Zur Chemie des Ecdysons, VII: Die Kristall- und Molekülstrukturanalyse des Insektenverpuppungshormons ecdyson mit der automatisierten Faltmolekülmethode

Huber, Robert; Hoppe, Walter

doi:10.1002/cber.19650980744

Cited by 219Steroid Chemistry and BiochemistryCrystal structures of chemical compoundsMolecular spectroscopy and chirality

Zur Chemie des Ecdysons, VII: Die Kristall- und Molekülstrukturanalyse des Insektenverpuppungshormons ecdyson mit der automatisierten Faltmolekülmethode

Huber, Robert, Hoppe, Walter·1965·Chemische Berichte

DOI 10.1002/cber.19650980744

Open this paper in CoChat — free account

Abstract

Abstract Die vollständige Struktur und Konfiguration des Insektenverpuppungshormons Ecdyson wird durch Röntgenstrukturanalyse der natürlichen, schweratomfreien Verbindung als 2β.3β.14α.22βF.25‐Pentahydroxy‐Δ7‐5β‐cholestenon‐(6) ermittelt.

Integrity signals

Registry

Crossref · 10.1002/cber.19650980744

Cites

4 of 4 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 structure of ecdysone was established eleven years after its isolation.
“This compound was named”
From Ecdysteroids (2021) · cites this paper as [6]

The determination of crystal structures
Lipson, H., & Cochran, W. G. (1957) · Cited by 256 · see citing works
Zur Chemie des Ecdysons, VI: Reaktionen des Ecdysonmoleküls
Karlson, P., Hoffmeister, H. M., Hummel, H., Hocks, P., & Spiteller, G. (1965) · Chemische Berichte · doi:10.1002/cber.19650980743 · Cited by 132 · see citing works
Zur Chemie Des Ecdysons
Karlson, P., Hoffmeister, H. M., Hoppe, W., & Huber, R. (1963) · Justus Liebig s Annalen der Chemie · doi:10.1002/jlac.19636620102 · Cited by 104 · see citing works
Zur Chemie des Ecdysons, II: Bestimmung des Sterin‐Skeletts und seiner Orientierung mit diffuser Röntgenstreuung in Kristallen von Ecdyson
Hoppe, W., & Huber, R. (1965) · Chemische Berichte · doi:10.1002/cber.19650980739 · Cited by 23 · see citing works

