Phytochemical investigation of the seeds of Althea officinalis L.

Article abstract of DOI:10.1080/14786411003650777

Phytochemical investigation of the seeds of Althea officinalis L. (Malvaceae) led to the isolation of three new phytoconstituents, identified as n-hexacos-2-enyl-1,5-olide (altheahexacosanyl lactone), 2-hydroxycalamene (altheacalamene) and 5,6-dihydroxyco

Full text of DOI:10.1080/14786411003650777

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Phytochemical investigation of the
seeds of Althea officinalis L.
Sunita Rani a , Suroor A. Khan a & M. Ali a
a Department of Pharmaceutical Chemistry, Jamia Hamdard
(Hamdard University), New Delhi 110062, India
Version of record first published: 27 Aug 2010.
To cite this article: Sunita Rani , Suroor A. Khan & M. Ali (2010): Phytochemical investigation of the
seeds of Althea officinalis L., Natural Product Research: Formerly Natural Product Letters, 24:14,
1358-1364
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Natural Product Research
Vol. 24, No. 14, 10 September 2010, 1358–1364
Phytochemical investigation of the seeds of Althea officinalis L.
*
Sunita Rani, Suroor A. Khan and M. Ali
Department of Pharmaceutical Chemistry, Jamia Hamdard (Hamdard University),
New Delhi 110062, India
(Received 27 April 2009; final version received 25 January 2010)
Phytochemical investigation of the seeds of Althea officinalis L. (Malvaceae)
led to the isolation of three new phytoconstituents, identified as
n-hexacos-2-enyl-1,5-olide (altheahexacosanyl lactone), 2ꢀ-hydroxycalamene
(altheacalamene)
and
5,6-dihydroxycoumarin-5-dodecanoate-6ꢀ-D-
glucopyranoside (altheacoumarin glucoside), along with the known
phytoconstituents lauric acid, ꢀ-sitosterol and lanosterol. The structures of
these compounds were established on the basis of spectral analysis and
chemical reactions.
Keywords: Althea
officinalis
2ꢀ-hydroxycalamene; coumarin glucoside
L.;
altheahexacosanyl
lactone;
1. Introduction
Althea officinalis L. (Malvaceae), commonly known as gulkhairo or marshmallow,
is a downy, perennial herb, distributed in the Himalayas from Kashmir to Himachal
Pardesh (National Institute of Science Communication and Information Resources,
2003). The seeds of this plant are demulcent, diuretic and febrifugal (Mhaskar,
Blatter, & Caius, 2000). In the Unani medicinal system, A. officinalis is prescribed as
an expectorant and is known to relieve bronchitic and bronchial catarrh (Indian
Council of Medical Research, 2004).
Malvalic acid and some fatty acids were previously extracted from the seeds of
this plant (Karawaya, Balbana, & Afifi, 1982; Mishina, Kornievskii, Shkurupii, &
Dolia, 1975). This article describes the isolation of hexadecanyl ꢁ-lactone,
hydroxycalamene and a coumarin glucoside along with the known compounds
lauric acid, ꢀ-sitosterol and lanosterol from the seeds of A. officinalis L.
2. Results and discussion
Compounds 2, 4 and 5 are the known phytoconstituents identified as lauric
acid, ꢀ-sitosterol (Chung, Ali, Chun, Lee, & Ahmad, 2007; Haba et al., 2007) and
lanostanol (Ali, 2001; Nes, Norton, Parish, Meenan, & Popjak, 1989), respectively.
