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Keywords = netamines

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45 pages, 6879 KB  
Review
Fused Tricyclic Guanidine Alkaloids: Insights into Their Structure, Synthesis and Bioactivity
by Nur Zahirah Abd Rani, Yean Kee Lee, Sarfraz Ahmad, Ramu Meesala and Iskandar Abdullah
Mar. Drugs 2022, 20(9), 579; https://doi.org/10.3390/md20090579 - 17 Sep 2022
Cited by 13 | Viewed by 3272
Abstract
A marine natural product possesses a diverse and unique scaffold that contributes to a vast array of bioactivities. Tricyclic guanidine alkaloids are a type of scaffold found only in marine natural products. These rare skeletons exhibit a wide range of biological applications, but [...] Read more.
A marine natural product possesses a diverse and unique scaffold that contributes to a vast array of bioactivities. Tricyclic guanidine alkaloids are a type of scaffold found only in marine natural products. These rare skeletons exhibit a wide range of biological applications, but their synthetic approaches are still limited. Various stereochemical assignments of the compounds remain unresolved. Batzelladine and ptilocaulins are an area of high interest in research on tricyclic guanidine alkaloids. In addition, mirabilins and netamines are among the other tricyclic guanidine alkaloids that contain the ptilocaulin skeleton. Due to the different structural configurations of batzelladine and ptilocaulin, these two main skeletons are afforded attention in many reports. These two main skeletons exhibit different kinds of compounds by varying their ester chain and sidechain. The synthetic approaches to tricyclic guanidine alkaloids, especially the batzelladine and ptilocaulin skeletons, are discussed. Moreover, this review compiles the first and latest research on the synthesis of these compounds and their bioactivities, dating from the 1980s to 2022. Full article
(This article belongs to the Section Synthesis and Medicinal Chemistry of Marine Natural Products)
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24 pages, 3654 KB  
Review
Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges
by Estelle Sfecci, Thierry Lacour, Philippe Amade and Mohamed Mehiri
Mar. Drugs 2016, 14(4), 77; https://doi.org/10.3390/md14040077 - 9 Apr 2016
Cited by 28 | Viewed by 10035
Abstract
Sessile marine sponges provide an abundance of unique and diversified scaffolds. In particular, marine guanidine alkaloids display a very wide range of biological applications. A large number of cyclic guanidine alkaloids, including crambines, crambescins, crambescidins, batzelladines or netamins have been isolated from Poecilosclerida [...] Read more.
Sessile marine sponges provide an abundance of unique and diversified scaffolds. In particular, marine guanidine alkaloids display a very wide range of biological applications. A large number of cyclic guanidine alkaloids, including crambines, crambescins, crambescidins, batzelladines or netamins have been isolated from Poecilosclerida marine sponges. In this review, we will explore the chemodiversity of tri- and pentacyclic guanidine alkaloids. NMR and MS data tools will also be provided, and an overview of the wide range of bioactivities of crambescidins and batzelladines derivatives will be given. Full article
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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9 pages, 589 KB  
Communication
Tricyclic Guanidine Alkaloids from the Marine Sponge Acanthella cavernosa that Stabilize the Tumor Suppressor PDCD4
by Tanja Grkovic, Johanna S. Blees, Magdalena M. Bayer, Nancy H. Colburn, Cheryl L. Thomas, Curtis J. Henrich, Megan L. Peach, James B. McMahon, Tobias Schmid and Kirk R. Gustafson
Mar. Drugs 2014, 12(8), 4593-4601; https://doi.org/10.3390/md12084593 - 21 Aug 2014
Cited by 18 | Viewed by 7312
Abstract
A cell-based high-throughput screen that assessed the cellular stability of a tumor suppressor protein PDCD4 (Programmed cell death 4) was used to identify a new guanidine-containing marine alkaloid mirabilin K (3), as well as the known compounds mirabilin G ( [...] Read more.
A cell-based high-throughput screen that assessed the cellular stability of a tumor suppressor protein PDCD4 (Programmed cell death 4) was used to identify a new guanidine-containing marine alkaloid mirabilin K (3), as well as the known compounds mirabilin G (1) and netamine M (2). The structures of these tricyclic guanidine alkaloids were established from extensive spectroscopic analyses. Compounds 1 and 2 inhibited cellular degradation of PDCD4 with EC50 values of 1.8 μg/mL and 2.8 μg/mL, respectively. Mirabilin G (1) and netamine M (2) are the first marine natural products reported to stabilize PDCD4 under tumor promoting conditions. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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