Flagged first, then by citations

Sorted by citations

Insights into the molecular basis of the hormonal control of molting and metamorphosis from Manduca sexta and Drosophila melanogaster
Riddiford, L. M., Hiruma, K., Zhou, X., & Nelson, C. A. (2003) · Insect Biochemistry and Molecular Biology · doi:10.1016/j.ibmb.2003.06.001 · Cited by 547 · see citing works
Phytoecdysteroids: Biological aspects
Dinan, L. (2001) · Phytochemistry · doi:10.1016/s0031-9422(01)00078-4 · Cited by 392 · see citing works
Conformation of non-aromatic ring Compounds—XXV
ALTONA, C., Geise, H. J., & Romers, C. (1968) · Tetrahedron · doi:10.1016/0040-4020(68)89003-9 · Cited by 380 · see citing works
Regulation of crustacean molting: A review and our perspectives
Chang, E. S., & Mykles, D. L. (2011) · General and Comparative Endocrinology · doi:10.1016/j.ygcen.2011.04.003 · Cited by 347 · see citing works
Lipid Metabolism and Function in Insects
Gilbert, L. I. (1967) · Advances in insect physiology · doi:10.1016/s0065-2806(08)60208-8 · Cited by 327 · see citing works
The Structure of the Juvenile Hormone
Röller, H., Dahm, K. H., Sweely, C. C., & Trost, B. M. (1967) · Angewandte Chemie International Edition in English · doi:10.1002/anie.196701792 · Cited by 303 · see citing works
Roles of ecdysone in Drosophila development
Garen, A., Kauvar, L. M., & Lepesant, J. (1977) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.74.11.5099 · Cited by 281 · see citing works
Physiological and biochemical changes during the molt cycle in decapod crustaceans: an overview
Chang, E. S. (1995) · Journal of Experimental Marine Biology and Ecology · doi:10.1016/0022-0981(95)00106-9 · Cited by 229 · see citing works
Effects and applications of arthropod steroid hormones (ecdysteroids) in mammals
Dinan, L., & Lafont, R. (2006) · Journal of Endocrinology · doi:10.1677/joe.1.06900 · Cited by 200 · see citing works
“2) was isolated in 1954 (Butenandt & Karlson 1954) and its structure was unambiguously identified only in 1965 (Huber & Hoppe 1965), with the result that research on ecdysteroids has generally lagged far behind that on the various classes of vertebrate steroid hormones, in spite of the fact that…”
Ecdysteroid Chemistry and Biochemistry
Lafont, R., Dauphin‐Villemant, C., Warren, J. T., & Rees, H. H. (2011) · Elsevier eBooks · doi:10.1016/b978-0-12-384749-2.10004-4 · Cited by 167 · see citing works
PHYSIOLOGY OF GROWTH AND DEVELOPMENT: ENDOCRINE ASPECTS
Gilbert, L. I., & King, D. S. (1973) · Elsevier eBooks · doi:10.1016/b978-0-12-591601-1.50012-0 · Cited by 163 · see citing works
Diglyceride-carrying lipoproteins in insect hemolymph isolation, purification and properties
Haruo, C., Satoru, M., & Harashima, K. (1969) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(69)90068-x · Cited by 153 · see citing works
Biosynthesis of ecdysones in isolated prothoracic glands and oenocytes of Tenebrio molitor in vitro
Römer, F., Emmerich, H., & Nowock, J. (1974) · Journal of Insect Physiology · doi:10.1016/0022-1910(74)90105-x · Cited by 142 · see citing works
Ecdysteroid Chemistry and Biochemistry
Lafont, R., Dauphin‐Villemant, C., Warren, J. T., & Rees, H. (2005) · Elsevier eBooks · doi:10.1016/b0-44-451924-6/00035-1 · Cited by 136 · see citing works
An extensive ecdysteroid CoMFA
Dinan, L. N., Hormann, R. E., & Fujimoto, T. T. (1999) · Journal of Computer-Aided Molecular Design · doi:10.1023/a:1008052320014 · Cited by 137 · see citing works
Zur Chemie des Ecdysons, VI: Reaktionen des Ecdysonmoleküls
Karlson, P., Hoffmeister, H. M., Hummel, H., Hocks, P., & Spiteller, G. (1965) · Chemische Berichte · doi:10.1002/cber.19650980743 · Cited by 132 · see citing works
Recent Developments in Insect Steroid Metabolism
Svoboda, J. A., Kaplanis, J. N., Robbins, W. E., & Thompson, M. J. (1975) · Annual Review of Entomology · doi:10.1146/annurev.en.20.010175.001225 · Cited by 128 · see citing works
On the origin and metabolic fate of α-ecdysone in insects
Moriyama, H., Nakanishi, K., King, D., Okauchi, T., SIDDALL, J. B., & Hafferl, W. (1970) · General and Comparative Endocrinology · doi:10.1016/0016-6480(70)90099-7 · Cited by 127 · see citing works
Arthropod Molting Hormones
Hikino, H., & Hikino, Y. (1970) · Fortschritte der Chemie Organischer Naturstoffe/Fortschritte der Chemie organischer Naturstoffe/Progress in the chemistry of organic natural products · doi:10.1007/978-3-7091-7123-3_6 · Cited by 116 · see citing works
The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review