Compound 1, designated as altheahexacosanyl lactone, was obtained as a
colourless mass from the petroleum ether–chloroform (9 : 1) eluants. Its IR spectrum
*Corresponding author. Email: sakhan_pchem@yahoo.com
ISSN 1478–6419 print/ISSN 1029–2349 online
ß 2010 Taylor & Francis
DOI: 10.1080/14786411003650777
http://www.informaworld.com

Natural Product Research
1359
exhibited absorption bands due to a ꢁ-lactone ring at 1720 cmꢀ1 and conjugated
C¼C at 1640 cmꢀ1. Its positive FAB-MS exhibited a molecular ion peak at m/z 392,
corresponding to the molecular formula C26H48O2. It indicated three double
bond equivalents, which were adjusted in the unsaturated lactone ring. The mass
spectrum showed CnH2n, CnH2nþ2 and CnH2nꢀ1 ion peaks separated by 14 mass
units, and the intensities of the fragments decreased on increasing molecular
weight, suggesting a long aliphatic chain (Misra, Singh, Pandey, & Sharma, 1989;
Stoianova-Ivanova, Hadjieva, & Papow, 1969). There was a sudden increase in the
þ
ion peak at m/z 295 [(CH2)20CH3] due to the expulsion of the ꢁ-lactone having
1
a mass unit of m/z 97 [C5H5O2]þ. The H-NMR spectrum of 1 displayed a double
doublet at ꢁ 5.63 (J ¼ 6.3, 5.7 Hz), integrated for one proton, assigned to vinylic H-3.
A doublet at ꢁ 5.45 (J ¼ 6.3 Hz) was ascribed to cis-oriented vinylic H-2. Two
doublets at ꢁ 4.16 (J ¼ 3.6 Hz) and 4.13 (J ¼ 3.9 Hz) were attributed to oxygenated
methylene protons H2-5. Broad multiplets at ꢁ 1.61 with half widths of 8.6 Hz were
accounted to a ꢀ-oriented H-4 methine proton. The remaining methylene protons
appeared at ꢁ 1.31 (1 ꢁ CH2) and ꢁ 1.18 (19 ꢁ CH2). The primary methyl protons
Me-26 appeared as a three-proton triplet at ꢁ 0.84 (J ¼ 7.2 Hz). The 13C-NMR
spectrum exhibited important carbon signals at ꢁ 173.61 assigned for a C-1 ester
carbon and at ꢁ 130.85 and 128.78 for C-2 and C-3 vinylic carbons, respectively.
The methylene carbons appeared in the range between ꢁ 37.09 and 22.65. The
terminal methyl carbon signal appeared at ꢁ 14.09. The 1H–1H COSY spectrum of 1
showed correlations of H2-5 with H-4 and H-3. The HMBC spectrum of 1 exhibited
the interaction of C-1 with H-2 and C-5 with H-4 and H-3. Based on this evidence,
the structure of 1 has been elucidated as n-hexacos-2-enyl-1,5-olide. This is a new
ꢁ-lactone isolated from a plant source for the first time.
O
O
1
5
H
6
7
25
26
CH
2
4
(CH )
3
2 17
3
ꢁ-Lactone type compounds have also been isolated from Malvastrum coromandalia-
num (Alam, Chopra, Ali, & Niwa, 1996), Phyllanthus fraternus (Gupta & Ali, 2000),
Desmotrichum fimbrianum (Roy, Ali, Sharma, & Ramachandran, 2002) and Oryza
sativa (Chung et. al., 2007).
Compound 3, designated as altheacalamene, was obtained as a brown
amorphous powder from chloroform–methanol (99 : 1). Its IR spectrum showed
absorption bands for a hydroxyl group (3470 cmꢀ1) and an aromatic ring (1525,
1081 cmꢀ1). Its FAB-MS displayed a molecular ion peak at m/z 218 corresponding to
the molecular formula of a hydroxycalamene type sesquiterpene, C15H22O.
