Axinelloside A, an unprecedented highly sulfated lipopolysaccharide inhibiting telomerase, from the marine sponge, Axinella infundibula.
Axinelloside A was isolated from the lipophilic extract of the Japanese marine sponge Axinella infundibula as a strong human telomerase inhibitor (IC(50) 2.0 microg/mL). It has the molecular weight of 4780.4 as the monoisotopic mass of the 19 sodium salt. The chemical structure was elucidated mainly by spectroscopic methods (2D NMR and MS). Axinelloside A consists of twelve sugars, e.g., a scyllo-inositol, a D-arabinose, 5 D-galactoses, and 5 L-fucoses, together with an (R)-3-hydroxy-octadecanoic acid, 3 (E)-2-hexadecenoic acids, and 19 sulfates.
Warabi
Kaoru
K
Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Hamada
Toshiyuki
T
Nakao
Yoichi
Y
Matsunaga
Shigeki
S
Hirota
Hiroshi
H
van Soest
Rob W M
RW
Fusetani
Nobuhiro
N
D000818:Animals; D002236:Carbohydrate Conformation; D002247:Carbon Isotopes; D006367:HeLa Cells; D006801:Humans; D008070:Lipopolysaccharides / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D011134:Polysaccharides / Q000737:chemistry / Q000494:pharmacology*; D011161:Porifera / Q000737:chemistry*; D011522:Protons; D012015:Reference Standards; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry*; D019098:Telomerase / Q000037:antagonists & inhibitors*
D002247:Carbon Isotopes; D008070:Lipopolysaccharides; D011134:Polysaccharides; D011522:Protons; D013431:Sulfates; C505704:axinelloside A; D019098:Telomerase