8-Oxoadenine (1) was found as a main secondary metabolite of a far-eastern Thorectidae sponge. In addition, a related minor compound, 9-methyl-8-oxoadenine (2), was isolated for the first time as a natural product, along with the previously known 3-methyladenine (3). Two known trihydroxylated sterols of the Δ7 series (4, 5) were also identified. Structural identification of 1–5 was carried out by analysis of spectroscopic data.
ChoBP, EvansFE. (1991) Structure of oxidatively damaged nucleic-acid adducts. 3. Tautomerism, ionization and protonation of 8-hydroxyadenosine studied by N-15-NMR-spectroscopy. Nucleic Acids Research, 19, 1041–1047.
2.
LindsayBS, AlmeidaAMP, SmithCJ, BerlinkRGS, da RochaRM, IrelandCM. (1999) 6-Methoxy-8-oxoguanine, an unusual purine from the ascidian Symplegma rubra. Journal of Natural Products, 62, 1573–1575.
3.
MoonB, BakerBJ, McClintockJB. (1998) Purine and nucleoside metabolites from the Antarctic sponge Isodictya erinacea. Journal of Natural Products, 61, 116–118.
4.
KilldayKB, YarwoodD, SillsMA, MurphyPT, HooperJNA, WrightAE. (2001) Microxine, a new cdc2 kinase inhibitor from the Australian marine sponge Microxina species. Journal of Natural Products, 64, 525–526.
5.
ZelnikR, HaraguchiM, MatidaAK, LavieD, FrolowF, WeisAL. (1986) X-ray molecular structure of caissarone, a novel purine derivative from the sea-anemone Bunodosoma caissarum. Journal of the Chemical Society-Perkin Transactions 1, 12, 2051–2053.
6.
CiminoG, de GiulioA, de RosaS, de StefanoS, PulitiR, MattiaCA, MazzarellaL. (1985) Isolation and X-ray crystal structure of a novel 8-oxopurine compound from a marine sponge. Journal of Natural Products, 48, 523–528.
7.
MakarievaTN, DenisenkoVA, DmitrenokPS, GuziiAG, SantalovaEA, StonikVA, MacMillanJB, MolinskiTF. (2005) Oceanalin A, a hybrid alpha, omega-bifunctionalized sphingoid tetrahydroisoquinoline beta-glycoside from the marine sponge Oceanapia sp. Organic Letters, 7, 2897–2900.
8.
MakarievaTN, GuziiAG, DenisenkoVA, DmitrenokPS, SantalovaEA, PokanevichEV, MolinskiTF, StonikVA. (2005) Rhizochalin A, a novel two-headed sphingolipid from the sponge Rhizochalina incrustata. Journal of Natural Products, 68, 255–257.
9.
FujiiT, ItayaT. (1998) Five Nx-methyladenines: their chemistry, physico-chemical properties, and biological activities. Heterocycles, 48, 1673–1724.
10.
FujiiT, ItayaT. (1999) Systematic tables of mono-and poly-N-methylated adenines: acid dissociation constants and UV and NMR spectral data. Heterocycles, 51, 1673–1724.
11.
StollerC, BraekmanJC, DalozeD, VandevyverG. (1988) 3-Methyladenine from the marine sponge Tepsentia genitrix. Journal of Natural Products, 51, 383–384.
12.
PiccialliV, SicaD. (1987) Four new trihydroxylated sterols from the sponge Spongionella gracilis. Journal of Natural Products, 50, 915–920.
13.
ZengC, IshibashiM, KobayashiJ. (1993) Biemnasterol, a new cytotoxic sterol with the rare 22,25-diene side chain, isolated from the marine sponge Biemna sp. Journal of Natural Products, 56, 2016–2018.
14.
YamaguchiY, NakanishiY, ShimokawaT, HashiguchiS, HayashiA. (1992) Structure elucidation of oxygenated sterols from eggs of sea hare, Aplysia juliana. Chemisrty Letters, 1713–1714.
15.
ShubinaLK, FedorovSN, LevinaEV, AndriyaschenkoPV, KalinovskyAI, StonikVA, SmirnovIS. Comparative study on polyhydroxylated steroids from echinoderms. (1998) Comparative Biochemistry and Physiology Part B, 119, 505–511.
