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A flavonoid (3, 7, 3'-Trihydroxy-4'-methoxyflavone) (1) and a flavonoid glycoside (3, 3'-dihydroxy-4'-methoxyflavone-7-O-β-D-glucopyranoside) (2) were isolated from the tuber root of Butea superba Roxb. The structures were determined on the basis of spectral analysis, including 2D-NMR techniques. These compounds show higher inhibitory effects on cAMP phosphodiesterase than caffeine and theophylline.
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J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000) 169
Flavonoid and Flavonoid glycoside from
Butea superba Roxb. and their cAMP
Phosphodiesterase Inhibitory Activity
Sophon Roengsumran,1 Amorn Petsom,1 Nattaya Ngamrojanavanich,1
Thanatip Rugsilp,1 Pailin Sittiwicheanwong,1 Prapas Khorphueng,1
Wichai Cherdshewasart,2 and Chaiyo Chaichantipyuth3
A flavonoid (3, 7, 3'-Trihydroxy-4'-methoxyflavone) (1) and a flavonoid
glycoside (3, 3'-dihydroxy-4'-methoxyflavone-7-O-β-D-glucopyranoside) (2) were
isolated from the tuber root of Butea superba Roxb. The structures were determined
on the basis of spectral analysis, including 2D-NMR techniques. These compounds
show higher inhibitory effects on cAMP phosphodiesterase than caffeine and
theophylline.
Key Words: Butea superba, flavonoid, flavonoid glycoside, cAMP
phosphodiesterase inhibition
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.
Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojanavanich, Thanatip Rugsilp, Pailin Sittiwicheanwong,
Prapas Khorphueng, Wichai Cherdshewasart, and Chaiyo Chaichantipyuth…………………………………….
170 J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000)
ฟลาวอนอยด และฟลาวอนอยดไกลโคไซดจากกวาวเครอแดง และ
ฤทธิ์ตอตานไซคลกเอเอมพฟอสโฟไดเอสเทอเรส
โสภณ เรงส าราญ, อมร เพชรสม, นาตยา งามโรจนวนชย, ธนาธิป รักศลป,
ไพลิน สิทธิวิเชยรวงศ, ประภาส ขอพึ่ง, วิชัย เชดชวศาสตร และ ชัยโย ชัยชาญทพยุทธ (2543)
วารสารวิจัยวทยาศาสตร จุฬาลงกรณมหาวทยาลัย 25(1)
ฟลาวอนอยด (3, 7, 3'-ไทรไฮดรอกซ-4'-เมธอกซิฟลาโวน) (1) และฟลาวอนอยด
ไกลโคไซด (3, 3'-ไดไฮดรอกซ-4'-เมธอกซฟลาโวน-7-O-β-D-กลโคไพราโนไซด) (2) แยกได
จากสวนรากของกวาวเครอแดง ไดทํ าการหาสูตรโครงสรางของสารดงกลาวโดยอาศยผลการ
วิเคราะหทางสเปกโตรสโคป ซึ่งประกอบดวยเทคนิค 2D-NMR สารประกอบทั้งสองชนิด
แสดงผลในการยบยั้งไซคลกเอเอมพ ฟอสโฟไดเอสเทอเรสอยางแรง
คํ าส าคัญ กวาวเครอแดง ฟลาวอนอยด ฟลาวอนอยดไกลโคไซด การยบยั้ง
ไซคลกเอเอมพฟอสโฟไดเอสเทอเรส
Flavonoid and Flavonoid glycoside from Butea superba Roxb. and
their cAMP Phosphodiesterase Inhibitory Activity……………………………………………………………………….
J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000) 171
INTRODUCTION
Butea superba Roxb. is a plant in the
Family Papilionaceae and has the
characteristics of being a crawler that wraps
itself around large trees. One branch has 3
leaves, the flowers are of a yellowish orange
color and the plant grows out in the open.
The long tuber root of the plant is buried
under the ground like the tuber root of a yam.
