Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities

Abstract

Three new sulfated steroid monoglycosides, leptaochotensosides A–C (1–3), and a new sulfated polyhydroxylated steroid (4) were isolated from the alcoholic extract of the Far Eastern starfish Leptasterias ochotensis. The structures of compounds 1–4 were established by extensive nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS) analyses and chemical transformations. Although the isolated compounds did not show any apparent cytotoxicity against melanoma RPMI-7951 and breast cancer T-47D cell lines, leptaochotensoside A (1) demonstrated inhibition of T-47D cell colony formation in a soft agar clonogenic assay at nontoxic doses. In addition, this compound decreased the epidermal growth factor (EGF)-induced colony formation of mouse epidermal JB6 Cl41 cells. The cancer preventive action of 1 is realized through regulation of mitogen-activated protein kinase (MAPK) signaling pathway.

Chemical Constituents and Bioactivities of Starfishes: An Update

“…Compound 97 was from Protoreaster linckii . The starfish Leptasterias ochotensis produced compounds 101 – 103 . The starfish Astropecten polyacanthus and Evasterias retifera yielded compounds 104 and 106 ,, respectively.…”

“…Compound 93 demonstrated significant inhibition of RPMI‐7951 and T‐47D cell colony formation . Compound 101 could inhibit the T‐47D cell colony formation at nontoxic doses . In addition, it also decreased the colony formation of mouse epidermal JB6 Cl41 cells induced by epidermal growth factor (EGF).…”

“…In addition, it also decreased the colony formation of mouse epidermal JB6 Cl41 cells induced by epidermal growth factor (EGF). 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 …”

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

“…For both sea stars and brittle stars, the sulfate group is located in the hydrophobic part (aglycone) of the molecule, whereas in holothurians the sulfate group is placed within the hydrophilic moiety (glycone) (Kornprobst et al 1998). The structural differences of asterosaponin and triterpene glycosides showed that not only the presence but also the position of the sulfate groups may be important, resulting in potentially different biological activities of saponins (Maier 2008;Malyarenko et al 2015).…”

In Silico Investigation of Echinodermata Secondary Metabolites as Human Immunodeficiency Virus Type 1 (Hiv-1) Reverse Transcriptase Inhibitors

“…Hence, novel compounds/ new chemical entities that are peculiar to marine environments are likely to differ from those of terrestrial organisms. Previous researches have shown echinoderm compounds with reported antiviral activities include imbricantine from Dermasterias imbricata [5,6], four new sulfated polar steroids from the Far Eastern starfish Leptasterias ochotensis [7], hedathiosulfonic acids A and B from Echinocardium cordatum [6,8], lysastroside from Lysastrosoma anthosticta [6,9], and ten saponin compounds from Certonardoa semiregularis [10]. In silico analyses may offer valuable research information and reduce the costs of drug development by reducing sample numbers in in vitro and in vivo studies [11].…”