El limonoíde clausenolido-1-metil eter (1) fue aislado de corteza de Clausena heptaphylla. La estructura del compuesto fue determinada por metodos espectroscópicos, incluyendo 2D RMN, espectrometría de masas (EM) y comparación de los datos espectroscópicos y constantes físicas con los publicados en la literatura. Este es el primer informe del aislamiento de clausenolido-1-metil eter (1) de Clausena heptaphylla.Abstract  From the stem bark of Clausena heptaphylla, the limonoid  clausenolide-1-methyl ether (1) was isolated. The structure of the compound was elucidated by extensive spectroscopic studies, including 2D NMR and MS measurements and by comparison with spectroscopic and physical data from the literature. This is the first report of occurrence of clausenolide-1-methyl ether (1) in Clausena heptaphyll

BEGUM, Rokeya

KAISAR, Mohammad A.

MAHMOOD HASAN, Choudhury

MUKHLESUR RAHMAN, M.

RAHMAN, Mohammad S.

RASHID, Mohammad A.

SARWARUDDIN CHOWDHURY, A. M.

Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas

  
© 2011 The Authors 
© 2011 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas  10 (2):  136 - 138 
BLACPMA ISSN 0717 7917 
 
Artículo Original | Original Article 
136 
 
 
Clausenolide-1-methyl ether from Clausena heptaphylla W&A  
 [Clausenolido-1-metil éter de Clausena heptaphylla W & A] 
 
 
Rokeya BEGUM1,2, Mohammad A. KAISAR3, Mohammad S. RAHMAN3, A. M. SARWARUDDIN CHOWDHURY1, 
M. MUKHLESUR RAHMAN4, Choudhury MAHMOOD HASAN3 & Mohammad A. RASHID3 
 
 
 
 
1Department of Applied Chemistry and Chemical Engineering, University of Dhaka, Dhaka-1000, Bangladesh. 
2(On leave from the Department of Agricultural Chemistry, Sher-e-Bangla Agricultural University, Dhaka-1207, Bangladesh).  
3Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Dhaka, Dhaka-1000, Bangladesh. 4Centre for 
Pharmacognosy and Phytotherapy, The School of Pharmacy, University of London, 29–39 Brunswick Square, London WC1N 1AX, UK 
 Contactos | Contacts: Mohammad A. RASHID - E-mail address: rashidma@univdhaka.edu 
 
 
 
 
Abstract  
From the stem bark of Clausena heptaphylla, the limonoid  clausenolide-1-methyl ether (1) was isolated. The structure of the compound was elucidated by 
extensive spectroscopic studies, including 2D NMR and MS measurements and by comparison with spectroscopic and physical data from the literature. This 
is the first report of occurrence of clausenolide-1-methyl ether (1) in Clausena heptaphylla. 
 
Keywords: Clausena heptaphylla, clausenolide-1-methyl ether 
 
 
 
 
 
Resumen 
El limonoíde clausenolido-1-metil eter (1) fue aislado de corteza de Clausena heptaphylla. La estructura del compuesto fue determinada por metodos 
espectroscópicos, incluyendo 2D RMN, espectrometría de masas (EM) y comparación de los datos espectroscópicos y constantes físicas con los publicados en 
la literatura. Este es el primer informe del aislamiento de clausenolido-1-metil eter (1) de Clausena heptaphylla. 
 
Palabras Clave: Clausena heptaphylla, clausenolido-1-metil eter 
 
 
 
 
 
  
Recibido | Received: August 22, 2010. 
Aceptado en versión corregida | Accepted in revised form: February 16, 2011. 
Publicado en línea | Published online: March 30, 2011. 
Este artículo puede ser citado como  /  This article must be cited as::  Rokeya BEGUM, Mohammad A. KAISAR, Mohammad S. RAHMAN, A. M. SARWARUDDIN 
CHOWDHURY, M. MUKHLESUR RAHMAN, Choudhury MAHMOOD HASAN, Mohammad A. RASHID, 2011. Claudenolide-1-methyl ether from Clausena heptaphylla W & 
A. Bol Latinoam Caribe Plant Med Aromat 10(2): 136 - 138.  
Begum et al Clausenolide-1-methyl éter from Clausena heptaphylla W & A 
 
INTRODUCTION 
Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/137 
 
Clausena heptaphylla W & A (Bengali name: 
Panbilash, Karanphul, Pomkaphur, Family: Rutaceae) 
is a small bushy shrub that is distributed throughout 
Bangladesh, India and other parts of south east Asia 
(Haque  1986). The plant is reported to have antiseptic 
property. Clausena species are known to be useful in 
paralysis, ulcerated nose, headache, muscular pain and 
malarial fever.
 