This plant reproduces through seeds and the
propagation of its tuber root. This plant can
be found growing in forests in Thailand’s
northern regions, eastern regions and along
Kanchanaburi Province. The tuber and stem
of the plant are used in medicines believed to
give strength and power and increase male
sexual performance. Thus, this plant has
come to be known as one type of miracle
herb. Since Butea superba Roxb. helps to
enhance human health, it is therefore very
interesting to investigate the chemical
constituents of this plant and their biological
activity. The bioactivity of each constituent
was tested for an inhibitory effect towards
cAMP phosphodiesterase, which has been
shown to be important in controlling bodily
function and involved a wide number of
diseases [1].
Table 1. 1H NMR spectral data of compounds 1 and 2 (500 MHz DMSO).
12
Position 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)
-OCH33.79 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)
Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojanavanich, Thanatip Rugsilp, Pailin Sittiwicheanwong,
Prapas Khorphueng, Wichai Cherdshewasart, and Chaiyo Chaichantipyuth…………………………………….
172 J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000)
Table 2. 13C NMR (125 MHz DMSO) and 2D Long-Range 1H-13C Correlations in the HMBC
Spectra of Compounds 1 and 2.
12
Position δCHMBC δCHMBC
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'
-OCH355.2 55.2
1" 100.1
2" 73.2
3" 76.5
4" 69.8
5" 77.2
6" 60.8
EXPERIMENTAL
General Experimental Procedures
All commercial grade solvents were
distilled prior to use. Melting points were
determined on a Fisher-Johns melting point
apparatus and are reported uncorrected. The
optical rotation was determined on a JASCO
DIP-370 digital polarimeter. Measurements
of UV spectra were carried out on a Milton-
Roy Spectronic 3000 Array UV/VIS
spectrophotometer. IR spectra were recorded
on a Perkin-Elmer model 1760X FT-IR
spectrophotometer. Spectra of solid samples
were recorded as KBr pellets. The 1H and
13C NMR spectra were recorded at 500.00
and 125.65 MHz, respectively, on a JEOL
JNM-A500 NMR spectrometer. LREIMS
were obtained with a Fisons Instruments
model Trio 2000 mass spectrometer at 70 eV.
Plant Materials
The tubers of Butea superba Roxb.
were collected from Amphur Muang,
Lumpang Province, Thailand in May 1997.
Botanical identification was claimed through
comparison with a voucher specimen No.
BKF 70163 in the herbarium collection of
Royal Forest Department of Thailand.
Extraction and Isolation
Powdered sun dried roots (16.0 kg) of
Butea superba were repeatedly extracted
with MeOH (5x10 L). The MeOH extracts
were filtered and evaporated under reduced
pressure to obtain a dark-red gummy residue
Flavonoid and Flavonoid glycoside from Butea superba Roxb. and
their cAMP Phosphodiesterase Inhibitory Activity……………………………………………………………………….
J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000) 173
(106.0 g) of MeOH crude extract. This
MeOH crude extract was subsequently re-
extracted with hexane and then CHCl3 to
leave the final insoluble residue (72.0 g). The
hexane and CHCl3 extract fractions were
evaporated under reduce pressure to give a
hexane crude extract (21.0 g) and CHCl3
crude extract (12.0 g), respectively. The
CHCl3 crude extract (12.0 g) was subjected
to silica gel column chromatography using
gradient elution with CHCl3 and MeOH in a
stepwise fashion. Compound 1 was eluted
with 5% MeOH in CHCl3. Similar fractions
were combined and the solvent was removed
under reduced pressure to give compound 1
(135.0 mg) after recrystallization from
MeOH and CHCl3. The final residue (72.0 g)
was separated by column chromatography on
Silica gel using gradient elution with
increasing amounts of MeOH in CHCl3 to
give compound 2 (60.0 mg) from 10% of
MeOH in CHCl3 fraction. Compound 2 was
recrystallized from MeOH and CHCl3.
