Journal of Ethnopharmacology 158 (2014) 437441

Contents lists available at ScienceDirect

Journal of Ethnopharmacology
journal homepage: www.elsevier.com/locate/jep

Ethnopharmacological communication

Inhibitory effects of avonoids from stem bark of Derris indica

on the formation of advanced glycation end products
Pornpat Anusiri a, Siwattra Choodej b, Pranom Chumriang c,
Sirichai Adisakwattana d, Khanitha Pudhom b,n
a

Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand

Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
c
Mangrove Extension, Learning and Development Center 5, Satun 91000, Thailand
d
Department of Nutrition and Dietetics, Faculty of Allied Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand
b

art ic l e i nf o

a b s t r a c t

Article history:
Received 14 May 2014
Received in revised form
7 October 2014
Accepted 21 October 2014
Available online 4 November 2014

Ethnopharmacological relevance: Derris indica (Lamk.) Bennet has been used in traditional medicine in
many countries for the treatment of bronchitis, whooping cough, rheumatic joints and dipsia in diabetes.
In addition, several studies have revealed that this plant displayed various pharmacological activities
including anti-diabetic. The present study was designed to isolate the active compounds from its stem
bark and evaluate their inhibitory activity on the formation of advanced glycation end products.
Material and methods: The EtOAc extract of the stem bark of Derris indica was isolated by column
chromatographic techniques. The structures of isolated compounds were established on the basis of
extensive spectroscopic methods. All compounds were assayed for their inhibitory effects on advanced
glycation end products formation using BSAmethylglyoxal assay.
Results: Chromatographic fractionation of the EtOAc extract of Derris indica stem bark led to the isolation
of two new pyranoavonoids, derrisins A and B (12), along with 11 known avonoids (313). The
inhibitory activities of the compounds on the formation of advanced glycation end products were
evaluated. Derrisin B (2) was the most active compound with IC50 value of 18.0 mM, and displayed
stronger inhibitory activity compared with positive control aminoguanidine.
Conclusions: This study provided the possibility that a pyranoavonoid (2) found in Derris indica might
have therapeutic potential as an inhibitor against the formation of advanced glycation end products.
& 2014 Elsevier Ireland Ltd. All rights reserved.

Keywords:
Derris indica
Flavonoid
Pyranoavonoid
Advanced glycation end products
Antiglycation

1. Introduction
Advanced glycation end products (AGEs) are unstable and
irreversible substances generated in the glycation process, a nonenzymatic reaction that initiates from a complex cascade of several
reactions between reducing sugars and free amino groups. AGEs can
react with other free amino groups leading to protein modication
such as alternative protein half-life, immune system, and enzyme
function. Thus they contribute to the pathophysiology of age-related
diseases, including diabetes, atherosclerosis, end-stage renal disease,
and neurodegenerative disease (Brownlee, 1995). More particularly,
the presence and accumulation of AGEs play an important role in the
development and complications of diabetes (Ahmed, 2005; Goldin
et al., 2006). Due to the emerging evidence about the adverse effects
of AGEs on the patients with diabetes, the use of anti-AGEs therapy

Corresponding author. Tel.: 66 22 187 641; fax: 66 22 541 309.

E-mail address: khanitha.p@chula.ac.th (K. Pudhom).

http://dx.doi.org/10.1016/j.jep.2014.10.053
0378-8741/& 2014 Elsevier Ireland Ltd. All rights reserved.

has thus attracted considerable attention from the researchers in

recent years.
Derris indica (Fabaceae), also known as Pongamia pinnata (L.)
Pierre, Pongamia pinnata (L.) Merr., Pongamia glabra Vent. and
Millettia pinnata (L.) Panigrahi, is widely distributed throughout
the mangrove areas in the southern part of Thailand. This plant is
traditionally used for bronchitis, rheumatic joints and to stop dipsia
in diabetes (Yadav et al., 2004). The stembark of this plant has been
used for treatment of diabetes, malaria, bleeding piles, beriberi,
anthelmintic, elexteric hemorrhoid, ophthalmopathy, vaginopathy,
skin diseases, gentitalia, sinus, stomach pain, intestinal disorder and
wound treatment (Al Muqarrabun et al., 2013). Various extracts from
the leaves, pods, roots, and stems of this plant displayed signicant
anti-diabetic activity (Rao et al., 2009; Badole and Bodhankar,
2009; Semalty et al., 2012; Sikarwar and Patil, 2012), as well as
the ethanolic extract of the owers considerably reduced the blood
glucose concentration in alloxan-induced diabetic rat (Punitha and
Manoharan, 2006). However, the inhibitory activity against the AGEs
formation of this plant has not been reported yet. In the present

