Gallic acid esters from the stem bark of Mimusops elengi L.

Article abstract of DOI:10.1080/14786410902833989

Phytochemical investigation of the ethanolic extract of the stem bark of Mimusops elengi L. (Sapotaceae) led to the isolation of new gallic acid esters, characterised as phenyl propanoxyl gallate (1), β-D-glucopyranosyl (6′→1″)-β-D-glucopyranosyl-4″-(4″-e

Full text of DOI:10.1080/14786410902833989

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Gallic acid esters from the stem bark of
Mimusops elengi L.
Nida Akhtar a , Mohd. Ali b & Mohd. Sarwar Alam a
a Department of Chemistry, Faculty of Science , Jamia Hamdard
(Hamdard University) , New Delhi–110 062, India
b Department of Pharmacognosy and Phytochemistry, Faculty of
Pharmacy , Jamia Hamdard (Hamdard University) , New Delhi–110
062, India
Published online: 19 May 2010.
To cite this article: Nida Akhtar , Mohd. Ali & Mohd. Sarwar Alam (2010) Gallic acid esters from
the stem bark of Mimusops elengi L., Natural Product Research: Formerly Natural Product Letters,
24:10, 962-972, DOI: 10.1080/14786410902833989
To link to this article: http://dx.doi.org/10.1080/14786410902833989
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Natural Product Research
Vol. 24, No. 10, 15 June 2010, 962–972
Gallic acid esters from the stem bark of Mimusops elengi L.
Nida Akhtara, Mohd. Alib and Mohd. Sarwar Alam
*
a
aDepartment of Chemistry, Faculty of Science, Jamia Hamdard (Hamdard University),
New Delhi – 110 062, India; bDepartment of Pharmacognosy and Phytochemistry, Faculty of
Pharmacy, Jamia Hamdard (Hamdard University), New Delhi – 110 062, India
(Received 17 December 2008; final version received 20 March 2009)
Phytochemical investigation of the ethanolic extract of the stem bark of
Mimusops elengi L. (Sapotaceae) led to the isolation of new gallic acid
esters, characterised as phenyl propanoxyl gallate (1), ꢀ-D-glucopyranosyl
(60!100)–ꢀ-D-glucopyranosyl-400-(400-ethylphenyl) gallate (2), 20-(1000-gerany-
loxy)-ꢀ-D-glucopyranosyl (60!100)-ꢀ-D-glucopyranosyl-400-phenoxy gallate
(3), ꢀ-D-glucopyranosyl (60!100)–ꢀ-D-glucopyranosyl 3,4,5-trihydroxy
benzoate (4), ꢀ-D-glucopyranosyl-(6’!100)–ꢀ-D-glucopyranosyl-400-(4000-
n-butylphenyl) 3,4,5-trihydroxy benzoate (5), ꢀ-D-glucopyranosyl(6’!100)-
ꢀ-D-rhamnosyl 3,4,5-trihydroxy benzoate (6) and ꢀ-D-(20-phenyl glucopyr-
anosyl)-(60!100)–(200, 400-diphenylrhamnopyranosyl)-3,4,5-trihydroxylbenzoate
(7), along with the known compounds: farnon-3-one, stigmasta-5-en-3-ꢀ-ol,
olean-18-en-2-one-3-ol, lup-20(29)-en-3ꢀ-ol and stigmasta-5-en-3ꢀ-D-glu-
copyranoside. Their structures were elucidated on the basis of spectroscopic
analyses and chemical reactions.
Keywords: Mimusops elengi L.; Sapotaceae; stem bark; ethanolic extract;
gallic acid esters
1. Introduction
Mimusops elengi L. (Sapotaceae) is a large glabrous evergreen tree found in the
western Peninsula of India (Anonymous, 2003). The tree is planted throughout India
for its ornamental foliage and the fragrance of its flowers (Kirtikar & Basu, 1993). Its
bark is acrid, sweet, cardiotonic, alexipharmic, stomachic, anthelmintic, astringent,
and is also used to cure biliousness and diseases of the gums and teeth (Drury, 1873;
Kirtikar & Basu, 1993). It has exhibited antimicrobial, anti-ulcer, hypotensive, anti-
HIV and spasmolytic activities (Banerji, Prakash, Patnaik, & Nigam, 1982; Dar,
Behbahanian, Malik, & Jahan, 1999; Mundhada & Takte, 2005; Sahu, Mandal,
Banerjee, & Siddiqui, 2001; Shah, Gandhi, Shah, Goswami, & Santani, 2003).
Ursolic acid, betulinic acid, the fatty acid ester of ꢁ-spinasterol (Misra, Nigam, &
Mitra, 1974), 3ꢀ,6ꢀ,19ꢀ,23-tetrahydroxy-urs-12-ene, 1ꢀ-hydroxy-3ꢀ-hexanoyllup-
20(29)-ene-23,28-dioic acid and basic acid have been isolated from its bark (Jahan
et al., 2001; Varshney & Logani, 1969).
