Secondary metabolome and its defensive role in the aeolidoidean <i>Phyllodesmium longicirrum</i>, (Gastropoda, Heterobranchia, Nudibranchia)

Bogdanov, Alexander; Hertzer, Cora; Kehraus, Stefan; Nietzer, Samuel; Rohde, Sven; Schupp, Peter J.; Wägele, Heike; König, Gabriele M.

doi:10.3762/bjoc.13.50

Cited by 16 publications

(29 citation statements)

References 62 publications

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“…The soft coral reef holobiont consists of symbiotic interactions among multiple organisms, encompassing eukaryotes, fungi, archaea, bacteria, and even viruses identified in recent metagenome sequencing [ 45 ]. Sarcophine ( 3 ), a major metabolite of soft coral species, is proposed to play a defensive role in the symbiont system [ 2 , 46 ]. Primarily, the proteasome is a conserved system for almost all forms of life.…”

Section: Discussionmentioning

confidence: 99%

A High-Content Screening Assay for the Discovery of Novel Proteasome Inhibitors from Formosan Soft Corals

et al. 2018

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The ubiquitin-proteasome system (UPS) is a major proteolytic pathway that safeguards protein homeostasis. The main 26S proteasome consists of a 20S catalytic core proteasome and a 19S substrate recognition proteasome. UPS dysfunction underlies many important clinical diseases involving inflammation, tumors, and neurodegeneration. Currently, three 20S proteasome inhibitors, bortezomib, carfilzomib, and ixazomib, have been approved for the treatment of multiple myeloma. We aim to screen UPS inhibitors for biomedical purposes. The protein interaction network of human cytomegalovirus UL76 targets UPS, resulting in aggregations of ubiquitinated proteins termed aggresomes. In this study, we demonstrated that cell-based high-content measurements of EGFP-UL76 aggresomes responded to bortezomib and MG132 treatment in a dose-dependent manner. Employing this high-content screening (HCS) assay, we screened natural compounds purified from Formosan soft corals. Four cembrane-based compounds, sarcophytonin A (1), sarcophytoxide (2), sarcophine (3), and laevigatol A (4), were found to enhance the high-content profiles of EGFP-UL76 aggresomes with relative ratios of 0.2. By comparison to the mechanistic action of proteasome inhibitors, compounds 1 and 3 modulated the accumulation of ubiquitinated proteins, with a unique pattern likely targeting 19S proteasome. We confirmed that the EGFP-UL76 aggresome-based HCS system greatly improves the efficacy and sensitivity of the identification of proteasome inhibitors.

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Section: Discussionmentioning

confidence: 99%

A High-Content Screening Assay for the Discovery of Novel Proteasome Inhibitors from Formosan Soft Corals

et al. 2018

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“…The aeolids Phyllodesmium briarieum, P. longicirrum and P. magnum possess several diterpenes along with some sesquiterpenes, possibly obtained from their octocoral prey [182,228]. Further studies report four polycyclic chatancin diterpenes in Australian specimens of P. longicirrum, along with other deterrent compounds against fish [229,230]. Tritoniopsins A-D (70) (Figure 8) are found in the dendronotid Tritoniopsis elegans in China, from its coral prey Cladiella krempfi [86,231].…”

Section: Tricyclic Diterpenoidsmentioning

confidence: 95%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata. Sesterterpenoids are only found in nudibranchia, while triterpenoids, carotenoids, and steroids are only reported for nudibranchia, pleurobranchoidea, and anaspidea. Many of these compounds are obtained from their diet, while others are biotransformed, or de novo biosynthesized by the molluscs. Overall, a huge variety of structures is found, indicating that chemodiversity correlates to the amazing biodiversity of this fascinating group of molluscs.

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“…Secogorgosterol 1409, methylsarcoate analogue 1410, 2R-isosarcophine 1411, bisepoxide 1412 and isobisglaucumlides B 1413 and C 1414 were isolated from extracts of an Australian collection of the nudibranch Phyllodesmium longicirrum. 626 Of the new MNPs, 1412 exhibited feeding deterrent activity towards the tropical puffer sh Canthigaster solandri. Diacylguanidine actinode 1415 was reported from skin tissue of the dorid nudibranch Actinocyclus papillatus.…”

Section: Molluscsmentioning

confidence: 99%