Licochalcones
Title: Licochalcones
Literature References: Oxygenated chalcones isolated from licorice root, a traditional medicine prepared from various species of Glycyrrhiza (Leguminosae). Exhibit antiparasitic and antitumor activity and appear to interfere with mitochondrial respiration. Four have been identified, A-D, as well as a closely related compound, echinatin. Isoln of A and B from G. glabra L. and structure: T. Saitoh, S. Shibata, Tetrahedron Lett. 50, 4461 (1975); of C and D from G. inflata: K. Kajiyama et al., Phytochemistry 31, 3229 (1992). Mechanism of action study: H. Haraguchi et al., ibid. 48, 125 (1998); L Zhai et al., J. Antimicrob. Chemother. 43, 793 (1999).
 
Derivative Type: Licochalcone A
CAS Registry Number: 58749-22-7
CAS Name: (2E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one
Molecular Formula: C21H22O4
Molecular Weight: 338.40
Percent Composition: C 74.53%, H 6.55%, O 18.91%
Literature References: Synthesis: A. Islam, M. A. Hossain, Indian J. Chem. 32B, 713 (1993). HPLC determn in biological fluids: L. Nadelmann et al., J. Chromatogr. B 695, 389 (1997). Antileishmanial activity: M. Chen et al., Antimicrob. Agents Chemother. 38, 1339 (1994). Antimalarial activity: eidem, ibid. 1470. Effect on human cancer cell lines: E. J. Park et al., Planta Med. 64, 464 (1998).
Properties: Yellow needles from methanol-water, mp 100°. uv max in methanol: 264, 308, 378 nm (log e 3.96, 3.97, 4.31).
Melting point: mp 100°
Absorption maximum: uv max in methanol: 264, 308, 378 nm (log e 3.96, 3.97, 4.31)
 
Derivative Type: Licochalcone B
CAS Registry Number: 58749-23-8
CAS Name: (2E)-3-(3,4-Dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one
Molecular Formula: C16H14O5
Molecular Weight: 286.28
Percent Composition: C 67.13%, H 4.93%, O 27.94%
Properties: Yellow needles from methanol-water, mp 197°. uv max in methanol: 262, 366 nm (log e 3.71, 4.27).
Absorption maximum: uv max in methanol: 262, 366 nm (log e 3.71, 4.27)
 
Derivative Type: Licochalcone C
CAS Registry Number: 144506-14-9
CAS Name: (2E)-3-[4-Hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl]-1-(4-hydroxyphenyl)-2-propen-1-one
Molecular Formula: C21H22O4
Molecular Weight: 338.40
Percent Composition: C 74.53%, H 6.55%, O 18.91%
Properties: Amorphous. uv max in methanol: 250, 308sh, 358 nm (log e 3.88, 3.95, 4.24).
Absorption maximum: uv max in methanol: 250, 308sh, 358 nm (log e 3.88, 3.95, 4.24)
 
Derivative Type: Licochalcone D
CAS Registry Number: 144506-15-0
CAS Name: (2E)-3-(3,4-Dihydroxy-2-methoxyphenyl)-1-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propen-1-one
Molecular Formula: C21H22O5
Molecular Weight: 354.40
Percent Composition: C 71.17%, H 6.26%, O 22.57%
Properties: Pale yellow needles from methanol-water, mp 113°. uv max in methanol: 254, 359 nm (log e 3.86, 4.30).
Melting point: mp 113°
Absorption maximum: uv max in methanol: 254, 359 nm (log e 3.86, 4.30)

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