*Corresponding author. Email: mali_hamdard@yahoo.co.in; maliphyto@gmail.com
ISSN 1478–6419 print/ISSN 1029–2349 online
ß 2010 Taylor & Francis
DOI: 10.1080/14786410902833989
http://www.informaworld.com

Natural Product Research
963
2. Results and discussion
Compound 1, designated as elengigallate, was obtained as a pale brown amorphous
powder from chloroform:methanol (93:7) eluants. It gave a blue colour with aqueous
ferric chloride solution, indicating the phenolic nature of the molecule. Its IR
spectrum exhibited distinctive absorption bands for hydroxyl groups (3391,
3110 cmꢀ1), an ester group (1723 cmꢀ1) and unsaturation (1608 cmꢀ1). It had
a molecular ion peak at m/z 288 in its mass spectrum, corresponding to a molecular
formula of C16H16O5, for an alkylated diphenyl-type molecule. The 1H NMR
spectrum of 1 displayed two one-proton doublets at ꢂ 7.28 (J ¼ 2.5 Hz) and 7.26
(J ¼ 2.5 Hz) assigned to meta-coupled H-2 and H-6 aromatic protons. Two
multiplets at ꢂ 6.93 and 6.90 integrating for two protons each and a one-proton
multiplet at ꢂ 6.88 were attributed to aromatic protons of the second ring. A two-
proton broad multiplet at ꢂ 3.55 was associated with the oxygenated methylene
proton H2-90. Two two-proton multiplets at ꢂ 2.74 and 1.52 were ascribed to H2-70
and H2-80, methylene protons. The 13C NMR spectrum of 1 showed important
signals for an ester carbon at 167.49 (C-7), aromatic carbons between ꢂ 158.74 and
107.10, oxygenated methylene carbons at ꢂ 60.76 (C-90) and methylene carbons at
ꢂ 29.04 (C-70), 28.71 (C-80). The DEPT spectrum of 1 exhibited the presence of three
methylene, seven methine and six quaternary carbons. The HMBC spectrum of 1
showed correlations of C-7 with H-2/H-6 and H2-90, and C-10 with H2-70 and C-20/60.
Acid hydrolysis of 1 yielded gallic acid (TLC comparable). On the basis of this
spectral data analysis and chemical reactions, the structure of 1 has been elucidated
as phenyl propanoxyl gallate.
Compound 2, named mimusopstannin, was obtained as a brown-coloured
amorphous mass from chloroform:methanol (93:7) eluants. It responded positively
to a test for phenols and glycosides. Its IR spectrum exhibited distinctive absorption
bands for hydroxyl groups (3369, 3290 and 3160 cmꢀ1), an ester group (1722 cmꢀ1
)
and unsaturation (1606 cmꢀ1). On the basis of mass and 13C NMR spectra its
molecular weight was established as 598, consistent with the molecular formula of
a gallic acid diglucoside substituted with a phenoxy group, C27H34O15. The 1H NMR
spectrum of 2 showed a two-proton doublet at ꢂ 7.51 (J ¼ 2.6 Hz) assigned to meta-
coupled H-2 and H-6 protons. Two multiplets at ꢂ 7.45 and 5.23, integrating for two
protons each, were ascribed to aromatic H-2000, H-6000and H-3000, H-5000 protons,
respectively. Two doublets at ꢂ 5.23 (J ¼ 7.2 Hz) and 5.01 (J ¼ 7.1 Hz) were attributed
to anomeric H-10 and H-100 protons, respectively. The remaining sugar protons
appeared between at ꢂ 4.56 and 3.38. The deshielded signals at ꢂ 4.03 (H-400) and 3.46
(H2-60) supported the location of the phenoxy ring at C-400 and another sugar linkage
at C-60. A two-proton multiplet at ꢂ 2.73 and a three-proton triplet at ꢂ 0.82
(J ¼ 7.8 Hz) were accounted to methylene H2-7000 protons attached to the phenyl ring
and primary methyl H3-8000 protons, respectively. The 13C NMR spectrum of 2
exhibited signals for an ester carbon in deshielded range at ꢂ 169.13 (C-7), aromatic
carbons between ꢂ 159.06 and 110.16, a C-7000 methylene carbon at ꢂ 18.12, a methyl
carbon at ꢂ 8.9, anomeric carbons at ꢂ 102.97 (C-10) and 100.09 (C-100), and sugar
carbons between ꢂ 75.50 and 60.88. The C-60 at ꢂ 65.84 and C-400 at ꢂ 69.88 were
shifted in a deshielded region due to the attachment of the second sugar moiety and
phenoxy group, respectively. The DEPT spectrum of 2 showed the presence of
one methyl, three methylene, 16 methine and seven quarternary carbons. The HMBC

964
N. Akhtar et al.
spectrum of 2 displayed the interaction of C-7 with H-2/6 and H-10, C-100 with H2-60
and H-200, and C-1000 with H-400 and H-2000/6000. Acid hydrolysis of 2 yielded gallic acid
and glucose (TLC comparable). On the basis of the above findings, the structure of 2
has been elucidated as ꢀ-D-glucopyranosyl (6’!100)–ꢀ-D-glucopyranosyl-400-(4000-
ethylphenyl) gallate.
Compound 3, designated as elengitannin, was obtained as a yellowish brown
amorphous mass from chloroform:methanol (93:7) eluants. It gave a positive test for
phenols and glycosides. Its IR spectrum exhibited absorption bands for hydroxyl
groups (3435, 3260 cmꢀ1), an ester group (1722 cmꢀ1) and unsaturation (1610 cmꢀ1).
On the basis of mass and 13C NMR spectra its molecular weight was established as
698, consistent with a molecular formula C34H50O15, corresponding to a gallic acid
diglycoside attached to monoterpenic and phenyl moieties. The mass spectrum
showed prominent ion fragments at m/z 239 [C6H10O5–C6H5]þ, 255 [C6H10O6–
C6H5]þ, 459 [M–239]þ and 443 [M–255]þ, indicating the location of the phenyl ring
to the terminal sugar moiety. The ion fragments arising at m/z 153 [CO–
C6H3(OH)3]þ, 169 [OCO–C6H3(OH)3]þ and 313 [C6H10O5–CO C6H3(OH)3]þ
supported the attachment of gallic acid with a glucose moiety. The ion peaks
generated at m/z 141 [C10H21]þ and 157 [C10H21O]þ suggested that an acyclic
1
monoterpenic moiety was linked to the sugar residue. The H NMR spectrum of 3
showed a 2-proton doublet at ꢂ 7.45 (J ¼ 2.3 Hz) assigned to meta-coupled H-2 and
H-6 protons, and three multiplets at ꢂ 7.43 (2H), 7.40 (2H) and 6.92 (1H) ascribed to
the remaining aromatic protons. Two one-proton doublets at ꢂ 5.26 (J ¼ 7.1 Hz) and
4.96 (J ¼ 6.9 Hz) were attributed to anomeric H-10 and H-100 protons, respectively.
