Fitoterapia 71 2000.

722724

Phytochemical communication

New constituents from Gliricidia sepium

H.M.T.B. HerathU , Susila deSilva
Natural Products Programme, Institute of Fundamental Studies, Kandy, Sri Lanka

Received 23 March 2000; accepted in revised form 11 May 2000

Abstract
The heart wood of Gliricidia sepium stem yielded stigmastanol glucoside 1. and 3X ,4Xdihydroxy-trans-cinnamic acid octacosylester 2, along with three other known constituents.
2000 Elsevier Science B.V. All rights reserved.
X

Keywords: Gliricidia sepium; Stigmastanol glucoside; 3 ,4 -Dihydroxy-trans-cinnamic acid octacosylester;

Isoflavonoids; Sterols; Triterpenes

Plant. Gliricidia sepium H.B et K. Fabaceae., stems 1.26 kg. were collected from
Ratnapura, Sabaragamuwa Province in Sri Lanka, in January 1997 and authenticated by S. Ekanayake on comparison with herbarium specimens at the National
Herbarium, Royal Botanic Gardens, Peradeniya, Sri Lanka.
Use in traditional medicines and other reported activities. No report for use in
traditional medicine. Insecticidal activity against some insect species such as
southern armyworm, cabbage looper and yellow wolly bear w1x.
Previously isolated constituents. Phenolics w2x, hydrocarbons w3,4x, flavonoids w59x,
saponins w10x, 12-hydroxyrotenoids w11x.
New-isolated constituents. 7,2X-Dihydroxy-6,4X-dimethoxyisoflavone w12x yield: 24.2
mg, 1.92 = 10y5 %, dry wt.., stigmasterol glucoside w13x 34 mg, 2.70 = 10y5 .,
U

Corresponding author. Tel.: q94-8-232-002; fax: q94-8-232-131.

E-mail address: herath@ifs.ac.lk H.M.T.B. Herath..
0367-326Xr00r$ - see front matter 2000 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X 0 0 . 0 0 2 1 9 - 7

H.M.T.B. Herath, S. deSil a r Fitoterapia 71 (2000) 722724

723

betulinic acid w14x 28.2 mg, 2.23 = 10y5 ., and two new natural products, stigmastanol glucoside 1. 14.6 mg, 1.15 = 10y5 . and 3X ,4X-dihydroxy-trans-cinnamic acid
octacosylester 2. 26 mg, 2.06 = 10y5 . from the CH2 Cl2 extract of the stem heart
wood.

Stigmastanol glucoside 1.. Colourless crystals MeOHrCH2 Cl2 ., mp 208C; IR

bands KBr.: 3408, 1628, 1379 and 1065 cmy1 ; 1 H-NMR 500 MHz, D2 O.:
4.351H, d, J 7.8 Hz, H-1X ., 4.15 1H, m, H-3., 3.85 1H, dd, J 11.8, 2.4 Hz, Ha-6X .,
3.68 1H, q, J 11.87, 5.7 Hz, Hb-6X ., 3.13.45 4H, m, H-2X , 3X , 4X , 5X ., 0.61.4 3H
each, 6 = CH3 .; 13 C-NMR 125 MHz, D2 O.: 101.1 C-1X ., 77.0 C-5X ., 76.6 C-3X .,
74.0 C-4X ., 70.7 C-2X ., 62.1 C-6X ., 57.1 C-14., 56.4 C-17., 46.2 C-24., 45.7 C-5.,
43.0 C-13., 40.4 C-12., 38.5 C-10., 37.1 C-4., 36.5 C-20., 34.4 C-22., 32.6
C-7,9., 30.6 C-2,8., 29.4 C-25., 28.9 C-6., 28.5 C-16., 26.3 C-23., 24.4 C-15.,
23.3 C-28., 21.4 C-11., 19.8 C-27., 19.0 C-26., 18.8 C-21., 16.6 C-19., 12.2

