Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp.

Longeon, Arlette; Copp, Brent R.; Quévrain, Elodie; Roué, Mélanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cécile; Bourguet‐Kondracki, Marie‐Lise

doi:10.3390/md9050879

Cited by 54 publications

(53 citation statements)

References 19 publications

(32 reference statements)

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“…In particular, the positive ion mode HR-ESIMS of 1 and 2 displayed M+2 isotopic pseudomolecular peaks in the ratio of 1:1 and 1:2:1, respectively, accounting for the presence of one or two bromine atoms and for the molecular formula C 9 H 13 BrNO + and C 12 H 15 Br 2 N 2 + . Taken together, MS evidence and the comparison of the 1 H-NMR data ( Figure S4), with the data reported in the literature [45,46], allowed the assignment of…”

Section: Bioassay-guided Isolation and Structural Elucidation Of 1 Andsupporting

confidence: 67%

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Identification of Quorum Sensing Activators and Inhibitors in The Marine Sponge Sarcotragus spinosulus

et al. 2020

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Marine sponges, a well-documented prolific source of natural products, harbor highly diverse microbial communities. Their extracts were previously shown to contain quorum sensing (QS) signal molecules of the N-acyl homoserine lactone (AHL) type, known to orchestrate bacterial gene regulation. Some bacteria and eukaryotic organisms are known to produce molecules that can interfere with QS signaling, thus affecting microbial genetic regulation and function. In the present study, we established the production of both QS signal molecules as well as QS inhibitory (QSI) molecules in the sponge species Sarcotragus spinosulus. A total of eighteen saturated acyl chain AHLs were identified along with six unsaturated acyl chain AHLs. Bioassay-guided purification led to the isolation of two brominated metabolites with QSI activity. The structures of these compounds were elucidated by comparative spectral analysis of 1HNMR and HR-MS data and were identified as 3-bromo-4-methoxyphenethylamine (1) and 5,6-dibromo-N,N-dimethyltryptamine (2). The QSI activity of compounds 1 and 2 was evaluated using reporter gene assays for long- and short-chain AHL signals (Escherichia coli pSB1075 and E. coli pSB401, respectively). QSI activity was further confirmed by measuring dose-dependent inhibition of proteolytic activity and pyocyanin production in Pseudomonas aeruginosa PAO1. The obtained results show the coexistence of QS and QSI in S. spinosulus, a complex signal network that may mediate the orchestrated function of the microbiome within the sponge holobiont.

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Section: Bioassay-guided Isolation and Structural Elucidation Of 1 Andsupporting

confidence: 67%

“…Compound 2 (5,6-dibromo-N,N-dimethyltryptamine) is a natural indole alkaloid that has also been previously isolated from the marine sponge Hyrtios sp. with strong antimicrobial, neurological, and antidepressant activity [45,46].…”

Section: Inhibition Of Production Of the Virulence Factors Pyocyanin mentioning

confidence: 99%

Identification of Quorum Sensing Activators and Inhibitors in The Marine Sponge Sarcotragus spinosulus

et al. 2020

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“…Indole derivatives derived from marine invertebrates exhibit diverse and potent bioactivities, such as antioxidant; PLA2 (phospholipase A2) inhibition activity; antimicrobial activity; anti-angiogenic effect; anti-inflammtory, PPAR-γ agnostic, cytotoxicity, the reported compound mucronatin A, which shared the same carbon skeleton, exhibited moderate AchE inhibitory activity [7,[11][12][13][14][15][16]. Hence, in our search for the biological activities of isolated compounds, the cytotoxicity, and AchE inhibitory A C C E P T E D M A N U S C R I P T…”

Section: Accepted Manuscriptmentioning

confidence: 98%

Acetylcholinesterase inhibitory dimeric indole derivatives from the marine actinomycetes Rubrobacter radiotolerans

Huang

Liu

et al. 2015

Fitoterapia

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“…42) Likewise, the conversion of M3 to M4 may be concurrent with decarboxylation, although the exact mechanism was not determined here. M4 itself was found in several marine sources, such as marine sponges Rhopaloeides odorabile and Hyritios sp., 43) marine sponge Spongosorites sp., 44) and marine bryozoan Cryptpsula pallasiana sp. 45) It is also known to be an intermediate in the synthesis of marine natural products, such as arborescidines, 46) and is an endogenous ligand for aryl hydrocarbon receptor for treatment of cancer or immune system diseases.…”

Section: Discussionmentioning

confidence: 99%

Pharmacokinetics and Metabolism of Streptochlorin and Its Synthetic Derivative, 5-Hydroxy-2′-isobutyl Streptochlorin, in Mice

Zhou

Choi

Kim

et al. 2018

Biological & Pharmaceutical Bulletin

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The purpose of this study was to investigate the pharmacokinetics and metabolism of streptochlorin and its derivative 5-hydroxy-2′-isobutyl streptochlorin (HIS) in mice. Plasma concentration of streptochlorin declined rapidly resulting in a high sustemic plasma clearance (CL p ) (5.8 1.7 L/h/kg), a large volume of distribution (V ss ) (1.4 0.9 L/kg) and a short half-life (t 1/2 ) (0.4 0.1 h) after a single intravenous administration (5 mg/kg). Oral bioavailability (F) was 10.3 3.4% after a single oral administration (10 mg/kg). HIS also showed a rapid plasma decline with a high CL p (11.3 8.8 L/h/kg), a high V ss (0.8 1.0 L/kg) and a short t 1/2 (0.070 0.004 h) following intravenous administration. It was not detected in plasma after oral administration. Metabolic stability studies using mouse liver microsomes and S9 fractions predicted a high hepatic clearance for both compounds, consistent with the in vivo data. Metabolite identification studies revealed three metabolic pathways for streptochlorin: monooxygenation, glucuronidation of the indole moiety and oxidative opening of the 4-chlorooxazole ring. HIS was metabolized via monooxygenation of the isobutyl chain and glucuronidation of the indole ring. These results may aid in structural optimization to mitigate the metabolic liability of streptochlorin.Key words streptochlorin; 5-hydroxy-2′-isobutyl streptochlorin; pharmacokinetics; metabolism Terrestrial organisms have been a rich source of natural products for drug discovery and development for thousands of years. Since the mid-twentieth century, studies have shown that marine creatures, especially microbes, have provided many bioactive compounds with novel structures. These include compounds such as ziconotide which is an analgesic agent for severe and chronic pain treatment, trabectedin, an anticancer drug, and eribulin for metastatic breast cancer and liposarcoma treatment.

show abstract

Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp.

Cited by 54 publications

References 19 publications

Identification of Quorum Sensing Activators and Inhibitors in The Marine Sponge Sarcotragus spinosulus

Identification of Quorum Sensing Activators and Inhibitors in The Marine Sponge Sarcotragus spinosulus

Acetylcholinesterase inhibitory dimeric indole derivatives from the marine actinomycetes Rubrobacter radiotolerans

Pharmacokinetics and Metabolism of Streptochlorin and Its Synthetic Derivative, 5-Hydroxy-2′-isobutyl Streptochlorin, in Mice

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