The remaining sugar protons resonated between ꢂ 4.03 and 3.19. The shifting of the
1H NMR signal at ꢂ 3.62 (H-400), 3.43 (H2-60) in the deshielded region indicated the
attachment of a phenoxy group at C-400 and another sugar–sugar moiety at C-60. The
oxygenated methylene protons appeared as broad signals at ꢂ 3.43 (H2-6), 3.21 (H2-
100) and 3.19 (H2-1000). A three-proton doublet at ꢂ 1.03 (J ¼ 6.1 Hz) and a six-proton
broad signal at ꢂ 0.79 were associated with the secondary C-8000 methyl and two C-9000
and C-10000 methyl protons, respectively. The other methine and methylene protons
resonated between ꢂ 2.51 and 1.18. The 13C NMR spectrum of 3 displayed signals for
an ester carbon at ꢂ 167.49 (C-7), aromatic carbons between 158.68 and 110.27,
anomeric carbons at ꢂ 107.14 (C-10) and 102.94 (C-100), sugar carbons between ꢂ 76.81
and 61.93, and monoterpenic carbons in the range ꢂ 60.90–11.51. The HMBC
spectrum of 3 showed correlation of C-7 with H-10 and H-2/6, C-100 with H-200 and
H2-60, and C-1a with H-400 and C-1000 with H-20 and H2-2000. Acid hydrolysis of 3
yielded gallic acid (TLC comparable). On the basis of the above-mentioned findings,
the structure of 3 has been elucidated as 20-(1000-geranyloxy)-ꢀ-D-glucopyranosyl
(60!100)-ꢀ-D-glucopyranosyl-400-phenoxy gallate.
Compound 4, designated as gallic acid diglucoside, was obtained as colourless
amorphous powder from chloroform:methanol (23:2) eluants. Its IR spectrum
exhibited absorption bands for hydroxyl groups (3366, 3210 and 3060 cmꢀ1) and an
ester group (1723 cmꢀ1). It had a molecular ion peak at m/z 494 in its mass spectrum,
corresponding to a molecular formula of gallic acid diglycoside, C19H26O15. The
1H NMR spectrum of 4 displayed two one-proton doublets at ꢂ 7.52 (J ¼ 3.0 Hz)
and 7.44 (J ¼ 3.0 Hz) assigned to meta-coupled aromatic H-2 and H-6 protons,
respectively. Two one-proton doublets at ꢂ 4.99 (J ¼ 6.6 Hz) and 4.96 (J ¼ 6.6 Hz) were
ascribed to anomeric protons H-10 and H-100, respectively. Two broad signals at ꢂ 3.38

Natural Product Research
965
and 3.28, both integrating for two-protons each, were attributed as corresponding to
oxygenated methylene protons H2-60 and H2-600, and a deshielded signal at ꢂ 3.38
indicated that the second sugar proton was attached to the H2-60 group. The remaining
carbinol protons of the sugar units appeared between ꢂ 4.04 and 3.40. The 13C NMR
spectrum of 4 showed an important signal for an ester carbon at ꢂ 170.12 (C-7),
aromatic carbons in the range of ꢂ 162.98–111.36, anomeric carbons at ꢂ 110.22 (C-10)
and 102.89 (C-100) and sugar carbons between ꢂ 75.50 and 60.90. The presence of C-60
resonance in the deshielded region at ꢂ 65.84 supported attachment of the second sugar
moiety at C-60. The HMBC spectrum of 4 showed interactions of C-7 with H-10
and H-2/6, and C-100 with H2-60 and H-200. Acid hydrolysis of 4 yielded gallic acid and
D-glucose (TLC comparable). On the basis of this spectral data analysis and
chemical reactions, the structure of 4 has been established as ꢀ-D-glucopyranosyl
(60!100)–ꢀ-D-glucopyranosyl 3,4,5-trihydroxy benzoate.
Compound 5, designated as gallic acid phenoxy diglucoside, was obtained as a
pale brown coloured amorphous powder from chloroform:methanol (23:2)
eluants. It gave a positive test for phenols and glycosides. Its IR spectrum
exhibited characteristic absorption bands for hydroxyl groups (3362, 3310 and
3260 cmꢀ1) and an ester group (1722 cmꢀ1). On the basis of mass and 13C NMR
spectra its molecular weight was established as 626, consistent with the molecular
formula C29H38O15 for a gallic acid diglucoside substituted with a phenyl ring.
