920
R. Maurya et al. / Phytochemistry 65 (2004) 915–920
recrystallized fromMeOH, mp 88–89 ꢁC, [ꢂ]D29 À80.0ꢁ
(c=0.30, CHCl3). Positive FAB-MS m/z: 721 [M+Na]+.
1H and 13C NMR: Table 2.
Burke, A.J., O’Sullivan, W.I., 1997. Flavonoid epoxides. Part 20.
Some unusual reactions of dimethyldioxirane (DMD) with flavonoid
compounds. Tetrahedron 53, 8491–8500.
Chopra, R.N.; Chopra, J.C.; Handa, K.L.; Kapur, L.D., 1958. Indi-
genous Drugs of India, 2nd ed. Dhar, U.N. and Sons Pvt., Ltd.,
Calcutta, pp. 522.
3.6. Marsuposide (4)
Eade, R.A., McDonald, F.J., Simes, J.H., 1975. Extractives of
Australian timbers. XV. Synthesis of 7,40-di-O-methylbayin. Aust.
J. Chem. 28, 2011–2018.
Ferrari, F., Lima, R.A., Bettolo, G.B.M., 1984. 2,4,20-Trihydroxy-40-
methoxybenzil from Zollernia paraensis. Phytochemistry 23, 2691–
2692.
Light yellow crystals, mp 156–158 ꢁC, [ꢂ]D26 +8.4ꢁ
(c=0.225, MeOH). IR (KBr) ꢁmax cmÀ1: 3300, 1680,
1608, 1510, 1444. UV (MeOH) lmax nm: 211, 240, 282,
333; (+NaOAc) nm: 211, 261, 283, 344. Positive FAB-
MS m/z: 435 [M+H]+, 457 [M+Na]+, 418, 327, 299,
Fink, K., Fink, R.M., 1949. Application of filter paper partition
chromatography to quantitative analysis of volatile and non volatile
organic acids. Proc. Soc. Exptl. Biol. Med. 70, 654–656.
Gadre, S.Y., Marathe, K.G., 1988. Acid catalysed isomerization of
Z-a-phenylcinnamic acid and their conversion to isomeric
isoaurones. Synth. Commun. 18, 1015–1027.
1
107. H and 13C NMR: Table 3. Marsuposide heptaa-
cetate (4a), crystallized frommixture of n-hexane and
29
ꢁ
EtOAc, mp 108–109 C, [ꢂ]D À29.0ꢁ (c=0.25, CHCl3).
Positive FAB-MS m/z: 729 [M+H]+, 751 [M+Na]+.
1H and 13C NMR: Table 3.
Gray, T.I., Pelter, A., Ward, R.S., 1979. Photochemical reaction of
6-methoxybenzofuran-2,3-dione with styrene and d-ethoxystyrene.
Tetrahedron 35, 2539–2543.
3.7. Vijayoside (5)
Grayer, R. J., 1989. Flavonoids. In: Dey, P. M., Harborne, J. B (Eds.),
Methods in Plant Biochemistry, Vol. 1. Academic Press Ltd,
London, pp. 292.
Yellow needles frommixture of H 2O–MeOH (19:1),
mp 202–204 ꢁC, [ꢂ]D19 +25.60 (c=0.5, MeOH). UV
(MeOH) lmax nm: 219, 238, 260, 320, 358; (+NaOAc)
nm: 219, 238, 267, 320, 367. IR (KBr) ꢁmax cmÀ1: 3228,
1617, 1554, 1448, 1422. Positive FAB-MS m/z: 433
Handa, S.S., Singh, R., Maurya, R., Satti, N.K., Suri, K.A., Suri,
O.P., 2000. Pterocarposide, an isoaurone C-glucoside from Pter-
ocarpus marsupium. Tetrahedron Letters 41, 1579–1581.
Indian Council of Medical Research (ICMR), 1998. Collaborating
Centres, New Delhi, Flexible dose open trial of Vijayasar in case of
newly-diagnosed non-insulin-dependent diabetes mellitus. Indian J.
Med. Res. 108, 24–29.
1
[M+H]+. H and 13C NMR: Table 4.
Jain, S.K., 1968. Medicinal Plants. National Book Trust, New Delhi.
pp. 116–118.
3.8. Vijayosine (6)
Kricka, L.J., Ledwith, A., 1973. Cation radicals: reaction of meth-
oxylated benzyl and bibenzil derivatives with tris-(p-bromophenyl)
ammoniumyl hexachloroantimonate. J. Chem. Soc. Perkin Trans. 1
294.
29
ꢁ
Pale yellow amorphous powder, mp 296–198 C, [ꢂ]D
+32.14 (c=0.056, DMSO). IR (KBr) ꢁmax: 3450, 1710,
1608, 1460, 1302 cmÀ1). UV (DMSO) lmax nm: 221,
268, 274 nm. EIMS m/z 598 [M]+, 299. H NMR (200
1
Maurya, R., Ray, A.B., Duah, F.K., Slatkin, D.J., Schiff Jr, P.L.,
1982. Marssupsin, a new benzofuranone from Pterocarpus marsu-
pium Roxb. Heterocycles 19, 2103–2107.
MHz, DMSO-d6) ꢀ: 11.90 (2H, s, OH), 8.90 (2H, d,
J=9.1 Hz, H-6), 8.26 (2H, s, OH), 6.98 (2H, d, J=9.1
Hz, H-5), 4.85 (2H, d, J=9.1Hz, H-100), 3.10–4.40
(sugar protons). 13C NMR (50.32 MHz, DMSO-d6) ꢀ:
192.0 (2ꢀCO), 160.5 (2ꢀC-4), 158.8 (2ꢀC-2), 128.3
(2ꢀC-6), 123.4 (2ꢀC-1), 113.0 (2ꢀC-5), 108.9 (2ꢀC-3),
82.6 (2ꢀC-500), 79.9 (2ꢀC-300), 79.5 (2ꢀC-200), 74.2
(2ꢀC-100), 71.5 (2ꢀC-400), 62.3 (2ꢀC-600).
Maurya, R., Ray, A.B., Duah, F.K., Slatkin, D.J., Schiff Jr, P.L.,
1984. Constituents of Pterocarpus marsupium Roxb. J. Nat. Prod.
47, 179–181.
Moriarty, R.M., Prakash, O., Prakash, I., Musallam, H.A., 1984.
Intramolecular participation in hypervalent iodine oxidation, the
synthesis of coumaran-3-ones, aurone, and isoaurone. J. Chem.
Soc., Chem. Commun 1342–1343.
Ohshima, Y., Okuyama, T., Takashashi, K., Takizawa, T., Shibata,
S., 1988. Isolation and High Perforance Liquid Chromatography
(HPLC) of isoflavonoids fromthe Pueraria root. Planta Medica 54,
250–254.
Acknowledgements
Pelter, A., Ward, R.S., Gray, T.I., 1976. The carbon-13 nuclear mag-
netic resonance spectra of flavonoids and related compounds.
J. Chem. Soc. Perkin Trans. 1 2475–2483.
We thank ICMR, New Delhi for financial support of
this work.
Seher, A., Seifen, F., 1959. Separation and identification of synthetic
antioxidants by thin layer chromatography. Anstrichmittel 61, 345–
351.
Seshadri, T.R., 1972. Polyphenols of Pterocarpus and Dalbergia
woods. Phytochemistry 11, 881–898.
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