Title: Yingzhaosu
Literature References: Family of sesquiterpenes isolated from the roots of Yingzhao, (Artabotrys uncinatus (L.) Merr.) a traditional Chinese herbal medicine for treatment of malaria. Yingzhaosu A & C contain a peroxy group which is needed for antimalarial activity. Isoln of A: X.-T. Liang et al., Acta Chim. Sin. 37, 215 (1979), C.A. 92, 146954 (1980); of C: L. Zhang et al., J. Chem. Soc. Chem. Commun. 1988, 523. Structure of C: eidem, Sci. China Ser. B 32, 800 (1989). Total synthesis of A: X.-X. Xu et al., Tetrahedron Lett. 32, 5785 (1991); stereocontrolled synthesis: W.-S. Zhou in Newer Trends Essent. Oils. Flavours, Sel. Pap. Int. Symp., K. L. Dhar et al., Eds. (Tata McGraw-Hill, New Delhi, India, 1993) pp 43-50. Enantioselective synthesis of C: X.-X. Xu, H.-Q. Dong, J. Org. Chem. 60, 3039 (1995).
Derivative Type: Yingzhaosu A
CAS Registry Number: 73301-54-9
CAS Name: (3S,4E)-5-[(1S,4S,5S,8R)-4,8-Dimethyl-2,3-dioxabicyclo[3.3.1]non-4-yl]-2-methyl-4-pentene-2,3-diol
Additional Names: (+)-yingzhosu A
Molecular Formula: C15H26O4
Molecular Weight: 270.36
Percent Composition: C 66.64%, H 9.69%, O 23.67%
Literature References: Contains a unique dioxabicyclo[3.3.1]nonane ring system.
Properties: Isolated as solid, mp 95-96°. [a]D25 +226° (in CHCl3).
Melting point: mp 95-96°
Optical Rotation: [a]D25 +226° (in CHCl3)
Derivative Type: Yingzhaosu C
CAS Registry Number: 121067-52-5
CAS Name: (3R,6S)-rel-a,a,6-Trimethyl-6-(4-methylphenyl)-1,2-dioxane-3-methanol
Molecular Formula: C15H22O3
Molecular Weight: 250.33
Percent Composition: C 71.97%, H 8.86%, O 19.17%
Literature References: Occurs naturally as an enantiomeric mixture of the (3R,6S), (3S,6R) with a predominance of the former.
Properties: Oily substance. [a]D14 +2.89° (c = 2.15 in methanol); (6S,3R): [a]D +189.3° (c = 0.93 in CHCl3); (3S,6R): [a]D -185.4° (c = 0.78 in CHCl3).
Optical Rotation: [a]D14 +2.89° (c = 2.15 in methanol); [a]D +189.3° (c = 0.93 in CHCl3); [a]D -185.4° (c = 0.78 in CHCl3)
Therap-Cat: Antimalarial. |