The 1H NMR spectrum of 5 showed two one-proton doublets at ꢂ 7.51
(J ¼ 2.7 Hz) and 7.44 (J ¼ 2.7 Hz) assigned to meta-coupled aromatic H-2 and H-6
protons, respectively. Two multiplets at ꢂ 6.92 and 6.88, integrated for two-
protons each, were ascribed the aromatic H-2000, H-6000 and H-3000, H-5000 protons,
respectively. Two one-proton doublets at ꢂ 5.48 (J ¼ 7.0 Hz) and 4.94 (J ¼ 7.2 Hz)
were attributed correspondingly to anomeric H-10 and H-100. The remaining sugar
protons appeared in the range of ꢂ 4.53–3.28. The shifting of oxygenated
methylene H2-60 protons at ꢂ 3.40 and 3.36, and the carbinol H-400 proton at ꢂ
4.04 in the deshielded region indicated the attachment of the second sugar moiety
at C-60 and a phenyl group at C-400. Three two-proton signals as a multiplet at ꢂ
2.51 and as broad signals at ꢂ 0.92 and 0.87 were associated with the methylene
H2-7000, H2-8000 and H-900 protons. A three-proton triplet at ꢂ 0.62 (J ¼ 6.5 Hz) was
accounted to primary C-10000 methyl protons. The 13C NMR spectrum of 5
displayed signals for an ester carbon at ꢂ 171.66 (C-7), aromatic carbons between
ꢂ 167.43 and 108.71, anomeric carbons at ꢂ 100.10 (C-10) and 103.12 (C-100), other
sugar carbons in the range of ꢂ 76.90–61.07, methylene carbons at ꢂ 33.16 (C-7000),
29.15 (C-8000) and 28.98 (C-9000), and methyl carbons at ꢂ 17.09 (C-10000). The
DEPT spectrum of 5 showed the presence of one methyl, five methylene, 16
methine and seven quaternary carbons. The HMBC spectrum of 5 exhibited
correlation of C-7 with H-2/6 and H-10, C-100 with H2-60 and H-200, C-1000 with
H-400 and H-2000/6000, and C-10000 with H2-9000. Acid hydrolysis of 5 yielded gallic
acid and glucose. On the basis of the above-mentioned data, the structure of 5
has been elucidated as ꢀ-D-glucopyranosyl-(60!100)–ꢀ-D-glucopyranosyl-400-(4000-n-
butylphenyl)3,4,5-trihydroxy benzoate.
Compound 6, designated as elengibenzyl diglycoside, was obtained as a brown
coloured amorphous mass from chloroform:methanol (9:1) eluants. It gave a positive
test for phenols and glycosides. Its IR spectrum exhibited characteristic absorption
bands for hydroxyl groups (3384 and 3280 cmꢀ1) and an ester group (1722 cmꢀ1).

966
N. Akhtar et al.
On the basis of mass and 13C NMR spectra, its molecular weight was established as
478, consistent with the molecular formula of a gallic acid diglycoside, C19H26O14.
1
The H NMR spectrum of 6 showed two one-proton deshielded doublets at ꢂ 7.58
(J ¼ 2.5 Hz) and 7.51 (J ¼ 2.5 Hz) assigned to meta-coupled H-2 and H-6,
respectively. Two one-proton doublets at ꢂ 5.54 (J ¼ 7.1 Hz) and 5.01 (J ¼ 7.2 Hz)
were ascribed correspondingly to anomeric H-10 and H-100 protons. The remaining
sugar protons appeared in the range of ꢂ 4.09–3.38. A three-proton doublet at ꢂ 1.20
(J ¼ 6.2 Hz) was accounted to the C-600 methyl proton of rhamnose unit. The shifting
of the C-60 oxygenated methylene protons in the deshielded region at ꢂ 3.38 indicated
the attachment of a second monosaccharide unit at C-60. The 13C NMR spectrum of
6 displayed signals for an ester carbon at 169.11 (C-7), anomeric signals at ꢂ 102.97
(C-10) and 100.12 (C-100), other sugar carbons in the range ꢂ 75.54–63.08, a methyl
carbon at ꢂ 17.88 (C-600) and aromatic carbons between ꢂ 158.65 and 110.19.
The HMBC spectrum of 6 showed the correlations C-7 with H-10 and H-2/H-6, C-100
with H2-60 and H-200, and C-600 with H-500. Acid hydrolysis of 6 yielded gallic acid,
glucose and rhamnose (TLC comparable). On the basis of the above-mentioned
discussion, the structure of 6 has been elucidated as ꢀ-D-glucopyranosyl (60!100)-ꢀ-D-
rhamnosyl 3,4,5-trihydroxy benzoate.
Compound 7, designated as gallic acid triphenoxy diglycoside, was obtained
as a light brown amorphous powder from chloroform:methanol (9:1) eluants.
It responded positively to the test for phenols and glycosides. Its IR spectrum
exhibited characteristic absorption bands for hydroxyl groups (3480, 3396 and
3285 cmꢀ1), an ester group (1723 cmꢀ1) and unsaturation (1607 cmꢀ1). On the basis
of mass and 13C NMR spectra its molecular weight was established as 706, consistent
with the molecular formula C37H38O14 of a gallic acid diglucoside substituted with
0
phenyl rings. The prominent ion fragments generated at m/z 391, 315 [C4 –O
fission]þ suggested that rhamnose was the terminal sugar to which two phenyl rings
were attached. The ion peaks arising at m/z 153 [C7–O fission]þ and 125 [C1–C7
fission]þ indicated the location of the gallic acid moiety attached to the glucose. The
1H NMR spectrum of 7 showed two one-proton doublets at ꢂ 7.98 (J ¼ 2.3 Hz) and
7.69 (J ¼ 2.3 Hz) assigned to meta-coupled aromatic H-2 and H-6 protons,
respectively. Seven multiplets between ꢂ 7.86 and 6.73 were ascribed to the other
aromatic protons. Two one-proton doublets at ꢂ 5.17 (J ¼ 7.1 Hz) and 5.12
(J ¼ 7.0 Hz) were attributed to anomeric H-10 and H-100 protons, respectively.
A three-proton doublet at ꢂ 1.30 (J ¼ 6.5 Hz) was accounted to the C-600 secondary
methyl proton of the rhamnose unit. The remaining sugar protons resonated in the
range ꢂ 4.29–3.35. The deshielded two-proton oxygenated methylene proton signal at
ꢂ 3.35 indicated the attachment of the second sugar unit at C-60. The 13C NMR
spectrum of 7 showed signals for an ester carbon at ꢂ 169.13 (C-7), aromatic carbons
in the range ꢂ 158.49–110.24, anomeric carbons at ꢂ 103.01 (C-10) and 100.13
(C-100), sugar carbons between ꢂ 75.48 and 60.91, and a methyl carbon at ꢂ 17.94
(C-600). The HMBC spectrum of 7 exhibited that C-7 interacted with H-10 and H2/6,
C-100 interacted with H-200 and H2-60 and aromatic C-1 interacted with aromatic H-2/
H-6, H-20/200 and H-400. Acid hydrolysis of 7 yielded gallic acid, glucose and
rhamnose (TLC comparable). On the basis of the above-mentioned findings, the
structure of 7 has been elucidated as ꢀ-D-(20-phenylglucopyranosyl)-(60!100)–
(200, 400-diphenylrhamnopyranosyl)-3,4,5-trihydroxybenzoate (Figure 1).

