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Butea Superba Sci - Flavonoid and Flavonoid Glycoside From Butea Superba and Their cAMP Phosphodiesterase Inhibitory Activity
Butea Superba Sci - Flavonoid and Flavonoid Glycoside From Butea Superba and Their cAMP Phosphodiesterase Inhibitory Activity
1
Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
2
Department of Biology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
3
Department of Pharmacognocy, Faculty of Pharmaceutical Sciences, Chulalongkorn University,
Bangkok 10330, Thailand.
INTRODUCTION
Butea superba Roxb. is a plant in the give strength and power and increase male
Family Papilionaceae and has the sexual performance. Thus, this plant has
characteristics of being a crawler that wraps come to be known as one type of miracle
itself around large trees. One branch has 3 herb. Since Butea superba Roxb. helps to
leaves, the flowers are of a yellowish orange enhance human health, it is therefore very
color and the plant grows out in the open. interesting to investigate the chemical
The long tuber root of the plant is buried constituents of this plant and their biological
under the ground like the tuber root of a yam. activity. The bioactivity of each constituent
This plant reproduces through seeds and the was tested for an inhibitory effect towards
propagation of its tuber root. This plant can cAMP phosphodiesterase, which has been
be found growing in forests in Thailand’s shown to be important in controlling bodily
northern regions, eastern regions and along function and involved a wide number of
Kanchanaburi Province. The tuber and stem diseases [1].
of the plant are used in medicines believed to
Position 1 2
δH (J in Hz) δH (J in Hz)
2
3
4
5 7.96 d (8.8) 8.05 d (8.8)
6 6.94 dd (2.1, 8.8) 7.15 dd (2.1, 8.8)
7
8 6.85 d (2.1) 7.22 d (2.4)
9
10
1'
2' 8.35 d (2.1) 8.40 d (2.0)
3'
4'
5' 6.98 d (8.8) 6.98 d (8.8)
6' 7.50 dd (2.1, 8.8) 7.52 dd (2.1, 8.8)
-OCH3 3.79 s 3.78 s
1" 5.10 d (7.6)
2" 3.30 dd (7.6, 9.5)
3" 3.35 t (9.5)
4" 3.18 t (9.5)
5" 3.45 m
6"a 3.45 dd (12.0, 2.5)
6"b 3.70 dd (12.0, 4.5)
Table 2. 13C NMR (125 MHz DMSO) and 2D Long-Range 1H-13C Correlations in the HMBC
Spectra of Compounds 1 and 2.
Position 1 2
δC HMBC δC HMBC
2 158.9 159.1
3 146.8 147.0
4 174.6 174.8
5 127.3 4, 7, 9 127.1 4, 7, 9
6 115.2 5, 7, 8, 10 115.7 5, 7, 8, 10
7 162.6 161.5
8 102.1 6, 7, 9, 10 103.5 6, 7, 9, 10
9 157.4 157.1
10 116.6 118.5
1' 124.2 123.5
2' 153.4 1', 3', 4', 6' 153.6 1', 3', 4', 6'
3' 157.3 157.1
4' 146.9 146.6
5' 113.6 1', 3', 4' 113.7 1', 4', 6'
6' 130.0 1', 2, 4', 5' 130.1 1', 3', 4', 5'
-OCH3 55.2 55.2
1" 100.1
2" 73.2
3" 76.5
4" 69.8
5" 77.2
6" 60.8
EXPERIMENTAL
General Experimental Procedures were obtained with a Fisons Instruments
All commercial grade solvents were model Trio 2000 mass spectrometer at 70 eV.
distilled prior to use. Melting points were Plant Materials
determined on a Fisher-Johns melting point The tubers of Butea superba Roxb.
apparatus and are reported uncorrected. The were collected from Amphur Muang,
optical rotation was determined on a JASCO Lumpang Province, Thailand in May 1997.
DIP-370 digital polarimeter. Measurements Botanical identification was claimed through
of UV spectra were carried out on a Milton- comparison with a voucher specimen No.
Roy Spectronic 3000 Array UV/VIS BKF 70163 in the herbarium collection of
spectrophotometer. IR spectra were recorded Royal Forest Department of Thailand.
on a Perkin-Elmer model 1760X FT-IR
spectrophotometer. Spectra of solid samples Extraction and Isolation
were recorded as KBr pellets. The 1H and Powdered sun dried roots (16.0 kg) of
13
C NMR spectra were recorded at 500.00 Butea superba were repeatedly extracted
and 125.65 MHz, respectively, on a JEOL with MeOH (5x10 L). The MeOH extracts
JNM-A500 NMR spectrometer. LREIMS were filtered and evaporated under reduced
pressure to obtain a dark-red gummy residue
compound 1. Similarly, in the 13C-NMR herb will also help control the numerous
spectra of compound 2 (Table 2), 7-O- diseases mentioned beforehand.
glycosylation was confirmed by the
diagnostic [6] upfield shift of C-7 (-0.24 ACKNOWLEDGEMENTS
ppm) and by downfield shifts of the ortho- We thank the Graduate School and
related C-8 (+1.45 ppm) and C-6 (+0.55 Department of Chemistry, Faculty of
ppm) and para-related C-10 (+1.99 ppm) Science, Chulalongkorn University, for
carbon with respect to compound 1. The 1H financial support and the staff of the
and 13 C NMR data indicated the β- Scientific and Technology Research
configuration at an anomeric position for the Equipment Centre, Chulalongkorn
glucopyranosyl unit (Table 1 and 2). University, for recording highfield NMR
Therefore, the structure of compound 2 was spectra and performing 2D NMR
assigned as 3,3'-dihydroxy-4'- experiments. We also thank Mr. Thanase U.
methoxyflavone-7-O-β-D-glucopyranoside. Patriyakul of Eiwlee Industrial for providing
From the bioactivity testing of some plant materials.
compound 1 and compound 2, it was found that
both of these compounds were effective in REFERENCES
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