Das, N., Mishra, S. K., Bishayee, A., Ali, E. S., & Bishayee, A. (2021) · Acta Pharmaceutica Sinica B · doi:10.1016/j.apsb.2020.10.012 · Cited by 115 · see citing works
Discovery of Insect Antiallatotropins
Bowers, W. S. (1976) · Springer eBooks · doi:10.1007/978-1-4684-7947-8_27 · Cited by 112 · see citing works
Die Struktur des Juvenilhormons
Röller, H., Dahm, K. H., Sweeley, C. C., & Trost, B. M. (1967) · Angewandte Chemie · doi:10.1002/ange.19670790411 · Cited by 111 · see citing works
4D-QSAR Analysis of a Set of Ecdysteroids and a Comparison to CoMFA Modeling
Ravi, M., Hopfinger, A. J., Hormann, R. E., & Dinan, L. N. (2001) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci010076u · Cited by 107 · see citing works
Nonsteroidal Ecdysone Agonists
Nakagawa, Y. (2005) · Vitamins and hormones · doi:10.1016/s0083-6729(05)73005-3 · Cited by 103 · see citing works
Ecdysones from the pupa of the tobacco hornworm, Manduca sexta (Johanson)
Kaplanis, J. N., Thompson, M. J., Yamamoto, R. T., Bobbins, W. E., & Louloudes, S. J. (1966) · Steroids · doi:10.1016/0039-128x(66)90002-x · Cited by 102 · see citing works
Ecdysone metabolism
Koolman, J. (1982) · Insect Biochemistry · doi:10.1016/0020-1790(82)90081-6 · Cited by 102 · see citing works
Insect Hormones: Alpha Ecdysone and 20-Hydroxyecdysone in Bracken Fern
Kaplanis, J. N., Thompson, M. J., Robbins, W. E., & Bryce, B. M. (1967) · Science · doi:10.1126/science.157.3795.1436 · Cited by 101 · see citing works
Conformation of non-aromatic ring compounds—LII
HOOG, A. J. D., Buys, H. R., ALTONA, C., & Havinga, E. (1969) · Tetrahedron · doi:10.1016/s0040-4020(01)82869-6 · Cited by 98 · see citing works
Assay for ecdysone (Molting hormone) activity using the house fly, Musca domestica L.
Kaplanis, J. N., Tabor, L. A., Thompson, M. J., Robbins, W. E., & Shortino, T. J. (1966) · Steroids · doi:10.1016/0039-128x(66)90003-1 · Cited by 94 · see citing works
The Chemistry and Biology of Juvenile Hormone
Röller, H., & Dahm, K. H. (1968) · Elsevier eBooks · doi:10.1016/b978-1-4831-9827-9.50018-6 · Cited by 92 · see citing works
What Goes Up Must Come Down
Ou, Q., & King‐Jones, K. (2013) · Current topics in developmental biology/Current Topics in Developmental Biology · doi:10.1016/b978-0-12-385979-2.00002-2 · Cited by 86 · see citing works
Ecdysone, an Insect Steroid Hormone, and Its Mode of Action
Karlson, P., & Sekeris, C. E. (1966) · Elsevier eBooks · doi:10.1016/b978-1-4831-9825-5.50015-4 · Cited by 85 · see citing works
Metabolism of Steroids in Insects
Thompson, M. J., Kaplanis, J. N., Robbins, W. E., & Svoboda, J. A. (1973) · Advances in lipid research · doi:10.1016/b978-0-12-024911-4.50013-1 · Cited by 80 · see citing works
A new model for 20‐hydroxyecdysone and dibenzoylhydrazine binding: A homology modeling and docking approach
Wurtz, J., Guillot, B., Fagart, J., Moras, D., Tietjen, K., & Schindler, M. (2000) · Protein Science · doi:10.1110/ps.9.6.1073 · Cited by 79 · see citing works
“The 3D structure of 20E was derived from the X-ray structure of ecdysone~Huber & Hoppe, 1965!”
Method
Phytoecdysteroids: Diversity, biosynthesis and distribution
Dinan, L., Harmatha, J., Volodin, V., & Lafont, R. (2009) · Ecdysone: Structures and Functions · doi:10.1007/978-1-4020-9112-4_1 · Cited by 77 · see citing works
Spatially Discrete, Light-Driven Protein Expression
Lin, W., Albanese, C., Pestell, R. G., & Lawrence, D. S. (2002) · Chemistry & Biology · doi:10.1016/s1074-5521(02)00288-0 · Cited by 77 · see citing works
Ecdyson, das H�utungshormon der Insekten
Karlson, P. (1966) · Die Naturwissenschaften · doi:10.1007/bf00601742 · Cited by 76 · see citing works
Conformation of non-aromatic ring compounds—XXIV
Geise, H. J., ALTONA, C., & Romers, C. (1967) · Tetrahedron · doi:10.1016/s0040-4020(01)83329-9 · Cited by 75 · see citing works
Hormonal Control of Metabolism in Insects
Steele, J. E. (1976) · Advances in insect physiology · doi:10.1016/s0065-2806(08)60256-8 · Cited by 73 · see citing works
The Ecdysial Glands of Arthropods
Herman, W. S. (1967) · International review of cytology · doi:10.1016/s0074-7696(08)61838-0 · Cited by 71 · see citing works
Effects of α-ecdysone, β-ecdysone and inokosterone on the in vitro evagination of Drosophila leg discs and the subsequent differentiation of imaginal integumentary structures
Mandaron, P. (1973) · Developmental Biology · doi:10.1016/0012-1606(73)90322-9 · Cited by 67 · see citing works
20-hydroxy-ecdyson, isoliert aus insekten