Flavonoid (3, 7, 3'-Trihydroxy-4'-
methoxyflavone) (compound 1): pale yellow
needle crystal, mp 258-260°C (d) [lit 288(d),
but no spectroscopic data for verification],
(found: C, 64.0; H, 3.9, C16H12O6 required:
C, 64.0; H, 4.0); UV λmax EtOH nm 254, 316
and 365; IR νKBrmax cm-1; 3340-3000, 2940,
1650, 1594, 1575, 1500, 1450, 1380, 1260,
1090, 1020, 790; 1H and 13C-NMR Table 1;
EIMS m/z (rel. int.) 300[M+] (25), 282 (30),
268 (100), 253 (25), 132 (60).
Flavonoid glycoside (3,5'-Dihydroxy-
4'-methoxyflavone-7-O-β-D-
glucopyranoside) (compound 2); white
amorphous solid; mp 210-212°C, (found: C,
57.0; H, 4.5, C22H22O11 requires: C, 57.1; H,
4.8); [α]25D+9.5 (c 1.05, MeOH); UV λmax
EtOH nm 267, 290 and 355; νKBrmax cm-1;
3600-3100, 2900, 1650, 1550, 1450, 1300,
1260, 1060-1030, 891, 800; 1H and 13C-NMR
Table 1 and 2; EIMS m/z (rel. int.) 282 (20),
268 (100), 253 (23), 133 (12), 132 (90).
1 R = H
Scheme 1
(2) R =
Scheme 2
Bioassay
Phosphodiesterase activity was determined
from the amount of inorganic phosphate liberated
during the reaction by the malachite green
method [2, 3]. Phosphodiesterase assay solutions
were prepared as follows: (a) the enzyme
solution contains phosphodiesterase (0.037
unit mL-1), 5-nucleotidase (1.67 unit mL-1),
MgCl2 (5 mM) and Tris HCl (0.2 M); (b)
reaction mixture A contains malachite green
(0.33 mM), polyvinyl alcohol (3.87g L-1) and
ammonium molybdate in 6 M HCl (8.33
mM). The test sample was dissolved in 1.5 %
dimethyl sulfoxide in water. The reaction
was performed by the addition of cAMP (10
mM, 100 µL) to the enzyme solution (400 µL)
at 30°C. Then the sample solution (500 µL),
reagent mixture A (1.0 mL) and 25% sodium
citrate (200 µL) were added to the above
solution successively at 5 minute intervals.
The absorbance of the colour complex was
O
O
OH
OMe
OH
H
H
RO
H
H
H
H
2
3
4
5
6
7
8
9
10
1'
2'
3'
4'
5'
6'
O
H
HO
H
HO
H
H
OH
H
OH
HH
1"
2"
3"
4"
5"
6"
Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojanavanich, Thanatip Rugsilp, Pailin Sittiwicheanwong,
Prapas Khorphueng, Wichai Cherdshewasart, and Chaiyo Chaichantipyuth…………………………………….
174 J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000)
observed at 630 nm using a UV/VIS
spectrophotometer referred against a mixed
reagent blank. A calibration curve, obtained
by this procedure using potassium
dihydrogen phosphate solution of a known
concentration, was used to determine the
amount of phosphate present in the assay.
For control experiment, dimethyl sulfoxide
was added instead of the solution of the
sample to minimize the effects of the solvent
and theophylline and caffeine were used as
positive controls for phosphodiesterase assay.
The IC50 valves of compound (1) and (2)
were determined from the calibration curve
of sample concentration against cAMP
phosphodiesterase activity.
RESULTS AND DISCUSSION
The 3, 7, 3'-Trihydroxy-4'-
methoxyflavonone (compound 1) was
obtained from a chloroform soluble crude
extract from the root of Butea superba by
silica-gel column chromatography using a
gradient elution with chloroform and
methanol. The IR spectrum of 1 showed a
broad absorption band between 3000 and
3340 cm-1 of OH stretching and a strong
absorption band at 1650 cm-1, which was
consistent with a conjugated carbonyl group.
The carbon-carbon double bond stretching
vibration of the aromatic phenyl group was
also observed at 1594, 1575 and 1500 cm-1.
