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

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Title: Allopregnane derivatives possessing marine medaka embryonic teratogenicity from starfish Asterias amurensis.
Authors: Li, Xiaodong1 (AUTHOR), Lu, Zhen1 (AUTHOR), Wang, Derui1,2 (AUTHOR), Yan, Zhi1 (AUTHOR), Yin, Xiuli1 (AUTHOR), Li, Ke1,3 (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
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Header DbId: enr
DbLabel: Energy & Power Source
An: 193684578
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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Items – Name: Title
  Label: Title
  Group: Ti
  Data: Allopregnane derivatives possessing marine medaka embryonic teratogenicity from starfish Asterias amurensis.
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  Data: <searchLink fieldCode="AR" term="%22Li%2C+Xiaodong%22">Li, Xiaodong</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Lu%2C+Zhen%22">Lu, Zhen</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Wang%2C+Derui%22">Wang, Derui</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yan%2C+Zhi%22">Yan, Zhi</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yin%2C+Xiuli%22">Yin, Xiuli</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Li%2C+Ke%22">Li, Ke</searchLink><relatesTo>1,3</relatesTo> (AUTHOR)<i> kli@yic.ac.cn</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Oceanology+%26+Limnology%22">Journal of Oceanology & Limnology</searchLink>. Mar2026, Vol. 44 Issue 2, p784-795. 12p.
– Name: Subject
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  Data: *<searchLink fieldCode="DE" term="%22Teratogenicity+testing%22">Teratogenicity testing</searchLink><br />*<searchLink fieldCode="DE" term="%22Starfishes%22">Starfishes</searchLink><br />*<searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance+spectroscopy%22">Nuclear magnetic resonance spectroscopy</searchLink><br />*<searchLink fieldCode="DE" term="%22Saponins%22">Saponins</searchLink><br />*<searchLink fieldCode="DE" term="%22Metabolites%22">Metabolites</searchLink><br />*<searchLink fieldCode="DE" term="%22Pregnanolone%22">Pregnanolone</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: 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]
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RecordInfo BibRecord:
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      – Type: doi
        Value: 10.1007/s00343-025-4296-9
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      – Code: eng
        Text: English
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        PageCount: 12
        StartPage: 784
    Subjects:
      – SubjectFull: Teratogenicity testing
        Type: general
      – SubjectFull: Starfishes
        Type: general
      – SubjectFull: Nuclear magnetic resonance spectroscopy
        Type: general
      – SubjectFull: Saponins
        Type: general
      – SubjectFull: Metabolites
        Type: general
      – SubjectFull: Pregnanolone
        Type: general
    Titles:
      – TitleFull: Allopregnane derivatives possessing marine medaka embryonic teratogenicity from starfish Asterias amurensis.
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          Name:
            NameFull: Li, Xiaodong
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            NameFull: Lu, Zhen
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            NameFull: Wang, Derui
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            NameFull: Yan, Zhi
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            NameFull: Yin, Xiuli
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            NameFull: Li, Ke
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            – D: 01
              M: 03
              Text: Mar2026
              Type: published
              Y: 2026
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              Value: 20965508
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              Value: 44
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            – TitleFull: Journal of Oceanology & Limnology
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