Hocks, P., & Wiechert, R. (1966) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)99901-0 · Cited by 66 · see citing works
Cuticle: Formation, Moulting and Control
Gnatzy, W., & Römer, F. (1984) · Springer eBooks · doi:10.1007/978-3-642-51593-4_33 · Cited by 66 · see citing works
A comparative study of the ring glands from wild type and 1(2)gl mutant Drosophila melanogaster
Aggarwal, S. K., & King, R. C. (1969) · Journal of Morphology · doi:10.1002/jmor.1051290204 · Cited by 65 · see citing works
ECDYSONE AND ECDYSONE ANALOGUES: THEIR ASSAY ON THE FLESHFLY Sarcophaga peregrina
Ohtaki, T., Milkman, R., & Williams, C. M. (1967) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.58.3.981 · Cited by 60 · see citing works
Zur chemie des ecdysterons
Hoffmeister, H. M., & Grützmacher, H. (1966) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)70018-9 · Cited by 59 · see citing works
Uptake and turnover of cholesterol-14C in Y-organs of the crab Hemigrapsus as a function of the molt cycle
Spaziani, E., & Kater, S. B. (1973) · General and Comparative Endocrinology · doi:10.1016/0016-6480(73)90085-3 · Cited by 58 · see citing works
Effects and interactions of juvenile hormone and β-ecdysone on Drosophila imaginal discs cultured in vitro
Chihara, C. J., & Fristrom, J. W. (1973) · Developmental Biology · doi:10.1016/0012-1606(73)90005-5 · Cited by 54 · see citing works
Hormonal Interactions between Plants and Insects
Williams, C. M. (1970) · Elsevier eBooks · doi:10.1016/b978-0-12-654750-4.50012-8 · Cited by 53 · see citing works
STUDIES OF THE PROTHORACICOTROPIC HORMONE IN THE TOBACCO HORNWORM,MANDUCA SEXTA
Safranek, L., & Williams, C. M. (1980) · Biological Bulletin · doi:10.2307/1540765 · Cited by 51 · see citing works
Quantitative structure‐activity analysis of larvicidal 1‐(substituted benzoyl)‐2‐benzoyl‐1‐tert‐butylhydrazines against Chilo suppressalis
Oikawa, N., Nakagawa, Y., Nishimura, K., Ueno, T., & Fujita, T. (1994) · Pesticide Science · doi:10.1002/ps.2780410210 · Cited by 51 · see citing works
Cyasterone, an insect metamorphosing substance from cyathula capitata: structure
Hikino, H., Hikino, Y., Nomoto, K., & Takemoto, T. (1968) · Tetrahedron · doi:10.1016/s0040-4020(01)98686-7 · Cited by 51 · see citing works
The Extraction and Determination of Ecdysones in Arthropods
Morgan, E. D., & Poole, C. F. (1976) · Advances in insect physiology · doi:10.1016/s0065-2806(08)60253-2 · Cited by 51 · see citing works
Conformational analysis of sterols: Comparison of X‐ray crystallographic observations with data from other sources
Duax, W. L., Griffin, J. F., Rohrer, D. C., & Weeks, C. M. (1980) · Lipids · doi:10.1007/bf02534032 · Cited by 50 · see citing works
Ecdysteroids
Lafont, R., Balducci, C., & Dinan, L. (2021) · Encyclopedia · doi:10.3390/encyclopedia1040096 · Cited by 49 · see citing works
Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones
Arif, Y., Singh, P., Bajguz, A., & Hayat, S. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23158664 · Cited by 50 · see citing works
“Later, its structure was reported via X-ray crystallography [2].”
Background
The crustacean cuticle: structure, composition and mineralization
Nagasawa, H. (2011) · Frontiers in Bioscience-Elite · doi:10.2741/412 · Cited by 49 · see citing works
“The hormone responsible for molting was first isolated from the silkworm, Bombyx mori, after much experimental effort across a long period of time (18), and later its chemical structure was determined by X-ray crystallography (19).”
Background
Fraenkel's pupariation factor identified at last
Verleyen, P., Clynen, E., Huybrechts, J., Lommel, A. V., Bosch, L. V., LOOF, A. D., Žd̕árek, J., & Schoofs, L. (2004) · Developmental Biology · doi:10.1016/j.ydbio.2004.05.021 · Cited by 49 · see citing works
Ecdysteroids in Plants and their Pharmacological Effects in Vertebrates and Humans
(2015) · Studies in Natural Products Chemistry · doi:10.1016/b978-0-444-63473-3.00005-8 · Cited by 48 · see citing works
Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs
Nakagawa, Y., Hattori, K., Shimizu, B., Akamatsu, M., Miyagawa, H., & Ueno, T. (1998) · Pesticide Science · doi:10.1002/(sici)1096-9063(199808)53:4 · Cited by 48 · see citing works
Die Kristall- und Molekülstruktur von Phyllochlorinester
Hoppe, W., Will, G., Gassmann, J., & Weichselgartner, H. (1969) · Zeitschrift für Kristallographie · doi:10.1524/zkri.1969.128.1-2.18 · Cited by 48 · see citing works
