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the jervine (1) soln. (50 mg of 1 dissolved in 250 ml of EtOH) was added to each flask, and the incubation
was continued for 12 d.
Microbial Metabolism of Jervine (1). After 12 d of incubation, the incubation mixtures were pooled
and filtered. The filtrate was passed through a MCI-gel CHP20P column, and washed with H2O to
remove sugars; then, successive extraction with 20% aq. MeOH, 60% aq. MeOH, and MeOH gave the
Fractions A, B, and C, resp. Each fraction was evaporated to dryness in vacuo and analyzed by TLC
(CHCl3/MeOH/H2O 65 :35 :10; visualization by spraying with 10% H2SO4 soln.). Fr. C was chromato-
graphed repeatedly through a column on SiO2 (CHCl3/MeOH 10 :1) to afford 2 (8.8 mg). Fr. B was
subjected repeatedly to CC (SiO2; CHCl3/MeOH 5 :1; Sephadex LH-20; 70% MeOH) to furnish 3
(4.6 mg) and 4 (6.1 mg). Fr. A was dissolved in 10% aq. MeOH and subjected to CC (RP SiO2 (ODS);
H2O/MeOH 100 :10 ! 0 :100) to give 5 (3.6 mg).
Jervine (1). Colorless prisms. C27H39NO3. ESI-MS: 426 ([M þ H]þ). [a]D23 ¼ ꢀ58.2 (c ¼ 3.08,
MeOH). Jervine (1) was isolated from the roots of Veratrum dahuricum with purity of 99.0% by HPLC
analysis in our laboratory. The chemical structure was identified by detailed NMR analysis and
comparing its data with those in the literature [17]. An X-ray diffraction analysis of (ꢀ)-varatrobasine
(¼ jervine-11b-ol) has been reported previously [18]. We performed the X-ray-analysis of 1 (Fig. 3) to
establish the absolute configuration of (ꢀ)-jervine.
Fig. 3. X-Ray crystal structure of 1
7a-Hydroxyjervine (¼(3b,7a,22S,23R)-3,7-Dihydroxy-17,23-epoxyveratraman-11-one ¼ (3S,3’R,
3a’S,6S,6’S,6aS,6bS,7a’R,9R,11aS,11bR)-2,3,3’a,4,4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-Hexadecahydro-3,6-di-
hydroxy-3’,6’,10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2’(3’H)-furo[3,2-b]pyridin]-11(1H)-one;
3). White amorphous powder. [a]2D3 ¼ ꢀ113.4 (c ¼ 0.81, MeOH). IR (KBr): 3370, 2951, 2177, 1623, 1070.
1H- and 13C-NMR: Tables 2 and 1, resp. 2D-NMR (HMBC; 500 MHz, CD3OD): HꢀC(3)/C(4), HꢀC(7)/
C(5), HꢀC(7)/C(8), HꢀC(15)/C(14). ESI-MS: 442 ([M þ H]þ). HR-ESI-MS: 442.2952 ([M þ H]þ,
C27H40NOþ4 ; calc. 442.2957).
14a-Hydroxyjervine (¼(3b,22S,23R)-3,14-Dihydroxy-17,23-epoxyveratraman-11-one ¼ (3S,3’R,
3a’S,6’S,6aR,6bR,7a’R,9R,11aS,11bR)-2,3,3’a,4,4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-Hexadecahydro-3,6b-di-
hydroxy-3’,6’,10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2’(3’H)-furo[3,2-b]pyridin]-11(1H)-one;
4). White amorphous powder. [a]2D3 ¼ ꢀ54.6 (c ¼ 0.76, MeOH). IR (KBr): 3361, 2947, 2170, 1617, 1073.
1H- and 13C-NMR: Tables 2 and 1, resp. 2D-NMR (HMBC; 500 MHz, CD3OD): HꢀC(3)/C(4), HꢀC(7)/
C(8), HꢀC(15)/C(14). ESI-MS: 442 ([M þ H]þ). HR-ESI-MS: 442.2956 ([M þ H]þ, C27H40NOþ4 ; calc.
442.2957).
1b,7a-Dihydroxyjervine (¼(1b,3b,7a,22S,23R)-1,3,7-Trihydroxy-17,23-epoxyveratraman-11-one ¼
(1R,3R,3’R,3a’S,6S,6’S,6aS,6bS,7a’R,9R,11aS,11bR)-2,3,3’a,4,4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-Hexadeca-