Novel cyclopropane fatty acids from the phospholipids of the Caribbean sponge Pseudospongosorites suberitoides.
The cyclopropane fatty acids 17-methyl-trans-4,5-methyleneoctadecanoic acid, 18-methyl-trans-4,5-methylenenonadecanoic acid, and 17-methyl-trans-4,5-methylenenonadecanoic acid were characterized for the first time in nature in the phospholipids (mainly PE, PG and PS) of the hermit-crab sponge Pseudospongosorites suberitoides. Pyrrolidine derivatization was the key in identifying the position of the cyclopropyl and methyl groups in the acyl chains and (1)H NMR was used to determine the trans stereochemistry of the cyclopropane ring. The phospholipids from the sponge also contained an interesting series of iso-anteiso Delta(5,9) fatty acids with chain-lengths between 17 and 21 carbons, with the fatty acids (5Z,9Z)-18-methyl-5,9-nonadecadienoic acid and the (5Z,9Z)-17-methyl-5,9-nonadecadienoic acid being described for the first time in sponges. The anteiso alpha-methoxylated fatty acid 2-methoxy-12-methyltetradecanoic acid was also identified for the first time in nature in the phospholipids of this interesting marine sponge. The novel cyclopropyl fatty acids could have originated from the phospholipids of a cyanobacterium living in symbiosis with the sponge.
Carballeira
Néstor M
NM
Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, 00931-3346 Puerto Rico. nmcarballeira@uprrp.edu
Montano
Nashbly
N
Vicente
Jan
J
Rodriguez
Abimael D
AD
D000818:Animals; D017691:Caribbean Region; D000458:Cyanobacteria / Q000737:chemistry / Q000502:physiology; D003521:Cyclopropanes / Q000737:chemistry* / Q000302:isolation & purification*; D005227:Fatty Acids / Q000737:chemistry* / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010743:Phospholipids / Q000737:chemistry* / Q000302:isolation & purification; D011161:Porifera / Q000737:chemistry* / Q000145:classification / Q000382:microbiology*; D011759:Pyrrolidines / Q000737:chemistry; D013045:Species Specificity; D013229:Stearic Acids / Q000737:chemistry / Q000302:isolation & purification; D013559:Symbiosis / Q000502:physiology
D003521:Cyclopropanes; D005227:Fatty Acids; D010743:Phospholipids; D011759:Pyrrolidines; D013229:Stearic Acids; C028775:cyclopropane fatty acids; C032519:pyrrolidine