The important ion fragments arising at m/z 203 [MꢀME]þ, 175 [M–C3H7]þ, 160
[175–Me]þ and 145 [160–Me]þ indicated the location of one hydroxyl, one isopropyl
1
and two methyl functions in the molecule. The H-NMR spectrum of 3 showed two
doublets at ꢁ 7.50 (J ¼ 9.2 Hz) and 6.92 (J ¼ 3.0 Hz) assigned to ortho-coupled H-9
and meta-coupled H-6, respectively. A double doublet at ꢁ 6.53 with coupling
interactions of 9.2, 3.0 Hz was attributed to an ortho, meta-coupled H-3 proton. A
broad multiplet at ꢁ 4.35 with a half width of 16.7 Hz was ascribed to an ꢂ-oriented
carbinol H-2 proton. A broad signal at ꢁ 2.50 was accounted to C-15 methyl protons

1360
S. Rani et al.
attached to a C-7 aromatic carbon. Three doublets at 1.36 (J ¼ 6.3 Hz), 1.24
(J ¼ 6.1 Hz) and 0.86 (J ¼ 6.9 Hz), all integrated for three protons each, were
associated to C-11, C-13 and C-14 secondary methyl protons, respectively. Two
multiplets at ꢁ 2.27 (w1/2 ¼ 14.5 Hz) and 2.09 (w1/2 ¼ 14.1 Hz) and a multiplet at ꢁ 1.89
were assigned to methine H-4, H-1 and methylene H2-3 protons, respectively. The
presence of the half width of 14.5 Hz of the signal at ꢁ 2.27 and of 14.1 Hz of the
signal at ꢁ 2.09 suggested ꢂ-orientation of the methine H-4 and H-1 protons,
respectively. The 13C-NMR spectrum of 3 showed the presence of one carbinol
carbon at ꢁ 67.53 (C-2), aromatic carbons between ꢁ 115.28 and 131.64,
methyl carbons between ꢁ 15.61 and 28.40, a methylene carbon at ꢁ 23.33 (C-3)
and methine carbons at ꢁ 29.86 (C-1) and 28.40 (C-4). The DEPT spectrum of 3
exhibited the presence of four methyl, one methylene, seven methine and three
quaternary carbons. The HMBC spectrum of 3 showed correlations of C-2 with H-1,
H2-3 and H3-11, and C-7 with H3-15, H-6 and H-8. On the basis of the above
mentioned data, the structure of 3 has been elucidated as 2ꢀ-hydroxycalamene.
11
CH
3
9
1
OH
10
5
8
2
3
7
H C
3
4
6
15
12
H C
CH
14
3
3
13
Compound 6, named altheaecoumaryl glucoside, was obtained as a colourless mass
from chloroform–methanol (4 : 1) eluants. Its UV spectrum revealed absorption
maxima at 255, 301 and 345 nm, indicating the coumarin nature of the molecule.
Its IR spectrum showed characteristic absorption bands for a hydroxyl group at 3350
and 3210 cmꢀ1, an ester group at 1726 cmꢀ1, conjugated C¼C at 1620 cmꢀ1 and an
aromatic ring at 1056 cmꢀ1. The FAB-MS of compound 6 displayed a molecular ion
peak at m/z 522, consistent with the molecular formula of coumarin glycoside
combined with C-12 ester C27H38O10. The important ion peaks arising at m/z 359
[MꢀC6H11O5]þ, 343 [MꢀC6H11O5]þ, 163 [C6H11O5]þ, 183 [CO(CH2)10CH3]þ, 339
[Mꢀ183]þ and 176 [359ꢀ183]þ suggested the location of one sugar unit and C12-ester
linkage attached to the coumarin. The 1H-NMR spectrum of 6 displayed two sets of
ortho-coupled doublets, one-proton each, at ꢁ 7.51 (J ¼ 9.2 Hz) and 6.87 (J ¼ 9.2 Hz)
assigned correspondingly to aromatic H-7 and H-8 protons. Two doublets at ꢁ 6.63
(J ¼ 7.5 Hz) and 5.34 (J ¼ 7.5 Hz) were attributed to cis-oriented vinylic H-3 and H-2
protons, respectively. The anomeric proton H-100 of the sugar molecule appeared as a
doublets at ꢁ 5.06 (J ¼ 7.1 Hz). The other sugar protons resonated between ꢁ 4.13 and