Natural Product Research
967
HO
4
3
2
6
6’
6’’
5’
4’
HO
9’
7
1
HO
COO (CH )
OH
OH
2 3
1’
2’
5
4’’
3’
OH
HO
R
1 = H,
R2
=
5
1
O
1’’’
O
H
2’’’
6’’’
3
2
7
1
4
6’
R2O
CH
7’’’
CH
CO
O
O
H
2
2
2
3
5
8’’’
O
6
O
H
1’
CH
4’
9’’’
O
OH
H
10’’’CH
6’’
OR1
O
O
H
H
O
3
O
6’’
CH
4’’
R2
=
1’’
R
1 = H,
1’’
6
O
H
OH
R2
=
O
R1 = H
2
HO
O
2’’’
H
OH
1’’’
6’’’
5’’
6’’
O
O
CH
OH
7’’’
3
CH2
1’’
8’’’
CH
3
O
1a
R2
=
6a
1c
1b
6’’
HO
R1
=
7
6b
6c
2’’’
O
9’’’
1’’’
6’’’
1’’
R2
=
OH
8’’’
R1
=
O
1a
3
10’’’
OH
6a
2a
OH
1’’
6’’
HO
O
R2
=
R1 = H,
4
4’’
OH
OH
OH
Figure 1. Structures of compounds 1–7.
3. Experimental
3.1. General experimental procedures
Melting points were determined on a Perfit melting point apparatus (Ambala, India)
and are uncorrected. IR spectra were recorded on KBr discs, using a Bio-Rad FT-IR
5000 spectrometer (FTS 135, Hongkong). UV spectra were measured with a Lambda
1
Bio 20 spectrophotometer (Perkin Elmer, Switzerland) in methanol. H and 13C
NMR spectra were scanned using Bruker Advance DRY 400 spectrospin and Bruker
Advance DRY 100 spectrospin instruments (Germany), respectively, in CDCl3 and
with TMS as an internal standard. FAB MS spectra were obtained using a Jeol-JMS-
DX 303 spectrometer (USA). Column chromatography was performed on silica gel
(Qualigens, Mumbai, India) 60–120 mesh. TLC was run on silica gel G (Qualigens,
Mumbai, India). Spots were visualised when exposed to iodine vapours, UV
radiation and by spraying reagents.

968
N. Akhtar et al.
3.2. Plant material
The barks of M. elengi were purchased from the Khari Baoli local market of Delhi
and authenticated by Dr H.B. Singh, Taxonomist, NISCAIR, CSIR, New Delhi.
A voucher specimen (no. PRL/JH/03/05) is deposited in the Herbarium of the
Phytochemical Research Laboratory, Faculty of Pharmacy, Jamia Hamdard,
New Delhi.
3.3. Extraction and isolation
The bark of M. elengi was dried in an oven at 45ꢁC for 2–3 days and coarsely
powdered. The ground bark (3 kg) was extracted with ethanol in a Soxhlet
apparatus. The ethanol extract was concentrated under reduced pressure to yield
a dark brown viscous mass (120 g, 4.0%). The extract was dissolved in a minimum
amount of methanol and adsorbed on silica gel (60–120 mesh) for preparation of the
slurry. The air-dried slurry was chromatographed over the silica gel column packed
in petroleum ether (60–80ꢁC). The column was eluted with petroleum ether,
petroleum ether:chloroform (9:1, 3:1, 1:1, 1:3 v/v), chloroform, chloroform:methanol
(99:1, 98:2, 95:5, 9:1, 3:1, 1:1, 1:3 v/v) and methanol successively, in order of increas-
ing polarity, to isolate the following compounds.
Elengigallate (1): Elution of the column with chloroform:methanol (93:7) gave a pale
brown amorphous powder of 1, recrystallised from methanol; 115 mg (0.003%); Rf:
0.64 (toluene : ethyl acetate : formic acid; 5:4:1); m.p. 255–256ꢁC; UV ꢃmax (MeOH):
215, 255 nm (log " 4.8,2.7); IR ꢄmax (KBr): 3391, 3110, 2921, 2845, 1723, 1608, 1431,
1
1340, 1196, 1113, 1062, 1030, 970, 918, 870 and 757 cmꢀ1; H NMR (DMSO-d6):
ꢂ 7.28 (1H, d, J ¼ 2.5 Hz, H-2), 7.25 (1H, d, J ¼ 2.5 Hz, H-6), 6.93 (2H, m, H-20, H-60),
6.90 (2H, m, H-30, H-50), 6.88 (1H, m, H-40), 3.55 (2H, brm, H2-90), 2.74 (2H, m, H2-
70), 1.52 (2H, m, H2-80); 13C NMR (DMSO-d6): ꢂ 141.31 (C-1), 110.40 (C-2), 145.22
(C-3), 158.74 (C-4), 148.17 (C-5), 111.48 (C-6), 167.49 (C-7), 151.99 (C-10), 139.79
(C-20), 107.10 (C-30), 112.30 (C-40), 120.48 (C-50), 137.79þ(C-60), 29.04 (C-70), 28.71
(C-80), 60.76 (C-90); þve FABMS m/z (rel. int.): 288 [M] (C16H16O5) (71.3).
