Cited by 38Steroid Chemistry and BiochemistryEstrogen and related hormone effectsPhytochemical Studies and Bioactivities

Photochemical transformation of 20-hydroxyecdysone: Production of monomeric and dimeric ecdysteroid analogues

Harmatha, Juraj, Buděšínský, Miloš, Vokáč, Karel·2002·Steroids

Abstract

Structural modification of 20-hydroxyecdysone (20E) based on photochemical transformation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and 14-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B(II)-bioassay compared with the original 20E.

Integrity signals

Registry

Crossref · 10.1016/s0039-128x(01)00140-4

Cites

17 of 17 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • The chemical space provided by natural ecdysteroids is being extended by the preparation and biological assessment of numerous semi-synthetic analogues.

    “The chemical space provided by the natural ecdysteroids is being extended by the preparation and biological assessment of numerous semi-synthetic analogues (e.g., [37][38][39][40][41]).”

    From Ecdysteroids (2021) · cites this paper as [39]

Cites

Flagged first, then by citations

Cited by

Sorted by citations

Authors
Harmatha, J., Buděšínský, M., & Vokáč, K.
Affiliations
Czech Academy of Sciences (CZ)
Corresponding author
Harmatha, Juraj
Venue
Steroids
Publisher
Elsevier BV
Published
2002-02
Volume
67
Issue
2
Pages
127-135
ISSN
0039-128X (ISSN-L)
OpenAlex
W2015410853
Cited by
38
References
17
Citations by year
2026: 2 · 2024: 1 · 2021: 5 · 2017: 2 · 2016: 1 · 2015: 2 · 2014: 1 · 2013: 1 · 2012: 3
FWCI
0.46
Type
journal article
Language
en
Open access
closed
Locations
  • Steroids (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • Ministerstvo Školství, Mládeže a Tělovýchovy (LB98233)
  • Grantová Agentura České Republiky (203/98/0451, Z4 055 905)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
Keywords
20-hydroxyecdysone, photochemical transformation, steroid structure elucidation
MeSH terms
Animals, Chromatography, High Pressure Liquid, Drosophila melanogaster, Ecdysterone, Models, Molecular, Molecular Conformation, Magnetic Resonance Spectroscopy, Photochemistry, Receptors, Steroid, Spectrophotometry, Infrared, Structure-Activity Relationship, Dimerization, Ecdysteroids

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review