Structure elucidation of the new citharoxazole from the Mediterranean deep‐sea sponge <i>Latrunculia (Biannulata) citharistae</i>

Genta‐Jouve, Grégory; Francezon, Nellie; Puissant, Alexandre; Auberger, Patrick; Vacelet, Jean; Pérez, Thierry; Fontana, Angelo; Al‐Mourabit, Ali; Thomas, Olivier P.

doi:10.1002/mrc.2772

Cited by 14 publications

(17 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The benzoxazole moiety in makaluvamine W ( 433 ) is also found in citharoxazole ( 435 ), isolated from the sponge Latrunculia (Biannulata) citharistae in 2011 ( Figure 60 ). The latter compound represented the first oxazole derivative in this family at that time [ 329 ].…”

Section: Miscellaneousmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

View full text Add to dashboard Cite

Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.

show abstract

Section: Miscellaneousmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

View full text Add to dashboard Cite

show abstract

“…The only compound in the study that fulfilled all of the criteria to be considered lead-like was from an organism of the Animalia Kingdom, citharoxazole, which was isolated from the deep-sea Mediterranean sponge, Latrunculia (Biannulata) citharistae from a depth of 103 m off La Ciotat, Banc de Banquiere in France by Genta-Jouve et al (Figure 20) [45]. No biological assessment was performed at the time and subsequent to its isolation, no further research has been reported on this interesting compound, presenting it as an attractive option for further investigation.…”

Section: Resultsmentioning

confidence: 99%

“…Structure of citharoxazole, a lead-like compound isolated from the deep-sea Mediterranean sponge, Latrunculia (Biannulata) citharistae [45]. …”

Section: Figurementioning

confidence: 99%

A Chemometric Analysis of Deep-Sea Natural Products

Pilkington

2019

Molecules

View full text Add to dashboard Cite

Deep-sea natural products have been created by unique marine organisms that thrive in a challenging environment of extreme conditions for its inhabitants. In this study, 179 deep-sea natural products isolated from 2009 to 2013 were investigated by analysing their physicochemical properties that are important indicators of the ADMET (Absorption, Distribution, Metabolism, Excretion and Toxicity) profile of a compound. The study and analysis of these molecular descriptors and characteristics enabled the defining of these compounds in various chemical spaces, particularly as an indication of their drug-likeness and position in chemical space and is the first to be conducted to analyse deep-sea derived natural products. It was found that ~40% of all deep-sea natural products were drug-like and 2/3 were within Known Drug Space (KDS), highlighting the high drug-likeness of a significant proportion of deep-sea natural products, most of which have already been shown to have notable biological activities, that should be further investigated as potential therapeutics. Furthermore, this study was able to reveal the general structural differences between compounds from Animalia, Bacteria and Fungi organisms where it was observed that natural products from members of the Animalia kingdom are structurally more varied than compounds from bacteria and fungi. It was also noted that, in general, fungi-derived compounds occupy a more favourable position in drug-like chemical space and are a rich and promising source of biologically-active natural products for the purposes of drug development and therapeutic application.

show abstract

“…192 and Monanchora unguifera, 193 and the synthesis of mirabilin B, along with the a biosynthetic proposal, has been recently reported from Snider's group. 195 Bioassay-and LC-MS-guided fractionation of a new species of deep-sea sponge belonging to the genus Latrunculia, collected by dredging at a depth of 230 m off the Aleutian Islands, Alaska, led to the isolation of two new brominated pyrroloiminoquinones, dihydrodiscorhabdin B (175) as a dark green solid and discorhabdin Y (176) as a purple solid, along with six known pyrroloiminoquinone alkaloids, discorhabdins A, C, E, and L, dihydrodiscorhabdin C, and a benzene derivative. 195 Bioassay-and LC-MS-guided fractionation of a new species of deep-sea sponge belonging to the genus Latrunculia, collected by dredging at a depth of 230 m off the Aleutian Islands, Alaska, led to the isolation of two new brominated pyrroloiminoquinones, dihydrodiscorhabdin B (175) as a dark green solid and discorhabdin Y (176) as a purple solid, along with six known pyrroloiminoquinone alkaloids, discorhabdins A, C, E, and L, dihydrodiscorhabdin C, and a benzene derivative.…”

Section: Order Poeciloscleridamentioning

confidence: 99%

Recent advances in deep-sea natural products

2014

View full text Add to dashboard Cite

Covering: 2009 to 2013. This review covers the 188 novel marine natural products described since 2008, from deep-water (50->5000 m) marine fauna including bryozoa, chordata, cnidaria, echinodermata, microorganisms, mollusca and porifera. The structures of the new compounds and details of the source organism, depth of collection and country of origin are presented, along with any relevant biological activities of the metabolites. Where reported, synthetic studies on the deep-sea natural products have also been included. Most strikingly, 75% of the compounds were reported to possess bioactivity, with almost half exhibiting low micromolar cytotoxicity towards a range of human cancer cell lines, along with a significant increase in the number of microbial deep-sea natural products reported.

show abstract

Structure elucidation of the new citharoxazole from the Mediterranean deep‐sea sponge Latrunculia (Biannulata) citharistae

Cited by 14 publications

References 16 publications

Marine Pyrrole Alkaloids

Marine Pyrrole Alkaloids

A Chemometric Analysis of Deep-Sea Natural Products

Recent advances in deep-sea natural products

Contact Info

Product

Resources

About