Damage-induced accumulation of phytoecdysteroids in spinach: A rapid root response involving the octadecanoic acid pathway
Schmelz, E. A., Grebenok, R. J., Galbraith, D. W., & Bowers, W. S. (1998) · Journal of Chemical Ecology · doi:10.1023/a:1022588610232 · Cited by 47 · see citing works
The moulting hormone activity of ecdysterone and inokosterone isolated from Achyranthis Radix
Kobayashi, M., TAKEMOTO, T., Ogawa, S., & Nishimoto, N. (1967) · Journal of Insect Physiology · doi:10.1016/0022-1910(67)90141-2 · Cited by 47 · see citing works
Chromatographic procedures for phytoecdysteroids
Lafont, R., Morgan, E. D., & Wilson, I. D. (1994) · Journal of Chromatography A · doi:10.1016/0021-9673(94)85205-7 · Cited by 46 · see citing works
Neuropeptide signaling mechanisms in crustacean and insect molting glands
Covi, J. A., Chang, E. S., & Mykles, D. L. (2011) · Invertebrate Reproduction & Development · doi:10.1080/07924259.2011.588009 · Cited by 46 · see citing works
“Several years later, the structure of ecdysone was determined and its source traced to the prothoracic gland (PG; Huber and Hoppe 1965; Karlson et al. 1965).”
Background
Insect Hormones and Antihormones in Plants
Bowers, W. S. (1991) · Elsevier eBooks · doi:10.1016/b978-0-12-597183-6.50017-6 · Cited by 45 · see citing works
INSECT HORMONES AND INSECT CONTROL
Schneiderman, H. A. (1972) · Elsevier eBooks · doi:10.1016/b978-0-12-490950-2.50006-1 · Cited by 44 · see citing works
Dormantinol, a possible precursor in solanidine biosynthesis, from budding Veratrum grandiflorum
Kaneko, K., Tanaka, M. W., & Mitsuhashi, H. (1977) · Phytochemistry · doi:10.1016/s0031-9422(00)94367-x · Cited by 41 · see citing works
Recovering Phase Information from Intensity Data
Karle, J. (1986) · Science · doi:10.1126/science.232.4752.837 · Cited by 41 · see citing works
Insect Hormones
Wyatt, G. R. (1972) · Biochemical Actions of Hormones · doi:10.1016/b978-0-12-452802-4.50018-4 · Cited by 41 · see citing works
Structure of cyasterone, a novel C29 insect-moulting substance from
TAKEMOTO, T., Hikino, Y., Nomoto, K., & Hikino, H. (1967) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)89896-8 · Cited by 40 · see citing works
Pterosteron, polypodin B und ein neues ecdysonartiges steroid (viticosteron E) aus vitex megapotamica (verbenaceae)
Rimpler, H. (1969) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)87684-x · Cited by 39 · see citing works
De novo assembly of the olive fruit fly (Bactrocera oleae) genome with linked-reads and long-read technologies minimizes gaps and provides exceptional Y chromosome assembly
Bayega, A., Djambazian, H. H. V., Tsoumani, K. T., Gregoriou, M., Sagri, E., Drosopoulou, E., Mavragani‐Tsipidou, P., Giorda, K., Tsiamis, G., Bourtzis, K., et al. (2020) · BMC Genomics · doi:10.1186/s12864-020-6672-3 · Cited by 39 · see citing works
“In order to identify the developmental stage-specific genes, we clustered all expressed genes using Dirichlet process Gaussian process (DPGP) [96] which jointly models data clusters with a Dirichlet process and temporal dependencies with Gaussian processes.”
BackgroundInfluential
Ecdysteroid Agonists and Antagonists
Dinan, L. N., & Hormann, R. E. (2005) · Elsevier eBooks · doi:10.1016/b0-44-451924-6/00036-3 · Cited by 38 · see citing works
Insect Hormones and Insect Chemical Ecology
Morgan, E. D., & Wilson, I. D. (1999) · Elsevier eBooks · doi:10.1016/b978-0-08-091283-7.00053-9 · Cited by 38 · see citing works
Protein structure based rational design of ecdysone agonists
HOLMWOOD, G., & Schindler, M. (2009) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2009.01.008 · Cited by 36 · see citing works
Crystal Structures of Ecdysteroids: The Role of Solvent Molecules in Hydrogen Bonding and Isostructurality
Fábián, L., Argay, G., Kálmán, A., & Báthori, M. (2002) · Acta Crystallographica Section B Structural Science · doi:10.1107/s0108768102005608 · Cited by 35 · see citing works
“The new unit-cell volumes are 2745.5 (5) and 2740.8 (7) AÊ 3, the mean of which is even larger than that reported by Huber & Hoppe (1965).”
BackgroundInfluential
Die Prothorakaldr�sen der Larve vonTenebrio molitor L. (Tenebrionidae, Coleoptera) und ihre Ver�nderungen w�hrend eines H�utungszyklus
Römer, F. (1971) · Cell and Tissue Research · doi:10.1007/bf00936078 · Cited by 35 · see citing works
Phytoecdysteroids: Structure, Sources, and Biosynthesis in Plants
Baltaev, U. A. (2000) · Russian Journal of Bioorganic Chemistry · doi:10.1023/a:1026662505403 · Cited by 34 · see citing works
