Two New Steroidal Monoglycosides, Anthenosides A1 and A2, and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera

Abstract

Two new polyhydroxysteroidal glycosides, anthenosides A1 (1) and A2 (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1–3 contain a 2-acetamido-2-deoxy-4-O-methyl-β-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%.

Chemical Constituents and Bioactivities of Starfishes: An Update

“…Compounds 113 – 118 were from the starfish Anthenea aspera . Compounds 113 and 114 contain a 2‐acetamido‐2‐deoxy‐4‐ O ‐methyl‐ β ‐ d ‐glucopyranosyl residue, which has not been found previously in the starfish steroidal glycosides . Compound 115 has an unoxidized Δ 22 ‐24‐nor‐cholestane in its structure .…”

“…It was reported that the cancer‐preventive action of 101 is realized through regulation of mitogen‐activated protein kinase (MAPK) signaling pathway . Both compounds 113 and 114 at 50 μ m slightly inhibited cell viability of human cancer T‐47D cells and they inhibited colony formation of human cancer RPMI‐7951 cells and T‐47D cells by 16 % and 40 %, respectively …”

Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

“…The concentrated methanol extract of A. laevigatus was subjected to sequential separation by column chromatography using Amberlite XAD-2 silica gel followed by reversed-phase HPLC on Discovery C18 and YMC-Pack Pro C18 columns to yield four new polyhydroxylated steroids (1−4), along with two known compounds 5 and 6 ( Figure 1). The known polyhydroxylated steroids were identified by analysis of their 1 H-, 13 C-NMR, and ESIMS spectra and comparison with those reported earlier for (24S)-5α-cholestane-3β,5,6β,15α,24-pentaol (5) and related sulfated compounds previously isolated from the starfish Luidia clathrata and Henricia leviuscula [16,17], and (25S)-5α-cholestane-3β,5,6β,15α,16β,26-hexaol (6) from the starfish L. clathrata [18]. The molecular formula of compound 1 was established to be of C 27 H 48 O 7 from the [M + Na] + sodium adduct ion peak at m/z 507.3292 in the (+)HRESIMS spectrum and the [M -H]deprotonated ion peak at m/z 483.3321 in the (-)HRESIMS spectrum ( Figure S1).…”

“…Elyakov Pacific Institute of Bioorganic Chemistry which celebrated its 55th anniversary in 2019. Continuing our research on biologically active steroid metabolites from the starfish species inhabiting the Vietnamese sea waters [11][12][13][14][15], herein, we describe the results of our investigation of steroid constituents from the methanolic extract of the starfish Anthenoides laevigatus Liao & A.M. Clark, 1989 (order Valvatida, family Goniasteridae), collected off the coastal waters of the Qui Nhon Province, Vietnam. We have isolated and structurally studied four new polyhydroxylated steroids 1−4, along with two previously known related steroids 5 and 6.…”

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

“…Anthenoside A1 (11) inhibited RPMI-7951 cell colony formation, and anthenoside A2 (12) showed a more significant inhibiting effect against colonies of T-47D cells. [27] pustulosa, collected at a depth of 6 m (20°09.030 N; 107°44.359 E). The steroid composition of the extract was also studied, and three known ketosteroids 20-22 and six sterols 23-28 were isolated.…”