ChemInform Abstract: Lissodendrins A (I) and B (II): 2‐Aminoimidazole Alkaloids from the Marine Sponge Lissodendoryx (Acanthodoryx) fibrosa.

Mokhlesi, Amin; Hartmann, Rudolf; Achten, Elisabeth; Chaidir, Elisabeth; Hartmann, Thomas; Lin, Wenhan; Proksch, Peter

doi:10.1002/chin.201625213

Cited by 2 publications

(3 citation statements)

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“…Compound 45 was a structurally unique bromopyrrole alkaloid, and it could be biogenetically synthesized by condensation of oroidin and 3-hydroxypyridine derived from nicotinic acid. [39] Compounds 47-49 were isolated from the Far-Eastern marine sponge Monanchora pulchra and characterized as novel pentacyclic guanidine alkaloids. Compounds 47 and 48 included a pentacyclic tetrahydrofuran moiety, which was replaced by the 2,3,4,7-tetrahydrooxepine moiety in compound 49.…”

Section: Guanidine Alkaloidsmentioning

confidence: 99%

“…Compounds 45 and 46 were obtained from marine sponge Lissodendoryx ( Acanthodoryx ) fibrosa containing an amino imidazole and two phenol moieties. Compound 45 was a structurally unique bromopyrrole alkaloid, and it could be biogenetically synthesized by condensation of oroidin and 3‐hydroxypyridine derived from nicotinic acid [39] . Compounds 47 – 49 were isolated from the Far‐Eastern marine sponge Monanchora pulchra and characterized as novel pentacyclic guanidine alkaloids.…”

Section: Structural Diversitymentioning

confidence: 99%

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Recent Advances on Marine Alkaloids from Sponges

Bian

Wang

Zhou

et al. 2020

Chemistry & Biodiversity

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Alkaloids from marine secondary metabolites have received extensive attention from pharmacists in recent years. Miscellaneous alkaloids derived from marine sponges possessed various pharmacological activities including cytotoxicity, antimicrobial, antioxidant, and so on. Herein, we summarized 149 marine alkaloids from sponges based on their structures and bioactivities reported from 2015 to 2020 and analyzed the production environment of marine sponges with rich alkaloids. Moreover, we discussed biosynthesis routes of pyrrole and guanidine alkaloids from marine sponges Agelas and Monanchora. This article will be beneficial for future research on drugs from marine natural products.

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Section: Guanidine Alkaloidsmentioning

confidence: 99%

Section: Structural Diversitymentioning

confidence: 99%

Recent Advances on Marine Alkaloids from Sponges

Bian

Wang

Zhou

et al. 2020

Chemistry & Biodiversity

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“…2-Aminoimidazole marine alkaloids have various biological activities, including anticancer [12], antimicrobial [13,14], antivirus properties [15], ABCB1-mediated MDR reversal activity [16] as well as both leukotriene B4 receptor [17] and epidermal growth factor (EGF) receptor antagonist activities [10]. Lissodendrins B (Figure 1) is a 2-aminoimidazole marine alkaloid first extracted from the EtOAc fraction of the sponge Lissodendoryx (Acanthodoryx) fibrosis in 2016 [18]. The compound was devoid of cytotoxicity, and its total synthesis was performed by our group [19].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Marine Lissodendrins B Analogues as Modulators of ABCB1-Mediated Multidrug Resistance

Wang,

Zhang,

Wei

et al. 2023

Marine Drugs

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Multidrug resistance (MDR) caused by ATP-Binding Cassette Subfamily B Member 1 (ABCB1, P-glycoprotein, P-gp) is a major barrier for the success of chemotherapy in clinics. In this study, we designed and synthesized a total of 19 Lissodendrins B analogues and tested their ABCB1-mediated MDR reversal activity in doxorubicin (DOX)-resistant K562/ADR and MCF-7/ADR cells. Among all derivatives, compounds D1, D2, and D4 with a dimethoxy-substituted tetrahydroisoquinoline fragment possessed potent synergistic effects with DOX and reversed ABCB1-mediated drug resistance. Notably, the most potent compound D1 merits multiple activities, including low cytotoxicity, the strongest synergistic effect, and effectively reversing ABCB1-mediated drug resistance of K562/ADR (RF = 1845.76) and MCF-7/ADR cells (RF = 207.86) to DOX. As a reference substance, compound D1 allows for additional mechanistic studies on ABCB1 inhibition. The synergistic mechanisms were mainly related to the increased intracellular accumulation of DOX via inhibiting the efflux function of ABCB1 rather than from affecting the expression level of ABCB1. These studies suggest that compound D1 and its derivatives might be potential MDR reversal agents acting as ABCB1 inhibitors in clinical therapeutics and provide insight into a design strategy for the development of ABCB1 inhibitors.

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ChemInform Abstract: Lissodendrins A (I) and B (II): 2‐Aminoimidazole Alkaloids from the Marine Sponge Lissodendoryx (Acanthodoryx) fibrosa.

Abstract: Lissodendrins A (I) and B (II): 2-Aminoimidazole Alkaloids from the Marine Sponge Lissodendoryx (Acanthodoryx) fibrosa. -(MOKHLESI, A.; HARTMANN, R.; ACHTEN, E.; CHAIDIR, E.; HARTMANN, T.; LIN, W.; DALETOS*, G.; PROKSCH, P.; Eur. J. Org. Chem. 2016, 4, 639-643, http://dx.

Cited by 2 publications

References 1 publication

Recent Advances on Marine Alkaloids from Sponges

Recent Advances on Marine Alkaloids from Sponges

Design, Synthesis, and Biological Evaluation of Marine Lissodendrins B Analogues as Modulators of ABCB1-Mediated Multidrug Resistance

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