2602
T. FURUMOTO et al.
tion of saturated NaCl (10 ml) and 5% Na S O (10 ml).
2
high-yield of a naphthoquinone by a hairy root culture of
Sesamum indicum. Phytochemistry, 33, 1095–1098
2
4
The Et O solution obtained was dried over Na SO and
2
2
4
(
1993).
concentrated to dryness. A solution of the residue
7
)
)
Shimomura, K., Sudo, H., Saga, H., and Kamada, H.,
Shikonin production and secretion by hairy root cultures
of Lithospermum erythrorhizon. Plant Cell Rep., 10,
(0.39 g), Ag2O (0.23 g) and Na2SO4 (0.2 g) in dry Et2O
(4 ml) was stirred for 20 min, and then filtered through
Celite, before the filtrate was concentrated to dryness.
The residue was purified by silica gel TLC (acetone–
hexane, 1:9) to give 1 (50 mg, 16% yield).
2
82–285 (1991).
8
Gamborg, O. L., Miller, R. A., and Ojima, K., Nutrient
requirements of suspension cultures of soybean root
cells. Exp. Cell Res., 50, 151–158 (1968).
2
-Geranyl-1,4-naphthoquinone (1). Pale brown oil.
UV ꢁmax (EtOH) nm (log "): 247 (4.28), 251 (4.28), 263
9) Perry, N. B., Blunt, J. W., and Munro, M. H. G., A
cytotoxic and antifungal 1,4-naphthoquinone and related
compounds from a New Zealand brown alga, Land-
sburgia quercifolia. J. Nat. Prod., 54, 978–985 (1991).
10) Jacobsen, N., and Torssell, K., Synthesis of naturally
occurring quinones. Acta Chem. Scand., 27, 3211–3216
(1973).
1) Jayasinghe, L., Balasooriya, B. A. I. S., Padmini, W. C.,
Hara, N., and Fujimoto, Y., Geranyl chalcone derivatives
with antifungal and radical scavenging properties from
the leaves of Artocarpus nobilis. Phytochemistry, 65,
ꢂ1
sh (4.15), 331 (3.49). IR ꢂ
1
(KBr) cm : 1665, 1619,
595, 1329, 1301, 1262. H-NMR ꢀH (CDCl3): 1.59
max
1
0
0
(
8
3H, br.s, H-9 ), 1.64 (3H, br.s, H-10 ), 1.67 (3H, br.s, H-
0
0
0
), 2.09 (4H, m, H-4 and H-5 ), 3.27 (2H, br.d,
0
J ¼ 7:3 Hz, H-1 ), 5.08 (1H, tqq, J ¼ 6:8, 1.4, 1.4 Hz, H-
0
0
6
), 5.21 (1H, ttq, J ¼ 7:3, 1.2, 1.2 Hz, H-2 ), 6.74 (1H, t,
1
J ¼ 1:8 Hz, H-3), 7.70 (2H, m, H-6 and H-7), 8.04 (1H,
13
m, H-5), 8.08 (1H, m, H-8). C-NMR ꢀ (CDCl ): 16.1
C
3
0 0 0 0 0
(
C-10 ), 17.7 (C-9 ), 25.7 (C-8 ), 26.4 (C-5 ), 27.9 (C-1 ),
0
0
0
0
3
1
1
1
9.7 (C-4 ), 118.1 (C-2 ), 123.9 (C-6 ), 126.1 (C-5),
26.5 (C-8), 131.8 (C-7 ), 132.2 (C-4a), 132.4 (C-8a),
33.56 (C-7), 133.63 (C-6), 134.6 (C-3), 140.0 (C-3 ),
50.8 (C-2), 185.3 and 185.4 (C-1 and C-4). EIMS m=z
1
287–1290 (2004).
12) Merza, J., Aumond, M.-C., Rondeau, D., Dumontet, V.,
Ray, A.-M. L., S e´ raphin, D., and Richomme, P.,
Prenylated xanthones and tocotrienols from Garcinia
virgata. Phytochemistry, 65, 2915–2920 (2004).
13) Herbert, R. B., ‘‘The Biosynthesis of Secondary Metab-
olites’’ second edition, Chapman and Hall, New York,
pp. 104–110 (1989).
0
þ
(
rel. int.): 294 (M , 46), 279 (11), 251 (22), 225 (43),
þ
2
11 (100). HR-EIMS m=z (M ): Calcd. for C H O :
2
20
22
2
94.1620. Found: 294.1623.
1
4) Inoue, K., Ueda, S., Nayeshiro, H., Moritome, N., and
Inouye, H., Biosynthesis of naphthoquinones and an-
thraquinones in Streptocarpus dunnii cell cultures.
Phytochemistry, 23, 313–318 (1984).
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