Two New Sarasinosides from the Sponge Melophlus Sarasinorum

Abstract

Two new 30-norlanostane-type oligoglycosides (6, 7) along with five known sarasinosides A 1 (1), A 2 (2), A 3 (3), M (4), L (5) were isolated from the ethanol extract of the Australian sponge Melophlus sarasinorum. The skeleton of new sarasinoside A 4 (6) possesses a rare 8α,9α-oxido-8,9-seco-moiety. Sarasinoside A 5 (7) proved to be a 9-deoxy-congener of the previously described sarasinoside L (5). Compounds 1-7 have identical pentasaccharide chains and differ in the aglycone portions. The structures have been elucidated on the basis of NMR, MALDI-TOF MS and GC analyses.

Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung

“…106 Später beschrieb diese Gruppe noch Sarasinosid M ( 157 ; Abbildung 28) aus dem indonesischen Schwamm Melophlus sarassinorum 107. 108 Sechs Jahre später isolierte eine von Oh und Shin geleitete Forschungsgruppe erneut Sarasinosid M ( 157 ) gemeinsam mit Sarasinosid Q ( 158 ) aus dem tropischen Schwamm Lipastrotethya sp. in Chuuk, Mikronesien (Abbildung 28).…”

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

“…Finally, Santalova et al . [ 18 ] have isolated two new 14-nor-methyl-lanostane triterpene glycosides, sarasinosides A 4 ( 22 ) and A 5 ( 23 ), along with known sarasinosides A 1 ( 1 ), A 2 ( 2 ), A 3 ( 3 ), M ( 21 ) and L ( 20 ) from the Australian collection of the same species.…”

“…The rearrangements led to relative compounds in certain triterpenoids isolated from higher plants is carried out via intermediates with Δ 14(15) -unsaturation [ 16 ]. More oxidized aglycones in sarasinosides E, F, H 1 , H 2 , I 1 , I 2 , J–L and A 5 ( 11 , 12 , 14 – 20 , 23 , respectively) contain additional oxy-, methoxy- or ketone groups, while aglycones of sarasinosides M and A 4 ( 21 , 22 ) are 8,9- seco -derivatives having unique 8α,9α-epoxy-8(14),9(11),24-triene and 8α,9α-epoxy-7(8),9(11)-diene structural fragments ( Chart 1 ) [ 14 , 15 , 16 , 17 , 18 ].…”

A new sarasinoside congener, sarasinoside M2, from a marine sponge collected in the Solomon Islands

“…4) The difference between 1 and 3 was found only in a sugar moiety: the internal Glc in 3 is replaced by Xyl in 1. In the aglycon of 1, the difference of the chemical shift from that of 3 was less than 0.1 ppm in the 1 H NMR spectrum, and less than 1.5 ppm (C9) in the 13 C NMR spectrum. The absolute configuration of the aglycon of 1 was not determined.…”

“…The absolute configuration of the aglycon of 1 was not determined. Besides 1 and 3, sarasinoside A 4 , 13) eryloside L, 14) jereisterol A, 15) Fig. 2.…”