Novel Monounsaturated Fatty Acids from the Sponges Amphimedon compressa and Mycale laevis

Carballeira, Néstor M.; Negrón, Vilmary; Reyes, Elba D.

doi:10.1021/np50081a009

Cited by 32 publications

(31 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This specimen of A. complanata contains a very complex phospholipid fatty acid profile typical of sponges belonging to the genus Amphimedon (4,5,7). Noteworthy is its ability to extend the n-7 and n-9 families of even-numbered chain monounsaturated fatty acids from 9-18:1 and 11-18:1 to 21-30:1 and 23-30:1, respectively.…”

Section: Discussionmentioning

confidence: 99%

“…Recent efforts have concentrated on the C 16 family of α-methoxylated fatty acids, such as the 2-methoxy-5(Z)-hexadecenoic acid, 2-methoxy-6(Z)-hexadecenoic acid, and the 2-methoxyhexadecanoic acid, which were identified in the phospholipids of several Caribbean sponges such as Amphimedon compressa (4). Both 2-methoxy-5(Z)-hexadecenoic acid and 2-methoxyhexadecanoic acid occur more often in the phospholipids of sponges than their ∆6 analogs (5).…”

mentioning

confidence: 99%

See 1 more Smart Citation

The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of Amphimedon complanata

Carballeira

Alicea

2001

Lipids

Self Cite

View full text Add to dashboard Cite

The phospholipid fatty acid composition of the sponge Amphimedon complanata was reinvestigated, and the 2-methoxy-13-methyltetradecanoic acid, 2-methoxy-14-methylpentadecanoic acid, and 2-methoxy-13-methylpentadecanoic acid were identified for the first time in nature. Structure characterization was accomplished by means of gas chromatographic retention times and gas chromatography-mass spectrometry. These acids could have originated from bacteria in symbiosis with the sponge.

show abstract

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of Amphimedon complanata

Carballeira

Alicea

2001

Lipids

Self Cite

View full text Add to dashboard Cite

show abstract

“…Thus, the saturated acids 2-metoxy-14 : 0, 2-metoxy-15 : 0, and 2-metoxy-18 : 0 were found in the sponge C. fallax [38], and 2-metoxy- 16 : 0 was found in the sponge A. compressa [23]. In several species of sponges (A. nompressa, Mycale laevis, M. laxissima, Tethya crypta, and C. fallax), there was the unsaturated acid 2-metoxy-16 : 1∆5 [23,35,38]. In sponges ∆6-monoenes with metoxy-group were found 2-metoxy-16 : 1∆6 in Spheciospongia cuspidifera [42], 2-metoxy-14 : 1∆6, 2-metoxy-15 : 1∆6, and 2-metoxy-13-methyl-14 : 1∆6 FA in C. fallax [38], 2-metoxy-17: 1∆6 and 2-metoxy-18: 1∆6 in S. cuspidifera [21].…”

Section: Fatty Acids With Additional Functional Groupsmentioning

confidence: 99%

Fatty Acids and Other Lipids of Marine Sponges

Rodkina

2005

Russ J Mar Biol

View full text Add to dashboard Cite

At the present, the structure of lipids and fatty acids (FA) of almost 250 species of marine sponges has been studied. It was shown that sponges are leaders in FA diversity among aquatic animals. The great majority of the works on research of FA structure in sponges was focused on representatives of the class Demospongiae and was carried out on organisms from tropical and subtropical areas, whereas sponges from the boreal region remain poorly studied.

show abstract

“…In addition, we recovered a number of unsaturated fatty acids often considered algal/protist biomarkers, including eicosatetraenoic (ara- Shalabi, 1994;Carballeira et al, 1992). We also failed to detect brominated long-chain fatty acids, which have been reported as major fatty acids for A. terpenensis (Garson, Zimmermann, Battershill, Holden, & Murphy, 1994;Garson et al, 1993).…”

Section: Amphimedon Queenslandica Contains Fatty Acids and Sterols mentioning

confidence: 94%

Lipidomics of the sea sponge Amphimedon queenslandica and implication for biomarker geochemistry

et al. 2017

View full text Add to dashboard Cite

Demosponges are a rich natural source of unusual lipids, some of which are of interest as geochemical biomarkers. Although demosponges are animals, they often host dense communities of microbial symbionts, and it is therefore unclear which lipids can be synthesized by the animal de novo, and which require input from the microbial community. To address this uncertainty, we analyzed the lipids of Amphimdeon queenslandica, the only demosponge with a published genome. We correlated the genetic and lipid repertoires of A. queenslandica to identify which biomarkers could potentially be synthesized and/or modified by the sponge. The fatty acid profile of A. queenslandica is dominated by an unusual Δ 5,9 fatty acid (cis-5,9-hexacosadienoic acid)-similar to what has been found in other members of the Amphimdeon genus-while the sterol profile is dominated by C 27 -C 29 derivatives of cholesterol. Based on our analysis of the A. queenslandica genome, we predict that this sponge can synthesize sterols de novo, but it lacks critical genes necessary to synthesize basic saturated and unsaturated fatty acids. However, it does appear to have the genes necessary to modify simpler products into a more complex "algal-like" assemblage of unsaturated fatty acids. Ultimately, our results provide additional support for the poriferan affinity of 24-isopropylcholestanes in Neoproterozoic-age rocks (the "sponge biomarker" hypothesis) and suggest that some algal proxies in the geochemical record could also have animal contributions.

show abstract

Novel Monounsaturated Fatty Acids from the Sponges Amphimedon compressa and Mycale laevis

Cited by 32 publications

References 11 publications

The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of Amphimedon complanata

The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of Amphimedon complanata

Fatty Acids and Other Lipids of Marine Sponges

Lipidomics of the sea sponge Amphimedon queenslandica and implication for biomarker geochemistry

Contact Info

Product

Resources

About