Title: Gardenins
Literature References: A group of flavones isolated from the resinous exudate of leaf buds of Gardenia lucida Roxb. Rubiaceae, a small spiny tree occurring throughout India. Isoln of the main flavonoid pigment, gardenin A (originally thought to be the only component and referred to in early literature as "gardenin"): J. Stenhouse, C. G. Groves, J. Chem. Soc. 1877, 552; Ann. 200, 311 (1880); K. J. Balakrishna, T. R. Seshadri, Proc. Indian Acad. Sci. 27A, 91 (1948). Isoln and structure of gardenins B, C, D, E: A. V. R. Rao et al., Indian J. Chem. 8, 398 (1970). Isoln of B from Citrus jambhiri lush. Rutaceae and synthesis: B. P. Chaliha et al., Tetrahedron 21, 1441 (1965). Structure of A: P. K. Bose, J. Indian Chem. Soc. 22, 233 (1945). Revised structure: A. V. R. Rao, K. Venkataraman, Indian J. Chem. 6, 677 (1968). Synthesis of A: M. Krishnamurti et al., ibid. 8, 575 (1970); M. Kamalam, A. V. R. Rao, ibid. 573; of C: A. J. Kalra et al., ibid. 11, 96 (1973); of E: eidem, ibid. 1092. Antineoplastic activity and cytotoxicity: J. Edwards et al., J. Nat. Prod. 42, 85 (1979). 13C-NMR study: M. Iinuma et al., Chem. Pharm. Bull. 28, 708 (1980).
Derivative Type: Gardenin A
CAS Registry Number: 21187-73-5
CAS Name: 5-Hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
Molecular Formula: C21H22O9
Molecular Weight: 418.39
Percent Composition: C 60.28%, H 5.30%, O 34.42%
Properties: Golden yellow needles from ethanol, mp 162-163°. Sol in alcohol, chloroform. All the gardenins give a green color with alcoholic ferric chloride.
Melting point: mp 162-163°
Derivative Type: Gardenin B
CAS Registry Number: 2798-20-1
Additional Names: 5-O-Desmethyltangeretin
Molecular Formula: C19H18O7
Molecular Weight: 358.34
Percent Composition: C 63.68%, H 5.06%, O 31.25%
Properties: Fine yellow needles from benzene/petr ether, mp 176-177°. uv max (ethanol): 292, 330 nm (log e 4.40, 4.35); (l% AlCl3): 310, 350 nm (log e 4.48, 4.49).
Melting point: mp 176-177°
Absorption maximum: uv max (ethanol): 292, 330 nm (log e 4.40, 4.35); (l% AlCl3): 310, 350 nm (log e 4.48, 4.49)
Derivative Type: Gardenin C
CAS Registry Number: 29550-05-8
Molecular Formula: C20H20O9
Molecular Weight: 404.37
Percent Composition: C 59.40%, H 4.99%, O 35.61%
Properties: Yellow flakes from ethyl acetate-petr ether, mp 179-180°. uv max (methanol) 304, 323 nm (log e 4.18, 4.20).
Melting point: mp 179-180°
Absorption maximum: uv max (methanol) 304, 323 nm (log e 4.18, 4.20)
Derivative Type: Gardenin D
CAS Registry Number: 29202-00-4
Molecular Formula: C19H18O8
Molecular Weight: 374.34
Percent Composition: C 60.96%, H 4.85%, O 34.19%
Properties: Cryst, mp 190-192°. uv max (ethanol): 256, 280, 343 nm.
Melting point: mp 190-192°
Absorption maximum: uv max (ethanol): 256, 280, 343 nm
Derivative Type: Gardenin E
CAS Registry Number: 29550-07-0
Molecular Formula: C19H18O9
Molecular Weight: 390.34
Percent Composition: C 58.46%, H 4.65%, O 36.89%
Properties: Golden yellow needles from ethyl acetate/petr ether, mp 234-235°. uv max (methanol): 280, 325 nm (log e 4.37, 4.36).
Melting point: mp 234-235°
Absorption maximum: uv max (methanol): 280, 325 nm (log e 4.37, 4.36)
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