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Abstract

The ethanol extract of the root bark of Terminalia sericea yielded an unreported stilbene glycoside, 3'5'-dihydroxy-4-(2-hydroxy-ethoxy) resveratrol-3-O-beta-rutinoside (1) together with known compounds resveratrol-3-beta-rutinoside glycoside (2), 3',4,5'-Trihydroxystilbene (resveratrol) (3), triterpenoic acid arjungenin and a mixture of beta-sitosterol and stigmasterol. Structure determination of the isolated compounds was achieved on the basis of spectroscopic measurements.
Joseph et al., Afr. J. Trad. CAM (2007) 4 (4): 383 – 386
383
Research Communication
ISSN 0189-6016©2007
ISOLATION OF A STILBENE GLYCOSIDE AND OTHER CONSTITUENTS OF TERMINALIA
SERICEAE
Joseph, C. C.*1, Moshi, M.J.2, Innocent, E.2 and Nkunya, M. H. H.1
1Department of Chemistry, University of Dar es Salaam, P.O. Box 35061, Dar es Salaam, Tanzania;
2Institute of Traditional Medicine, Muhimbili University College of Health Sciences
University of Dar es Salaam, P.O. Box 65005, Dar es Salaam, Tanzania
*E-mail: Cosam@chem.udsm.ac.tz
Abstract
The ethanol extract of the root bark of Terminalia sericea yielded an unreported stilbene glycoside,
3'5'-dihydroxy-4-(2-hydroxy-ethoxy) resveratrol-3-O-β-rutinoside (1) together with known compounds
resveratrol-3-β-rutinoside glycoside (2), 3',4,5'-Trihydroxystilbene (resveratrol) (3), triterpenoic acid arjungenin
and a mixture of β-sitosterol and stigmasterol. Structure determination of the isolated compounds was achieved
on the basis of spectroscopic measurements.
Key words: Terminalia sericea, stilbenes, combretastatin, resveratrol, glycosides.
Introduction
Terminalia sericea Burch. Ex. DC (Combretaceae) is widely distributed in the tropical and warm
temperate regions, especially in Africa (Watt and Breyer-Brandwijk, 1962; Hutchings et al., 1996). The plant
has wide spread traditional uses in eastern and southern African countries (Arnold and Gulumian, 1984;
Kokwaro, 1976; Msonthi and Magombo, 1983). Among some of its proven biological activities, include
inhibition of topoisomerase II (Wall et al., 1996), antibacterial, and antifungal activity (Eloff, 1999; Fyhrquist et
al., 2002; 2004). However, there is scanty information on compounds that are responsible for the exhibited
biological activities of the plant. The stilbene glycoside, resveratrol-3-O-β-rutinoside (2) (Bombardelli et al.,
1975), and pentacyclic triterpenes of the oleanane skeleton, together with their glucosides (Bombardelli et al.,
1974; 1975) have been isolated. This includes also a triterpene, sericoside (Maeda and Fukuda, 1996). Skin
lightening preparations containing sericoside have been patented in Japan (Maeda and Fukuda, 1996). A β-D-
glucoside (4) of resveratrol was isolated from wine, a compound that is considered to be responsible for the
protective ability of wines against coronary heart disease (Jeandet et al., 1991).
We hereby report the isolation of a an unreported stilbene glycoside 1, resveratrol-3-O-β-rutinoside (2),
resveratrol (3) and other known compounds such as sericic acid, stigmasterol, β-sitosterol and triterpenoid acid
were also isolated from the ethanol extract of the root bark of T. sericeae occurring in Tanzania.
Materials and Methods
Materials
Petroleum ether, dichloromethane, ethyl acetate (EtOAc), methanol (MeOH), chloroform (CHCl3), and
ethanol were purchased from Fisher Scientific UK Ltd (Bishop Meadow Road, Loughborough, Leicestershire,
LE 11 5RG, UK). Precoated silica gel plates (60 F254, 250 µm) were purchased from Merck and sephadex LH-
20 from Pharmacia.
Afr. J. Traditional,
Complementary and
Alternative Medicines
www.africanethnomedicines.net
Joseph et al., Afr. J. Trad. CAM (2007) 4 (4): 383 – 386
384
1: R =
2: R = H 3
13
5
3'
5' αβ
HO
H
HOH
OH
A
B
OH
1"
2"
13
5
3'
5' αβ
HO
H
HOR
O
A
B
OO
O
OH
OH
OH
OHOH
HO
CH3
OH
HO
O
O
HO
HO
OH
4
OH
Collection of Plant materials
The root barks of T. sericea were collected from Iringa region, and identified by Mr. Frank Mbago.