H.M.T.B. Herath, S. deSil a r Fitoterapia 71 (2000) 722724

724

C-18., 11.9 C-29.; EIMS 70 eV., mrz rel. int.%.: 416 Mq gluc; 8., 368 10.,
275 10., 228 8., 157 15., 111 20., 80 60., 40 60., 43 100..
3X ,4 X-Dihydroxy-trans-cinamic acid octacosyl ester 2 .. Colourless prisms
CH2 Cl2rhexane., mp 9899C; IR bands KBr.: 3424, 1628, 1212, 758 and 655
cmy1 ; 1 H-NMR 500 MHz, CDCl3 .: 7.57 1H, d, J 15.9 Hz, H-3., 7.08 1H, d, J
2.0 Hz, H-2X ., 6.97 1H, dd, J 8.2, 1.9 Hz, H-6X ., 6.84 1H, d, J 8.1 Hz, H-5X ., 6.25
1H, d, J 15.9 Hz, H-2., 4.25 2H, t, J 13.4, 6.7 Hz, CO2 CH2 ., 1.75 2H, m,
CO2 CH2CH2 ., 1.42 2H, m, CO2 CH2 CH2CH2 ., 1.39 br s, methylene chain.,
0.89 3H, t, J 8.8 Hz, CH3 .; 13 C-NMR 125 MHz, CDCl3 .: 170.0 C-1., 150.9 C-3X
and C-4X ., 145.0 C-3., 127.0 C-1X ., 122.5 C-5X ., 115.6 C-6X ., 114.8 C-2., 114.4
C-2X ., 65.0 CO2 CH2 ., 32.2 CO2 CH2 CH2 ., 30.0 CH2 CH2 CH3 ., 29.8
methylene chain., 29.6 CO2 CH2 CH2 CH 2 ., 29.0 CH2 ., 26.3 CH2 CH3 .,
22.9 CH2 ., 14.2 terminal CH3 .. EIMS 70 eV. mrz rel. int.%.: 574 Mqq 2,
13., 572 Mq, 7., 183 91., 182 100., 180 68., 165 72., 164 64..

Acknowledgements
Authors wish to thank Swedish Agency for Research Co-operation with Developing Countries SAREC. for the financial support, Dr Ulla Jacobson Department of
Organic Chemistry, Royal Institute of Technology, Stockholm, Sweden for the
NMR spectral data, Prof. V. Kumar and his group at the Department of Chemistry,
University of Peradeniya for valuable discussions and suggestions, and to Mr
R.G.U. Jayalal at the Institute of Fundamental Studies for the technical assistance.

References
w1x
w2x
w3x
w4x
w5x
w6x
w7x
w8x
w9x
w10x
w11x
w12x
w13x
w14x

Sievers AF, Archer WA, Moore RH, McGovran ER. J Econ Entamol 1949;42:549.
Ramamoorthy M, Paliwal K. J Chem Ecol 1993;19:1691.
Sharma N, Qadry JS, Subramanian B, Ali M, Sharma AK, Alam MS. Orient J Chem 1993;9:143.
Hariharan V, Rangaswami S, Subramoni IV. Curr Sci India. 1971;40:106.
Nair AGR, Subramanian SS. Curr Sci India. 1962;31:504.
Manners GD, Jurd L. Phytochemistry 1979;18:1037.
Jurd L. Tetrahedron Lett 1976;21:1741.
Jurd L, Manners GD. J Agric Food Chem 1977;25:723.
Herath HMTB, Dassanayake RS, Priyadarshani AMA, de Silva S, Wannigama GPW, Jamie J.
Phytochemistry 1998;47:117.
Kojima K, Zhu XB, Ogihara Y. Phytochemistry 1998;48:885.
Rastrelli L, Berger I, Kubelka W, Caceres A, De Tommasi N, De Simone F. J Nat Prod
1999;62:188.
Fukai T, Wang QH, Inami R, Nomura T. Heterocycles 1990;31:643.
Alam MS, Chopra N, Ali M, Niwa M. Phytochemistry 1996;41:1197.
Misra G, Mitra CR. Phytochemistry 1967;6:453.