Acid hydrolysis: Compound 1 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. The solution was extracted with EtOAc
(3 ꢂ 10 mL), washed with water (2 ꢂ 10 mL), dried over Na2SO4 and evaporated to
give 3-phenyl propanol; IR ꢄmax 3450 cmꢀ1. The aqueous phase was dried under
reduced pressure, dissolved in methanol and crystallised to get needles of gallic acid,
m.p. 235–238ꢁC decomposition.
Mimusopstannin (2): Further elution of the column with chloroform:methanol (93:7)
furnished a brown coloured amorphous powder of 2, recrystallised from methanol;
110 mg (0.003%); Rf: 0.42 (toluene:ethyl acetate:formic acid; 5:4:1); m.p. 298–300ꢁC
(decomp.); UV ꢃmax (MeOH): 253 nm (log " 5.7); IR ꢄmax (KBr): 3369, 3290, 3160,
1
2921, 2850, 1722, 1606, 1578, 1494, 1439, 1349, 1101, 1047 and 967 cmꢀ1; H NMR
(DMSO-d6): ꢂ 7.51 (2H, d, J ¼ 2.6 Hz, H-2, H-6), 7.45 (2H, m, H-2000, H-6000), 7.39
(2H, m, H-3000, H-5000), 5.23 (1H, d, J ¼ 7.2 Hz, H-10), 5.01 (1H, d, J ¼ 7.1 Hz, H-100),
4.56 (2H, m, H-50, H-500), 4.47 (2H, m, H-20, H-200), 4.03 (1H, m, H-400), 3.87 (1H, m, H-
40), 3.61 (2H, m, H-30, H-300), 3.46 (2H, brs, H2-60), 3.38 (2H, brs, H2-600), 2.73
(2H, m, H2-7000), 0.82 (3H, t, J ¼ 7.8 Hz, Me-8).; 13C NMR (DMSO-d6): ꢂ 146.09

Natural Product Research
969
(C-1), 139.66 (C-2), 159.06 (C-3), 152.58 (C-4), 148.09(C-5), 136.30 (C-6), 169.13
(C-7), 102.97 (C-10), 71.78 (C-20), 69.85 (C-30), 69.28 (C-40), 73.00 (C-50), 65.84 (C-60),
100.09(C-100), 71.76 (C-200), 69.28 (C-300), 69.88 (C-400), 75.50 (C-500), 60.88 (C-600),
158.57 (C-1000), 114.16 (C-2000), 112.85 (C-3000), 141.44 (C-4000), 111.42 (C-5000), 110.16
(C-6000), 18.2 (C-7000), 8.9 (C-8000); þve FABMS m/z (rel. int.): 598 [M]þ (C27H34O15)
(1.1), 127 (31.7).
Acid hydrolysis: Compound 2 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. It was dried under reduced pressure and the
residue was dissolved in methanol to separate gallic acid, m.p. 236–237ꢁC. The
residue was redissolved in water and analysed by paper chromatography along with
standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2) was used as
the developing solvent system. The paper was sprayed with aniline hydrogen
phthalate. The sugar was identified as D-glucose.
Elengitannin (3): Further elution of the column with chloroform:methanol (93:7)
afforded yellowish brown amorphous mass of 3, recrystallised from methanol;
189 mg (0.006%); Rf: 0.68 (toluene:ethyl formate:formic acid; 10:10:3); m.p.: 286–
287ꢁC; UV ꢃmax (MeOH): 219, 253 nm (log " 2.1,1.1); IR ꢄmax (KBr): 3435, 3260,
2922, 2846, 1722, 1610, 1583, 1495, 1440, 1348, 1210, 1102 and 1062 cmꢀ1; 1H NMR
(DMSO-d6): ꢂ 7.45 (2H, d, J ¼ 2.3 Hz, H-2, H-6), 7.43 (2H, m, H-2a, H-6a), 7.40
(2H, m, H-3a, H-5a), 6.92 (1H, m, H-4a), 5.26 (1H, d, J ¼ 7.1 Hz, H-10), 4.96
(1H, d, J ¼ 6.9 Hz, H-100), 4.03 (2H, m, H-50, H-500), 3.83 (2H, m, H-20, H-200), 3.62
(1H, m, H-400), 3.51 (2H, m, H-30, H-300), 3.49 (1H, m, H-40) 3.43 (2H, brs, H2-60),
3.21 (2H, brs, H2-1000), 3.19 (2H, brs, H2-1000), 2.51 (2H, m, H-3000, H-700), 1.92
(2H, m, H2-2000), 1.21 (2H, m, H-4000), 1.18 (4H, brs, H2-5000, H2-6000), 1.03
(3H, d, J ¼ 6.1 Hz, Me-8000), 0.79 (6H, brs, H3-9000, H3-10000); 13C NMR: ꢂ 141.32 (C-
1), 140.07 (C-2), 158.68 (C-3), 148.19 (C-4), 152.03 (C-5), 139.74 (C-6), 167.49 (C-7),
107.14 (C-10), 75.46 (C-20), 70.05 (C-30), 69.35 (C-40), 76.81 (C-50), 65.91 (C-60),
102.94 (C-100), 73.49 (C-200), 69.35 (C-300), 72.11 (C-400), 76.81 (C-500), 61.93 (C-600),
60.90 (C-1000), 31.47 (C-2000), 36.84 (C-3000), 29.29 (C-4000), 29.29 (C-5000), 22.21 (C-6000),
34.38 (C-7000), 18.93 (C-8000), 13.78 (C-9000), 11.51 (C-10000), 148.19 (C-1a), 112.29 (C-2a),
111.32 (C-3a), 108.76 (C-4a), 110.27 (C-5a), 112.00(C-6a); þ ve FABMS m/z (rel. int.):
698 [M]þ (C34H50O15), 459 (10.2), 443 (12.6), 329 (17.8), 313 (11.5), 255 (22.6), 239
(19.2), 169 (21.3), 157 (26.2), 153 (29.8), 141 (24.8).
