American Journal of Plant Sciences, 2011, 2, 657-659
doi:10.4236/ajps.2011.25078 Published Online November 2011 (
Copyright © 2011 SciRes. AJPS
Phytochemical Study of Glycosmis Mauritiana
Javed Intekhab1, Mohammad Aslam1, Hira Khalid2
1Natural Products Research Division, Post Graduate Department of Chemistry, G. F. College (Rohilkhand University), Shahjahanpur,
India; 2Post Graduate Department of Chemistry, Government College, Lahore, Pakistan
Email: Javed786khan_khan@
Received February 20th, 2011; revised March 25th, 2011; accepted April 6th, 2011.
Three quinolinone alkaloids, two acridone alkaloids and a flavones glycoside were isolated from the aerial parts of
Glycosmis mauritiana. These compounds were characterized as 7, 8-Dimethoxy-2,2,6-trimethyl-pyrano quinolin-5-one,
4-Methoxy 1-methyl quinolin-2-one, 6-Hydroxy N-methyl 2,3-furo-qu inolin-4-one, 1-Hydroxy-10-methyl acridone, 1-
Hydroxy-2, 3-dimethoxy-10-methylacridin-9-one and Luteolin-4'-O-[α-L-rhamnopyranosyl-(12)-{α-L-rhamnopyra-
nosyl-(16)}-β-D-glycopyranoside]. The isolated compounds were characterized by UV, IR and N. M. R (
1H, 13C)
Keywords: Glycosmis Mauritiana, Rutaceae, Flavanone Glycoside
1. Introduction
Glycosmis mauritiana (syn. Limonia pentaphylla Auct;
Glycosmis pentaphylla Auct.; Limonia mauritiana Lam.)
commonly known as Ash-sheora, Orange berry, Rum
Berry and Gin Berry. Glycosmis mauritiana is native of
India, Malaysia, China, Sri Lanka, Myanmar, Thailand,
Indonesia and Malaya. Glycosmis mauritiana is a small
tree or shrub, widely used in Hindu medicine [1-3].
Plants of this genus used as a traditional medicine for the
treatment of various diseases [4]. The genus Glycosmis
(Family Rutaceae) is a rich source of quinolone, quina-
zoline, furoquinoline, carbazole, acridone type of alka-
loids and also sulphur-containing amides, coumarins and
flavonoids [4-7]. Plant flavonoids have been shown in
current years to be of essential meaning to mankind as
well as to plants. The several thousand polyphenols that
have been described in plants can be grouped into dis-
tinct classes, most of which are found in fruits and vege-
tables. Flavonoids are particularly common in higher
plants belonging families Leguminoseae, Rutaceae, Pri-
mulaceae, Polygonaceae, Salicaceaem, Pinaceae, Rosa-
ceae, Asteraceae, Lamiaceae, Bignoniaceae, Moraceae,
Betulaceae, Rubiaceae, and Mytaceae. Flavanoids, are
the largest group of naturally occurring phenolic com-
pounds, which occur in different plant parts both in the
free state and as glycosides [8-11].
Flavonoids have been shown to have a wide range of
biological activities, including antiallergic, antibacterial,
antiinflammatory, antimutagenic, antioxidant, antiprolif-
erative, antithrombotic, antiviral and hepatoprotective [8-
15]. These flavonoids also showed antitumor and anti-
HIV effect, strong antioxidative effects and provide
powerful scavengers against superoxide, hydrogen per-
oxide, hydroxyl radicals, nitric oxide and peroxynitrite
produced by various chemicals and biological systems
moreover they have anticarcinogenic properties [16].
2. Results and Discussion
The compound was isolated as yellow semi solid from
the ethyl acetate extract by the elution with CHCl3:
MeOH (5:14). The compound showed positive test for
sugar and flavonoid moiety suggested that the compound
might be a flavanoid glycoside. The UV spectrum of the
compound showed absorption bands at 257, 269 and 337
nm characteristic of flavonoid [17-20]. The methanol UV
spectra of this compound showed two peaks at 257 and
269 nm, respectively, indicating that the B-ring is either
3', 4'- or 3', 4', 5'-oxygenation. The IR spectrum of the
compound exhibited absorption bands at 3421 (O-H),
2925 (C-H), 1654 (α, β-unsaturated C=O), 1620 (C=C),
1517, 1493 (aromatic), and 1108 - 1018 (glycosidic na-
ture) cm1 functionalities. Mass spectrum exhibited a
molecular ion peak at m/z 740 (M + H) which corre-
sponded to the molecular formula C33H40O19 [17-20].
