1106 J ournal of Natural Products, 2003, Vol. 66, No. 8
Notes
nm to give 7 (0.7 mg).10 Compound 7 was treated with (S)-1-
phenyletheylamine (2 µL) in THF (50 µL), followed by acetyl-
ation with Ac2O in pyridine, to give 8.9 Identification of 8 was
carried out using HPLC with a silica gel column (YMC A-004,
300 × 4.6 mm) eluting with n-hexane-CH2Cl2-i-PrOH (20:
20:1) at a flow rate of 2.0 mL/min with detection at 254 nm.
The tR’s of authentic (3R)-5-O-acetyl-1-[(S)-phenylethyl]meva-
lonamide and (3S)-5-O-acetyl-1-[(S)-phenylethyl]mevalona-
mide were 14.7 and 15.8 min, respectively, and 8 was identical
to the former on the chromatogram.
(CH2, C-6), 17.9 (CH, C-21), 16.5 (CH3, C-26), 16.3 (CH3, C-18);
FABMSm/z629[MH-H2O]+(4),467[MH-OCOCH2C(OH)(CH3)CH2-
COOH - H2O]+ (25); HRFABMS m/z 629.4081 (calcd for
C
37H57O8 [(MH - H2O)+], 629.4053).
An ti-in fla m m a tor y Test. The mouse ear inflammatory
test was conducted according to Gschwendt’s method.15 The
experiment complied with regulations concerning animal
experimentation and the care of experimental animals of the
Faculty of Agriculture at Shinshu University.
(25S,3′S)-(+)-12r-Hyd r oxy-3r-(3′-h yd r oxy-4′-m eth oxy-
Ack n ow led gm en t. We thank Ms. K. Hashimoto of Shin-
shu University for providing the NMR spectra.
ca r b on yl-3′-m et h ylb u t yr yloxy)-24-m et h ylla n ost a -8,24-
(31)-d ien -26-oic a cid (5): colorless powder; [R]23 +17.0° (c
D
2.62, CHCl3); IR (film) νmax 3483, 2948, 1710, 1645, 1457, 1376,
1204 cm-1; FABMS m/z 627 [MH - H2O]+ (8), 451 [MH -
OCOCH2C(OH)(CH3)CH2COOCH3 - H2O]+ (78); HRFABMS
m/z 627.4243 (calcd for C38H59O7 [(MH - H2O)+], 627.4261).
Meth yla tion of 4 a n d 5. Methylation of 5 (5 mg) in MeOH
(1 mL) with ethereal diazomethane for 2 h gave 9 quantita-
tively. Compound 9 was also prepared from 4 in the same
manner.
Su p p or tin g In for m a tion Ava ila ble: Table of 13C and 1H NMR
spectra for 1, 3-5, and 9 and a figure showing NOEs and coupling
constants of the A ring of 6. This material is available free of charge
Refer en ces a n d Notes
(1) Yasukawa, K.; Ikeya, Y.; Mitsuhashi, H.; Iwasaki, M.; Aburada, M.;
Nakagawa, S.; Takeuchi, M.; Takido, M. Oncology 1992, 49, 68-71.
(2) Yasukawa, K.; Takido, M.; Takeuchi, M.; Nakagawa, S. Chem. Pharm.
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(4) Bowers, A.; Halsall, T. G.; Sayer, G. C. J . Chem. Soc. 1954, 3070-
3084.
(+)-12r,28-Dih ydr oxy-3r-(3′-h ydr oxy-3′-m eth ylglu tar yl-
oxy)-24-m eth ylla n osta -8,24(31)-d ien -26-oic a cid (6): color-
1
less powder; [R]21 +25.6° (c 0.43, MeOH); H NMR (CDCl3,
D
500 MHz) δ 5.19 (1H, brs, H-3), 5.00, 4.93 (each 1H, brs, H-31),
3.98 (1H, d, J ) 8.1 Hz, H-12), 3.82, 3.52 (each 1H, d, J )
11.3 Hz, H-28), 3.20 (1H, q, J ) 7.1 Hz, H-25), 2.77, 2.71 (each
1H, d, J ) 15.3 Hz, H-2′), 2.77, 2.65 (each 1H, d, J ) 15.6 Hz,
H-4′), 2.58, 2.08 (each 1H, m, H-11), 2.26, 2.08 (each 1H, m,
H-23), 2.05 (1H, m, H-17), 2.03 (2H, m, H-7), 2.04, 1.28 (each
1H, m, H-16), 1.89, 1.70 (each 1H, m, H-2), 1.68, 1.28 (each
1H, m, H-22), 1.67, 1.21 (each 1H, m, H-15), 1.64 (1H, m, H-5),
1.62, 1.45 (each 1H, m, H-6), 1.52, 1.44 (each 1H, m, H-1), 1.44
(1H, m, H-20), 1.42 (3H, s, 3-CH3), 1.34 (3H, d, J ) 7.1 Hz,
H-26), 1.09 (3H, s, H-30), 1.02 (1H, d, J ) 6.4 Hz, H-21), 1.02
(3H, s, H-29), 0.94 (3H, s, H-19), 0.58 (3H, s, H-18); 13C NMR
(CDCl3, 125 MHz) δ 177.4 (C, C-27), 174.6 (C, C-5′), 171.8 (C,
C-1′), 149.5 (C, C-24), 134.8 (C, C-8), 132.9 (C, C-9), 110.5 (CH2,
C-31), 73.9 (CH, C-3), 73.2 (CH, C-12), 69.7 (C, C-3′), 65.1 (CH2,
C-28), 49.7 (C, C-14), 49.6 (C, C-13), 46.2 (CH, C-5), 46.0 (CH,
C-25), 45.7 (CH2, C-2′), 45.1 (CH2, C-4′), 43.1 (CH, C-17), 42.3
(C, C-4), 36.6 (C, C-10), 36.0 (CH, C-20), 34.3 (CH2, C-22), 32.6
(CH2, C-11), 32.0 (CH2, C-15), 31.7 (CH2, C-23), 30.6 (CH2, C-1),
27.7 (CH2, C-16), 27.3 (CH3, 3′-CH3), 26.4 (CH2, C-7), 24.5 (CH3,
C-30), 23.2 (CH2, C-2), 21.7 (CH3, C-29), 19.4 (CH3, C-19), 18.2
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