Voucher specimen no. IMPP 001-0144 is kept in the Herbarium of the Institute of Traditional Medicine,
Muhimbili University College of Health Sciences, University of Dar es Salaam.
Extraction and isolation
Air-dried and powdered plant material (2 Kg) was cold extracted sequentially in petroleum ether (2.0 L;
40-60˚C), dichloromethane (2.0 L) and then ethanol (2.0 L). The amounts of both the petroleum ether and
dichloromethane extracts were very small to the extent that these extracts could not be worked on further. The
ethanol extract was then fractionated by vacuum liquid chromatography (VLC) eluting with a mixture of
EtOAc/petroleum ether followed by MeOH/EtOAc to give 4 bulked fractions. Thin layer chromatography (TLC)
was performed on pre-coated plates (silica gel 60 F254, 250 µm on polyester backing, Merck) eluting with
mixtures consisting of petroleum ether (b.p. 40-60˚C) and EtOAc; detection by UV and an anisaldehyde spray
reagent (Jean, 1996). Column chromatography on silica gel 60 mesh (0.063-0.2 mm, Merck) eluting with
mixtures of increasing polarity consisting of petroleum ether and EtOAc. Gel filtration was performed on
Sephadex® LH-20 (Pharmacia) eluting with MeOH or a mixture of MeOH/CHCl3. VLC was performed on
silica gel 60 (Merck), eluting with petroleum ether containing increasing amounts of EtOAc. Recrystallisation
was achieved from MeOH/CHCl3, 9:1 v/v. Flash chromatography (FC) employed Merck silica gel 60 (0.063-0.2
mm, Merck) and petroleum ether (b.p. 40-60˚C)-EtOAc mixtures. Repeated column chromatography on silica
gel of fraction 1 yielded compound 2 and 3. Compound 1 was obtained from fraction 4 after repeated column
chromatography followed by gel chromatography over Sephadex® LH-20 eluting with a mixture of methanol
and water (1:1 v/v).
Spectra
1H NMR spectra were recorded on a Bruker AM 400 spectrometer operating at 400 MHz. CD3OD, CDCl3
or d6-DMSO were used as solvents. Chemical shifts are given in δ values relative to the internal standard TMS
(δ = 0). Mass spectra were determined by direct inlet on a VG 7070 E instrument at 70 eV.
Results
The unreported stilbene glycoside, 3΄5΄-dihydroxy-4-(2 hydroxy-ethoxy) resveratrol-3-O-β-rutinoside (1), was
isolated as a reddish gum.1H-NMR (CDCl3): δ 7.49 (1H, d, J = 8.6 Hz, H-2 or H-6), 6.99 (1H, d, J = 16.3 Hz,
Joseph et al., Afr. J. Trad. CAM (2007) 4 (4): 383 – 386
385
H- α), 6.85 (1H, d, J = 16.3 Hz, H-β), 6.74 (1H, d, J = 2 Hz, H-2’), 6.66 (1H, d, J = 2 Hz, H-6΄), 6.47 (1H, d, J
= 2 Hz, H-4΄), 4.90 (1H, d, H = 1΄΄΄), 4.75 (1H, d, H = 1΄΄), 3.90 (1H, dd, J = 1.61 Hz, 3.4 Hz, H = 4΄΄), 3.71
(1H, m, H = 3΄΄΄), 3.68 (2H, m, H-1΄΄΄΄), 3.58 (2H, m, H-2΄΄΄΄), 3.56 (1H, dd, J = 3.8 Hz, 5.4 Hz, H-3΄΄), 3.46
(1H, d, J = 5.7 Hz, H-2΄΄), 3.44 (1H, m, H-2΄΄΄), 3.35 ( 1H, m, H-4΄΄΄), 1.22 (d, d, J = 6.15 Hz, Me-6΄΄΄). 13C-
NMR (CDCl3): δ 159.32 (C-3΄), 158.48 (C-5΄), 157.41 (C-4), 140.39 (C-1΄), 129.29 (C-β), 127.98 (C-2/6),
125.64 (C-C-a), 115.58 (C-3/5), 107.16 (C-C-2΄), 106.76 (C-C-6΄), 103.10 (C-C-4΄), 101.33 (C-1΄΄΄), 101.15 (C-
1΄΄), 76.93 (C-3΄΄΄), 75.85 (C-5΄΄), 73.94 (C-2΄΄), 73.08 (C-4΄΄΄), 72.49 (C-1΄΄΄΄), 71.35 (C-3΄΄΄), 71.08 (C-4΄΄),
70.33 (C-2΄΄΄), 68.82 (C-5΄΄΄), 66.60 (C-6΄΄), 61.24 (C-2΄΄΄΄), 16.93 (C-6΄΄΄). EIMS m/z (rel. int.): 580 [M]+
(C28H36O13), 564 (55), 537 (100), 391 (15), 375 (20), 229 (10). Compounds 2, 3 and 4 were also isolated.