The UV spectrum exhibited absorption
maxima at 254 and 365 nm which are
characteristic absorption bands of a flavone
skeleton [4]. The molecular formula of
C16H12O6 was established for compound 1
from the elemental analysis, LREIMS and 1H
and 13C NMR data (Tables 1 and 2). The 1H
and 13C NMR spectra together with 2D NMR
experiments allowed the complete structure
of compound 1 to be established. The
occurrence of flavonoid (1) was clearly
determined from the 1H 500 MHz NMR
spectrum which displayed six aromatic
protons at δ 6.85 (d, J=2.1 Hz), 6.94 (dd,
J=2.1, 8.8 Hz), 6.98 (d, J=8.8 Hz), 7.50 (dd,
J=2.1, 8.8 Hz), 7.96 (d, J=8.8 Hz), and 8.35
(d, J=2.1 Hz) and one methyl proton singlet
at 3.79 ppm. Detailed analysis of the 2D 1H
and 13C NMR spectrum, including COSY,
NOESY, HMQC and HMBC supported the
structure of 3, 7, 3'-Trihydroxy-4'-
methoxyflavone (1). Although compound 1
is a known compound isolated as a minor
constituents of quebracho tannin extract [5],
its 1H and 13C NMR spectral data have not
been published before.
The 3, 3'-Dihydroxy-4'-
methoxyflavone-7-O-β-D-glucopyranoside
(compound 2) was isolated as an amorphous
white solid powder from MeOH extract
residue by silica gel column chromatography
using CHCl3-MeOH as the eluent. The IR
spectrum of compound 2 displayed
absorption at 3100-3600 cm-1 of OH
stretching, and strong absorption at 2900 cm-
1 of C-H stretching. The absorption band of a
conjugated carbonyl group appeared at 1650
cm-1. The molecular formula of compound 2
was assigned as C22H22O11 based on
elemental analysis and 1H and 13C NMR
(Table 1 and 2) while its EI-MS showed no
molecular ion peak pointing to its glycoside
nature. The 1H NMR spectrum of compound
2 in DMSO showed the presence of a sugar
moiety by one proton doublet at δ 5.10
(J=7.6 Hz, H-1''), one proton doublet of
doublets at δ 3.30 (J=7.6, 9.5 Hz, H-2''), one
proton triplet at δ 3.35 (J=9.5 Hz, H-3''), one
proton triplet at δ 3.18 (J=9.5 Hz, H-4'') and
one proton multiplet at δ 3.45 (H-5''). Two
protons of C-6'' included one proton showed
doublet of doublets at δ 3.45 (J=12.0, 2.5 Hz,
H-6''a) and another one proton showed
doublet of doublets at δ 3.70 (J=12.0, 4.5 Hz,
H-6''b). The chemical shifts at δ 6.98, 7.15,
7.22, 7.52, 8.05 and 8.40 were assigned to
flavonoid protons at C-5', C-6, C-8, C-6', C-5
and C-2' respectively, on the basis of their
similarity to signals observed for compound 1.
Their 1H and 13C-NMR spectra indicate
that glycoside 2 has a glycone portion
identical to that in compound 1. In the 1H
NMR spectra (Table 1), an unusual pattern of
7-O-glycosylation was indicated by
downfield shifts of H-6 (ca. +0.21 ppm) and
H-8 (ca. +0.36 ppm) with respect to
Flavonoid and Flavonoid glycoside from Butea superba Roxb. and
their cAMP Phosphodiesterase Inhibitory Activity……………………………………………………………………….
J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000) 175
compound 1. Similarly, in the 13C-NMR
spectra of compound 2 (Table 2), 7-O-
glycosylation was confirmed by the
diagnostic [6] upfield shift of C-7 (-0.24
ppm) and by downfield shifts of the ortho-
related C-8 (+1.45 ppm) and C-6 (+0.55
ppm) and para-related C-10 (+1.99 ppm)
carbon with respect to compound 1. The 1H
and 13C NMR data indicated the β-
configuration at an anomeric position for the
glucopyranosyl unit (Table 1 and 2).