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P. Anusiri et al. / Journal of Ethnopharmacology 158 (2014) 437441

study, we report the isolation and structure elucidation of two new

pyranoavonoids, derrisins A and B (12), together with 11 known
avonoids, from the stem bark of Derris indica, and their inhibitory
effects on the formation of AGEs.

2. Materials and methods

2.1. General
Optical rotations were measured on a Perkin-Elmer 341 polarimeter using methanol as a solvent. Melting points were measured
using a Fisher-Johns melting point apparatus. UV spectra were
recorded on a Shimadzu UV-160 UVvisible spectrometer. NMR
spectra were acquired on a Varian Mercury-400 Plus NMR spectrometer with TMS as internal standard. HR-ESI-MS was carried out on
a micrOTOF-Q II ESI mass spectrometer. Single-crystal X-ray diffraction analysis was performed on an Oxford Gemini S Ultra diffractometer. Silica gel 60 (Merck, 230400 mesh) and Sephadex LH20
(GE healthcare life science) were used for column chromatography.
2.2. Plant material
Stem bark of Derris indica was collected from mangrove area in
Satun province, Thailand, in November 2012. The plant sample was
identied by one of the authors (P. Chumriang). Avoucher specimen (CUCHEM-2012-04) has been deposited at Department of
Chemistry, Faculty of Science, Chulalongkorn University.
2.3. Extraction and isolation
2.3.1. Preparation of the EtOAc extract
The air-dried stem bark of Derris indica (2 kg) was roughly ground
and macerated in MeOH (  3, each for two days), and ltered. The
MeOH extract was concentrated, suspended in H2O, and then
partitioned with EtOAc to obtain the EtOAc crude extract (27 g).
The extract was subjected to quick column chromatography
over silica gel using a gradient of increasing EtOAc in hexane from
10% to 100%, and a gradient of increasing MeOH in CH2Cl2 from 5%
to 20% to give 11 fractions (F1F11) in consideration of a similar
TLC pattern. Fraction F3 was separated by silica gel column
chromatography using mixtures of EtOAc and hexane (from 3:17
to 1:1), and further recrystallization with CHCl3 afforded compound 4 (50.6 mg, 0.19% w/w). Fraction F6 was subjected to silica
gel column chromatography with a gradient system of acetone
hexane (from 3:17 to 6:4) to furnish compound 7 (14.7 mg).
Fraction F7 was reapplied to a silica gel column with EtOAc
hexane (from 1:9 to 1:1) to afford compound 13 (3.7 mg, 0.017% w/w)
and 12 subfractions. Subfraction F7.2 was further subjected to a
Sephadex LH-20 column using MeOH as eluent to yield compound 8
(7.1 mg, 0.026% w/w), while subfraction F7.5 was separated by silica
gel column chromatography eluted with EtOAchexane (from 2:8 to
1:1) to yield compounds 1 (4.0 mg, 0.015% w/w) and 5 (248.6 mg,
0.92% w/w). Subfraction F7.6 was also puried by silica gel column
chromatography using EtOAc-hexane (from 2:8 to 1:1) to give
compound 11 (3.9 mg, 0.014% w/w). Subfraction F7.7 was chromatographed on silica gel eluted with a gradient system of acetonehexane
from 3:17 to 4:6 to yield compound 3 (21.1 mg, 0.078% w/w), and
subfraction F7.10 afforded compound 9 (9.6 mg, 0.036% w/w) after
purication with silica gel column chromatography using the same
solvent system as that of subfraction F7.7. Isolation of fraction F8 by
silica gel column chromatography eluted with acetonehexane (from
1:9 to 1:1) yielded compound 12 (47.4 mg, 0.18% w/w) and 18
subfractions. Subfractions 8.14 and 8.17 were subsequently repeated
by column chromatography using the same solvent system to give
compounds 2 (25.5 mg, 0.094% w/w) and 6 (171.8 mg, 0.64% w/w),