Compound 2, resveratrol-3-O-β-rutinoside, exhibited a weak antibacterial activity against Escherichia coli at 4
mg/ml. The compound was not tested on the other organisms due to its paucity.
Discussion
Compound 1 was obtained as a red gum. Its structure was established on the basis of extensive
spectroscopic analysis, in particular H/H-COSY, HMQC, HMBC and MS measurements, as well as from
comparison of the observed spectral data with those reported in the literature for the main skeleton (Bombardelli
et al., 1975., Breitmaier and Voelter, 1989., Dorman et al., 1970). Thus, the aromatic region of the 1H and 13C
NMR spectra exhibited features which were virtually the same as those observed for the stilbene moiety in
resveratrol-3-O-β-rutinoside (2) and this indicated the presence of a resveratrolyl unit in structure 1, as was
further also confirmed by the MS which consisted of a peak at m/z 228 due to the fragment ion corresponding to
3. Furthermore, the 1H NMR spectrum displayed two doublet at δ 4.94 and 4.75 which were assigned to
protons at anomeric carbon atoms, thereby indicating the presence of a disaccharide unit that consisted of a
rhamnoside and a glucoside unit, whereas the methyl carbon signal for the rhamnose unit was observed at δ
16.93 (Bombardelli et al., 1975., Breitmaier and Voelter, 1989., Dorman et al., 1970). The α-L-O-glycosidic
linkage between the two sugar units was indicated from the observed J values as well as the 13C NMR
resonances of the anomeric carbon atoms, which appeared at δ 101.18 and 101.33, respectively (Kasai et al.,
1977; 1979). The 1H and 13C NMR spectral features for the disaccharide unit were virtually the same as those
observed in the spectra of 2 and this indicated that, like in 2, glycoside 1 contained a rutinoside residue
(Bombardelli et al., 1975., Breitmaier and Voelter, 1989., Dorman et al., 1970). The 13C NMR spectrum with
DEPT 135 measurements of compound 1 indicated signals due to 14 carbon atoms in the region δ 16-101. Of
these signals, 12 were characteristic resonances observed for the rutinoside sugar residue in compound 2 as
reported in the preceeding discussion, also corresponding to literature data for the rutinoside 13C NMR
resonances for compound 2 (Bombardelli et al., 1975., Breitmaier and Voelter, 1989. Dorman et al., 1970). The
remaining two 13C NMR signals at δ 61.24 and 72.49 were attributed to a dioxymethylene group. These
spectral features, as well as the positions of the 13C NMR resonances in the high field region being comparable
to those observed for the resveratrolyl unit in compound 2 but having only slight differences led to the
conclusion that compound 1 must be having structural features similar to those of 2, the former compound
however bearing an additional hydroxyethane group. Addition of a two carbon atom in compound 1 as
compared to compound 2 was also indicated by the MS which exhibited a molecular ion peak at m/z 580, which
is 44 amu higher than the M+ peak for glycoside 2 (m/z 536). The additional 44 amu could be accounted for by
considering the presence of an additional CH2CH2O unit in compound 1.
As for compound 2, the position of the rutinoside sugar residue in glycoside 1 was deduced based on
the upfield shift of the 13C NMR resonances for C-3' and C-5' in ring A as compared to the corresponding
signals in the spectrum of 3. The position of the rutinoside sugar residue was further corroborated by long range
H/C interactions involving the anomeric proton at C-1'' as revealed in the HMBC spectrum.
Establishment of the position of the hydroxyethane group at C-4 was facilitated by considering the slight upfield
shift of the 13C NMR resonance for C-4 in compound 3 as compared to the corresponding signals in the
spectrum of glycoside 2. Apparently, the substitution could also be at C-5' in ring B which makes structure 1 to
be only tentative.
The MS of 1 consisted of the molecular ion peak at m/z 580 and a fragment ion peak at m/z 536 which
corresponds to the M+ peak for compound 2, being formed through rearrangement of 1 followed by extrusion of
Joseph et al., Afr. J. Trad. CAM (2007) 4 (4): 383 – 386
386
acetaldehyde. Cleavage of the sugar residue yielded a fragment ion at m/z 229 due to the resveratrolyl unit. The
MS fragmentation pattern of compound 1 is consistent with the proposed structure.
