377. Amarogentin

Nomenclature

CAS number: 21018-84-8
(4aS,5R,6S)-5-Ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3′,5-trihydroxy[1,1′-biphenyl]-2-yl)carbonyl]-β-d-glucopyranosyl]oxy]-1H,3H-pyrano[3,4-c]pyran-1-one; sweroside 2′-(3″,5″,3-trihydroxydiphenyl)-2″-carboxylic acid ester; [4aS-(4aα,5β,6α)]-3,3′,5-Trihydroxy[1,1′-biphenyl]-2-carboxylic acid 2-ester with 5-ethenyl-6-(β-d-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one.
C29H30O13; mol wt 586.54.
C 59.38%, H 5.16%, O 35.46%.

Description and references

Strongly bitter glucoside. Isoln from Swertia chirata Buch-Ham., Gentianaceae: Korte, Ber. 88, 704 (1955); 89, 2404 (1956); from Swertia japonica Makino: Inouye et al., Chem. Pharm. Bull. 18, 1856 (1970). Occurrence in gentianaceous plants: Inouye, Nakamura, J. Pharm. Soc. Jpn. 91, 755 (1971), C.A. 75, 95431b (1971). Structure: eidem, Tetrahedron Lett. 9, 4919 (1968); eidem, Tetrahedron 27, 1951 (1971).

Chemical structure

Properties

Colorless needles, mp 229-230° (monohydrate). [α]D20 116.6° (methanol). uv max: 230, 266, 306 nm (log ε 4.46, 4.07, 3.68). Slightly sol in benzene, water; freely sol in acetone, anhydr dioxane, tetrahydrofuran, methanol, ethanol. Practically insol in petr ether, ether, cyclohexane, CHCl3.