Sengosterone, an insect metamorphosing substance from Cyathula capitata: Structure
Hikino, H., Nomoto, K., & Takemoto, T. (1970) · Tetrahedron · doi:10.1016/s0040-4020(01)97887-1 · Cited by 34 · see citing works
Structure of sengosterone, a novel C29 insect-moulting substance from
Hikino, H., Nomoto, K., & Takemoto, T. (1969) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)87902-8 · Cited by 33 · see citing works
Diversity of Ecdysteroids in Animal Species
Lafont, R., & Koolman, J. (2009) · Springer eBooks · doi:10.1007/978-1-4020-9112-4_2 · Cited by 32 · see citing works
Ecdysterone and Turkesterone—Compounds with Prominent Potential in Sport and Healthy Nutrition
Todorova, V., Ivanova, S., Chakarov, D., Kraev, K., & Ivanov, K. (2024) · Nutrients · doi:10.3390/nu16091382 · Cited by 31 · see citing works
“The first ecdysteroid, ecdysone, was isolated from silkworm pupae by Butenandt and Karlson in 1954, and its structure was presented in 1965 by Huber and Hoppe [3,4].”
Background
Insect hormones V. The structures of ponasterones B and C
Nakanishi, K., Koreeda, M., Chang, M. L., & Hsu, H. Y. (1968) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)98900-2 · Cited by 31 · see citing works
Juvenile hormone of Hyalophora cecropia
Trost, B. M. (1970) · Accounts of Chemical Research · doi:10.1021/ar50028a002 · Cited by 30 · see citing works
Endocrine Mechanisms in Ticks: Effects of Insect Hormones and their Mimics on Development and Reproduction
Solomon, K. R., Mango, C. K. A., & Obenchain, F. D. (1982) · Elsevier eBooks · doi:10.1016/b978-0-08-024937-7.50016-0 · Cited by 29 · see citing works
REVIEW
(1983) · Hoppe-Seyler´s Zeitschrift für physiologische Chemie · doi:10.1515/bchm2.1983.364.2.1067 · Cited by 29 · see citing works
Structure of capitasterone, a novel C29 insect-moulting substance from
Takemoto, T., Nomoto, K., Hikino, Y., & Hikino, H. (1968) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)72794-8 · Cited by 30 · see citing works
Steroids
Grunwald, C. (1980) · Springer eBooks · doi:10.1007/978-3-642-67360-3_10 · Cited by 28 · see citing works
The moulting hormone activity of ponasterones on Musca domestica (Diptera) and Bombyx mori (Lepidoptera)
Kobayashi, M., Nakanishi, K., & Koreeda, M. (1967) · Steroids · doi:10.1016/0039-128x(67)90106-7 · Cited by 28 · see citing works
Regulation of Pupariation in Flies
Žd̕árek, J. (1985) · Elsevier eBooks · doi:10.1016/b978-0-08-030809-8.50015-0 · Cited by 28 · see citing works
Isolation of the diapause hormone from the silkworm, Bombyx mori
Isobe, M., Hasegawa, K., & Goto, T. (1973) · Journal of Insect Physiology · doi:10.1016/0022-1910(73)90206-0 · Cited by 28 · see citing works
Zur Synthese des Ecdysons. II. Mitteilung über Insektenhormone Synthesen von 2β, 3β‐Dihydroxy‐6‐keto‐A|B‐cis‐Steroiden
Wiechert, R., Kerb, U., Hocks, P., Furlenmeier, A. E., Fürst, A., Langemann, A., & Waldvogel, G. (1966) · Helvetica Chimica Acta · doi:10.1002/hlca.19660490517 · Cited by 28 · see citing works
Die Synthese von 5α‐Stigmastatrien‐(7. 22.25)‐ol‐(3β)
Sucrow, W., & Girgensohn, B. (1970) · Chemische Berichte · doi:10.1002/cber.19701030314 · Cited by 28 · see citing works
Arthropod moulting hormones from plants,Achyranthes andCyathula
Hikino, H., & Takemoto, T. (1972) · Die Naturwissenschaften · doi:10.1007/bf00591780 · Cited by 27 · see citing works
Distribution and dynamic state of sterols and steroids in the tissues of an insect, the roach Eurycotis floridana
Lasser, N. L., Edwards, A. M., & Clayton, R. B. (1966) · Journal of Lipid Research · doi:10.1016/s0022-2275(20)38968-9 · Cited by 27 · see citing works
Modern Steroid Problems
Wiechert, R. (1970) · Angewandte Chemie International Edition in English · doi:10.1002/anie.197003211 · Cited by 27 · see citing works
Die synthese des ecdysons
Kerb, U., Hocks, P., Wiechert, R., Furlenmeier, A. E., Fürst, A., Langemann, A., & Waldvogel, G. (1966) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)99727-8 · Cited by 27 · see citing works
Ecdysterone and its Activity on some Degenerative Diseases
Cahlíková, L., Macáková, K., Chlebek, J., Hošťálková, A., Kulhánková, A., & Opletal, L. (2011) · Natural Product Communications · doi:10.1177/1934578x1100600527 · Cited by 26 · see citing works
Past and present studies with ponasterones, the first insect molting hormones from plants
Nakanishi, K. (1992) · Steroids · doi:10.1016/0039-128x(92)90018-5 · Cited by 26 · see citing works

