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J. Braz. Chem. Soc. 2000, 4, 278-280

J. Braz. Chem. Soc. 2000, 4, 278-280

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Published by srinivasarao meneni
Further dihydrochalcones from Crotalaria ramosissima.
Further dihydrochalcones from Crotalaria ramosissima.

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Published by: srinivasarao meneni on Oct 04, 2009
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10/06/2009

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Further Dihydrochalcones from
Crotolaria
 
 ramosissima
 J.K. Kumar
a
 , T. Narender
a
 , M.S. Rao
a
 , P.S. Rao
a
 , G. Tóth*
,b
 , B. Balázs
b
 , and H. Duddeck*
,c
a
 Department of Chemistry, Kakatiya University, Warangal (A.P.) 506 009, India
b
Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry of the Technical University, Szent Gellért tér 4, H-1111 Budapest, Hungary
c
Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, D-30167 Hannover, Germany
Duas novas 2,3-diidrohalconas crotaramin (
2
) e crotin (
3
) foram isoladas da planta da Índia
Crotolaria ramosissima
. Suas estruturas foram elucidadas por meio de intenso uso de espectros-copia de RMN uni- e bidimensional, incluindo HMBC e NOESY.Two new dihydrochalcones, crotaramin (
2
) and crotin (
3
), have been isolated from the Indianplant
Crotolaria ramosissima
. Their structures have been elucidated by extensive one- andtwo-dimensional NMR spectroscopy including HMBC and NOESY.
Keywords:
dihydrochalcones,
Crotolaria ramosissima
 , structure elucidation, 1D and 2D
1
 H and 
13
C-NMR spectroscopy
Introduction
Crotolaria
 
ramosissima
is a weed plant belonging to thefamily
 Leguminoseae
. It is a much branched sticky woodyherb. The flowers are yellow tinged with purple. It isdistributed in some places of Tamilnadu and coastal areasof Andrha Pradesh. The plant contains waxes, and, whenflowering, a yellow exudate appears in the inflorescences.Recently
1
, we published the corrected structure of crotara-mosmin (
1
) from
crotolaria ramosissima
which appearedto be a dihydrochalcone, a class of compound which is rareas a plant secondary metabolite. Except
1
, only one otherinstance of a dihydrochalcone possessing a chromenylmoiety has been reported in the literature
2
. This is a syn-thetic compound and has an unsubstituted phenyl ring (seeScheme 1: X = Y = H). Our continued interest on
crotolariaramosissima
led to the identification of two more dihydro-chalcones, crotaramin (
2
) and crotin (
3
) (Scheme 1).
Results and Discussion
The identification of the two new dihydrochalcones wasbased on extensive 1D and 2D NMR spectroscopy asdescribed before
3,4
. The
1
H and
13
C chemical shifts arecollected in Table 1. The assignments were confirmed byDEPT experiments which allowed the differentiation be-tween the CH
n
(n = 0-3) fragments and further by HMQCexperiments providing the assignment of the hydrogens tothe directly attached carbon atoms. Long-range
1
H,
13
Ccorrelations (
via
more than one bond; HMBC, optimizedto a
13
C,
1
H coupling constant of 7 Hz) afforded the un-equivocal assignment of the quaternary carbons and theconnectivity within the carbon framework. For example,C-5’ and C-9’ gave rise to very close
13
C signals,
δ
= 159.7
Article
 J. Braz. Chem. Soc.
, Vol. 10, No. 4, 278-280, 1999.© 1999 Soc. Bras. QuímicaPrinted in Brazil.0103 5053 $6.00 + 0.00
1
OH H crotaramosmin
2
OCH
3
H crotaramin
3
OH OH crotinXY
OOHOXY
βα
2”1”2'3'4'10'5'6'7'8'9'123456
Scheme 1.
Structures of 
1
-
3
.
 
and 159.6, respectively. Their assignment could be accom-plished by an HMBC peak correlating the 159.6-signal tothose of the methyl protons H-1" and H-2". Only in onecase, C-2 and C-5 of 
3
, the signals were so close that theresolution in the
13
C domain of the HMBC spectrum wasnot good enough for a safe assignment.NOESY experiments were helpful in corroborating thebicyclic chromene structure because they ascertained thespatial proximity between H-8’ and the methyl protonsH-1" and H-2" (compare Scheme 2) so that a benzene ringcarrying a prenyl side chain could be excluded.The position of the hydroxyl groups was obvious fromthe
1
H,
1
H coupling constants:
3
 J 
(H-7’, H-8’) = 8.8 Hz(
ortho
-coupling); typical AA’XX’ sub-spectrum for H-2/H-3/H-5/H-6 in
2
; although the spin-system of H-2, H-5and H-6 in
3
is not entirely first-order, the coupling patterncould be detected and the respective constants are
3
 J 
(H-5,H-6)
8 Hz and
4
 J 
(H-2, H-6)
2 Hz. The
α
- and
β
-protonsshow the expected triplets.It turned out that
2
is the 4-
O
methyl ether of 
1
whereasan extra hydroxyl group in 3-position is present in
3
, ascompared to
1
. Both dihydrochalcones have not yet beendescribed in the literature.
Experimental
The plant material was collected in november 1997 nearthe city of Hyderabad. It was identified by Dr. V.S. Rajuand Dr. Ragan, Department of Botany, Kakatiya Univer-sity, Warangal. A voucher specimen is deposited in theDepartment of Botany.The fresh plant material (2 kg) was extracted withpetroleum ether in a soxhlet extractor. The extract wasconcentrated under reduced pressure to give a dark yellowsyrupy liquid. The concentrate was dissolved in MeOH and
Table 1.
 
1
H and
13
C chemical shifts of the dihydrochalcones
2
and
3
.
position
2
1
H
3
1
H
2
13
C
3
13
C1132.9134.027.166.76129.3115.44*36.85114.0143.64158.1141.956.856.79114.0115.48*67.166.66129.3120.7
α
3.193.1739.839.7
β
3.002.9429.629.8C=O203.9203.92’77.777.73’5.595.58128.2128.24’6.736.72115.8115.85’159.7159.76’113.4113.47’7.537.52130.8130.98’6.326.32108.3108.39’159.6159.610109.3109.31”1.461.4628.328.32”1.461.4628.328.35’-OH13.0513.024-MeO3.8055.3
* Asterisked values may be interchanged.
Scheme 2.
Section of the NOESY spectrum of 
3
.Vol. 10, No. 4, 1999Further Dihydrochalcones from
Crotolaria ramosissima
279

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