Novel Polycyclic Guanidine Alkaloids from Two Marine Sponges of the Genus <i>Monanchora</i>

Braekman, Jean‐Claude; Daloze, Désiré; Tavares, R.; Hajdu, Eduardo; Soest, R.W.M. van

doi:10.1021/np990403g

Cited by 91 publications

(109 citation statements)

References 14 publications

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“…DHPMs represent a heterocyclic system of remarkable pharmacological and therapeutic properties such as antiviral, antibacterial, and antitumor [5][6][7]. Several alkaloids-derivate DHPMs possessing biological and anti-HIV characters have been isolated from marine sources [8][9][10]. There is an inherent stereogenic center in DHPMs, and individual enantiomer is found to exhibit different or opposite pharmaceutical activities [11,12].…”

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confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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In this study, enantioselective Biginelli reaction of aldehyde, b-ketoester, and urea catalyzed by natural (2R, 3R)-tartaric acid has been investigated using density functional theory calculations. The results indicate that the most favorable pathway involves a protonated imine from aldehyde and urea in the first step. Tartaric acid forms H-bonds network with substrates enhancing the electrophilicity of protonated imine and the nucleophilicity of b-ketoester. (R)-3,4-Dihydropyrimidin-2-(1H)-ones is preferable for the reaction. The solvent effect is discussed in the prediction of enantiomeric excess (ee) values in ethanol and water.

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confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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“…18,19 Moreover, crambescidin 359 ( 11 ) isolated from the marine sponge Monanchom unguiculata in 2000, is the first member of this class devoid of the C-14 ester linkage. 14 …”

Section: Introductionmentioning

confidence: 99%

Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Shi

Moazami

Pierce

2017

Bioorganic & Medicinal Chemistry

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The pentacyclic guanidinium alkaloids (PGAs) are a family of marine natural products that possess a poly-cyclic guanidine-containing core and a long alkyl chain tethered spermidine-derived tail that is rarely observed in other natural products. These natural products exhibit potent activities on a wide range of organisms and therefore have attracted the attention of many synthetic chemists; however, the structure-activity relationships and mechanisms of action of PGAs remain largely elusive. Herein we summarize the structure, synthesis, toxicity and mechanisms of action of PGAs and highlight their potential as chemical probes and/or therapeutic leads.

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“…On the guidance of bioassay, we found crambescidin 800 (1), a pentacyclic guanidine alkaloid, from the Indonesian marine sponge of Monanchora ungiculata. Crambescidin 800 (1) and several related compounds have been isolated from marine sponge and have a variety of bioactivities such as cytotoxic, antiviral, and induction of cell differentiation [18][19][20][21][22]. This paper presents details of the protective effect of crambescidin 800 (1) against oxidative stress (Fig.…”

Section: Introductionmentioning

confidence: 99%

Crambescidin 800, a pentacyclic guanidine alkaloid, protects a mouse hippocampal cell line against glutamate-induced oxidative stress

et al. 2007

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Oxidative stress is implicated in the pathogenesis of neuronal degenerative diseases. In our search for protective substances against glutamate-induced oxidative stress using mouse hippocampal cell line HT22, we have isolated crambescidin 800, a pentacyclic guanidine alkaloid, from the Indonesian marine sponge, Monanchora ungiculata. Crambescidin 800 (1) protected HT22 cells against glutamate-induced oxidative toxicity at 0.06 lM (EC 50 ) concentration. Crambescidin 800 (1) also protected HT22 and neuroblastoma cells from the oxidative stress induced by a hypoxic condition or nitric oxide (NO). Crambescidin 800 (1) showed no effect on the depletion of intracellular glutathione (GSH) of HT22 cells induced by glutamate, and production of reactive oxygen species (ROS) and activation of mitogen-activated protein kinase (MAPK) were inhibited only by the high concentration (1 lM) of 1.

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Novel Polycyclic Guanidine Alkaloids from Two Marine Sponges of the Genus Monanchora

Cited by 91 publications

References 14 publications

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Crambescidin 800, a pentacyclic guanidine alkaloid, protects a mouse hippocampal cell line against glutamate-induced oxidative stress

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