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Isolation of Mangiferin from Bombax

malabaricum and Structure Revision of
Shamimin
ARTICLE in PLANTA MEDICA DECEMBER 2003
Impact Factor: 2.15 DOI: 10.1055/s-2003-45161 Source: PubMed

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Isolation of Mangiferin from Bombax

malabaricum and Structure Revision
of Shamimin
Abdelaaty A. Shahat1, 2, Rasmeia A. Hassan1, Naglaa M. Nazif1,
Sabine Van Miert2, Luc Pieters2, Faiza M. Hammuda1,
Arnold J. Vlietinck2

Abstract

Letter
1068

Repeated column chromatography of the n-BuOH fraction of the

70 % EtOH of the dried leaves of Bombax malabaricum led to the
isolation of mangiferin, a xanthone. Mangiferin was identified by
UV, 1H- and 13C-NMR spectroscopy and electrospray mass spectrometry. It was found to be identical to shamimin, a compound
for which originally a flavonol structure was proposed, and the
structure of which has to be revised.

Bombax is the common name for members of the Bombaceae, a

family including many commercially important members, e. g.,
the baobab, the balsa, the kapok and several species of the genera
Bombax and Ceriba whose seed fibres are used as filling materials. Bombax malabaricum DC. (syn. B. ceiba L. and Salmalia
malabaricum DC.) is also known as silk-cotton tree. It is widely
cultivated in Pakistan, India, China and Australia. B. malabaricum
was introduced into Egypt several decades ago as an ornamental
plant and shade tree [1], [2], [3]. All parts of the plant have medicinal significance, e. g., leaves are reported to have application in
skin eruptions and they are used to reduce blood sugar levels; roots
and flowers are regarded as having diuretic, laxative and restorative properties. The gum is useful in acute dysentery. Phytochemical investigations of different parts of this plant resulted in the isolation of naphthol and naphthoquinone derivatives, anthocyanins,
shamimin (a flavonoid C-glycoside), and lupeol [4], [5], [6].
Compound 1 was isolated from the n-BuOH fraction of the 70 %
alcoholic extract of the leaves of Bombax malabaricum by column
chromatography on polyamide, followed by column chromatography on Sephadex LH-20. Compound 1 was obtained as an
amorphous yellow powder. The 13C-NMR spectrum of compound 1 showed an obvious similarity with 1,3,6,7-tetrahydroxyxanthone; however, one of the singlets in the 1H-NMR spectrum
and a CH signal in the 13C-NMR spectrum were missing [7]. An
additional quaternary carbon atom was observed at d = 107.58,
which was attributed to C-2. Remaining signals in the 1H- and
13
C-NMR spectra were in agreement with a C-glycoside. Indeed,

Affiliation: 1 Department of Pharmaceutical Sciences, National Research Centre, Dokki, Cairo, Egypt 2 Department of Pharmaceutical Sciences, University
of Antwerp, Antwerp, Belgium
Correspondence: Dr. A. A. Shahat Department of Pharmaceutical Sciences
University of Antwerp Universiteitsplein 1 2610 Antwerp Belgium Fax:
+32 3 820 27 09 E-mail: shahat@uia.ua.ac.be
Received: April 8, 2003 Accepted: July 26, 2003
Bibliography: Planta Med 2003; 69: 10681070  Georg Thieme Verlag
Stuttgart New York ISSN 0032-0943

Materials and Methods

General experimental procedures: Column chromatography was
carried out on polyamide 6 S (Riedel-de Han, Germany) and Sephadex LH-20 (Pharmacia). TLC was carried out on silica gel 60 F254 plates (Merck); solvent system: EtOAc-HOAc-HCOOH-H2O
(30/0.8/1.2/8) v/v; detection: Neu's spray reagent (1 % diphenylboric acid ethanolamine complex), UV detection at 254 and 366
nm.
Electrospray ionisation (ESI) mass spectra were recorded on an
Autospec TOF MS (Micromass) of EBE time-of-flight design
equipped with an electrospray ionisation (ESI) source and microchannel plate (MCP) detector. The ESI source was operated at 4
kV and a cone voltage of + 40 V. 1H- and 13C-NMR spectra were
recorded in DMSO-d6 on a Bruker DRX-400 instrument. The chemical shifts were reported in d values (ppm) with TMS as the
internal standard. UV spectra were recorded in MeOH using a
Kontron Uvikon 931 instrument.

