Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedure
3.2. Collection, Extraction, and Isolation
3.3. Zeamide (1)
3.4. Methanolysis of Zeamide (1)
3.5. Hydrolysis of Zeamide (1)
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Sample Availability: Sample of compound 1 is available from the authors. |
Position | δC, Type b | δH, mult ( J in Hz) c | HMBC d | |
---|---|---|---|---|
1 | 65.7, CH2 | a | 4.24, ddd (10.9, 7.2, 4.2) | |
b | 3.96, ddd (10.9, 6.4, 2.7) | |||
2 | 55.5, CH | 3.91, ddd (9.0, 4.2, 2.7) | 1‴ | |
3 | 72.5, CH | 4.10, t (8.3) | 1, 2, 4, 5 | |
4 | 131.2, CH | 5.45, dd (15.3, 7.7) | 3, 6 | |
5 | 135.0, CH | 5.71, ddd (15.3, 6.9, 6.9) | 3, 6, 7 | |
6 | 33.5, CH2 | 2.02, m | 4, 5, 7 | |
7 | 30.5, CH2 | 1.37, m | ||
1′ | 76.5, CH | 4.01, ddd (9.9, 8.0, 2.7) | 6′ | |
2′ | 72.9, CH | 4.27, t (2.7) | 1′, 3′, 4′, 6′ | |
3′ | 72.9, CH | 3.36, dd (9.8, 2.7) | 4′ | |
4′ | 74.1, CH | 3.63, t (9.5) | 2′, 3′, 5′ | |
5′ | 77.3, CH | 3.41, t (9.3) | 4′, 6′ | |
6′ | 78.9, CH | 3.91, t (9.6) | 4′, 5′, 1″ | |
1′′ | 101.5, CH | 5.36, d (3.7) | 6′, 3″, 5″ | |
2″ | 71.1, CH | 3.76, dd (9.9, 3.7) | ||
3″ | 70.8, CH | 3.91, dd (9.9, 3.7) | ||
4″ | 71.1, CH | 3.88, br. s | 3″ | |
5″ | 64.9, CH | a | 4.36, br. d (12.7) | 1″, 3″ |
b | 3.54, dd (12.7, 2.2) | 1″, 3″ | ||
1‴ | 175.9, C | |||
2‴ | 37.4, CH2 | 2.21, t (7.6) | 1‴, 3‴ | |
3‴ | 27.2, CH2 | 1.58 | 1‴, 2‴ |
Fatty Acid Methyl Ester | |
---|---|
methyl 13-methyltetradecanoate ( iso-C15) | 22.6% |
methyl 14-methylpentadecanoate ( iso-C16) | 21.0% |
methyl hexadecanoate ( n-C16) | 25.4% |
methyl 10-methylhexadecanoate (10Me-C17) | 12.9% |
methyl 15-methylhexadecanoate ( iso-C17) | 14.2% |
methyl octadecanoate ( n-C18) | 3.9% |
Sphingosine | |
(2 S,3R,4E)-2-amino-4-tetracosene-1,3-diol (C24 d-erythro-sphingosine, d24:1) | 3.5% |
(2 S,3R,4E)-2-amino-4-pentacosene-1,3-diol (C25 d-erythro-sphingosine, d25:1) | 2.7% |
(2 S,3R,4E)-2-amino-4-hexacosene-1,3-diol (C26 d-erythro-sphingosine, d26:1) | 62.1% |
(2 S,3R,4E)-X-methyl-2-amino-4-hexacosene-1,3-diol (branched d27:1) | 3.4% |
(2 S,3R,4E)-2-amino-4-heptacosene-1,3-diol (C27 d-erythro-sphingosine, d27:1) | 4.5% |
(2 S,3R,4E)-2-amino-4-octacosene-1,3-diol (C28 d-erythro-sphingosine, d28:1) | 5.2% |
Total unsaturated sphingosines | 81.4% |
(2 S,3R)-2-amino-1,3-tetracosenediol (C24 d-erythro-dihydrosphingosine, d24:0) | 1.8% |
(2 S,3R)-X-methyl-2-amino-1,3-tetracosenediol (branched d25:0) | 1.1% |
(2 S,3R)-2-amino-1,3-pentacosenediol (C25 d-erythro-dihydrosphingosine, d25:0) | 1.3% |
(2 S,3R)-2-amino-1,3-hexacosenediol (C26 d-erythro-dihydrosphingosine, d26:0) | 11.4% |
(2 S,3R)-2-amino-1,3-heptacosenediol (C27 d-erythro-dihydrosphingosine, d27:0) | 1.8% |
(2 S,3R)-2-amino-1,3-octacosenediol (C28 d-erythro-dihydrosphingosine, d28:0) | 1.2% |
Total saturated sphingosines | 18.6% |
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Della Sala, G.; Teta, R.; Esposito, G.; Pawlik, J.R.; Mangoni, A.; Costantino, V. Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai. Molecules 2017, 22, 1455. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules22091455
Della Sala G, Teta R, Esposito G, Pawlik JR, Mangoni A, Costantino V. Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai. Molecules. 2017; 22(9):1455. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules22091455
Chicago/Turabian StyleDella Sala, Gerardo, Roberta Teta, Germana Esposito, Joseph R. Pawlik, Alfonso Mangoni, and Valeria Costantino. 2017. "Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai" Molecules 22, no. 9: 1455. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules22091455