Scalarane Sesterterpenoids

González, Miguel A.

doi:10.2174/157340710793237362

Cited by 63 publications

(53 citation statements)

References 109 publications

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“…Sesterterpenoids originate from geranylfarnesylpyrophosphate and are found primarily in fungi and marine organisms [1–3,11]. Examples of specific metabolites produced through various diverse cyclizations of the linear C 25 precursor include cytotoxic agents ophiobolin A [12] and bilosespene A [13], fungal and marine metabolites, respectively (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…1). Sesterterpenoids have been a subject of a lot of recent investigations aimed at structural, chemical, and biological characterizations and were found to show a broad spectrum of biological activities against bacteria, fungi, and nematodes [3,11,14]. Many of them exhibit strong anticancer activity via novel mode(s) of action.…”

Section: Introductionmentioning

confidence: 99%

“…Scalaranes are sesterterpenoids characterized by the typical tetracyclic carbon skeleton, which are exclusively isolated from sponges and shell molluscs (nudibranchs) [11]. Most of these natural products are involved in chemical defense of producer marine organisms and are of interest due to their potential application in medicine and as a molecular marker in the chemotaxonomic classification of sponges [11].…”

Section: Introductionmentioning

confidence: 99%

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Sesterterpenoids with Anticancer Activity

Evidente¹,

Kornienko²,

Lefranc³

et al. 2015

CMC

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Terpenes have received a great deal of attention in the scientific literature due to complex, synthetically challenging structures and diverse biological activities associated with this class of natural products. Based on the number of C5 isoprene units they are generated from, terpenes are classified as hemi- (C5), mono- (C10), sesqui- (C15), di- (C20), sester- (C25), tri (C30), and tetraterpenes (C40). Among these, sesterterpenes and their derivatives known as sesterterpenoids, are ubiquitous secondary metabolites in fungi, marine organisms, and plants. Their structural diversity encompasses carbotricyclic ophiobolanes, polycyclic anthracenones, polycyclic furan-2-ones, polycyclic hydroquinones, among many other carbon skeletons. Furthermore, many of them possess promising biological activities including cytotoxicity and the associated potential as anticancer agents. This review discusses the natural sources that produce sesterterpenoids, provides sesterterpenoid names and their chemical structures, biological properties with the focus on anticancer activities and literature references associated with these metabolites. A critical summary of the potential of various sesterterpenoids as anticancer agents concludes the review.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sesterterpenoids with Anticancer Activity

Evidente¹,

Kornienko²,

Lefranc³

et al. 2015

CMC

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“…Moreover, two deoxoscalarin-like metabolites [13], felixins D ( 4 ) and E ( 5 ) were isolated from I. felix in this study. Felixin D ( 4 ) was isolated as white powder and its molecular formula was established as C 30 H 46 O 6 from the HRESIMS at m / z 525.31849 (calcd C 30 H 46 O 6 + Na, 525.31866).…”

Section: Resultsmentioning

confidence: 90%

“…These data, together with the key HMBC correlations between protons and quaternary carbons (Table 1), such as H 2 -3, H-5, H 3 -19, H 3 -20/C-4; H 2 -6, H-9, H-14, H 3 -21/C-8; H 2 -1, H-5, H-9, H 2 -22/C-10; H 2 -11, H-14, H 2 -18, H 3 -23/C-13; H 2 -15, H 2 -18, H 3 -25/C-17; and H-16, H 2 -18, H 3 -25/C-24, established the carbon skeleton of 1 as a 24-homo-25-norscalarane derivative [13]. The oxymethylene unit at δ C 63.0 was correlated to the methylene protons at δ H 4.03 and 3.89 in the HMQC spectrum.…”

Section: Resultsmentioning

confidence: 99%

New Scalarane Sesterterpenoids from the Formosan Sponge Ircinia felix

Lai

Wang

et al. 2015

Marine Drugs

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Antimycobacterial Metabolites from Marine Invertebrates

Ancheeva

Chaidir²,

Kalscheuer

et al. 2016

Archiv der Pharmazie

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Marine organisms play an important role in natural product-based drug research due to accumulation of structurally unique and bioactive metabolites. The exploration of marine-derived compounds may significantly extend the scientific knowledge of potential scaffolds for antibiotic drug discovery. Development of novel antitubercular agents is especially significant as the emergence of drug-resistant Mycobacterium tuberculosis strains remains threateningly high. Marine invertebrates (i.e., sponges, corals, gorgonians) as a source of new chemical entities are the center of research for several scientific groups, and the wide spectrum of biological activities of marine-derived compounds encourages scientists to carry out investigations in the field of antibiotic research, including tuberculosis treatment. The present review covers published data on antitubercular natural products from marine invertebrates grouped according to their biogenetic origin. Studies on the structure-activity relationships of these important leads are highlighted as well.

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Scalarane Sesterterpenoids

Abstract: In this review we cover the names, structures, and occurrence of all the scalaranes since their discovery in 1972. We have given special attention to the biological properties of these polycyclic terpenoids of exclusive marine origin.

Cited by 63 publications

References 109 publications

Sesterterpenoids with Anticancer Activity

Sesterterpenoids with Anticancer Activity

New Scalarane Sesterterpenoids from the Formosan Sponge Ircinia felix

Antimycobacterial Metabolites from Marine Invertebrates

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