Die Kristall‐ und Molekülstrukturanalyse des Insektenhäutungshormons 20‐Hydroxy‐ecdyson (Ecdysteron)
Dammeier, B., & Hoppe, W. (1971) · Chemische Berichte · doi:10.1002/cber.19711040534 · Cited by 16 · see citing works
ChemInform Abstract: KRISTALL‐ UND MOLEKUELSTRUKTURANALYSE DES INSEKTENHAEUTUNGSHORMONS 20‐HYDROXY‐ECDYSON (ECDYSTERON)
Dammeier, B., & HOPPE, W. (1971) · Chemischer Informationsdienst Organische Chemie · doi:10.1002/chin.197129116
Zur Chemie des Ecdysons, II: Bestimmung des Sterin‐Skeletts und seiner Orientierung mit diffuser Röntgenstreuung in Kristallen von Ecdyson
Hoppe, W., & Huber, R. (1965) · Chemische Berichte · doi:10.1002/cber.19650980739 · Cited by 23 · see citing works
Zur Chemie Des Ecdysons
Karlson, P., Hoffmeister, H. M., Hoppe, W., & Huber, R. (1963) · Justus Liebig s Annalen der Chemie · doi:10.1002/jlac.19636620102 · Cited by 104 · see citing works
Ausscheidung von Ecdyson bei Insekten
Hoffmeister, H. M., Rufer, C., & Ammon, H. (1965) · Zeitschrift für Naturforschung B · doi:10.1515/znb-1965-0207 · Cited by 24 · see citing works

