Three New Spongian Diterpenes from the Fijian Marine Sponge <i>Spongia</i> sp

Gross, Harald; Wright, Anthony D.; Reinscheid, Uwe M.; König, Gabriele M.

doi:10.1177/1934578x0900400303

Cited by 11 publications

(15 citation statements)

References 30 publications

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“…Doriprismatica (Glossodoris) atromarginata presents furanoditerpenoids and scalarane sesterterpenes from its dietary sponges Spongia ( Hyatella ) sp. and Hyrtios spp., and these compounds display ichthyotoxicity against the mosquito fish, G. affinis —particularly, the activity of 12-deacetoxy-12-oxodeoxoscalarin ( 136 ) is noticeable [ 92 , 175 , 180 , 378 , 379 , 380 , 381 , 382 , 383 , 384 , 385 , 386 ]. Other NPs from chromodoridids were analyzed for ichthyotoxicity against G. affinis , including homoscalarane and scalarane compounds from Felimida (Glossodoris) dalli , Glossodoris rufomarginata , Glossodoris pallida , Glossodoris vespa , and Ardeadoris (Glossodoris) averni , and 12-deacetyl-23-acetoxy-20-methyl-12- epi- scalaradial ( 135 ) was the most potent of them [ 175 , 183 , 383 ].…”

Section: Ecological Activitymentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from different origins that provide the molluscs with potent chemicals that are ecologically and pharmacologically relevant. In this review, we analyze the bioactivity of more than 450 compounds from ca. 400 species of heterobranch molluscs that are useful for the snails to protect themselves in different ways and/or that may be useful to us because of their pharmacological activities. Their ecological activities include predator avoidance, toxicity, antimicrobials, antifouling, trail-following and alarm pheromones, sunscreens and UV protection, tissue regeneration, and others. The most studied ecological activity is predation avoidance, followed by toxicity. Their pharmacological activities consist of cytotoxicity and antitumoral activity; antibiotic, antiparasitic, antiviral, and anti-inflammatory activity; and activity against neurodegenerative diseases and others. The most studied pharmacological activities are cytotoxicity and anticancer activities, followed by antibiotic activity. Overall, it can be observed that heterobranch molluscs are extremely interesting in regard to the study of marine natural products in terms of both chemical ecology and biotechnology studies, providing many leads for further detailed research in these fields in the near future.

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Section: Ecological Activitymentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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“…The observed shifts in 13 C NMR spectrum of 2 (Table 1) for C-1 (−5.0 ppm, upfield), C-2 (+1.8 ppm, downfield), C-3 (+0.1 ppm, downfield) and C-4 (+0.6 ppm, downfield) are therefore consistent with the 2 Z configuration. Thus we propose for compound 2 the trivial name isomalyngamide K. In order to consolidate this hypothesis, the NMR analysis was complemented by the comparison of quantum-mechanically calculated 13 C NMR chemical shifts [21–23] with experimental ones. To increase the reliability of this comparison, the most indicative differences in chemical shifts were chosen that occur between the published data for malyngamide K ( 3 ) and the putative isomalyngamide K ( 2 ): C-1 (−5.0 ppm) and C-2 (+1.8 ppm).…”

Section: Resultsmentioning

confidence: 99%

The structure elucidation of isomalyngamide K from the marine cyanobacterium Lyngbya majuscula by experimental and DFT computational methods

Han

Reinscheid

Gerwick

et al. 2011

Journal of Molecular Structure

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a b s t r a c tThe 2Z-isomer of malyngamide K has been isolated along with the known compounds malyngamide C, deoxy-C and K, and characterized from a Papua New Guinea field collection of the cyanobacterium Lyngbya majuscula. The planar structure was deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. The absolute configurations were determined on the basis of spectroscopic techniques, chemical degradation and DFT theoretical calculations.

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“…They share the similar skeleton with abietane-type with furan ring connected on C-13 and C-14. Among them, two compounds (414 and 415) compose of a cyclopentanone ring A (Gross et al 2009). …”

Section: Type Icmentioning

confidence: 99%

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

et al. 2016

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Furanoditerpenoids are a special group of diterpenoids composing of one or more furan rings, which are rarely found in nature. This review aims to survey the various naturally occurring furanoditerpenoids and their pharmacological activities. A fairly large number of furanoditerpenoids have been reported from the families Euphorbiaceae, Fabaceae and Lamiaceae, and a few ones from the families Asteraceae, Codoniaceae, Dioscoreaceae, Fossombroniaceae, Jamesoniellaceae, Meliaceae, Menispermaceae, Olacaceae, Psathyrellaceae, Sapindaceae and Scapaniaceae. Their distribution correlates strongly with the taxonomic divisions. Most of these plants are widely used in traditional medicines, and furanoditerpenoids have therefore been disclosed with a wide range of bioactivities including anti-cancer, antiinflammation and anti-microorganism. To structure this review, the furanoditerpenoids were classified into seven types, including clerodane-type (Type I), labdane-type (Type II), cassane-type (Type III), abietane-type (Type IV), spongian-type (Type V), prenylbisabolane-type (Type VI) and miscellaneous type (Type VII). On the basis of 170 references, this review covers the distribution, phytochemistry, synthesis and pharmacological activities of furanoditerpenoids, describing 444 compounds. The information provided in this review might shed light on further research and development of furanoditerpenoids as potential therapeutic agents.

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Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp

Cited by 11 publications

References 30 publications

Bioactive Compounds from Marine Heterobranchs

Bioactive Compounds from Marine Heterobranchs

The structure elucidation of isomalyngamide K from the marine cyanobacterium Lyngbya majuscula by experimental and DFT computational methods

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

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