In the 1H NMR spectrum a singlet appeared at δ 12.13
applicable for C5-OH group, which was hydrogen, bonded
with carbonyl group at C-4. The 1H NMR spectrum of
this compound further displayed a one proton singlet
signals for the other two phenolic protons at δ 9.04 (1H,
Phytochemical Study of Glycosmis Mauritiana
H-3') and 10.80 (1H, H-7) [17-20].
The 1H-NMR demonstrated two one-proton doublets
at δ 7.82 (1H, d, J = 2.2 Hz) and δ 7.34 (1H, d, J = 8.3 Hz)
and one double doublet δ 7.74 (1H, dd, J = 2.2, 8.3 Hz)
assignable to H-2', H-5' and H-6' protons respectively.
The 1H NMR displayed one proton singlet at δ 6.74
could be assigned to H-3 proton [19]. In addition, the
methine carbon signal at δc 105.41 was attributed to C-3
in the 13C NMR spectrum, indicating a 3', 5, 7-trihydroxy
flavone [21].
The 1H NMR spectrum of the compound showed two
meta-coupled doublets at δ 6.49(1H, d, J = 2.2 Hz) and
6.26(1H, d, J = 2.2 Hz) each integrating for one proton,
were assigned to H-8 and H-6, respectively of ring A of 5,
7-dihydroxy flavone. The 1H NMR studies of the com-
pound showed it to be flavonoid with sugar moieties i.e.
glactose and rhamnose in a trisaccharide fashion. In the
1H NMR spectra the resonances of the anomeric protons
observed in the low-field region at δ 5.58 (1H, d, J = 7.9
Hz, H-1"), 5.46 (1H, d, J = 3.6 Hz, H-1'"), and 5.41 (1H,
d, J = 3.1 Hz, H-1"") applicable for three sugar anomeric
protons suggesting the presence of triglycoside linkage
[17-19]. The anomeric proton signals were consistent
with the β-configuration of one glactose and α-configu-
ration of two rhamnose moieties.
The downfield chemical shift of C-2" and C-6" and
slight upfield shift of C-1' and C-5'of galactopyranosyl
moiety provided evidence for the sites of attachment of
rhamnose to the galactose.
The structure was further supported by its 13C NMR
spectrum, which demonstrated a downfield signal at δ
181.5 clearly assignable to carbonyl carbon C-4 of the
pyron ring [20,21]. The three downfield signals appeared
at δ 160.47, 165.80 and 149.45 were assigned to C-5, C-7
and C-3' bearing hydroxyl group. Two signals at δ 99.93
and 94.86 assigned to C-6 and C-8 further supported that
hydroxyl group present at C-5 and C-7 [21]. Moreover, a
signal at δ 151.56 assigned to C-4' supports the attach-
ment of glycoside moiety to this compound at C-4' [21].
On acid hydrolysis, compound afforded β-D-galactose
and α-L-rhamnose were identified by Co-PC with those
of an authentic sample.
Thus on the basis of the above spectral evidences the
structure of the isolated compound was finally concluded
to be Luteolin-4'-O-[α-L-rhamnopyranosyl-(12)-{α-L-
3. Conclusions
Although several compounds have been isolated from
Glycosmis mauritiana among them Luteolin-4'-O-[α-L-
-β-D-glycopyranoside is new for this plant.
[1] P. G. Watermann and M. F. Grundon, “Chemistry and
Chemical Taxonomy of the Rutales,” Academic Press,
London, 1983.
[2] O. Hofer and H. Greger, “Sulfur-Containing Amides from
Glycosmis Species: Rutaceae,” W. Herz, H. Falk, G. W.
Kirby and R. E. Moore, Eds., Springer, New York, Vol.
80, 2000, p. 187.
