Ponasterone A
Title: Ponasterone A
CAS Registry Number: 13408-56-5
CAS Name: (2b,3b,5b,22R)-2,3,14,20,22-Pentahydroxycholest-7-en-6-one
Additional Names: 25-deoxyecdysterone; 25-deoxy-20-hydroxyecdysone
Molecular Formula: C27H44O6
Molecular Weight: 464.63
Percent Composition: C 69.80%, H 9.55%, O 20.66%
Literature References: Polyhydroxylated steroid with strong moulting hormone activity; first phytoecdysteroid to be isolated. Isoln with ponasterones B, C, D, from plant source, Podocarpus nakaii Hay., Podocarpaceae and structure determn: K. Nakanishi et al., Chem. Commun. 1966, 915; isoln from various Japanese ferns: T. Takemoto et al., Chem. Pharm. Bull. 21, 2336 (1973). Isoln from crustaceans: J. F. McCarthy, Steroids 34, 799 (1979). Stereochemical elucidation: H. Moriyama, K. Nakanishi, Tetrahedron Lett. 1968, 1111; using 13C-NMR: H. Hikino et al., Chem. Pharm. Bull. 23, 125 (1975). Chromatographic sepn: M. Hori, Steroids 14, 33 (1969). HPLC analysis: I. D. Wilson et al., J. Chromatogr. 238, 97 (1982); R. E. Isaac et al., ibid. 246, 317 (1982). Synthesis: G. Hüppi, J. B. Siddall, Tetrahedron Lett. 1968, 1113. Moulting hormone activity on houseflies, silkworms: M. Kobayashi et al., Steroids 9, 529 (1967); on various insects: W. E. Robbins et al., ibid. 16, 105 (1970). Hormonal regulation to increase yield from silkworms: T. Okauchi et al., US 3941879 (1976 to Takeda). Used to characterize ecdysteroid receptors in Drosophilia cells: P. Maroy et al., Proc. Natl. Acad. Sci. USA 75, 6035 (1978); B. A. Sage et al., J. Biol. Chem. 257, 6373 (1982). Review of ponasterones: K. Nakanishi, Bull. Soc. Chim. Fr. 1969, 3475. See also Ecdysteroids.
Properties: Crystals from ethanol, mp 259-260° (dec). [a]D15 +90° (methanol). uv max (methanol): 244, 326 nm (e 12400, 130).
Melting point: mp 259-260° (dec)
Optical Rotation: [a]D15 +90° (methanol)
Absorption maximum: uv max (methanol): 244, 326 nm (e 12400, 130)

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