Therefore, the structure of compound 2 was
assigned as 3,3'-dihydroxy-4'-
methoxyflavone-7-O-β-D-glucopyranoside.
From the bioactivity testing of
compound 1 and compound 2, it was found that
both of these compounds were effective in
inhibiting cAMP phosphodieterase. These two
compounds have IC50 = 190 and 58 µg/mL,
respectively. The cAMP phosphodiesterase
inhibition of both these compounds was more
effective than those of theophylline (IC50 = 615
µg/mL) and caffein (IC50 = 420 µg/mL). The
cAMP phosphodiesterase enzyme has a main
function in the hydrolysis of the intracellular
cAMP. Substances that inhibit cAMP
phosphodiesterase are therefore capable of
stimulating the functioning of the central
nervous system (CNS) and stimulating the
functioning of cells [7]. Thus, papaverin,
dipyridamole, caffeine and theophylline are
effective when the cAMP phosphodiesterase
is inhibited [8, 9]. Furthermore, substances
that have an effect in inhibiting cAMP
phosphodesterase also take part in controlling
numerous severe diseases, including diabetes
[10-13], hypertension [14, 15], asthma [16],
hepatomas [17], psoriasis [18] and possibly
cancer [19, 20]. In addition, substances that
inhibit phosphodiesterase are shown to have
effects in controlling platelet-aggregation
inhibition [21- 26].
Therefore, Butea superba Roxb. is
composed of flavonoids that are effective in
inhibiting the cAMP phosphodiesterase
enzyme, which are very beneficial to the
human body. At least, when taking this herb,
the body will begin to feel healthier. This
herb will also help control the numerous
diseases mentioned beforehand.
ACKNOWLEDGEMENTS
We thank the Graduate School and
Department of Chemistry, Faculty of
Science, Chulalongkorn University, for
financial support and the staff of the
Scientific and Technology Research
Equipment Centre, Chulalongkorn
University, for recording highfield NMR
spectra and performing 2D NMR
experiments. We also thank Mr. Thanase U.
Patriyakul of Eiwlee Industrial for providing
some plant materials.
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Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojanavanich, Thanatip Rugsilp, Pailin Sittiwicheanwong,
Prapas Khorphueng, Wichai Cherdshewasart, and Chaiyo Chaichantipyuth…………………………………….
176 J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000)
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Received: August 6, 1999
Accepted: February 1, 2000
Flavonoid and Flavonoid glycoside from Butea superba Roxb. and
their cAMP Phosphodiesterase Inhibitory Activity……………………………………………………………………….
J. Sci. Res. Chula. Univ., Vol. 25, No.1 (2000) 1
... The tuberous root has a long cylindrical shape. The root was found to contain flavonoids, flavonoid glycosides, isoflavonoids, and sterol compounds [5,6]. Flavonoids and flavonoid glycosides from B. superba showed cyclic adenosine monophosphate (AMP) phosphodiesterase inhibitor activity [5]. ...
... The root was found to contain flavonoids, flavonoid glycosides, isoflavonoids, and sterol compounds [5,6]. Flavonoids and flavonoid glycosides from B. superba showed cyclic adenosine monophosphate (AMP) phosphodiesterase inhibitor activity [5]. B. superba contained genistin, genistein, and daidzein that possessed potent antioxidant properties [7] and showed strong antimicrobial ability [3]. ...
... Flavonoids, one of the most diverse and widespread groups of natural compounds, are the major subclass of polyphenols and antioxidants in plants. BSE was also reported as a rich source of the flavonoid (3,7,3'-trihydroxy-4'-methoxyflavone) and the flavonoid glycoside (3,5'-dihydroxy-4'-methoxyflavone-7-O-ß-D-glucopyranoside) [5]. Furthermore, some documents showed that BSE contained four isoflavones (7,4'dimethoxyisoflavone, 7-hydroxy-6,4'-dimethoxyisoflavone, Formononetin, and Prunetin), a derivative isoflavonoid (Medicarpin) [6], and four isoflavones (Biochanin A, Genistin, Daidzein, and Genistein) [7,9]. ...
