Isolation of free deoxyribonucleosides and their bases from the acorn worm Ptychodera flava

doi:10.1016/0305-0491(85)90136-1

Comparative Biochemistry and Physiology Part B: Comparative Biochemistry

Volume 82, Issue 1, 1985, Pages 107-109

https://doi.org/10.1016/0305-0491(85)90136-1 Get rights and content

Abstract

1.
1. An aqueous extract of the acorn worm Ptychodera flava was investigated for hydrophilic constituents.
2.
2. Isolated from the extract were four deoxyribonucleasides (deoxyguanosine, deoxyinosine, deoxyuridine, and deoxythymidine) and three bases (hypoxanthine, uracil, and thymine).
3.
3. Free deoxyribonucleosides, especially deoxyinosine and deoxyuridine have rarely been isolated from marine invertebrates.

References (21)

T. Higa et al.
Halogenated phenol and indole constituents of acorn worms
Comp. Biochem. Physiol.
(1980)
L.A. Manson et al.
Some chemical properties of deoxyribose nucleosides
J. biol. Chem.
(1951)
J.F. Weber et al.
Isolation of allantoin and adenosine from the marine sponge Tethya aurantia
Comp. Biochem. Physiol.
(1981)
W. Bergmann et al.
Contributions to the study of marine products. XXXIX. The nucleosides of sponges III. Spongothymidine and spongouridine
J. org. Chem.
(1955)
W. Bergmann et al.
Contributions to the study of marine products. XL. The nucleosides of sponges IV. Spongosine
J. org. Chem.
(1956)
W. Bergmann et al.
Contributions to the study of marine products. XXXII. The nucleosides of sponges 1
J. org. Chem.
(1951)
E.R. Blout et al.
Absorption spectra. VIII. The infrared spectra of some purines and pyrimidines
J. Am. chem. Soc.
(1950)
D.M. Brown et al.
Deoxyribonucleosides and related compounds. Part II. A proof of furanose structure of the natural 2-deoxyribonucleosides
J. chem. Soc.
(1950)
A.F. Cook et al.
1-Methylisoguanosine, a pharmacologically active agent from a marine sponge
J. org. Chem.
(1980)
C.A. Dekker et al.
Uracil deoxyriboside
Nature
(1950)

There are more references available in the full text version of this article.

Cited by (7)

Aplysidine, a new nucleoside from the Okinawan marine sponge Aplysina Sp.
1992, Tetrahedron
Hydrophilic organic nitrogenous metabolites from marine bryozoans
1989, Comparative Biochemistry and Physiology -- Part B: Biochemistry and
- 1.
  1. Hydrophilic nitrogenous metabolites have been identified from extracts of marine bryozoans
- 2.
  2. Homarine and betaine were found in all extracts investigated.
- 3.
  3. A mixture of Cellaria spp. was found to have free nucleosides (inosine, 2′-deoxyadenosine and 2′-deoxyguanosine) and tetramethylammonium ion.
Unprecedented constituents of a new species of acorn worm
1987, Tetrahedron
A new species of acorn worm, recently discovered in deep underwater caves off the island of Maui, yielded after Chromatographic separation of the acetone extract the following secondary metabolites: (4 $S$ ,5 $R$ ,6 $S$ ,)-4-acetoxy-2.6-dibromo-5-hydroxy- cyclohex-2-enone ( $11$ ), its C-6 epimer ( $12$ ), (1 $R$ ,4 $S$ ,5 $R$ ,6 $S$ )-4-acetoxy-2,6-dibromo-1.5-dihydroxy-cyclohexene ( $13$ ), (4 $S$ ,5 $R$ ,6 $R$ )-4-acetoxy-2-bromo-5,6-epoxycyclohex-2-enone ( $14$ ), its deacetyl derivative $15$ , and 2,4-dibromoresorcinol ( $9$ ), in addition to phenols $1–4$ and indole $10$ as minor constituents. The structures of 1 $11–15$ were determined from spectroscopic data, and the absolute configurations by x-ray analysis of $11$ . $13$ , and $14$ . Although the species is morphologically related to the genus Ptychodera, the minor aromatic constituents are usually associated with the genus Balonoglossus. Epoxyenone $14$ shows in vitro P388 activity with an IC₅₀ of 10 ng/mL.
Pyrimidine as constituent of natural biologically active compounds
2005, Chemistry and Biodiversity
Forbesin: A novel sulfated glycolipid from the starfish asterias forbesi
1990, Journal of Natural Products
Studies of swedish marine organisms, part x. biologically active compounds from the marine sponge geodia baretti
1988, Journal of Natural Products

View all citing articles on Scopus

View full text

Article preview

Comparative Biochemistry and Physiology Part B: Comparative Biochemistry

Abstract

References (21)

Halogenated phenol and indole constituents of acorn worms

Comp. Biochem. Physiol.

Some chemical properties of deoxyribose nucleosides

J. biol. Chem.

Isolation of allantoin and adenosine from the marine sponge Tethya aurantia

Comp. Biochem. Physiol.

Contributions to the study of marine products. XXXIX. The nucleosides of sponges III. Spongothymidine and spongouridine

J. org. Chem.

Contributions to the study of marine products. XL. The nucleosides of sponges IV. Spongosine

J. org. Chem.

Contributions to the study of marine products. XXXII. The nucleosides of sponges 1

J. org. Chem.

Absorption spectra. VIII. The infrared spectra of some purines and pyrimidines

J. Am. chem. Soc.

Deoxyribonucleosides and related compounds. Part II. A proof of furanose structure of the natural 2-deoxyribonucleosides

J. chem. Soc.

1-Methylisoguanosine, a pharmacologically active agent from a marine sponge

J. org. Chem.

Uracil deoxyriboside

Nature

Cited by (7)

Aplysidine, a new nucleoside from the Okinawan marine sponge Aplysina Sp.

Hydrophilic organic nitrogenous metabolites from marine bryozoans

Unprecedented constituents of a new species of acorn worm

Pyrimidine as constituent of natural biologically active compounds

Forbesin: A novel sulfated glycolipid from the starfish asterias forbesi

Studies of swedish marine organisms, part x. biologically active compounds from the marine sponge geodia baretti