Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus

Abstract

Three new polyhydroxysteroidal glycosides, hesperuside A (1), B (2), and C (3), as well as a known novaeguinoside A (4), were isolated from the ethanol extract of starfish Craspidaster hesperus collected from the South China Sea. Their structures were elucidated by extensive spectroscopic methods and chemical evidence. The compounds 1–3 present unprecedented carbohydrate chain 3-O-methyl-β-d-galactopyranose, which differ from each other in the side chains. These compounds exhibited cytotoxicity against human tumor cells BEL-7402, MOLT-4, and A-549 in vitro.

Six New Polyhydroxysteroidal Glycosides, Anthenosides S1 – S6, from the Starfish Anthenea sibogae

“…We established the structures of six new polyhydroxysteroidal glycosides, anthenosides S1 – S6 ( 1 – 6 ), which were isolated along with a mixture of two previously known anthenosides J and K ( 7 and 8 ). All these substances were structurally related to glycosides of the same type from the starfish A. chinensis , A. aspera , and C. hesperus . In addition, the cytotoxicity of compounds 1 , 2 , 4 , and the obtained mixture of 7 and 8 against human breast cancer T‐47D cells, and their effects on the cell proliferation and colony formation of these cells in a soft agar clonogenic assay in vitro have been studied.…”

“…They contain highly oxygenated steroidal aglycons with carbohydrate moieties, consisting of one to three monosaccharide units attached to C(3) in the steroidal nucleus and/or to C(24), C(26), C(28) or C(29) in the side chain. Recently, glycosides belonging to a new structural type has been isolated from three tropical species of starfish Anthenea chinensis , Anthenea aspera , and Craspidaster hesperus . These substances have unusual structural features: rare positions of carbohydrate fragments attachment to C(7) and C(16) or only to C(16) of aglycons with Δ 8(14) ‐3 β ,4 β ,6 β ,7 β ,16 α ‐pentahydroxy, Δ 8(14) ‐3 β ( α ),6 β ,7 β ,16 α ‐tetrahydroxy or Δ 8(14) ‐3 α ,7 β ,16 α ‐trihydroxy substitutions and not oxidized side chains.…”

“…Recently, glycosides belonging to a new structural type has been isolated from three tropical species of starfish Anthenea chinensis, [8] [9] Anthenea aspera, [10] and Craspidaster hesperus. [11] These substances have unusual structural features: rare positions of carbohydrate fragments attachment to C (7) and C (16) or only to C (16) of aglycons with D 8(14) -3b,4b,6b,7b,16a-pentahydroxy, D 8(14) -3b(a),6b,7b,16a-tetrahydroxy or D 8(14) -3a,7b,16atrihydroxy substitutions and not oxidized side chains.…”

“…All these substances were structurally related to glycosides of the same type from the starfish A. chinensis, [8] [9] A. aspera, [10] and C. hesperus. [11] In addition, the cytotoxicity of compounds 1, 2, 4, and the obtained mixture of 7 and 8 against human breast cancer T-47D cells, and their effects on the cell proliferation and colony formation of these cells in a soft agar clonogenic assay in vitro have been studied.…”

Chemical Constituents and Bioactivities of Starfishes: An Update

“…Compounds 120 – 123 were generated by the starfish Anthenea chinensis Gay . Compounds 126 – 128 all present unprecedented carbohydrate chain 3‐ O ‐methyl‐ β ‐ d ‐galactopyranose, and they only differ from each other in the side chains . Compounds 129 and 130 were isolated as an inseparable mixture of epimers .…”