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This study investigated total phenolics content (TPC), total flavonoids content (TFC), antioxidant, toxicity, and cytotoxicity of B. superba ethanolic extract (BSE), which the plant is used in Thai traditional medicine. The toxicity was evaluated using a brine shrimp lethality assay and the cytotoxicity was done through Michigan Cancer Foundation (MCF-7) and prostate cancer (PC-3) cancer cell lines, particularly nuclear morphological changes and Deoxyribonucleic acid (DNA) fragmentation. The result found that BSE had low TPC and TFC (87.16 µg gallic acid equivalent (GAE)/mg and 38.29 µg CE/mg). The effective concentrations at 50% (EC50) and 99% (EC99) through 2,2-diphenyl-l-picrylhydrazyl (DPPH) and Ferric thiocyanate (FTC) assays were 3,610.10 (EC50/DPPH), 215.11 (EC50/FTC), 7,304.05 (EC99/DPPH), and 401.88 (EC99/FTC) µg/mL, respectively. Lethal concentration at 1% (LC1) and 50% (LC50) were 54.63 and 184.24 µg/mL Therapeutic index (TI) and margin of safety (MOS) assessment of BSE by DPPH and FTC assay were 0.051 (TIDPPH), 0.856 (TIFTC), 0.007 (MOSDPPH), and 0.136 (MOSFTC). BSE demonstrated an antiproliferative effects on MCF-7 and PC-3 cells in a dose-dependent manner, and induced apoptosis and DNA fragmentation in both cancer cells. In conclusion, BSE proposed to develop anticancer agents that could contribute to medicinal benefits.
... Blood platelets are, in fact, sentinel cells which contribute significantly to anti-infectious immunity (Chabert et al., 2017) [17] . Furthermore, K. africana due to its high flavonoid content, shows its ability to modulate megakaryopoiesis, which is the system of production and regulation of platelets (Roegsumran et al., 2000) [18] . These results are the same with those work of Alrawaiq and Abdullah (2014) [19] who showed that following the oral administration of quercetin to rats, the level of blood platelets increased. ...
... Interestingly, all doses of the BS treatments increased the strength, endurance, and the cross-sectional areas of both EDL and gastrocnemius similar to those found in the testosterone treatment. In a previous work by Roengsumran et al [17], flavonoid (3,7,3 -Trihydroxy-4 -methoxyflavone) and flavonoid glycoside (3,3 -dihydroxy-4 -methoxyflavone-7-O-β-D-glucopyranoside) were isolated from the tuber root of Butea superba Roxb., and the function of the compounds was investigated. They found that both flavonoid and flavonoid glycoside were influential in inhibiting cyclic adenosine monophosphate (cAMP) phosphodiesterase. ...
... e potential medicinal applications of B. superba to treat erectile dysfunction in mature human males have been reported [21]. Furthermore, it could promote penile blood flow [22] and enhance penile erection via the inhibition of cAMP phosphodiesterase activity [23,24]. Moreover, the antioxidative activity of BSE has been reported [25] to increase serum testosterone [21,26] and it could ameliorate cognitive and emotional deficits in olfactory bulbectomized mice by inhibiting AChE [27]. ...
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Butea superba Roxb. (B. superba) is a herb that has been used for rejuvenation, to improve sexual performance, or to prevent erectile dysfunction function. Alzheimer’s disease (AD) is a chronic neurodegenerative disorder that is the main cause of progressive dementia. This study aimed to investigate the amelioration for cognitive and memory dysfunction of B. superba ethanolic extract (BSE), a possible mechanism of action, and its toxicity. The results from the Y-maze test, novel object recognition test, and passive avoidance test exhibited that the administration of BSE at 50 mg/kg (BSL) and 200 mg/kg (BSH) could ameliorate scopolamine-induced cognitive impairment in all behavior testing. Moreover, BSE could prevent the cognitive deficit in a dose-dependent manner in a passive avoidance test. Furthermore, BSE inhibited acetylcholinesterase’s (AChE) ex vivo activity in the cerebral cortex and hippocampus. Also, the in vitro and ex vivo antioxidative effects of BSE revealed that BSE had free radical scavenging activities in both DPPH and FRAP assay. Furthermore, male rats treated with BSE at 200 mg/kg/day for two weeks could significantly increase serum testosterone compared with control (P0.05). These results suggest that BSE may not be toxic to the vital organ and blood. In conclusion, BSE has the potential to be developed as a health supplement product or medicine for AD prevention and treatment.