respectively. Fraction F10 was chromatographed on silica gel eluted

with acetoneCH2Cl2 (from 3:17 to 4:6), followed by MeOHCH2Cl2
(from 1:19 to 1:9) to obtain compound 10 (7.4 mg, 0.027% w/w).
2.3.2. Derrisin A (1)
Colorless crystals; mp. 195198 1C; []25
D  13.0 (c 0.1, MeOH); UV
(MeOH) max 254, 316 nm; 1H (400 MHz, CDCl3) and 13C NMR
(100 MHz, CDCl3) data, see Table 1; HR-ESI-MS mz 441.1598
[MH] , calcd. for C24H25O8, 441.1544. X-ray data of 1: C24H24O8,
Mr440.43, triclinic, a 9.2968(7) , b12.0179(12) , c 20.457
(2) , space group P1, Z4 and V2220.5(4) 3, m(Mo K)
0.099 mm  1, and F(000)928. Crystal dimensions: 0.34  0.08 
0.04 mm3. Independent reections: 13,081 (Rint 0.025). The nal R1
values were 0.056, wR2 0.136 (I42 (I)). CCDC number: 938525.
2.3.3. Derrisin B (2)
6.5 (c 0.1, MeOH); UV
White solid; mp. 160162 1C; []25
D
(MeOH) max 258, 313 nm; 1H (400 MHz, CDCl3) and 13C NMR
(100 MHz, CDCl3) data, see Table 1; HR-ESI-MS mz 367.1217
[MH]  , calcd. for C21H19O6, 367.1176.
2.4. Antiglycation assay in bovine serum albumin (BSA)methylglyoxal
(MGO) model
The BSAMGO assay was used for investigation of an inhibitor
on the middle stage of the glycation of protein, and was slightly
modied according to Peng et al. (2007). BSA solution (10 mg/mL
in 0.1 M PBS, 125 mL, pH 7.4) was mixed with MGO (1 mM, 115 mL).
Then, the indicated concentrations (0.1, 0.05, 0.025, 0.0125 and
0.00625 mM) of test compounds were added in BSAMGO reaction, and incubated at 37 1C for 7 days. After incubation, the
uorescence intensity was measured at the excitation wavelength
of 370 nm and an emission wavelength of 420 nm by using the
EnSpire Multilabel Plate Reader. The % inhibition of AGEs was
calculated based on the following equation and IC50 values were
Table 1
1
H (400 MHz) and
No.

13

C (100 MHz) NMR data (CDCl3) of compounds 1 and 2.

H (mult, J in Hz)

5.10 d (12.4)
4.58 dd (2.0, 12.4)

83.9
72.8
192.1
129.2
112.7
161.9
107.3
160.6
111.9
136.1
127.3
129.3
128.5
129.3
127.3
77.5
70.7
61.0
25.6
21.9
20.6
169.8
20.4
169.5

2
3
4
5
6
7
8
9
10
10
20
30
40
50
60
2
3
4
2-Me
2-Me
3-OAc

5.17 d (4.8)
6.26 d (4.8)
1.41 s
1.45 s
2.05 s

4-OAc

1.94 s

3-OH
3-OMe
3-OH
4-OH

3.70 d (1.6)

7.85 d (8.8)
6.63 d (8.8)

7.46m
7.39 m
7.40 m
7.39 m
7.46 m

H (mult, J in Hz)

7.93 d (8.8)
6.83 d (8.8)

8.10 m
7.48 m
7.46 m
7.48 m
8.10 m
3.90 dd (5.2, 6.4)
5.20 dd (5.2, 5.2)
1.44 s
1.55 s

3.80 s
3.28 d (5.6)
3.54 d (5.6)

C
154.8
141.3
174.5
126.9
116.2
155.6
110.0
157.5
118.1
130.8
128.3
130.7
128.7
130.7
128.3
79.2
71.5
62.0
25.0
22.0

60.1

P. Anusiri et al. / Journal of Ethnopharmacology 158 (2014) 437441

obtained from line graph between the % inhibition and the

concentration of compound. Aminoguanidine (AG) was used as
positive control.


