Bromotyrosine Alkaloids with Acetylcholinesterase Inhibitory Activity from the Thai Sponge <i>Acanthodendrilla</i> sp

Sirimangkalakitti, Natchanun; Olatunji, Opeyemi Joshua; Changwichit, Kanokwan; Saesong, Tongchai; Chamni, Supakarn; Chanvorachote, Pithi; Ingkaninan, Kornkanok; Plubrukarn, Anuchit; Suwanborirux, Khanit

doi:10.1177/1934578x1501001135

Cited by 10 publications

(7 citation statements)

References 33 publications

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“…Homoaerothioin (80) (Figure 11), also a derivative of tyrosine, extracted from the sponges Verongia aerophoba [138] and Acanthodendrilla sp. in Thailand [139], displays also low micromolar inhibitory activity against AChE. Fistularin 1 (81) (Figure 11), derivative of tyrosine, extracted from the sponges Aplysina fistularis forma fulva [140] and Acanthodendrilla sp.…”

Section: Derivatives Of Phenylalanine or Tyrosinementioning

confidence: 99%

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Marine Organisms as Alkaloid Biosynthesizers of Potential Anti-Alzheimer Agents

Lima

Medeiros

2022

Marine Drugs

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The incidence of neurodegenerative diseases, such as Alzheimer’s disease (AD), increases continuously demanding the urgent development of anti-Alzheimer’s agents. Marine organisms (MO) have to create their own defenses due to the adverse environment where they live and so synthesize several classes of compounds, such as akaloids, to defend themselves. Therefore, the identification of marine natural products with neuroprotective effects is a necessity. Being that AD is not only a genetic but also an environmental complex disease, a treatment for AD remains to discover. As the major clinical indications (CI) of AD are extracellular plaques formed by β-amyloid (Aβ) protein, intracellular neurofibrillary tangles (NFTs) formed by hyper phosphorylated τ-protein, uncommon inflammatory response and neuron apoptosis and death caused by oxidative stress, alkaloids that may decrease CI, might be used against AD. Most of the alkalolids with those properties are derivatives of the amino acid tryptophan mainly with a planar indole scaffold. Certainly, alkaloids targeting more than one CI, multitarget-directed ligands (MTDL), have the potential to become a lead in AD treatment. Alkaloids to have a maximum of activity against CI, should be planar and contain halogens and amine quaternization.

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Section: Derivatives Of Phenylalanine or Tyrosinementioning

confidence: 99%

“…Fistularin 1 (81) (Figure 11), derivative of tyrosine, extracted from the sponges Aplysina fistularis forma fulva [140] and Acanthodendrilla sp. [139], is another alkaloid with the same spirocyclohexadienylisoxazoline structural feature of purealidin Q (79). It is also effective against AChE [139].…”

Section: Derivatives Of Phenylalanine or Tyrosinementioning

confidence: 99%

Marine Organisms as Alkaloid Biosynthesizers of Potential Anti-Alzheimer Agents

Lima

Medeiros

2022

Marine Drugs

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“…The spiro moiety of compound 69 derived from bromotyrosine connected with an amide group through a five-carbon linker. [49] Compound 70 was the first bromotyrosine alkaloid with a β-alanine unit, and compound 71 was a rare N-substituted bromotyrosine alkaloid bearing a pyridinium ring. Both of them were obtained from Okinawan Verongid sponge.…”

Section: Bromotyrosine Alkaloidsmentioning

confidence: 99%

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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“…The assay was carried out according to the modified Ellman's method [7,[29][30][31]. Plant extracts were dissolved in methanol to make 10 mg/mL concentration, and was serially diluted with 50 mM Tris buffer to obtain a 1 mg/mL concentration containing not more than 10% of methanol.…”

Section: Cholinesterase Inhibitory Assaymentioning

confidence: 99%

Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species

Suciati¹,

Laili²,

Poerwantoro³

et al. 2020

jrp

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Alzheimer's disease (AD) is a neurodegenerative disorder, which is the most common cause of dementia. The aging population means that the number of people suffering from AD is expected to increase each year if there is no effective treatment found. One of the strategies for the treatment of AD is the use of cholinesterase inhibitors. Plants have been the source of many bioactive metabolites, including cholinesterase inhibitors. The objective of this study is to investigate the potency of several plant extracts from the genus Cassia as cholinesterase inhibitors. The cholinesterase inhibitory screening was carried out against two enzymes, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), according to the modified Ellman's method. The chemistry of the active fractions was studied by LC-MS/MS method. The results suggested that amongst six plant extracts from the genus Cassia investigated, the ethanolic extract of Cassia spectabilis showed the strongest inhibition against both AChE and BChE enzymes, with IC50 values of 39.5 and 36.9 µg/mL, respectively. Investigation on the n-hexane, ethyl acetate, and nbutanol fractions obtained from the C. spectabilis extract showed that the ethyl acetate and the n-butanol fractions gave better inhibitory activity compared to the n-hexane fraction. Based on the LC-MS/MS data, the two active fractions gave similar profile. Both fractions contained alkaloid cassine and spectaline, which may responsible for the cholinesterase inhibitory activity.

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Bromotyrosine Alkaloids with Acetylcholinesterase Inhibitory Activity from the Thai Sponge Acanthodendrilla sp

Cited by 10 publications

References 33 publications

Marine Organisms as Alkaloid Biosynthesizers of Potential Anti-Alzheimer Agents

Marine Organisms as Alkaloid Biosynthesizers of Potential Anti-Alzheimer Agents

Recent Advances on Marine Alkaloids from Sponges

Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species

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