They are also reputed as diuretic, 
astringent, insecticide, tonic and vermifuge (Yusuf et 
at., 1994). Previous phytochemical investigations of 
Clausena species led to the isolation of amides 
(Riemer et at., 1997), limonoids (Ngadjui et al., 
1989a; Thuy et al., 1999), carbazole and quinolone 
alkaloids (Ngadjui et al., 1989b; Wu et al., 1996; 
Begum et al., 2008), coumarins (Thuy et al., 1999; 
Huang et al., 1997), terpenes (He et al., 2002; Sohrab 
et al., 1999), cyclopeptide (Wang et al., 2005) and 
carboxamide (Milner et al., 1996). As a part of our 
work on Bangladeshi medicinal plants (Ara et al., 
2006; Islam et al., 2009, Jahan et al,. 2010.), we 
investigated C. heptaphylla and isolated a limonoid, 
clausenolide-1-methyl ether (1) which is the first 
report of its occurence from this plant.  
 
 
(1) 
 
XPERIMENTALS AND METHODS 
MR spectra 
  
 C. heptaphylla was collected from 
xtraction and isolation 
(210 g) of C. heptaphylla 
ESULTS 
e-1-methyl ether (1): White crystalline 
ISCUSSION 
ution electro-spray ionization (ESI-
The stem bark of
Barisal in May 2005 and was identified by Dr. 
Mahbuba Khanam, Director in charge, Bangladesh 
National Herbarium, Ministry of Environment and 
Forest, Dhaka, Bangladesh where a voucher specimen 
(accession number DACD-31,252) has been 
maintained for this collection.  
 
E
The powdered stem bark 
was soaked in 800 ml MeOH, for 5 days and then 
filtered and concentrated using rotary evaporator at 
low temperature and reduced pressure. A portion (5 
gm) of the concentrated methanol extract was 
fractionated by the modified Kupchan (VanWagenen 
et al., 1993) procedure into n-hexane, carbon 
tetrachloride, chloroform and aqueous soluble 
fractions. Evaporation of solvents from the extractives 
afforded n-hexane (0.2 g), carbon tetrachloride (1.94 
g), chloroform (1.85 g) and aqueous (1.00 g) soluble 
materials. The chloroform soluble material was 
subjected to vacuum liquid chromatography (VLC) 
over silica gel 60H, and the column was eluted with n-
hexane-EtOAc mixtures of increasing polarity yielding 
20 fractions, each  of 100 ml. VLC fractions eluted 
with 20 % ethyl acetate in hexane afforded compound 
1 (12.1 mg) as crystalline white mass. 
 
R
Clausenolid
mass; 1H NMR (400 MHz, CDCl3), δ. 1.10, 1.14, 1.22, 
1.43, 1.45, 1.54 (each 3H, s),  2.33 (1H, dd, J=14.0, 
3.4 Hz, Hα-6), 2.62 (1H, dd, J=16.0, 3.4 Hz, H-5), 2.72 
(1H, br.s, H-9), 2.87 (1H, dd, J=16.0, 14.0 Hz, Hβ-6), 
3.98 (1H, s, H-15), 4.51 (1H, br.s, H-11), 5.54 (1H, s, 
H-17), 6.35 (1H, d, J=1.5 Hz, H-22), 7.38 (1H, s, H-
21), 7.40 (1H, d, J=1.5 Hz, H-23), -OMe (3.22); 13C 
NMR: δ 108.5 (C-1), 79.9 (C-4), 54.7 (C-5), 37.0 (C-
6), 208.1 (C-7), 50.6 (C-8), 44.70 (C-9), 51.0 (C-10), 
67.1 (C-11), 43.4 (C-12), 41.0 (C-13), 65.7 (C-14), 
54.5 (C-15), 167.2 (C-16), 78.3 (C-17), 120.3 (C-20), 
141.1 (C-21), 109.9 (C-22), 143.0 (C-23), 30.8, 23.3, 
20.2, 19.3, 18.0, 17.3 (6×C-Me), 55.72 (OMe); 
C26H34O8  (ESI-TOFMS: [M+H]+  m/z  475.2010).   
 
E
General Experimental Procedures:  N
D(both 1D and 2D) were obtained on a  Ultra Shield 
Bruker DPX 400 NMR instrument,  using the residual 
solvent peaks (CDCl3 ) as internal standard. Mass 
spectrum was obtained with a LCT premier KD146 
TOF analyzer using positive mode ESI technique.
  
Plant material  
The high resol
TOF) mass spectrum of compound 1 displayed the 
pseudo-molecular ion peak [M+H]+ at  m/z 475.2010 
suggesting a molecular formula C26H34O8. The 13C 
NMR spectrum of this compound displayed 26 carbon 
resonances consistent with the molecular formula and 
Begum et al Clausenolide-1-methyl éter from Clausena heptaphylla W & A 
 
Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/138 
 
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singlets at δ 1.10, 1.14, 1.22, 1.43, 1.45 and 1.54, 
which were assigned to the methyl groups at C-13, C-4 
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Clausenolide-1-methyl ether from Clausena heptaphylla W&A [Clausenolido-1-metil éter de Clausena heptaphylla W & A]

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Clausenolide-1-methyl ether from Clausena heptaphylla W&A [Clausenolido-1-metil éter de Clausena heptaphylla W & A]

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