Acknowledgements
Financial support by Swedish International Development Agency (SIDA)/Department of Research
Cooperation (SAREC) within an overall research support to the Faculty of Science at the University of Dar es
Salaam is gratefully acknowledged. We also thank Prof. Berhanu M. Abegaz of the University of Botswana for
availing spectral analytical facilities to us. One of the authors (IE) thanks the Vlaamse Interuniversitaire Raad-
Flemish Interuniversity Council (VLIR) for fellowship.
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... Among Terminalia species, T. bellerica's roots and fruits have been extensively studied, with 85 secondary metabolites identified in the leaves. Major components found in T. bellerica include ellagitannins such as chebulagic acid, galloyl punicalagin, and hexoside [20] . Additionally, compounds like phenolics, saponins, lignans, triterpenoids, resveratrol, arjungenin, sitosterol, and stigmasterol have been isolated from the fruit and stem bark [20] . ...
... Major components found in T. bellerica include ellagitannins such as chebulagic acid, galloyl punicalagin, and hexoside [20] . Additionally, compounds like phenolics, saponins, lignans, triterpenoids, resveratrol, arjungenin, sitosterol, and stigmasterol have been isolated from the fruit and stem bark [20] . Terminalia species are rich in diverse bioactive compounds, including beta-cetosterol, tannins, gallic acid, ethyl gallate, ellagic acid, and glucosides [21] . ...
... It has been identified as a species with excellent potential for commercialization [14]. Phytochemical studies have revealed the presence of hydrolysable tannins (ellagic acid, flavogallonic acid dilactone, methyl-flavogallonate) lignans (anolignan b, termilignan b), stilbenes (resveratrol-3-O-β-rutinoside, resveratrol-3-(6 '-galloyl)-O-β-D-glucopyranoside), flavonoids (quercetin-3-(2 -galloylrhamnoside) and triterpenoids (arjunic acid, sericic acid, arjunglucoside I, sericoside, arjunetin) in the roots of T. sericea [15][16][17][18][19][20]. In a recent study [20], the chemical variability within T. sericea root bark samples representing several populations in Limpopo Province, South Africa, was attributed mainly to sericic acid, sericoside and resveratrol-3-O-β-rutinoside. ...
... mg/g from Tzaneen (Track 13; +++). Samples from Tshandama (TSA1-TSA5) (Tracks [18][19][20][21][22] and Tshitavha (TSH1-TSH5) (Tracks 23-27) contained high concentrations of all the major compounds, as reflected by the intense bands corresponding to the standards in these samples (all allocated +++). The congruent results between the quantitative analysis and the band intensities prove that the HPTLC method is reliable for QC (qualitative and quantitative) of T. sericea. ...
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Terminalia sericea is used throughout Africa for the treatment of a variety of conditions and has been identified as a potential commercial plant. The study was aimed at establishing a high-performance thin layer chromatography (HPTLC) chemical fingerprint for T. sericea root bark as a reference for quality control and exploring chemical variation within the species using HPTLC metabo3lomics. Forty-two root bark samples were collected from ten populations in South Africa and extracted with dichloromethane: methanol (1:1). An HPTLC method was optimized to resolve the major compounds from other sample components. Dichloromethane: ethyl acetate: methanol: formic acid (90:10:30:1) was used as the developing solvent and the plates were visualized using 10% sulfuric acid in methanol as derivatizing agent. The concentrations of three major bioactive compounds, sericic acid, sericoside and resveratrol-3-O-β-rutinoside, in the extracts were determined using a validated ultra-performance liquid chromatography-photodiode array (UPLC-PDA) detection method. The rTLC software (written in the R-programming language) was used to select the most informative retardation factor (Rf) ranges from the images of the analysed sample extracts. Further chemometric models, including principal component analysis (PCA) and hierarchical cluster analysis (HCA), were constructed using the web-based high throughput metabolomic software. The rTLC chemometric models were compared with the models previously obtained from ultra-performance liquid chromatography coupled with mass spectrometry (UPLC-MS). A characteristic fingerprint containing clear bands for the three bioactive compounds was established. All three bioactive compounds were present in all the samples, although their corresponding band intensities varied. The intensities correlated with the UPLC-PDA results, in that samples containing a high concentration of a particular compound, displayed a more intense band. Chemometric analysis using HCA revealed two chemotypes, and the subsequent construction of a loadings plot indicated that sericic acid and sericoside were responsible for the chemotypic variation; with sericoside concentrated in Chemotype 1, while sericic acid was more abundant in Chemotype 2. A characteristic chemical fingerprint with clearly distinguishable features was established for T. sericea root bark that can be used for species authentication, and to select samples with high concentrations of a particular marker compound(s). Different chemotypes, potentially differing in their therapeutic potency towards a particular target, could be distinguished. The models revealed the three analytes as biomarkers, corresponding to results reported for UPLC-MS profiling and thereby indicating that HPTLC is a suitable technique for the quality control of T. sericea root bark.
