Abstract

Three pregnane-type steroids, including a new metabolite, 3β-methoxy-5,20-pregnadiene (1) along with two known analogues, 3β-acetoxy-5,20-pregnadiene (2) and 5α-pregna-1,20-dien-3-one (3) were isolated from the soft coral Scleronephthya flexilis. Standard spectroscopic techniques were used to determine the structure of new steroid 1. The absolute stereochemistry of steroid 2 was confirmed by X-ray diffraction analysis. Steroid 3 exhibited potent activity against MOLT-4 tumor cells.

Highlights

  • Octocorals belonging to the Scleronephthya genus have been well-recognized as marine organisms containing large quantities of steroids that exhibit varying degrees of bioactivities, such as cytotoxicity and anti-inflammatory activity [1,2,3,4,5,6,7]

  • We evaluated whether the cytotoxicity of 3 is associated with apoptosis by examining the effect of 3 on cells stained with annexin V-FITC and propidium iodide (PI)

  • The structure of new steroid 1 was elucidated on the basis of spectroscopic methods

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Summary

Introduction

Octocorals belonging to the Scleronephthya genus have been well-recognized as marine organisms containing large quantities of steroids that exhibit varying degrees of bioactivities, such as cytotoxicity and anti-inflammatory activity [1,2,3,4,5,6,7]. In connection with our investigations of bioactive substances from marine organisms, a soft coral Scleronephthya flexilis Our chemical investigation of this organism led to the isolation of a new metabolite, 3β-methoxy-5,20-pregnadiene (1), and two known analogues, 3β-acetoxy-5,20-pregnadiene (2) [2,6,8,9] and 5α-pregna-1,20-dien-3-one (3) [1,2,4,6,10−17] (Scheme 1). The soft coral Scleronephthya flexilis and the structures of 3β-methoxy-5,20pregnadiene (1), 3β-acetoxy-5,20-pregnadiene (2), 5α-pregna-1,20-dien-3-one (3) and

Results and Discussion
General Experimental Procedures
Animal Material
Extraction and Isolation
X-ray Crystallographic Analysis of Compound 2
Bioassay Material
MTT Antiproliferative Assay
Determination of Mitochondrial Membrane Potential Disruption
Conclusions
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