3.66. The methylene H2-20 proton adjacent to an ester group appeared as two
one-proton doublets at ꢁ 2.30 (J ¼ 6.5 Hz) and 2.27 (J ¼ 7.5 Hz). The remaining
methylene protons resonated at ꢁ 1.59 (CH2-30) and 1.25 (8 ꢁ CH2). A triplet at ꢁ 0.87
(J ¼ 6.6 Hz) integrating for three protons was accounted to primary Me-120 methyl
protons. The 13C-NMR spectrum of 6 displayed a carbon signal at ꢁ 177.55 assigned
to the carbonyl carbon C-1. The aromatic carbons resonated between ꢁ 146.70 and

Natural Product Research
1361
112.30. The ester carbon C-10 appeared at ꢁ 174.01, whereas the adjacent carbon
C-20 and methyl carbon C-120 resonated at ꢁ 55.97 and 14.06, respectively. A signal
at ꢁ 102.74 was accounted to anomeric C-100 protons. The remaining signals between
ꢁ 73.87 and 61.74 were accounted to other carbons of the sugar unit. The HMBC
spectrum of 6 exhibited the correlation of C-6 with H-7 and H-100; C-1 with H-2
and H-3; and C-10 with H2-20. Acid hydrolysis of 6 yielded lauric acid and D-glucose.
On the basis of this evidence, the structure of 6 has been established as
5,6-dihydroxycoumarin-5-dodecanoate-6-ꢀ-D-glucopyranoside. It is an unknown
coumarin derivative isolated from a natural or synthetic source for the first time.
2
O
3
1
12'
H C
(CH )
4
2 10
O
O
3
1'
OH
O
9
8
5
6''
5''
6
O
H
O
H
7
H
OH
4''
HO
1''
H
2''
OH
3''
H
3. Experimental
3.1. General experimental procedures
Melting points were determined on a Perfit melting point apparatus and are
uncorrected. IR spectra were recorderd on KBr pellets using a Jasco FT-IR-5000
instrument. UV spectra were scanned in methanol on a Lamda Bio 20 spectro-
1
photometer. H-NMR (400 MHz) and 13C-NMR (75 MHz) spectra were recorded
on an Advance Dry 400, Bruker Spectrospin in CDCl3. Mass spectra were measured
in FAB ionisation mode with a JEOL-JMS-DX 303.
Silica gel G (Qualigens, 60–120 mesh, Mumbai, India) was used for column
chromatography. Silica gel G (Qualigens, Mumbai) was used for analytical
thin-layer chromatography (TLC). Spots were visualised by exposure to iodine
vapour, UV radiation and by spraying reagents.
3.2. Plant material
The seeds of A. officinalis were purchased from Khari Baoli market, Delhi, and
identified by Dr M.P. Sharma, Taxonomist, Department of Botany, Faculty of
Science, Jamia Hamdard, New Delhi. A voucher specimen (no. PRL/JH/07/06) has
been deposited in the Herbarium of the Department of Pharmacognosy and
Phytochemistry, Jamia Hamdard, New Delhi.
3.3. Extraction
The air dried defatted powdered seeds (3 kg) of A. officinalis were extracted with
ethanol in a Soxhlet apparatus for 72 h. The ethanolic extract was concentrated to

1362
S. Rani et al.
obtain a dark brown viscous mass (475 g). A small portion (2 g) of the extract was
analysed chemically to determine the presence of different chemical constituents.
3.4. Isolation
The viscous extracted mass was adsorbed on silica gel (60–120 mesh) to form slurry.
The slurry was air dried and chromatographed over a silica gel column packed in
petroleum ether. The column was eluted with petroleum ether, a mixture of petroleum
ether and chloroform (9 : 1, 3 : 1, 1 : 1 and 1 : 3), pure chloroform and finally a mixture
of chloroform and methanol (99.5 : 0.5, 99 : 1, 49 : 1, 19 : 1, 9 : 1, 4 : 1, 3 : 2 and 1 : 1).
