Three New Cytotoxic Steroidal Glycosides Isolated from Conus pulicarius Collected in Kosrae, Micronesia

Abstract

Three new sulfated steroidal glycosides (3–5), along with known cholesterol derivatives (1,2), were isolated from the visceral extract of the cone snail Conus pulicarius. The structure of each new compound was elucidated by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The three new compounds exhibited significant in vitro cytotoxicity (GI50 values down to 0.49 μM) against the K562 human leukemia cell line.

Marine natural products

“…643 The cone snail Conus pulicarius was the source of the moderately cytotoxic steroidal glycosides 1425-1427. 644 The synthesis, 3D structure and antiproliferative effects of conotoxin F-MiXXVIIA (C. miles), a member of the new G2 toxin superfamily have been reported. 645 Fieen-residue C-amidated conorfamide-Sr3 (C. spurius) blocks activity of Shaker subtype voltage-gated potassium channels.…”

Neuroactive Type-A γ-Aminobutyric Acid Receptor Allosteric Modulator Steroids from the Hypobranchial Gland of Marine Mollusk, Conus geographus

“…48 Several interesting steroid derivatives have been previously reported from cone snails, although neuroactivity was not investigated. 33,49 Several of these sterols have oxygenated sidechains, as found in 1−5, suggesting a potentially common biogenetic origin. Of note, 1−5 are specialized metabolites found in the C. geographus HB gland.…”

Sulfated and Sulfur-Containing Steroids and Their Pharmacological Profile

“…Three sulfated steroidal glycosides ( 40 – 42 ) were isolated from the visceral extract of the cone snail Conus pulicarius . The three new compounds exhibited significant in vitro cytotoxicity (GI 50 values down to 0.49 µM) against the K562 human leukemia cell line [ 73 ]. Three sulfated steroid monoglycosides, leptaochotensosides A–C ( 43 – 45 ), and a sulfated polyhydroxylated steroid ( 33 ) were isolated from the alcoholic extract of the Far Eastern starfish Leptasterias ochotensis [ 74 ].…”

“…The 3-(3-oxo-7α-methylsulfinyl-6β,17β-dihydroxy-4-androsten-17α-y1)-propionic acid γ-lactone called spironolactone (73) has been found and isolated in the human urine by Karim and Brown in 1972 [129]. The physiological properties and biogenesis of spironolactone in humans are well described in several reviews [130][131][132][133].…”