The Annonaceae are an old family of flowering plants belonging to the order Magnoliales, distributed mainly in tropical regions. Numerous Annonaceae species find ethnobotanical use for curing a broad range of diseases, among them cancer and infections by diverse pathogens. Hence, bioactive natural products from Annonaceae have received considerable interest in drug development. Beyond cytotoxic acetogenins, unique aporphine-derived polycyclic aromatic alkaloids are characteristic constituents of Annonaceae. Among them are unique tri- and tetracyclic aromatic alkaloids like azafluorenones, diazafluoranthenes, azaanthracenes, and azaoxoaporphines. The complex substitution pattern of these alkaloids represents a major challenge in structure elucidation of isolated natural products. Based on a broad spectrum of alkaloids available from our previous work, we present a GC-MS protocol for the identification of over 20 polycyclic aromatic alkaloids from Annonaceae. This collection of data will contribute to the future identification of the metabolite patterns of extracts from Annonaceae as an important source of novel bioactive secondary metabolites.
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http://dx.doi.org/10.3390/molecules27238217 | DOI Listing |
J Am Chem Soc
January 2025
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
A concise and convergent synthesis of the isosteroidal alkaloids veratramine and 20--veratramine has been accomplished. A Horner-Wadsworth-Emmons olefination joins two chiral building blocks of approximately equal complexity and a transition-metal catalyzed intramolecular Diels-Alder cycloaddition-aromatization cascade constructs the tetrasubstituted arene. Other key steps include a highly diastereoselective crotylation of an -sulfonyl iminium ion and an Eschenmoser fragmentation.
View Article and Find Full Text PDFProtoplasma
January 2025
CSIR-Central Institute of Medicinal and Aromatic Plants, P.O. CIMAP, Lucknow, 226015, Uttar Pradesh, India.
Catharanthus roseus leaves have been traditionally described to possess potent antidiabetic activity and some leaf-specific alkaloids, including vindoline, have been studied for their antidiabetic potential. The aim of the present study was to validate the antidiabetic property of the plant with special reference to vindoline. An Ayurveda-based method was used to prepare the Swaras [leaf juice extract (LJE)] of three familial C.
View Article and Find Full Text PDFChemistry
January 2025
Florida State University, Chemistry and Biochemistry, 95 Chieftan Way, 32306, Tallahassee, UNITED STATES OF AMERICA.
Since antiquity, alkaloid natural products have served as medicinal ingredients that still contribute as an inspiration for the development of novel therapeutics. For the synthetic chemist, much of the importance of natural products lies in their acting as a forcing-function for the invention of new synthetic strategies and tactics for molecular assembly. With this rich history in mind, it remains an important goal for chemists to build nitrogenous structures with greater efficiency, abiding by economies of synthesis.
View Article and Find Full Text PDFChemistry
January 2025
Department of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302, West Bengal, India.
All-carbon quaternary and tertiary stereocenters connected at the C2-position of functionalizable C3-alkylated indole nucleus are commonly occurring frameworks found in many indole alkaloids of medicinal importance. Their direct access is scarcely reported, a long-standing problem, and developing a unique yet simple method can pave the pathway to an entirely different retrosynthetic route for the total synthesis of these alkaloids. Herein, this problem is addressed by developing an unprecedented branch-selective allylation strategy employing a broad range of structurally and electronically different 3-alkenyl-indoles and allylboronic acids.
View Article and Find Full Text PDFEur J Med Chem
December 2024
Key Laboratory of Marine Drugs and Key Laboratory of Evolution and Marine Biodiversity (Ministry of Education), School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, 266003, China; Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao, 266237, China. Electronic address:
Bromodomain-containing protein 4 (BRD4) has been identified as a promising target in drug discovery, and the development of novel specific BRD4 bromodomain inhibitors will benefit anti-inflammatory drug discovery as well as bromodomain function role disclose. Herein, inspired by marine quinazolinone alkaloid penipanoid C, we designed and synthesized a series of quinazolin-4(3H)-ones with diverse linkers between two aromatic ring systems. Among them, compound 25 possessed good in vitro BRD4 inhibitory activities (IC = 3.
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