[3] B. C. Stone, “A Conspectus of the Genus Glycosmis
Correa: Studies in Malaysian Rutaceae, III,” Pro-
ceedings of the Academy of Natural Sciences of Phila-
delphia, Vol. 137, 1985, pp. 1-27.
[4] N. M. Cuong, T. V. Sung and W. C. Taylor, “Gly-
petelotine, a Sulphur-Containing Indole Alkaloid from
Glycosmis petelotii,” Phytochemistry, Vol. 52, No. 8.,
1999, pp. 1711-1714.
[5] M. Rahmani, C. Y. Ling, M. A. Sukari, H. B. M. Ismail,
S. Meon and N. Aimi, “7-Methoxyglycomaurin: A New
Carbazole Alkaloid from Glycosmis rupestris,” Planta
Medica, Vol. 64, No. 8, 1998, p. 780.
[6] T.-S. Wu, Feng-Chu, C., & Pei-Lin, W., “Flavonoids,
Amidosulfoxides and an Alkaloid from the Leaves of
Glycosmis citrifolia,” Phytochemistry, Vol. 39, No. 6,
1995, p. 1453-1457. doi:10.1016/0031-9422(95)00171-3
[7] C. W. J. Chang, W. Herz, H. Greger, H. Falk, O. Hofer, G.
W. Kirby, “Fortschritte Der Chemie Organischer Naturst-
Copyright © 2011 SciRes. AJPS
Phytochemical Study of Glycosmis Mauritiana
Copyright © 2011 SciRes. AJPS
offe/Progress in the Chemistry,” Springer, Berlin, Vol. 80,
2000, p. 188.
[8] R. E. Catherinefl, “Flavonoids in Health and Disease,”
2nd Edition, Marcel Dekker, Inc., New York, 2003.
[9] G. Erich, “The Science of Flavonoids,” Springer Science,
New York, 2006.
[10] C. G. Fraga, “Plant Phenolics and Human Health Pub-
lished,” John Wiley and Sons, Hoboken, 2010.
[11] W. Bylka and I. Matlawska, “Natural Flavonoids as An-
timicrobial Agents,” JANA, Vol. 7, No. 2, 2004, pp. 24-31
[12] L. G. Korkina and I. B. Afanas’ev, “Antioxidant and Che-
lating Properties of Flavonoids,” Advances in Pharma-
cology, Vol. 38, 1997, pp. 151-163.
[13] C. A. Rice-Evans, N. J. Miller and G. Paganga, “Struc-
ture-Antioxidant Activity Relationships of Flavonoids
and Phenolic Acids,” Free Radical Biology and Medicine,
Vol. 20, No. 7, 1996, pp. 933-956.
[14] S. Charles, N. I. Buer and A. Michael, “Djordjevic Fla-
vonoids: New Roles for Old Molecules,” Journal of Inte-
grative Plant Biology, Vol. 52, No. 1, 2010, pp. 98-111.
[15] A. R. Tapas, D. M. Sakarkar and R. B. Kakde, “Flavon-
oids as Nutraceuticals: A Review,” Tropical Journal of
Pharmaceutical Research, Vol. 7, No. 3, 2008, pp.
[16] O. M. Andersen and K. R. Markham, “Flavonoids: Chem-
istry, Biochemistry, & Applications,” CRC Press, Taylor
& Francis, London, 2006.
[17] K. R. Markham, “Techniques of Flavonoid Identifica-
tion,” Academic Press, London, 1982.
[18] T. J. Mabry, K. R. Markham and M. B. Thomas, “The
Systematic Identification of Flavonoids,” Springer, New
York, 1970, pp. 24-26, 147, 332-333.
[19] K. R. Markham and T. J. Mabry, “Ultraviolet-Visible and
Proton Magnetic Resonance Spectroscopy of Flavon-
oids,” In: J. B. Harborne, T. J. Mabry and H. Mabry, Eds.,
The Flavonoids, Chapman and Hall, London, 1975, pp.
[20] J. B. Harborne and H. Baxter, “The Handbook of Natural
Flavonoids,” John Wiley and Sons, Chichester, Vol. 1-2.
[21] P. K. Agrawal, “Carbon-13 NMR of Flavonoids,” El-
sevier, Amsterdam, 1999.