A New Sesquiterpenoid Hydroquinone from the Marine Sponge Dysidea arenaria

Qiu, Yun; Wang, Xiu Min

doi:10.3390/molecules13061275

Cited by 33 publications

(17 citation statements)

References 14 publications

(15 reference statements)

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“…Human adenoviruses (HAdV) are non-enveloped viruses with an icosahedral capsid containing a linear double-stranded DNA whose size ranges from 34 to 37 kb in size (Lion, 2014). Currently, more than 100 serotypes have been identified and grouped into 7 HAdV species (HAdV-A to -G) in Mastadenovirus genus (Qiu et al, 2018;HAdV Working Group, 2019). HAdV infections are common in the human population, as indicated by the high seroprevalence of anti-adenovirus antibodies (ranging from 80 to 90% in sub-Saharan Africa, and from 30 to 70% in Europe and North America), but in otherwise healthy adults, these infections are generally mild and self-limited (Grosso et al, 2017;Inturi et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Antiviral and Antiproliferative Potential of Marine Organisms From the Yucatan Peninsula, Mexico

et al. 2020

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Viral infections are one of the main human health problems in recent decades and the cancer remains one of the most lethal diseases worldwide. The development of new antiviral drugs for the treatment of human adenovirus (HAdV) infections continues to be a challenging goal for medicinal chemistry. There is no specific antiviral drug approved to treat infections caused by HAdV so far and the off-label treatments currently available show great variability in their effectiveness. In relation to cancer, most of the available drugs are designed to act on specific targets by altering the activity of involved transporters and genes. Taking into account the high antiviral and antiproliferative activity against tumor cell lines displayed by some marine natural products reported in the literature, sixty five marine organisms were selected: 51 sponges (Porifera), 13 ascidians (Chordata), and 1 gorgonian (Cnidaria), collected from Yucatan Peninsula, Mexico, to evaluate their antiviral activity against human adenovirus type 5 (HAdV5) and their anticancer properties against five human tumor cell lines, namely human lung carcinoma (A549), human skin melanoma (A2058), hepatocyte carcinoma (HepG2), breast adenocarcinoma (MCF7), and pancreas carcinoma (MiaPaca-2). Eleven extracts displayed anti-HAdV activity being the organic extracts of Dysidea sp., Agelas citrina, Chondrilla sp., Spongia tubulifera, and Monanchora arbuscula the five most active ones. On the other hand, 24 extracts showed antiproliferative activity against at least one tumor cell line, being the extracts of the ascidian Eudistoma amanitum and the sponge Haliclona (Rhizoniera) curacaoensis the most active ones. This work constitutes the first wide antiviral and antiproliferative screening report of extracts from the marine sponges, ascidians, and a gorgonian collected from the Yucatan Peninsula, Mexico.

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Section: Introductionmentioning

confidence: 99%

Antiviral and Antiproliferative Potential of Marine Organisms From the Yucatan Peninsula, Mexico

et al. 2020

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“…in 1987, and (+)‐isospongiaquinone ( 4 ) from the marine sponge Stelospongia conulata in 1978 (Figure ). Ilimaquinone has been shown to have remarkable biological activities, including antimicrobial, anti‐HIV, anti‐inflammatory, antiproliferative, and antisecretory activities. Smenospongine and isospongiaquinone have also been found to show antimicrobial and antiproliferative activities , …”

Section: Introductionmentioning

confidence: 99%

Unified Synthesis of the Marine Sesquiterpene Quinones (+)‐Smenoqualone, (–)‐Ilimaquinone, (+)‐Smenospongine, and (+)‐Isospongiaquinone

et al. 2017

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The marine sesquiterpene quinones (+)‐smenoqualone, (–)‐ilimaquinone, (+)‐smenospongine, and (+)‐isospongiaquinone were efficiently synthesized in a unified manner starting from a known trans‐decalin derivative, which is accessible from (+)‐5‐methyl Wieland–Miescher ketone. The synthetic method involved the following key steps: (i) assembly of the whole carbon skeleton by coupling the decalin segment to an aromatic moiety; (ii) p‐quinone formation by strategic salcomine oxidation of phenolic intermediates; (iii) direct conversion of (–)‐ilimaquinone into (+)‐isospongiaquinone by pTsOH‐induced isomerization of the C‐4 olefinic double bond; (iv) site‐selective amination of a dimethoxy‐p‐quinone intermediate by substitution of the C‐18 methoxy group with an amino group; and (v) one‐step construction of the requisite tetracyclic core structure by sequential BF3·Et2O‐induced rearrangement/cyclization of an olefinic decalin intermediate having an aromatic moiety. The syntheses of (+)‐smenoqualone and (+)‐smenospongine are reported here for the first time.

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“…Nakijiquinones G-I from Okinawan marine sponges, belonging to family Spongilidae, were found to be a sesquiterpenoid quinone with antimicrobial potency [15]. Novel sesquiterpenoid hydroquinones from Dysidea arenaria, a marine sponge, were found moderately inhibitory for enzyme HIV reverse transcriptase (RT) [16]. Peyssonoic acids A and B, novel sesquiterpene hydroquinones, with a novel carbon skeleton, isolated from crustose marine red alga Peyssonnelia sp [17] were found inhibitory for bacterial pathogen Pseudoalteromonas bacteriolytica in marine algae and Lindra thalassiae, a fungal pathogen of marine algae.…”

Section: Terpenoids/isoprenoids/modified Terpenesmentioning

confidence: 99%

Antimicrobial lead compounds from marine plants

Kurhekar¹

2020

Phytochemicals as Lead Compounds for New Drug Discovery

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A New Sesquiterpenoid Hydroquinone from the Marine Sponge Dysidea arenaria

Cited by 33 publications

References 14 publications

Antiviral and Antiproliferative Potential of Marine Organisms From the Yucatan Peninsula, Mexico

Antiviral and Antiproliferative Potential of Marine Organisms From the Yucatan Peninsula, Mexico

Unified Synthesis of the Marine Sesquiterpene Quinones (+)‐Smenoqualone, (–)‐Ilimaquinone, (+)‐Smenospongine, and (+)‐Isospongiaquinone

Antimicrobial lead compounds from marine plants

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