Various fractions were collected separately and matched by TLC to check homoge-
neity. Similar fractions (having the same Rf values) were combined and crystallised.
The isolated compounds were recrystallised to obtain the pure compounds. The
following compounds were isolated from the A. officinalis seed extract.
3.4.1. Altheahexacosanyl lactone (1)
Elution of the column with a petroleum ether–chloroform (9 : 1) mixture furnished a
colourless mass of 1, recrystallised from acetone. Rf: 0.23 (n-hexane); m.p. ¼ 68–
69ꢂC; 98.5 mg ¼ (0.0003% yield); UV (MeOH) ꢃmax ¼ 201 nm (log " 3.6); IR (KBr)
ꢄmax ¼ 2923, 2843, 1720, 1640, 1470, 1280, 1120, 702 cmꢀ1; 1H-NMR (CDCl3) ¼ 5.63
(H, dd, J ¼ 6.3, 5.7 Hz, H-3), 5.45 (1H, J ¼ 6.3 Hz, H-2), 4.16 (1H, d, J ¼ 3.6 Hz,
H2-5a), 4.13 (1H, d, J ¼ 3.9 Hz, H2-5b), 1.61 (1H, brm, w1/2 ¼ 8.6 Hz, H-4b), 1.31
(2H, brs, CH2), 1.18 (38H, brs, 19 ꢁ CH2), 0.84 (3H, t, J ¼ 7.2 Hz, Me-26); 13C-NMR
(CDCl3) ¼ ꢁ 173.61(C-1), 130.85 (C-2), 128.78 (C-3), 68.13 (C-5), 38.72 (C-4), 37.09
(CH2), 34.05 (CH2), 32.75 (CH2), 31.92 (CH2), 31.59 (CH2), 30.34 (CH2), 29.69
(11 ꢁ CH2), 28.93 (CH2), 24.92 (CH2), 22.65 (CH2), 14.09 (CH3); FAB-MS m/z ¼ 392
[M]þ(C26H48O2) (5.9), 349 (1.1), 321 (1.2), 295 (23.6), 281 (5.3), 239 (5.7), 169 (7.2),
155 (8.9), 141 (10.2), 123 (11.5), 113 (12.0), 97 (100), 85 (41.5).
3.4.2. Lauric acid (2)
Elution of the column with chloroform afforded colourless crystals of 2,
recrystallised from methanol. m.p. ¼ 45–46ꢂC; lit. m.p. ¼ 44–48ꢂC (O’Neil, 2001);
100 mg (0.00033% yield); UV (MeOH) ꢃmax ¼ 207 nm; IR (KBr) ꢄmax ¼ 3305, 2975,
1
2854, 1700, 1272, 795 cmꢀ1; H-NMR (DMSO-d6) ¼ ꢁ 2.20 (1H, d, J ¼ 7.2, 5.7 Hz,
H2-2a), 2.17(1H, d, J ¼ 7.2 Hz, H2-2b), 1.47 (2H, brs, H2-3), 1.27 (16H, brs,
8 ꢁ CH2), 0.85 (3H, t, J ¼ 6.2 Hz, Me-12); 13C-NMR (CDCl3) ¼ ꢁ 183.12 (C-1), 39.96
(CH2), 33.97 (CH2), 31.84 (CH2); 29.62 (5 ꢁ CH2), 24.84 (CH2), 22.60 (CH2), 14.04
(CH3); FAB-MS m/z ¼ 201[M þ H]þ(C12H24O2).