Acid hydrolysis: Compound 3 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. The solution was dried under reduced
pressure and the residue was dissolved in methanol to isolate gallic acid, m.p. 235–
238ꢁC. The residue was redissolved in water and analysed by paper chromatography
along with standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2)
was used as the developing solvent system. The paper was sprayed with aniline
hydrogen phthalate. The sugar was identified as D-glucose.
Gallic acid diglucoside (4): Elution of the column with chloroform:methanol (23:2)
afforded a colourless amorphous powder of 4, recrystallised from methanol; 100 mg
(0.003%); Rf: 0.78 (toluene:ethyl acetate:formic acid; 5:4:1); m.p. 310–312ꢁC; UV
ꢃ
max (MeOH): 253 nm (log " 6.3); IR ꢄmax (KBr): 3366, 3210, 3060, 2928, 2850, 1723,
1
1606, 1581, 1494, 1429, 1360, 1187, 1102, 1058, 975, 914 and 755 cmꢀ1; H NMR
(DMSO-d6): ꢂ 7.52 (1H, d, J ¼ 3.0 Hz, H-2), 7.44 (1H, d, J ¼ 3.0 Hz, H-6), 4.99

970
N. Akhtar et al.
(1H, d, J ¼ 6.6 Hz, H-10), 4.96 (1H, d, J ¼ 6.6 Hz, H-100), 4.04 (2H, m, H-50, H-500), 3.86
(1H, m, H-20), 3.84 (1H, m, H-200), 3.40 (4H, m, H-30, H-300, H-40, H-400), 3.38 (2H, brs,
H2-60), 3.28 (2H, brs, H2-600); 13C NMR (DMSO-d6): 139.85 (C-1), 138.62 (C-2),
158.64 (C-3), 162.98 (C-4), 152.62 (C-5), 111.36 (C-6), 170.12 (C-7), 110.22 (C-10),
73.00 (C-20), 64.84 (C-30), 69.26 (C-40), 75.50 (C-50), 65.84 (C-60), 102.89 (C-100), 73.09
(C-200), 69.31 (C-300), 69.26 (C-400), 75.50 (C-500), 60.90 (C-600); FAB-MS m/z (rel. int.):
494 [M]þ (C19H26O15).
Acid hydrolysis: Compound 4 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. The solution was dried under reduced
pressure and the residue was dissolve in methanol to separate gallic acid, m.p. 236–
239ꢁC. The residue was dissolved in water and analysed by paper chromatography
along with standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2)
was used as the developing solvent system. The paper was sprayed with aniline
hydrogen phthalate. The sugar was identified as D-glucose.
Gallic acid phenoxy diglucoside (5): Further elution of the column with
chloroform:methanol (23:2) afforded a pale brown amorphous powder of 5,
recrystallised from methanol; 800 mg (0.026%); Rf: 0.64 (toluene:ethyl formate:
formic acid; 10:10:3); m.p. 187–188ꢁC; UV ꢃmax (MeOH): 259 nm (log " 5.2);
IR ꢄmax (KBr): 3362, 3310, 3260, 2930, 2850, 1722, 1611, 1494, 1332, 1196, 1104
and 1027 cmꢀ1
;
1H NMR (DMSO-d6): ꢂ 7.51 (1H, d, J ¼ 2.7 Hz, H-2), 7.44
(1H, d, J ¼ 2.7 Hz, H-6), 6.92 (2H, m, H-2000, H-6000), 6.88 (2H, m, H-3000, H-5000), 5.48
(1H, d, J ¼ 7.0 Hz, H-100), 4.94 (1H, d, J ¼ 7.2 Hz, H-10), 4.53 (2H, m, H-50, H-500),
4.45 (2H, m, H-20, H-200), 4.04 (1H, m, H-400), 3.91 (1H, m, H-40), 3.63 (2H, m,
H-30, H-300), 3.40 (1H, d, J ¼ 10.8 Hz, H2-6a), 3.36 (1H, d, J ¼ 10.8 Hz, H2-60b), 3.32
(1H, d, J ¼ 10.1 Hz, H2-100a), 3.28 (1H, d, J ¼ 10.1 Hz, H2-100b), 2.51 (2H, m, H2-7000),
0.92 (2H, brs, H2-8000), 0.87 (2H, brs, H2-9000), 0.62 (3H, t, J ¼ 6.5 Hz, Me-10000);
13C NMR (DMSO-d6): ꢂ 141.76 (C-1), 136.12 (C-2), 152.65 (C-3), 120.43 (C-4),
167.43 (C-5), 111.36 (C-6), 171.66 (C-7), 100.10 (C-10), 73.16 (C-20), 69.44 (C-30),
66.01 (C-40), 76.90 (C-50), 63.19 (C-60), 103.12 (C-100), 72.58 (C-200), 70.02(C-300),
71.94 (C-400), 76.81 (C-500), 61.07 (C-600), 158.31 (C-1000), 115.89 (C-2000), 112.85
(C-3000), 141.03 (C-4000), 110.18 (C-5000), 108.71 (C-6000), 33.16 (C-7000), 29.15 (C-8000),
28.98 (C-9000), 17.99 (C-10000); þve FABMS m/z (rel. int.): 626 [M]þ (C29H38O15).
Acid hydrolysis: Compound 5 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. The solution was dried under reduced
pressure and the residue was dissolved in methanol to separate gallic acid, m.p. 237–
239ꢁC. The residue was redissolved in water and analysed by paper chromatography
along with standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2)
was used as the developing solvent system. The paper was sprayed with aniline
hydrogen phthalate. The sugar was identified as D-glucose.