... But, rutin exhibited stronger inhibitory effects than quercetin. This result agrees with previous reports on the inhibitory effects exhibited by some flavonoids and flavonoid glycosides (Roengsumran et al. 2000). Lines and Ono (2006) reported that quercetin markedly downregulated the activity of PDE-5 activity in vitro. ...
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This study demonstrates the effects of rutin and quercetin and their various combinations on phosphodiesterase-5 (PDE-5), arginase, acetylcholinesterase (AChE), and angiotensin-I-converting enzyme (ACE) activities in vitro. The effects of the flavonoids against Fe²⁺- and sodium nitroprusside (SNP)-induced lipid peroxidation in rats’ corpus cavernosum tissues were also investigated. Quercetin and rutin were dissolved in dimethylsulfoxide (DMSO) to a final concentration of 1 mM each. Thereafter, their combinations (50% quercetin + 50% rutin [Q1:R1]; 75% quercetin + 25% rutin [Q3:R1]; 25% quercetin + 75% rutin [Q1:R3]) were prepared. Our findings revealed that both flavonoids inhibited PDE-5, arginase, AChE, and ACE activities. Rutin exhibited significantly higher inhibitory effects on PDE-5, AChE, and ACE activities compared to quercetin. Considering the combinations, Q1:R3 was more potent compared to Q1:R1 and Q3:R1. Both flavonoids inhibited Fe²⁺- and SNP-induced lipid peroxidation in rat’s corpus cavernosa tissues. Rutin also showed higher inhibitory effects on Fe- and SNP-induced lipid peroxidation. Similarly, the combinatorial effects of the flavonoids revealed that Q1:R3 significantly inhibited malondialdehyde (MDA) production compared to Q1:R1 and Q3:R1. In conclusion, our findings suggest that the combination of quercetin and rutin is more potent than their individual effect.
... The plant crude extracts were shown to exhibit acetylcholinesterase (AChE) inhibitory properties with Alzheimer's disease prevention benefits [1], and anti-proliferation activity on the growth of human breast adenocarcinoma cells (MCF-7) [2]. Flavonoid (3,7,3'-Trihydroxy-4'-methoxyflavone) and flavonoid glycosides (3,3'-dihydroxy-4'-methoxyflavone-7-O-β-D-glucopyranoside) isolated from tuberous roots had an inhibiting effect upon cAMP phosphodiesterase [3]. The tuberous formononetin and prunetin exhibited moderate cytotoxicity on human oral cavity carcinoma cells and breast cancer cells [4]. ...
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... The tuberous roots and stems are used in traditional therapies as anti-aging and alternative medicines for the purposes of rejuvenation, promotion of sexual vigor and treatment of erectile dysfunction in mature males [1]. In tuberous roots, the chemical constituents, flavonoid (3,7,3 0 -trihydroxy-4 0 -methoxyflavone) and flavonoid glycosides (3,3 0 -dihydroxy-4 0 -methoxyflavone-7-O-b-D-glucopyranoside), were found to harbour cAMP phosphodiesterase inhibitory activity [2], whereas formononetin and prunetin showed moderate cytotoxic activity on human oral cavity carcinoma cells (KB) and breast cancer cells (BC) [3]. In addition, the plant crude extracts were also shown to act as antimicrobial agents [4], antioxidant [5], acetylcholinesterase (AChE) inhibitor for protection of Alzheimer's disease [6] and anti-proliferation agents for retarding growth of human breast adenocarcinoma cells (MCF-7) [1]. ...