3.4.3. Altheacalamene (3)
Elution of the column with chloroform–methanol (99 : 1) yielded a brown amorphous
powder of 3, recrystallised from chloroform–ethyl acetate (1 : 5); Rf ¼ 0.68 (petroleum
ether, chloroform, methanol, 1 : 4 : 1); m.p. ¼ 270ꢂC; 120 mg (0.0004% yield); UV
(MeOH) ꢃmax ¼ 217, 285, 303 nm (log " 4.3, 5.1, 3.1, 2.1); IR (KBr) ꢄmax ¼ 3470, 2936,
2850, 1651, 1525, 1400, 1081 cmꢀ1; 1H-NMR (DMSO-d6) ¼ ꢁ 7.50 (1H, d, J ¼ 9.2 Hz,

Natural Product Research
1363
H-9), 6.92 (1H, d, J ¼ 3.0 Hz, H-6), 6.53 (1H, dd, J ¼ 9.2, 3.0 Hz, H-8), 4.35 (1H, brm,
w1/2 ¼ 16.7 Hz, H-2ꢂ), 2.50 (3H, brs, Me-15), 2.27 (1H, m, w1/2 ¼ 14.5 Hz, H-4), 2.09
(1H, m, w1/2 ¼ 14.1 Hz, H-1), 1.89 (2H, m, H2-3), 1.36 (3H, d, J ¼ 6.3 Hz, Me-11), 1.24
(3H, d, J ¼ 6.1 Hz, Me-13), 0.86 (3H, d, J ¼ 6.9 Hz, Me-14); 13C-NMR
(DMSO-d6) ¼ ꢁ 29.86 (C-1), 67.53 (C-2), 23.33 (C-3), 28.40 (C-4), 128.13 (C-5),
127.42 (C-6), 131.64 (C-7), 115.28 (C-8), 125.62 (C-9), 128.69 (C-10), 15.61 (C-11),
29.86 (C-12), 18.26 (C-13), 23.33 (C-14), 28.40 (C-15); FAB-MS m/z ¼ 218
[M]þ(C15H220) (11.7), 203 (15.8), 201 (9.6), 175 (42.3), 160 (18.1), 145 (63.2).
3.4.4. ꢀ-Sitosterol (4)
Elution of the column with chloroform–methanol (19 : 1) gave colourless crystals of
4, recrystallised from methanol. Rf ¼ 0.30 (chloroform : methanol, 1 : 1); m.p. ¼ 138–
139ꢂC; lit. m.p. 140ꢂC (O’Neil, 2001); 120 mg (0.0004% yield); UV (MeOH)
ꢃmax ¼ 205 nm; IR (KBr) ꢄmax ¼ 3465, 2955, 2845, 1640, 1475, 1365, 1210, 1105 cmꢀ1
;
1H-NMR (CDCl3) ¼ ꢁ 5.30 (d, J ¼ 5.5 Hz, H-6), 3.51(1H, brs, w1/2 ¼ 16.5 Hz, H-3ꢂ),
1.01(3H, brs, Me-19), 0.97 (3H, d, J ¼ 6.5 Hz, Me-21), 0.86 (3H, d, J ¼ 6.0 Hz,
Me-26), 0.83 (3H, d, J ¼ 6.03 Hz, Me-29), 0.81 (3H, d, J ¼ 6.0 Hz, Me-27), 0.67 (3H,
brs, Me-18). FAB-MS m/z ¼ 414 [M]þ (C29H50O).
3.4.5. Lanostanol (5)
Elution of the column with chloroform–methanol (9 : 1) afforded a colourless
crystalline mass of 5, recrystallised from methanol; Rf ¼ 0.86 (n-butanol, acetic acid,
water, 5 : 1 : 2); m.p. ¼ 138–140ꢂC; lit. m.p. 138–140ꢂC (Nes et al., 1989); 100 mg
(0.00033% yield); UV (MeOH) ꢃmax ¼ 209 nm (log “ 5.3).; IR (KBr) ꢄmax ¼ 3404,
2919, 2850, 2851, 1607, 1401, 1262, 1198, 129, 1095, 1025, 803 cmꢀ1 1H-NMR
;
(DMSO-d6) ¼ ꢁ 3.67 (1H, dd, J ¼ 5.5, 9.1 Hz, H-3ꢂ), 1.23 (9H, brs, Me-28, Me- 29,
Me-30), 1.16 (3H, brs, Me-19), 1.08 (3H, d, 71, J ¼ 6.7 Hz, Me-21), 1.06 (3H, brs,
Me-18), 0.85 (3H, d, J ¼ 6.8 Hz, Me-26), 0.83 (3H, d, J ¼ 6.8 Hz, Me-27); FAB-MS
m/z ¼ 430[M]þ(C30H540).