%inhibition F 0 F t =F 0  100
Ft and F0 respectively represent the uorescence intensity of
the sample and the control of mixtures.
2.5. Statistical analysis
All data were expressed as mean 7S.E.M. of ve determinations. The data analysis was performed by one-way analysis of
variance (ANOVA), followed by Tukey's HSD test. The p value
o0.05 was considered to be signicant.

3. Results and discussion

3.1. Isolation and structure elucidation
Repeated open column chromatography on silica gel and
Sephadex LH-20 of the EtOAc crude extract led to the isolation
of two new pyranoavonoids (12) and 11 known compounds,
including pongachromene (3), pongaavone (4), karanjin (5),
pongaglabol methyl ether (6), lacneolatin B (7), pongaglabrone
(8), pongapin (9), 5-methoxy-3,4-methylenedioxy(8,7,4,5)-avone (10), 3,7-dimethoxy-2-(4-methoxy phenyl)-avone (11), setin tetramethyl ether (12), and desmethoxy kanugin (13) (Fig. 1).
The structures of the known compounds were determined by
comparison of their NMR spectroscopic data with those in the
literature (Talapatra et al., 1980, 1982; Gupta et al., 1982; Garcez

439

et al., 1988; Tanaka et al., 1992; Das et al., 1994; Yoshioka et al.,
2004; Koysomboon et al., 2006; Lee and Park, 2012 ).
Compound 1 was isolated as colorless needle-like crystals and its
molecular formula C24H24O8 was deduced from HR-ESI-MS at mz
441.1598 [M H] (calcd 441.1544), implying 13 degrees of unsaturation. The 1H NMR data, taken in conjunction with the UV absorption
maxima at 254 and 316 nm, were indicative of a avanone skeleton.
The 1H NMR spectrum of 1 (Table 1) displayed characteristic signals
for two tertiary methyls (H 1.41 s, 1.45 s), two acetyl methyls (H 1.94
s, 2.05 s), and one unsubstituted phenyl ring (H 7.39 m, 2H; 7.40 m,
1H; 7.46 m, 2H). In addition, signals for ortho-coupled aromatic
protons at H 6.63 and 7.85 (each d, J8.8 Hz) were observed,
attributable for an additional aromatic ring. Analysis of 13C NMR
and HSQC data further revealed the presence of two tertiary methyls,
two acetyl methyls, four oxygenated methines, one oxygenated
quaternary carbon, 12 aromatic carbons (two oxygenated), and three
carbonyls (two esters and one ketone). On the basis of the above NMR
data, compound 1 had a tetracyclic skeleton due to nine units of the
13 unsaturations coming from three carbonyl groups and six carbon
carbon double bonds of two aromatic rings. The existence of a 2,2dimethyl-3,4-diacetyl-3,4-dihydro-2H-pyran moiety was corroborated by strong COSY correlations between H-3 and H-4, and HMBC
correlations from both tertiary methyls (2-Me  2) to oxygenated
C-2 and C-3 (Fig. 2). The location of two acetyl groups at C-3 and
C-4 was conrmed by HMBC correlations from H-3 and H-4 to
their carbonyl carbons. Indeed, the NMR data of 1 were very similar to
those of 3-methoxy-(3,4-dihydro-3,4-diacetoxy)-2,2-dimethylpyrano-(7,8:5,6)-avone (Koysomboon et al., 2006), except for the
replacement of the 2,3 double bond by the CH(2)CH(OH)(3) unit
in 1. Finally, a single-crystal X-ray diffraction study conrmed the
gross structure of 1 and allowed the determination of its relative

Fig. 1. Structures of compounds 113 isolated from the stem bark of Derris indica.