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Seasonal changes are major factors affecting environmental conditions which induce multiple stresses in plants, leading to changes in protein relative abundance in the complex cellular plant metabolic pathways. Proteomics was applied to study variations in proteome composition of Butea. superba tubers during winter, summer and rainy season throughout the year using two-dimensional polyacrylamide gel electrophoresis coupled with a nanoflow liquid chromatography coupled to electrospray ionization quadrupole-time-of-flight tandem mass spectrometry. A total of 191 protein spots were identified and also classified into 12 functional groups. The majority of these were mainly involved in carbohydrate and energy metabolism (30.37 %) and defense and stress (18.32 %). The results exhibited the highest numbers of identified proteins in winter-harvested samples. Forty-five differential proteins were found in different seasons, involving important metabolic pathways. Further analysis indicated that changes in the protein levels were due mainly to temperature stress during summer and to water stress during winter, which affected cellular structure, photosynthesis, signal transduction and homeostasis, amino-acid biosynthesis, protein destination and storage, protein biosynthesis and stimulated defense and stress mechanisms involving glycolytic enzymes and relative oxygen species catabolizing enzymes. The proteins with differential relative abundances might induce an altered physiological status within plant tubers for survival. The work provided new insights into the better understanding of the molecular basis of plant proteomes and stress tolerance mechanisms, especially during seasonal changes. The finding suggested proteins that might potentially be used as protein markers in differing seasons in other plants and aid in selecting B. superba tubers with the most suitable medicinal properties in the future.
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Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxyl-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxy-phenyl)ethanone (2), eight pterocarpans (3-10), and eleven isoflavonoids (11-21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D and 2D NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities. Compounds 3, 7, 8, and 11 showed promising α-glucosidase inhibitory activity (IC50 = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μM, respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC50 = 6.54 ± 0.04 μM). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure-activity relationships are discussed.
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Butea superb (BS) root has been used for Thai traditional medicine. It was believed for its sexual performance increasing property in aged person. There was a report that administration of B. superba root ethanolic extract orally everyday for a period of time to male rats could induce penile erection by increasing intracavernous pressure. However, acute effect of the single oral administration of ethanolic extracts from various parts of BS root on intracavernous pressure and blood pressure in adult male rat had not been investigated. Then the objective of this project was to investigate the acute effect of single administration of three dosages of ethanolic extract from fresh or dried stele of BS roots or fresh or dried cortex of BS roots at the dosage of 1, 10 and 100 mg kg-1 orally on intracavernous pressure and blood pressure in adult male Sprague Dawley rats were measured during anaesthetized condition. It was found that one-hour after single administration of every dosages of ethanolic extract from fresh or dried stele of BS roots or fresh or dried cortex of BS roots to adult male rats could significantly increase the intracavernous pressure without altering blood pressure, both systolic and diastolic. Low dosage of ethanolic extract of each BS root studied, seem to increase intracavernous pressure more effectively than the high dosage used. It was concluded that one-hour after treatment of BS extract could induce intracavernous pressure without altering blood pressure in adult male rats and low dosage of BS extract was more effective.
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As a follow-up to Dr Markham's highly successful publication, The Systematic Identification of Flavonoids (1970) co-authored with T.J. Mabry and M.B. Thomas, this book presents a more extensive, up-to-date and thorough guide to techniques used in flavonoid research. The techniques are discussed in the approximate order in which they are normally needed by the researcher and extensive cross-referencing is used throughout to guide the reader to the next recommended technique. Tech- niques covered include: chromatography, recrystallization, UV-visible spectroscopy, hydrolysis and product analysis, derivation degradation, 1 H-NMR, 13 C-NMR, and mass spectroscopy. The book, as a self-contained laboratory manual, contains extensive tabulations of reference data, discusses examples of a wide range of spectra, and features diagrams of flavonoid structures, reaction schemes and appara- tus. Of special interest and importance to the beginner are the tables of trivial names, the list of sources of flavonoid standards and a discussion of the means for proving a new flavonoid identical to a known standard.
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