3.4.6. Althaeacoumaryl glucoside (6)
Elution of the column with a chloroform–methanol (4 : 1) mixture furnished a
colourless mass of 6, recrystallised from methanol. Rf ¼ 0.82 (chloroform–ethyl
acetate; 4 : 1); m.p. ¼ 93ꢂC; 150 mg (0.0005% yield); UV (MeOH) ꢃmax ¼ 229, 255,
301, 345 nm (log " 4.1, 3.6, 3.5, 3.9); IR (KBr) ꢄmax ¼ 3350, 3210, 2926, 2850, 1726,
1620, 1460, 1056 cmꢀ1; 1H-NMR (CDCl3) ¼ ꢁ 7.51(1H, d, J ¼ 9.2 Hz, H-7), 6.87(1H,
d, J ¼ 9.2 Hz, H-8), 6.63 (1H, d, J ¼ 7.5 Hz, H-3), 5.34 (1H, d, J ¼ 7.5 Hz, H-2), 5.06
(1H, d, J ¼ 7.1 Hz, H-100), 4.13 (1H, m, H-500), 3.86 (1H, dd, J ¼ 6.5, 7.1 Hz, H-3), 3.84
(1H, brs, H-300), 3.81 (1H, brs, H-400), 3.66 (2H, brs, H2-600), 2.30 (1H, d, J ¼ 7.5 Hz,
H2-20a), 2.27 (1H, d, J ¼ 7.5 Hz, H2-20b), 1.59 (2H, brs, CH2-30), 1.25 (16H, brs,
8 ꢁ CH2), 0.87 (3H, t, J ¼ 6.5 Hz, Me-120);13C-NMR (CDCl3): ꢁ 177.55 (C-1), 112.30
(C-2), 114.2 (C-3), 119.25 (C-4), 146.70 (C-5), 143.31 (C-6), 129.24 (C-7), 128.55
(C-8), 127.04 (C-9), 174.01(C-10), 55.97 (C-20), 36.96 (C-30), 33.97 (C-40), 31.85 (C-50),
29.63 (C-60), 29.63 (C-70), 27.17 (C-80), 24.71 (C-90), 22.61 (C-100), 20.75 (C-110),
14.06 (C-120), 102.74 (C-100), 71.85 (C-200), 70.11 (C-300), 68.62 (C-400), 73.87 (C-500),

1364
S. Rani et al.
61.74 (C-600); FAB-MS m/z ¼ 522[M]þ (C27H38O10) (7.8), 359 (18.3), 343 (9.5), 339
(22.7), 183 (16.4), 176 (12.5), 163 (5.3), 155 (33.2), 113 (27.1), 97 (67.8).
3.4.6.1. Hydrolysis of 6. Compound 6 (40 mg) was dissolved in ethanol (5 mL), to
which conc. HCl (2 mL) was added and the reaction mixture heated for 1 h on a steam
bath. It was cooled and extracted with petroleum ether (3 ꢁ 5 mL) to separate lauric
acid (co-TLC comparable). The reaction mixture was dried under reduced pressure
and the residue dissolved in chloroform to isolate 5,6-dihydroxycoumarin, IR
ꢄmax ¼ 1721, 3410, 3250 cmꢀ1, [M]þ 178 [C9H6O4]þ. The residue was dissolved in a
minimum amount of water and chromatographed on silica gel TLC with a standard
sample of D-glucose using EtOAc–HOAc–H2O–MeOH (6 : 1 : 1 : 2), Rf ¼ 0.4.
References
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