Antifouling Diterpenoids from the Sponge Dendrilla antarctica.

Chem Biodivers

Universidad de Buenos Aires, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, C1428EGA, Buenos Aires, Argentina.

Published: February 2022

AI Article Synopsis

  • Two new compounds, 9,11-dihydrogracilin A and 9,11-dihydrogracillinone A, were discovered in the sponge Dendrilla antarctica, which was collected at a depth of 49 m near Tierra del Fuego.
  • The sponge's lack of epibionts and the abundance of these compounds led researchers to include them in paints designed to prevent marine fouling.
  • Tests showed that both compounds effectively inhibited the growth of various marine organisms, suggesting their potential as natural antifouling agents.

Article Abstract

Two nor-diterpenes, 9,11-dihydrogracilin A (1) and the previously unreported 9,11-dihydrogracillinone A (2), were isolated from the sponge Dendrilla antarctica. The sponge was collected by trawling at a depth of 49 m, from the research vessel Puerto Deseado, near the coast of Tierra del Fuego, farther north than the reported habitat for this species. Since these compounds were particularly abundant and the sponge was free from epibionts, both 1 and 2 were included in soluble-matrix paints and tested for antifouling activity in the ocean. The results obtained from these experiments clearly indicated a potent antifouling activity for both compounds against a variety of colonizing organisms, and established a probable role as natural antifoulants for these abundant secondary metabolites and other structurally related compounds previously isolated from Dendrilla spp.

Download full-text PDF

Source
http://dx.doi.org/10.1002/cbdv.202100618DOI Listing

Publication Analysis

Top Keywords

sponge dendrilla
8
dendrilla antarctica
8
antifouling activity
8
antifouling diterpenoids
4
sponge
4
diterpenoids sponge
4
antarctica nor-diterpenes
4
nor-diterpenes 911-dihydrogracilin
4
911-dihydrogracilin unreported
4
unreported 911-dihydrogracillinone
4

Similar Publications

Marine sponges usually host a wide array of secondary metabolites that play crucial roles in their biological interactions. The factors that influence the intraspecific variability in the metabolic profile of organisms, their production or ecological function remain generally unknown. Understanding this may help predict changes in biological relationships due to environmental variations as a consequence of climate change.

View Article and Find Full Text PDF

Two nitrogenous rearranged spongian nor-diterpenoids, dendrillic acids A and B, were isolated from a marine sponge sp. (order: Dendroceratida; family: Darwinellidae). The structures of the metabolites were elucidated on the basis of spectroscopic analysis as well as density functional theory prediction of NMR chemical shifts and application of the DP4+ algorithm.

View Article and Find Full Text PDF

Nature has been always a great source of possible lead compounds to develop new drugs against several diseases. Here we report the identification of a natural compound, membranoid G, derived from the Antarctic sponge displaying an inhibitory activity against human DNA topoisomerase 1B. The experiments indicate that membranoid G, when pre-incubated with the enzyme, strongly and irreversibly inhibits the relaxation of supercoiled DNA.

View Article and Find Full Text PDF

Antifouling Diterpenoids from the Sponge Dendrilla antarctica.

Chem Biodivers

February 2022

Universidad de Buenos Aires, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, C1428EGA, Buenos Aires, Argentina.

Article Synopsis
  • Two new compounds, 9,11-dihydrogracilin A and 9,11-dihydrogracillinone A, were discovered in the sponge Dendrilla antarctica, which was collected at a depth of 49 m near Tierra del Fuego.
  • The sponge's lack of epibionts and the abundance of these compounds led researchers to include them in paints designed to prevent marine fouling.
  • Tests showed that both compounds effectively inhibited the growth of various marine organisms, suggesting their potential as natural antifouling agents.
View Article and Find Full Text PDF

Total synthesis and biological evaluation of 7-hydroxyneolamellarin A as hypoxia-inducible factor-1α inhibitor for cancer therapy.

Bioorg Med Chem Lett

October 2021

Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.

7-Hydroxyneolamellarin A (7-OH-Neo A, 1), a natural marine product derived from sponge Dendrilla nigra, was first synthesized with 10% overall yield under the instruction of convergent synthetic strategy. We found that 7-OH-Neo A could attenuate the accumulation of hypoxia-inducible factor-1α (HIF-1α) protein and inhibit vascular epidermal growth factor (VEGF) transcriptional activity, showing well inhibitory effect on HIF-1 signaling pathway. Meantime, 7-OH-Neo A had the well anti-tumor activities, such as inhibiting tumor angiogenesis, proliferation, migration and invasion.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!