440

P. Anusiri et al. / Journal of Ethnopharmacology 158 (2014) 437441

conguration as depicted (Fig. 3). Compound 1 has thus been named

derrisin A.
Compound 2, a white solid, showed a [MH] ion at mz 367.1217
(calcd 367.1176), consistent with a molecular formula of C21H20O6. It
provided a typical avone UV spectrum (max 239, 258, and 312 nm).
The NMR data suggested that the structure of 2 was closely related to
that of pongaavone (4) (Koysomboon et al., 2006), except for the
appearance of two additional oxygenated methines [H 3.90 dd
(J5.2, 6.4 Hz), 5.20 dd (J5.2, 5.2 Hz); C 71.5, 62.0] as well as the
loss of a carboncarbon double bond in 4. Moreover, two exchangeable protons, observed at 3.28 (d, J8.0 Hz) and 3.54 (d, J8.0 Hz),
were assigned to OH-3 and OH-4, respectively, by the COSY correlations with their vicinal protons (Fig. 4a). An HMBC correlation between

Fig. 2. 1H1H COSY and selected HMBC correlations of 1.

Fig. 3. ORTEP diagram of compound 1.

the methoxyl protons and the double bond carbon C-3 conrmed its
location at the C-3 position. The relative conguration at C-3 and C-4
was deduced from the NOESY interactions to be the same as that of 1,
due to the correlations of H-3H-4 and OH-3 and OH-4 (Fig. 4b).
Therefore compound 2 was identied as a new pyranoavone and was
named derrisin B.

3.2. Inhibitory effects on AGEs formation of compounds isolated from

stem bark of Derris indica
All isolated compounds, except for compound 1, were further
evaluated for their inhibitory effects on the AGEs formation by using
the bovine serum albumin (BSA)methylglyoxal (MGO) antiglycation model (Peng et al., 2007). Since it is noted that not only AGEs
are derived from glucose, but reactive carbonyl species such as MGO
are crucial intermediates formed during glycation of proteins by
glucose (Thornelly et al., 1999; Nohara et al., 2002), thus MGO
should be included as a target. Aminoguanidine (AG) was used as a
positive control. At the screening dose of 0.1 mM, compound 2
displayed the most potent activity with 84.5% inhibition, whereas
compounds 5, 7 and 9 gave much weaker activity with the inhibition
of 14.4%, 8.8% and 18.5%, respectively. The remaining compounds did
not show any detectable activity at this dose. This also suggested
that the loss of the C-3, C-4 diol moiety caused a signicant loss
of activity, revealing from no activity observed in compound 4.
Additionally, it was subsequently found that the inhibitory effect of
compound 2 was in a dose-dependent manner (Fig. 5) with an IC50
value of 18.070.4 M. Since the current result revealed that derrisin
B (2) showed remarkable antiglycation activity, much greater than

Fig. 5. % AGEs inhibition of compound 2 in the BSAMGO model. Each value

represents the mean7SEM (n 5), (A) 27.72%72.24 at concentration of 6.25 mM,
(B) 61.89%71.82 at concentration of 25 mM, (C) 96.53%72.22 at concentration of
50 mM, and (D) 100.65%74.22 at concentration of 100 mM.

Fig. 4. (a) 1H1H COSY and selected HMBC correlations of compound 2. (b) Diagnostic NOESY correlations of compound 2.

P. Anusiri et al. / Journal of Ethnopharmacology 158 (2014) 437441

the antiglycative standard AG (IC50 477.1710.0 M), it provided

the possibility that this compound might have therapeutic potential
as an antiglycative agent for the treatment of diabetes.
4. Conclusion
This work demonstrates that the medicinal mangrove plant
Derris indica is a prolic source of avonoids. This is the rst report
of the inhibitory effects on the AGEs formation of avonoids
isolated from Derris indica. In particular, derrisin B (2), a new
pyranoavonoid, displaying potent activity when compared to
aminoguanidine, might be useful for the development of novel
AGEs inhibitor for the treatment of diabetes.
Acknowledgments
This work was supported by The 90th Anniversary of Chulalongkorn University Fund (Ratchadaphiseksomphot Endowment
Fund), and the Ratchadaphiseksomphot Endowment Fund of
Chulalongkorn University (RES560530208-AS).
Appendix A. Supporting information
Supplementary data associated with this article can be found in
the online version at http://dx.doi.org/10.1016/j.jep.2014.10.053.
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