... isolating metabolites from root bark material of T. sericea have previously been reported [26][27][28], details on the isolation procedures are not available, making them difficult to replicate. Previous methods involved several solvent partitioning steps, followed by silica gel chromatographic separation, to isolate the aglycones and glycosides, respectively. ...
... The presence of an anomeric proton at δ H 5.24 and carbon signals at δ C 94.6, 78.2, 77.2 and 69.9 ( Figure S3) support the presence of the sugar moiety. The molecular ion (m/z 689.389) is consistent with the molecular formula C 36 Figure S4) obtained corresponded to that reported in literature [27,28,34]. ...
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Terminalia sericea Burch. ex. DC. (Combretaceae) is a popular remedy for the treatment of infectious diseases. It is widely prescribed by traditional healers and sold at informal markets and may be a good candidate for commercialisation. For this to be realised, a thorough phytochemical and bioactivity profile is required to identify constituents that may be associated with the antibacterial activity and hence the quality of raw materials and consumer products. The aim of this study was to explore the phytochemistry and identify the antibacterial constituents of T. sericea root bark, using a metabolomic approach. The chemical profiles and antibacterial activities of 42 root bark samples collected from three districts in the Limpopo Province, South Africa, were evaluated. Dichloromethane:methanol (1:1) extracts were analysed using ultraperformance liquid chromatography (UPLC)-mass spectrometry (MS), and chemometric models were constructed from the aligned data. The extracts were tested against Bacillus cereus (ATCC 11778), Staphylococcus epidermidis (ATCC 12223), Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 8739), Klebsiella pneumoniae (ATCC 13883), Pseudomonas aeruginosa (ATCC 27853), Shigella sonnei (ATCC 9292) and Salmonella typhimurium (ATCC 14028), using the minimum inhibition microdilution assay. Nine compounds; sericic acid, sericoside, resveratrol-3-O-β-rutinoside, ellagic acid, flavogallonic acid dilactone, methyl-flavogallonate, quercetin-3-(2′′-galloylrhamnoside), resveratrol-3-(6′′-galloyl)-O-β-d-glucopyranoside and arjunetin, were isolated from the root bark. All the compounds, with the exception of sericic acid, sericoside and resveratrol-3-O-β-rutinoside, were isolated for the first time from the root bark of T. sericea. Chemometric analysis revealed clustering that was not population specific, and the presence of three groupings within the samples, characterised by sericic acid, sericoside and an unidentified compound (m/z 682/4.66 min), respectively. The crude extracts from different populations displayed varied antibacterial activities against S. typhimurium (minimum inhibitory concentrations (MICs) 0.25–1.0 mg/mL), but similar activity towards Bacillus cereus (1.0 mg/mL). Several compounds present in the root bark were highly active towards all or most of the pathogens tested, but this activity was not reflected by the chemical profiles of extracts prepared from the individual samples. Among the pure compounds tested, only flavogallonic acid dilactone and methyl-flavogallonate exhibited broad-spectrum activity. A biochemometric analysis indicated that there was no consistent association between the levels of phytochemicals and the activity of the active or non-active extracts. Although it was deduced that the major constituents of T. sericea root bark contributed to the chemotypic variation, further investigation of the interactions of compounds present in the root bark may provide antibacterial efficacies not evident when examining compounds singularly. The data reported herein will provide information that is fundamentally important for the development of quality control protocols.
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... 38 The resveratrol glycoside piceid is also present in T. ferdinandiana 22 and the African species T. sericea. 39 Piceid (and other glycosylated stilbenes) blocks IL-17 production in stimulated human mononuclear cells. 40 A variety of other stilbenes have also been reported in the southern and eastern African species T. brownii and T. laxiflora. ...
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... Furthermore, stilbenes are classified into monomeric and oligomeric stilbenes (Shen et al. 2009). Monomeric stilbenes occur in 23 plant families, including the Combretaceae family, from which a series of tubulin polymerization inhibitors, the combretastatins, and resveratrol and its glycosides are known , Shen et al. 2009, Joseph et al. 2007Fig. 20 Fig 19). ...
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