TY - JOUR
T1 - Studies on terpenoids and steroids - 18 balaenonol, balaenol and isobalaendiol
T2 - Three new 14(15)-ene-quinone-methide triterpenoids from cassine balae
AU - Chandrasiri Fernando, H.
AU - Leslie Gunatilaka, A. A.
AU - Tezuka, Yasuhiro
AU - Kikuchi, Tohru
N1 - Funding Information:
Isolation of ~~~~ial(3) This WBS isolated from the same combined column fractions fmm which ~h~~~~no~ was isolated (SW a&we}_ bLC separatkm [Si gel; 0.5 mm; eluant-~i~~~:M~ (97:3), F& 0.36 and then with hexane:EtOAc (4:8), F$ 0.41 afforded isobataendiol (3) as an orange red crystalline soiii (23 mg, 0.0023%), m.p. 210-212 (from dichlommethane-ether); [alo t66’ tc, 4.5 in CHC ; UV (EKIH) 266 (log E 3.02), 441 (4.01) nm ; IR (KBr) 3500-3200, 1584,1526,1442,1379, and 1204 cm’; for ‘H and '% NMR data,S BB Tab&s I and 2, rqwth@; MB, mh 436 @+, Acknowfedgement& We wish to thank Prof. Dr. Gunther Snakke for CD spectra of bafaenonof and bafaenof; P&t V. Kumar for an ~~~~ sample of their ~~~~ previously iscfated from C. balacr; Mis. S.C. Wan for careful pmparation of the manuscript; Natural Resources, Energy and Bciince Authority of Sri L&a and i~~~n~ Program for Chemical Science (Sweden) for financial assistance.
PY - 1989
Y1 - 1989
N2 - The three new 14(15)-ene-quinone-methide triterpenoids, balaenonol, balaenol and isobalaendiol, isolated from Cassine balae have been shown to be 3,21β-dihydroxy-2,22-dioxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,29-dinoroleanane (1), 3,21β-dihydroxy-2-oxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,29-dinoroleanane (2) and 3,21β,22β-trihydroxy-2-oxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,30-dinoroleanane (3), respectively, on the basis of spectroscopic evidence. The possible biosynthetic origin of these 14(15)-ene-quinone-methides from pristimerin is discussed.
AB - The three new 14(15)-ene-quinone-methide triterpenoids, balaenonol, balaenol and isobalaendiol, isolated from Cassine balae have been shown to be 3,21β-dihydroxy-2,22-dioxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,29-dinoroleanane (1), 3,21β-dihydroxy-2-oxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,29-dinoroleanane (2) and 3,21β,22β-trihydroxy-2-oxo-3,5,7,10(1),14(15)-pentaen-(14→15)-D:A-friedo-24,30-dinoroleanane (3), respectively, on the basis of spectroscopic evidence. The possible biosynthetic origin of these 14(15)-ene-quinone-methides from pristimerin is discussed.
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U2 - 10.1016/S0040-4020(01)89113-4
DO - 10.1016/S0040-4020(01)89113-4
M3 - Article
AN - SCOPUS:0000892824
SN - 0040-4020
VL - 45
SP - 5867
EP - 5876
JO - Tetrahedron
JF - Tetrahedron
IS - 18
ER -