Authors: Huber, R., & Hoppe, W.
Affiliations: Max Planck Society (DE)
ORCID: Huber, Robert
Venue: Chemische Berichte
Publisher: Wiley
Published: 1965-07
Volume: 98
Issue: 7
Pages: 2403-2424
ISSN: 0009-2940 (ISSN-L)
DOI: 10.1002/cber.19650980744
OpenAlex: W2053483325
Cited by: 219
References: 4
Citations by year: 2026: 1 · 2024: 3 · 2023: 3 · 2022: 4 · 2021: 2 · 2020: 4 · 2019: 1 · 2017: 4 · 2015: 1 · 2014: 1 · 2013: 4 · 2012: 2
FWCI: 10.30
Type: journal article
Language: en
Open access: closed
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 14814 d)
Locations: Chemische Berichte (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
Physical Sciences › Chemistry › Inorganic Chemistry › Crystal structures of chemical compounds
Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
Keywords: ecdysone, insect molting hormone, crystal structure, molecular structure, steroid structure determination, natural product structure
MeSH terms: Ecdysone, Hormones, Insecta

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

Zur Chemie des Ecdysons, VII: Die Kristall- und Molekülstrukturanalyse des Insektenverpuppungshormons ecdyson mit der automatisierten Faltmolekülmethode

Abstract

Integrity signals

Claims the paper makes

Claims other papers make about this one

Cites

Cited by

Related

Record

About these checks