Asterosaponin P1 from the starfish

Kicha, A. A.; Kalinovsky, Anatoly I.; Levina, E. V.; Stonik, Valentin A.; Elyakov, G. B.

doi:10.1016/s0040-4039(00)94305-3

Cited by 56 publications

(27 citation statements)

References 7 publications

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“…The position of the fourth hydroxyl group in the nucleus follows from the chemical shift of C14 at δ C 66.6 ppm and a upfield shift of signals of 18-CH 3 (δ H 0.96 and δ C 15.3 ppm) and C17 (δ C 55.9 ppm) in comparison with the spectra of 8,15β-dihydroxysteroids [13]. The multiplicity of signal H15 (CH) and spin coupling constants of H15 and H14 (J 14,15 9.6 Hz) ( Table 4) also confirms the α-configuration of hydroxyl group, since the J value is within 5.3-6.5 Hz in 15β-hydroxysteroids [14].…”

Section: Resultsmentioning

confidence: 64%

Steroid Compounds from Far Eastern Starfishes Henricia aspera and H. tumida

et al. 2005

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Six new natural compounds were isolated from two Far Eastern starfish species, Henricia aspera and H. tumida, collected in the Sea of Okhotsk. Two new glycosylated steroid polyols were obtained from H. aspera: asperoside A and asperoside B, which were shown to be (20R,24R,25S)-3-O-(2,3-di-O-methyl-beta-D-xylopyranosyl)-24-methyl-5alpha-cholest-4-ene-3beta,6beta,8,15a,16beta,26-hexaol and (20R,24R,25S,22E)-3-O-(2,4-di-O-methyl-beta-D-xylopyranosyl)-24-methyl-5alpha-cholest-22-ene-3beta,4beta,6beta,8,15alpha,26-hexaol, respectively. Two other glycosylated polyols, tumidoside A, with the structure elucidated as (20R,22E)-3-O-(2,4-di-O-methyl-beta-D-xylopyranosyl)-26,27-di-nor-24-methyl-5alpha-cholest-22-ene-3beta,4beta,6beta,8,15alpha,25-hexaol, and tumidoside B, whose structure was elucidated as (20R,24S)-3-O-(2,3-di-O-methyl-beta-D-xylopyranosyl)-5alpha-cholestan-3beta,4beta,6beta,8,15alpha,24-hexaol, were isolated from the two starfish species. (20R,24S)-Salpha-Cholestan-3beta,6beta,15alpha,24-tetraol and (20R,24S)-5alpha-cholestan-3beta,6beta,8,15alpha,24-pentaol were identified only in H. tumida. The known monoglycosides henricioside H1 and laeviuscolosides H and G were also identified in both species.

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Section: Resultsmentioning

confidence: 64%

Steroid Compounds from Far Eastern Starfishes Henricia aspera and H. tumida

et al. 2005

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“…Cytotoxic, antitumor Wang et al (2004a, b) Certonardoside Kicha et al (1983Kicha et al ( , 2000Kicha et al ( , 2004…”

Section: Halityle Regularismentioning

confidence: 99%

Chemical Biodiversity and Bioactivities of Saponins in Echinodermata with an Emphasis on Sea Cucumbers (Holothuroidea)

Kamyab

Kellermann

Kunzmann

et al. 2019

YOUMARES 9 - The Oceans: Our Research, Our Future

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Echinoderms are a source of a broad range of secondary metabolites with a large variety of bioactive properties. Although pigment and lipid derivatives are the major groups of bioactive compounds found in crinoids and ophiuroids, saponins represent the most abundant and diverse marine natural products (MNPs) in the phylum Echinodermata. This review is for researchers that are interested in MNPs derived from echinoderms, but with a particular focus on the structural diversity and biological function of saponins. Among the echinoderms, these steroidal compounds are mostly known for and structurally most diverse within sea cucumbers. Through compilation of extensive tables, this review provides a reference book, summarizing not only the major chemical classes of well-known secondary metabolites in the phylum Echinodermata but also further focusing on the presence of bioactive saponins in echinoderms in general and within different sea cucumber species in particular. The final compilation aims to correlate the vast structural diversity of saponins with known biological functions. The here presented data revealed that holothurians, holotoxins, cucumariosides, and echinosids are not only the most abundant saponin compounds in various genera of sea cucumbers but that these saponins can also be used as potential chemotaxonomic markers for different sea cucumber species. By studying the structure-function relationships of triterpene glycosides in echinoderms in general, or in particular within holothurians, the vast structural diversity, taxonomic distribution, and bioactivity of the molecules can be deciphered, which provides an opportunity to focus future research efforts on target species that contain MNPs with novel pharmacological activities.

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“…Steroid compounds 2-11 were isolated from starfishes. Compounds 2-10 were isolated and purified according to the procedures published previously [18][19][20][21][22][23]. Compound 11 was obtained by the following original protocol.…”

Section: Steroid Compoundsmentioning

confidence: 99%

Structural Analogues of Lanosterol from Marine Organisms of the ClassAsteroideaas Potential Inhibitors of Human andCandida albicansLanosterol 14α-demethylases

Kaluzhskiy

Shkel

Ivanchina

et al. 2017

Natural Product Communications

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Lanosterol 14α-demethylases (hemoproteins of the cytochrome P450(51) family) are involved in biosynthesis of different membrane sterols, including animal cholesterol, fungal ergosterol and C24-modified plant and protozoa sterols. In this study we have investigated 10 structural analogs of lanosterol isolated from echinoderms belonging to the class Asteroidea as potential ligands (competitive inhibitors) of human and Candida albicans cytochromes P450(51). The study was performed using the surface plasmon resonance method, spectrophotometric titration and enzyme assay. Among the compounds tested we found several selective ligands for human and Candida albicans cytochromes. Between selective ligands of the human lanosterol 14α-demethylase we found two novel inhibitors of this enzyme: henricioside Н 1 and levisculoside G from Henricia derjugini. With due consideration of obtained data, we conclude that marine organisms from the class Asteroidea can be a valuable source of new lead compounds for creation of selective inhibitors of cytochromes P450(51) family with less side effects due to their selective action on these enzymes in different types of organisms.

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Asterosaponin P1 from the starfish

Cited by 56 publications

References 7 publications

Steroid Compounds from Far Eastern Starfishes Henricia aspera and H. tumida

Steroid Compounds from Far Eastern Starfishes Henricia aspera and H. tumida

Chemical Biodiversity and Bioactivities of Saponins in Echinodermata with an Emphasis on Sea Cucumbers (Holothuroidea)

Structural Analogues of Lanosterol from Marine Organisms of the ClassAsteroideaas Potential Inhibitors of Human andCandida albicansLanosterol 14α-demethylases

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