Elengibenzyl diglycoside (6): Elution of the column with chloroform:methanol (9:1)
afforded a brown amorphous mass of 6, recrystallised from methanol; 98 mg
(0.003%); Rf: 0.62 (toluene:ethyl formate:formic acid; 10:10:3); m.p. 288–290ꢁC; UV
ꢃmax (MeOH): 216, 256 nm (log " 2.1,6.2); IR ꢄmax (KBr): 3384, 3280, 2921, 2851,
1
1722, 1606, 1496, 1438, 1364, 1175, 1100 and 1033 cmꢀ1; H NMR (DMSO-d6): ꢂ
7.58 (1H, d, J ¼ 2.5 Hz, H-2), 7.51 (1H, d, J ¼ 2.5 Hz, H-6), 5.54 (1H, d, J ¼ 7.1 Hz,
H-100), 5.01 (1H, d, J ¼ 7.2 Hz, H-10), 4.09 (1H, brm, H-50), 4.05 (1H, m, H-500), 3.89

Natural Product Research
971
(2H, m, H-20, H-200), 3.87 (2H, m, H-3000, H-300), 3.48 (2H, m, H-40, H-400), 3.38 (2H, brs,
H2-60), 1.20 (3H, d, J ¼ 6.2 Hz, Me-600); 13C NMR (DMSO-d6):139.70 (C-1), 111.83
(C-2), 158.65 (C-3), 148.13 (C-4), 152.70 (C-5), 110.19 (C-6), 169.11 (C-7), 102.97 (C-
10), 73.06 (C-20), 65.96 (C-30), 68.05 (C-40), 75.54 (C-50), 63.08 (C-60), 100.12 (C-100),
73.03 (C-200), 65.37 (C-300), 68.15 (C-400), 75.54 (C-500), 17.88 (C-600); þve FABMS m/z:
480 [M]þ (C19H26O14).
Acid hydrolysis: Compound 6 (20 mg) was dissolved in MeOH and 2 N HCl (1:1)
and heated until half of the volume was left. The solution was dried under reduced
pressure and the residue was dissolved in methanol to separate gallic acid, m.p. 234–
237ꢁC. The residue was redissolved in water and analysed by paper chromatography
along with standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2)
was used as the developing solvent system. The paper was sprayed with aniline
hydrogen phthalate. The sugars were identified as D-glucose and D-rhamnose.
Gallic acid triphenoxy diglycoside (7): Further elution of the column with
chloroform:methanol (9:1) yielded a light amorphous powder of 7, recrystallised
from methanol; 123 mg (0.004%); Rf: 0.63 (toluene:ethyl formate:formic acid;
10:10:3); m.p. 239–240ꢁC; UV ꢃmax (MeOH): 253, 356 nm (log " 5.2,1.3). IR ꢅmax
(KBr): 3480, 3396, 3285, 2919, 2850, 1723, 1607, 1493, 1439, 1350, 1187, 1104,
1050 and 968 cmꢀ1
;
1H NMR (DMSO-d6): ꢂ 7.98 (1H, d, J ¼ 2.3 Hz, H-2), 7.86
(1H, m, H-6a), 7.82 (2H, m, H-2b, H-6b), 7.69 (1H, d, J ¼ 2.3 Hz, H-6), 7.34
(2H, m, H-2c, H-6c), 7.34 (2H, m, H-3a, H-5a), 7.04 (2H, m, H-3b, H-5b), 6.87
(2H, m, H-3c, H-5c), 6.73 (3H, brm, H-4a, H-4b, H-4c), 5.17 (1H, d, J ¼ 7.1 Hz, H-
10), 5.12 (1H, d, J ¼ 7.0 Hz, H-100), 4.29 (2H, m, H-50, H-500), 4.16 (2H, m, H-20, H-200),
3.87 (2H, m, H-30, H-300), 3.81 (1H, m, H-400) 3.72 (1H, m, H-40), 3.35 (2H, brs, H2-
60), 1.30 (3H, d, J ¼ 6.5 Hz, Me-600); 13C NMR (DMSO-d6): oC 148.09 (C-1), 140.13
(C-2), 158.49 (C-3), 158.48 (C-4), 158.48 (C-5), 139.57 (C-6), 169.13 (C-7), 152.64
(C-1a), 141.57 (C-2a), 111.03 (C-3a), 139.57 (C-4a), 114.13 (C-5a), 146.94 (C-6a),
152.00 (C-1b), 146.43 (C-2b), 110.24 (C-3b), 135.89 (C-4b), 135.92 (C-5b), 141.13
(C-6b), 152.64 (C-1c), 144.10 (C-2c), 139.57 (C-3c), 135.89 (C-4c), 111.45 (C-5c),
140.01 (C-6c), 103.01 (C-10), 73.08 (C-20), 69.94 (C-30), 69.36 (C-40), 75.48 (C-50),
60.91 (C-60), 100.13 (C-100), 73.08 (C-200), 69.36 (C-300), 71.89 (C-400), 75.48 (C-500),
17.94 (C-6); þve FABMS m/z: 706 [M]þ (C37H38O14), 391 (19.6), 315 (70.5), 153
(25.2), 125 (21.3).
Acid hydrolysis: Compound 7 (20 mg) was dissolved in MeOH and 2 N HCl (1:1) and
heated until half of the volume was left. The solution was dried under reduced
pressure and the residue was dissolved in methanol to separate gallic acid, m.p. 235–
237ꢁC. The residue was redissolved in water and analysed by paper chromatography
along with standard samples of monosaccharides. Butanol:ethanol:water (4:1:2.2)
was used as the developing solvent system. The paper was sprayed with aniline
hydrogen phthalate. The sugars were identified as D-glucose and D-rhamnose.
Acknowledgements
The authors are thankful to the Head, Regional Sophisticated Center, Central Drug Research
Institute, Lucknow for recording spectral data of the compounds.

972
N. Akhtar et al.
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