygrayanane and features a caged oxa-tricyclo[3.3.1.0(3.7)]nonane ring system. Plausible biogenetic pathways for 1 were proposed. Compound 1 exhibited transcriptional activation effects on the xbp1 upstream promoter in IEC-6, 293T, and RAW264.7 cells. DOI: 10.1021/ol5020653 PMID: 25090103 [Indexed for MEDLINE]