Letter

the 1H- and 13C-NMR spectral data were in complete agreement

with those reported for mangiferin or 2-b-D-glucosyl-1,3,6,7-tetrahydroxyxanthone (listed without any assignment) [8]. This
structural proposal was confirmed by positive ion electrospray
mass spectrometry, showing a molecular ion at m/z = 423 ([M +
H]+). The NMR data were also in complete agreement with those
reported for shamimin or 6-b-D-glucosyl-3,5,7,2,4,5-hexahydroxyflavone reported before from Bombax ceiba (Fig. 1) [6].
However, the mass spectral data reported for shamimin, i. e., a
signal at m/z = 421 in negative FAB-MS, rather point towards a
compound with a molecular weight of 422, such as mangiferin,
whereas the putative structure of shamimin requires a molecular
weight of 480. On the other hand, the EI mass spectrum reported
for shamimin is in good agreement with the fragmentation pattern published before for mangiferin [9]. In addition, the 13CNMR assignments reported for shamimin contain two overlapping signals, C-2 and C-3, at d = 150.81, and C-3 and C-5 at
d = 143.70 and, as a consequence, the 1H- and 13C-NMR spectral
data could just as well be assigned to mangiferin. The same authors have reported a 1H- and 13C-NMR study of some acetylated
derivatives of shamimin [10]. Also for these derivatives, double
assignments are always needed to allow complete 13C assignments. In addition, heptaacetylmangiferin has a relative molecular mass of 716, and several EI-mass spectra of acetylated shamimin derivatives reported in the same study show a signal at m/z
= 716. Therefore, the NMR and MS data reported for acetyl derivatives of shamimin cannot support its structure. Also the optical
rotation reported for shamimin {[a]D24: + 30.558 (c 0.11, DMSO)} is
in good agreement with the [a]D value of mangiferin (+ 328). Finally, a direct comparison on TLC, and comparison of the UV, 1Hand 13C-NMR spectra of our compound isolated from Bombax
malabaricum, a sample of shamimin obtained from Faizi et al.,
and a commercially available sample of mangiferin, revealed
that the three compounds were identical. The UV spectra of all
three samples were identical to those reported before for mangiferin [8], showing a characteristic xanthone spectrum presenting
four maxima [11], whereas for a flavonol with a free hydroxyl
group in position 3 such as shamimin rather two bands (band I,
350 385 nm; band II, 250 280 nm) are expected [12]. Therefore, we conclude that the structure reported for shamimin [6]
is not correct and has to be revised, and that in fact it is identical
to mangiferin. Consequently, it should be noted that the hypotensive and hypoglycaemic activities reported for shamimin [5]
apply in fact to mangiferin.

Plant material: Leaves of Bombax malabaricum DC. were collected at Giza Street, Area of Imbaba, Giza, Egypt in May, 2000. The
plant was kindly identified by Prof. Dr. K. H. Al-Batanony, Professor of Taxonomy, Faculty of Science, Cairo University to whom
the authors are greatly indebted. A voucher specimen (Bombaceae/Bombax malabaricum/052000) is kept at the Herbarium
of the NRC, Dokki, Cairo, Egypt.
A reference sample of mangiferin was obtained from Extrasynthse, France. A sample of shamimin was obtained from Prof. S.
Faizi, University of Karachi, Pakistan [6].
Extraction and isolation: 500 g of the dried powdered leaves were
defatted with petroleum ether (40 60 8C). After drying, the residue was extracted with 70 % EtOH (4 1000 mL). The alcohol extract was evaporated under reduced pressure and kept in the refrigerator overnight. After filtration the supernatant was successively extracted with CHCl3, EtOAc and n-BuOH (5 300 mL
each). The n-BuOH fraction (4 g) was subjected to column chromatography on polyamide (60 3 cm) and eluted first with H2O
(150 mL), and then with a gradient of H2O and MeOH with an increasing amount of MeOH, in steps of 10 % (elution volume each
time 200 mL). Fractions eluted with 60 % MeOH were collected
and concentrated. Repeated column chromatography on Sephadex LH-20 (Pharmacia) (60 1.5 cm) using MeOH as eluent
(3 200 mL) gave compound 1 (98 mg).
Mangiferin (2-b-D-glucosyl-1,3,6,7-tetrahydroxyxanthone) (1). UV
(MeOH): lmax (log e) = 243 (4.56), 259 (4.61), 318 (4.26), 368 nm

Fig. 1 Structures of mangiferin (1) and

shamimin.

Letter Planta Med 2003; 69: 1068 1070

1069

Table 1

13

C- and H-NMR spectral data for mangiferin (1)

Letter

Carbon No.

13

1
2
3
4
4a
5
6
7
8
8a
9
9a
10a
1
2
3
4
5
6

161.76
107.56
163.81
93.31
156.21
102.56
154.17
143.76
108.00
111.63
179.07
101.29
150.82
73.09
70.62
79.14
70.26
81.53
62.78

C-NMR (d)

tra. Prof. S. Faizi (University of Karachi) is kindly acknowledged

for sending a sample of shamimin.

H-NMR [d, mult., J (Hz)]

6.35, s

6.84, s

7.36, s

4.58, d, J = 9.8Hz
4.03, dd, J = 9.1, 9.0 Hz
3.20, m
3.14, m
3.16, m
3.68, br d, J = 11.6 Hz
3.40, dd, J = 11.6, 5.5 Hz

(4.22) [8]. ESI-MS (positive ion mode): m/z = 423 ([M + H]+). 1HNMR (400 MHz, DMSO-d6): Table 1. 13C-NMR (100 MHz, DMSOd6): Table 1.

Acknowledgments
Dr. M. Claeys (Department of Pharmaceutical Sciences, University of Antwerp) is kindly acknowledged for recording mass spec-

1070

Letter Planta Med 2003; 69: 1068 1070

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