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Allopregnane derivatives possessing marine medaka embryonic teratogenicity from starfish Asterias amurensis.

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Bibliographic Details
Title:	Allopregnane derivatives possessing marine medaka embryonic teratogenicity from starfish Asterias amurensis.
Authors:	Li, Xiaodong¹ (AUTHOR), Lu, Zhen¹ (AUTHOR), Wang, Derui^1,2 (AUTHOR), Yan, Zhi¹ (AUTHOR), Yin, Xiuli¹ (AUTHOR), Li, Ke^1,3 (AUTHOR) kli@yic.ac.cn
Source:	Journal of Oceanology & Limnology. Mar2026, Vol. 44 Issue 2, p784-795. 12p.
Subject Terms:	Teratogenicity testing, Starfishes, Nuclear magnetic resonance spectroscopy, Saponins, Metabolites, Pregnanolone
Abstract:	Starfish are usually apex predators in marine benthic ecosystems, given that they have spines and use their secondary metabolites to defend against predators. Crude extracts of starfish have demonstrated their chemical defense function. However, the specific molecules utilized by starfish for chemical defense remain unknown. In this paper, we used a variety of chromatographic methods to systematically separate the secondary metabolites of starfish Asterias amurensis. The structures of the compounds were unambiguously solved by detailed nuclear magnetic resonance spectroscopy (NMR), mass spectra analysis, and time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. Three new compounds, 3β,6α,12α-trihydroxyl-5α-pregn-9(11)-en-3-O-sulfate sodium salt (1), 5α-pregn-9(11)-en-12,20-dione-3β,6α-diol-3-O-surfate sodium salt (2), and 6α-[O-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl-(1→3)-β-D-qumovopyranosyl]-5α-pregn-9(11)-en-20-one-3β-O-sulfate sodium salt (7), together with four known asterosaponins (3–6), were identified from the n-butanol extract of A. amurensis. A systematic assessment of the embryonic toxicity of the identified compounds was conducted using the model animal marine medaka (Oryzias melastigma). The findings suggest that compounds 1–7 exhibited no embryonic lethality. Compound 7 exhibits significant teratogenicity and has adverse effects on both cardiac function and voluntary movement. Integral analysis indicates that saponins and compounds containing sulphate groups have the potential to induce birth defects in embryos. [ABSTRACT FROM AUTHOR]
Database:	Energy & Power Source

Description
Abstract:	Starfish are usually apex predators in marine benthic ecosystems, given that they have spines and use their secondary metabolites to defend against predators. Crude extracts of starfish have demonstrated their chemical defense function. However, the specific molecules utilized by starfish for chemical defense remain unknown. In this paper, we used a variety of chromatographic methods to systematically separate the secondary metabolites of starfish Asterias amurensis. The structures of the compounds were unambiguously solved by detailed nuclear magnetic resonance spectroscopy (NMR), mass spectra analysis, and time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. Three new compounds, 3β,6α,12α-trihydroxyl-5α-pregn-9(11)-en-3-O-sulfate sodium salt (1), 5α-pregn-9(11)-en-12,20-dione-3β,6α-diol-3-O-surfate sodium salt (2), and 6α-[O-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl-(1→3)-β-D-qumovopyranosyl]-5α-pregn-9(11)-en-20-one-3β-O-sulfate sodium salt (7), together with four known asterosaponins (3–6), were identified from the n-butanol extract of A. amurensis. A systematic assessment of the embryonic toxicity of the identified compounds was conducted using the model animal marine medaka (Oryzias melastigma). The findings suggest that compounds 1–7 exhibited no embryonic lethality. Compound 7 exhibits significant teratogenicity and has adverse effects on both cardiac function and voluntary movement. Integral analysis indicates that saponins and compounds containing sulphate groups have the potential to induce birth defects in embryos. [ABSTRACT FROM AUTHOR]
ISSN:	20965508
DOI:	10.1007/s00343-025-4296-9