Discorhabdin Alkaloids from the Antarctic Sponge Latrunculia apicalis

Yang, Aimin; Baker, Bill J.; Grimwade, Julia E.; Leonard, Alan C.; McClintock, James B.

doi:10.1021/np50124a020

Cited by 63 publications

(98 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Discorhabdin-type alkaloids are characterized by their wide spectrum of in vitro anticancer activities [5,16]. Notably, the anticancer potency of the dimeric discorhabdins is similar to the monomeric discorhabdin with IC 50 values at a submicromolar level.…”

Section: Discussionmentioning

confidence: 99%

“…Some discorhabdins bear a heptacyclic backbone through further intramolecular cyclization via a bond formation between C-2 and N-18 and/or possess a thioether bridge between C-5 and C-8 [6,7,15]. The broad-spectrum anticancer activity of discorhabdins against various cancer cell lines, e.g., HCT-116 (human colon cancer cell line), P388 (murine leukemia cell line), and KB (human oral cancer cell line) have been reported [5,16]. Compared to monomeric discorhabdins, dimeric discorhabdins are highly uncommon.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

Janussen

Taşdemir

2020

Marine Drugs

View full text Add to dashboard Cite

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

Janussen

Taşdemir

2020

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…This cold-adapted porifera is rarely preyed upon by sea stars, which are the dominant spongivores in Antarctic benthic communities. The sponge contains alkaloids, namely dischorhabidins (e.g., dischorhabidin-G) that elicit a tube foot retraction response in the sea star Perkinaster focus (Yang et al 1995;Furrow et al 2003). Defensive alkaloids are apparently localized in the external part of the sponge body (dischorhabidins-G was found within 2 mm from the sponge surface), preserving the most vulnerable tissues, where the likelihood of predation from sea stars is highest.…”

Section: Chemically-mediated Interactions In Benthic Invertebratesmentioning

confidence: 99%

New trends in marine chemical ecology

Ianora

Boersma

Casotti

et al. 2006

Estuaries and Coasts: J ERF

123

View full text Add to dashboard Cite

This essay is the outcome of a colloquium convened in November 2005 at the Benthos Laboratory of the Stazione Zoologica Anton Dohrn in Ischia, Italy, on chemical ecology and the role of secondary metabolites in the structuring and functioning of marine biodiversity. The participants of the workshop are part of the European Network of Excellence MarBEF (Marine Biodiversity and Ecosystem Function), a consortium of 56 European marine institutes to integrate and disseminate knowledge and expertise on marine biodiversity. Here we review some of the new trends and emerging topics in marine chemical ecology. The first section deals with microbial chemical interactions. Microbes communicate with each other using diffusible molecules such as N-acylhomoserine lactones (AHL). These are regulators in cell-density-dependent gene regulation (quorum sensing) controlling microbial processes. In chemical interactions with higher organisms, microbes can act either as harmful pathogens that are repelled by the host's chemical defense or as beneficial symbionts. These symbionts are sometimes the true producers of the host's secondary metabolites that have defensive and protective functions for their hosts. We also describe how allelochemicals can shape phytoplankton communities by regulating competition for available resources, and also interactions among individuals of the same species. Compounds such as the diatom-derived unsaturated aldehydes have been demonstrated to act as infochemicals, and they possibly function as a diffusible bloom-termination signal that triggers an active cell death and bloom termination at sea. The same molecules have also been shown to interfere with the reproductive capacity of grazing animals deterring future generations of potential predators. Such compounds differ from those that act as feeding deterrents since they do not target the predator but its offspring. Many of the neurotoxins produced by dinoflagellates act as feeding deterrents, and laboratory experiments have shown that ingestion of these algae by some microzooplankton and macrozooplankton can cause acute responses such as death, incapacitation, altered swimming behavior, and reduced fecundity and egg-hatching success. These effects may rarely occur in nature because of low individual grazing rates on dinoflagellate cells and grazing on other food sources such as microflagellates and diatoms. We also consider the nutritional component of marine plant-herbivore interactions, especially in the plankton, and the information available on the effects of growing conditions of algae on the production of toxic metabolites. Species producing saxitoxins seem to consistently produce the highest amounts of toxins (on a per cell basis) in the exponential phase of growth, and there is a decrease in their production under nitrogen, but not under phosphorus stress, where the production actually increases. We try to explain the circumstances under which organisms defend themselves chemically and argue that the most likely explanatory model for ...

show abstract

“…MCMURDO SOUND SPONGES Extracts from Latrunculia apicalis elicit a significant tube-foot retraction response in Perknaster fuscus (McClintock et al, 1994). Fractionation of the extract yielded discorhabdin alkaloids (Yang, 1994;Yang et al, 1995). This group of pigments was first reported from sponge species found in temperate and tropical waters, and they are routinely toxic (Perry et al, 1988).…”

Section: Chemical Analyses Of Bioactivementioning

confidence: 99%

Secondary Metabolites as Mediators of Trophic Interactions Among Antarctic Marine Organisms1

Amsler¹,

McClintock²,

Baker³

2001

American Zoologist

Self Cite

View full text Add to dashboard Cite

SYNOPSIS. Secondary metabolites are widespread among lower phyla and understanding their functional role(s) in the producing organism has been under study in recent decades. Considerable progress has been made in understanding chemical ecological interactions among terrestrial organisms, and similar research in the marine realm has been initiated in recent years. Polar regions are more difficult to access and thus progress has been slower. Nevertheless, the extreme and often unique marine environments surrounding Antarctica as well as the many unusual trophic interactions in antarctic marine communities might well be expected to select for novel secondary metabolites and/or novel functional roles for secondary metabolites. Indeed, recent studies have documented novel, chemically-mediated interactions between molluscs and amphipods, between algae, urchins and anemones, and between sponges and their predators. The Porifera are the dominant phylum on the McMurdo Sound benthos, and representatives of this phylum have been shown to elaborate sea star feeding deterrents, inhibitors of fouling or infectious organisms, and metabolites which mediate predation via molt inhibition. As a result of studies on Antarctic sponges, new insights into functional roles of pigments and the ability of sponges to sequester metabolites have been gained, and a new mechanism of chemical defense has been described. Herein we describe recent results of our studies of trophic interactions between sponges and their predators that are mediated by specific sponge secondary metabolites. Moreover, we highlight unusual chemically-mediated interactions in antarctic marine invertebrates other than sponges.

show abstract

Discorhabdin Alkaloids from the Antarctic Sponge Latrunculia apicalis

Cited by 63 publications

References 10 publications

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

New trends in marine chemical ecology

Secondary Metabolites as Mediators of Trophic Interactions Among Antarctic Marine Organisms1

Contact Info

Product

Resources

About