Triterpenoid Constituents Isolated from the Bark of Abies sachalinensis

Abstract

Three new lanostane-type triterpenoids (1-3) were isolated from the bark of Abies sachalinensis along with a known compound (4). The structures of 1-4 were characterized by spectroscopic methods including NMR and MS. Compound 4 and some derivatives were tested for inhibitory effects on in vitro DNA topoisomerases I and II and found to be selective catalytic inhibitors of topoisomerase II activity with IC(50) values in the range 43-76 microM.

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

“…Similarly, purification of the filtrate afforded five known terpenoids. Based on their spectroscopic data (IR, MS and NMR) and comparison with literature values, the structures of the known compounds were elucidated as awashishinic acid ( 5 ) [7], abiesonic acid ( 6 ) [6], firmanoic acid ( 7 ) [8], (22 Z )-3,4- seco -9β H -lanosta-4(28),7,22,24-tetraen-23,26-olid-3-oic acid ( 8 ) [9], (25 R )-3,4- seco -9β H -lanosta-4(28),7-diene-3,26-dioic acid ( 9 ) [10], abiesolidic acid ( 10 ) [10–11], (23 R ,25 R )-3,4- seco -17,14- friedo -9β H -lanosta-4(28),6,8(14)-trien-26,23-olid-3-oic acid ( 11 ) [10], (24 E )-3,4- seco -9β H -lanosta-4(28),7,24-triene-3,26-dioic acid ( 12 ) [12], abiesanordine C ( 13 ) [13], methyl 13-oxo-podocarp-8(14)-en-15-oate ( 14 ) [14], 15-hydroxydehydroabietic acid ( 15 ) [15], methyl 15-hydroxydehydroabietate ( 16 ) [16], (12 E )-8-hydroxy-15-nor-12-labden-14-al ( 17 ) [17] and 8-hydroxy-14,15-dinor-11-labden-13-one ( 18 ) [13,18] (Fig. 1).…”

Two lanostane triterpenoids from Abies koreana

“…Considerable interest has continued in the 9bH-lanostane-type triterpenoids isolated from the needles, stem barks, seeds and resins of the genus Abies. The isolation and structure elucidation of 3,4-seco-9bH-lanost-7-enes and 3-oxo9bH-lanost-7-enes were reported widely in some Abies species including A. sibirica (Raldugin et al, , 1987(Raldugin et al, , 1991Roshchin et al, 1986;Shevtsov and Raldugin, 1988;Yaroshenko and Raldugin, 1989;Leibyuk et al, 1990;Kukina et al, 1988;Druganov et al, 2000), A. sachalinensis (Wada et al, 2002), A. veitchii (Tanaka and Matsunaga, 1991a), A. firma (Hasegawa et al, 1987a;Tanaka et al, 1990;Tanaka and Matsunaga, 1991b) and A. mariesii (Hasegawa et al, 1987b;Tanaka et al, 1999). These 9bH-lanost-7-enes have interesting stereochemical features that are different from euph-7-ene or tirucall-7-ene series of compounds.…”

Stereoselektive Synthese und Reaktionen von in Position 3 funktionalisierten sekundären Alkyllithiumverbindungen

“…[15] Das entsprechende Lithiumreagens reagierte mit Bu 2 S 2 oder ClCO 2 Et in 69 bzw. [16] an: Eine Reaktion von 5 d mit MeSO 3 H (10 Mol-%) ergab das trans-Lacton 13 in 70 % Ausbeute (d.r. = 97:3; Schema 2).…”