926
S. Marquina et al. / Phytochemistry 66 (2005) 921–927
+
HRFAB-MS m/z 461.3868 ([M + H] , calcd. for
Elegami, A.A., Bates, C., Gray, A.I., Mackay, S.P., Skellern, G.G.,
Waigh, R.D., 2003. Two new very unusual macrocyclic flavo-
noids from the water lily Nymphaea lotus. Phytochemistry 63,
C H O : 461.3876).
2
2
20 11
7
27–731.
3
.5. Acid hydrolysis of compound 1
Fiuza, M., Gomes, C., Teixeira, L.J., Girao da Cruz, M.T., Cordeiro,
M.N.D.S., Milhazos, N., Borges, F., Marques, P.M., 2004.
Phenolic acid derivatives with potential anticancer properties – a
structure–activity relationship study. Part 1: methyl, propyl and
octyl esters of caffeic and gallic acids. Bioorgan. Med. Chem. 12,
Compound 1 (7 mg) in 5% HCl (5 ml) was heated
until reflux began, this being maintained for 2 h. After
cooling, the non-polar product was extracted with
EtOAc. The EtOAc fraction was concentrated and
the nonpolar reaction product was separated by pre-
cipitation with ice to afford 1a (3 mg) m.p. 138–
3
581–3589.
Fossen, T., Andersen, Ø.M., 1997. Acylated anthocyanins from leaves
of the water lily Nymphaea x marliacea. Phytochemistry 46, 353–
357.
Fossen, T., Fr;ystein, N.A., Andersen, Ø.M, 1998a. Myricetin 3-
1
40 ꢁC; For NMR spectral data, see Table 1. The
rhamnosyl (1 ! 6) galactoside from Nymphaea
x marliacea.
aqueous layer was neutralized with 5% NaOH (5 ml)
and concentrated until dryness for identification. The
sugars were analyzed by silica gel TLC [EtOAc–
Phytochemistry 49, 1997–2000.
˚
Fossen, T., Larsen, A., Andersen, Ø.M, 1998b. Anthocyanins from
flowers and leaves of Nymphaea x marliacea cultivars. Phytochem-
istry 48, 823–827.
MeOH–H O–AcOH (11:2:2:2)] by comparison with
2
0
Fossen, T., Andersen, Ø.M., 1999. Delphinidin 3 -galloylgalactosides
from blue flowers of Nymphaea caerulea. Phytochemistry 50, 1185–
standard sugars.
1
Fossen, T., Larsen, A, Kiremire, B.T., Anderse, Ø.M, 1999. Flavo-
188.
0
0
3
.6. 7,3 ,4 -Trihydroxy-5-O-a-L-
rhamnopyranosylisoflavone (2)
˚
noids from blue flowers of Nymphaea caerulea. Phytochemistry 51,
1
133–1137.
2
D
0
Geibel, M., Geiger, M., Treutter, D., 1990. Tectochrysin 5- and
genistein 5-glucosides from the bark of Prunus cerasus. Phyto-
chemistry 29, 1351–1353.
Yellow amorphous powder; ½aꢀ –19ꢁ (MeOH, c 0.2);
UV (MeOH) k
(
(MeOH) nm (log e): 312 (4.6), 272
3.8), (+NaOAc–H BO ) 325, 273; IR (KBr) m
340, 1668; For H NMR (400 MHz, CD OD) and
3
max
ꢁ
cm
max
1
3
1
3
Gunn, C.R., Wiersema, J.H., Ritchie, C.A., Kirkbride, J.H., 1992.
Nymphaeaceae. In: Salisbury, R.A. (Ed.), Families and Genera of
Spermatophytes Recognized by the Agricultural Research Service.
Tech. Bull. U.S.D.A. 1976, pp. 1–218.
3
1
3
C NMR (100 MHZ, CD OD ), see Table 1; positive
3
+
FAB-MS: m/z 455 [M + Na] , 433 [M + H] HRFAB-
+
+
MS m/z 433.4885 ([M + H] , calcd. for C H O :
Holmgren, P.K., Holmgren, N.H., Barnett, L.C., 1990. Index Herbar-
iorum. Part I: The Herbaria of the World, eighth ed. New York
Botanical Garden, New York, USA.
2
1
20 10
4
33.4882).
Iribarren, A.M., Pomilo, A.B., 1984. Sitosterol 3-O-b-D-xylopyr-
anoside from Bauhinia candicans. Phytochemistry 23, 2087–
2
088.
Acknowledgements
Khalid, S.A., Gellert, M., Szendrei, K., Duddeck, H., 1989.
Prunetin 5-O-b-D-glucopyranoside, an isoflavone from the
peduncle of Prunus avium and P. cerasus. Phytochemistry 28,
Authors thank the support obtained from CONA-
CyT (project 34699-N). S.M. thanks the fellowship
1
560–1561.
Kurihara, H., Kawabata, J., Hatano, M., 1993. Geraniin, a hydroly-
sable tannin from Nymphaeae tetragona Georgi (Nymphaceae).
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Zanis, M., 1999. Phylogeny, classification and floral evolution
of water lilies (Nymphaeaceae; Nymphaeales): a synthesis of
non-molecular rbcl, matK, and 18S rDNA data. Syst. Bot. 24,
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