Constituents of the trunk bark of Maquira coriacea

Ž .Fitoterapia 72 2001 841�843

Phytochemical communication

Constituents of the trunk bark ofMaquira coriacea

A.-C. Mitaine-Offer a,�, M. Sauvainb, C. Petermanna,M. Zeches-Hanrota`

aLaboratoire de Pharmacognosie, UMR 6013 CNRS, CPCBAI, Bat. 18, Moulin de la Housse,ˆBP 1039, 51087 Reims cedex, France

bInstitut de Recherche pour le De�eloppement, UR R043 Pharmacochimie des Substances´Naturelles, Faculte de Pharmacie, 35 chemin des Maraıchers, 31062 Toulouse cedex 04, France´ ˆ

Received 5 February 2001; accepted in revised form 15 May 2001

Abstract

The isolation of 14 known triterpenoids and phytosterols from the trunk bark of Maquira( )coriacea, and complete spectral data of a cardenolide, k-strophanthin-� 1 , are reported.

� 2001 Elsevier Science B.V. All rights reserved.

Keywords: Maquira coriacea; Cardenolides; Phytosterols; Triterpenoids

Ž . Ž .Plant. Maquira coriacea Karsten C.C. Berg Moraceae trunk barks were col-lected from the Amazonian rain forest region of Beni, Bolivia, in the Chacobo

Ž .community, in October 1993, and identified by Dr S. Bergeron IRD . A voucherŽ .specimen N� SB691 was deposited at the National Herbarium of Bolivia, La Paz,

Bolivia.

Uses in traditional medicine and other reported activities. The latex is used in the� �Brazilian Amazon region as dart poison 1 . The ethanolic extract of the trunk

� �barks was shown to have antiplasmodial activity 2 .

� �Previously isolated constituents. Cardenolides from the seeds 1 ; quaternary nitro-� �gen compounds from the latex 3 .

� Corresponding author. Tel.: �33-380-393-236.Ž .E-mail address: acoffer@u-bourgogne.fr A.-C. Mitaine-Offer .

0367-326X�01�$ - see front matter � 2001 Elsevier Science B.V. All rights reserved.Ž .PII: S 0 3 6 7 - 3 2 6 X 0 1 0 0 3 1 7 - 3

( )A.-C. Mitaine-Offer et al. � Fitoterapia 72 2001 841�843842

� � Ž . � �New-isolated constituents. �-Amyrin 4 yield: 4.35% on dried wt. , lupeol 5Ž . � � Ž . � � Ž .1.57 , 3�-hydroxyolean-12-en-11-one acetate 6 0.11 , cycloartenol 4 0.1 , �-

� � Ž . � � Ž . � � Ž .sitosterol 4 0.08 , �-amyrin acetate 4 0.007 , lupeol acetate 5 0.005 , glutinol� � Ž . � � Ž . � � Ž .acetate 7 0.001 , ursolic acid 8 0.0006 , 3-O-�-feruloyl-ursolic acid 8 0.0006 ,

� � Ž . � � Ž .stigmast-5-ene-3�,7�-diol 9 0.0003 , stigmast-5-ene-3�,7�-diol 9 0.0004 , 3-O-Ž . � � Ž .6�-O-palmitoyl -�-D-glucopyranosyl-�-sitosterol 10 0.001 , 3-O-�-D-gluco-

� � Ž . ( ) � � Ž .pyranosyl-�-sitosterol 10 0.001 , k-strophanthin-� 1 11 0.001 .

( ) � � Ž . Ž .k-strophanthin-� 1 . � �32.6� c 0.50, CHCl ; FAB-MS positive mode m�z:D 3Ž .� � � 1 13 Ž711 M � H ; revised 12 H- and C-NMR data in Table 1 assignments were

1 1 .made on the basis of H- H-COSY, HMQC, and HMBC experiments .

Table 11 13Ž . Ž . ( ) Ž .H-NMR 300 MHz and C-NMR 75 MHz for k-strophantin-� 1 � ppm, CDCl as solvent3

Position � �H C

1 nd 23.82 nd 25.0

Ž .3 4.15 br s 74.54 nd 34.65 73.76 nd 35.57 nd 21.78 nd 41.29 nd 39.2

10 54.611 nd 17.7

( )A.-C. Mitaine-Offer et al. � Fitoterapia 72 2001 841�843 843

Ž .Table 1 Continued

12 nd 39.513 49.414 84.515 nd 31.516 nd 26.7

Ž .17 2.77 dd, J 9.4, 5.2 Hz 50.4Ž .18 0.85 s 15.4Ž .19 10.05 s 208.0

20 175.1Ž . Ž .21 5.00 d, J 18.3 Hz , 4.90 dd, J 18.3, 1.5 Hz 73.6Ž .22 5.89 s 117.3

23 175.1Ž .Cym-1 4.83 dd, J 9.4, 1.6 Hz 96.8Ž . Ž .Cym-2 2.15 m , 1.65 m 35.5Ž .Cym-3 3.80 m 76.8Ž .Cym-4 3.30 m 81.5Ž .Cym-5 3.90 m 68.9Ž .Cym-6 1.30 d, J 6.3 Hz 17.9Ž .OCH 3.43 s 57.53Ž .Glc-1 4.35 d, J 7.7 Hz 104.2Ž .Glc-2 3.30 m 73.4Ž .Glc-3 3.45 m 75.9Ž .Glc-4 3.45 m 70.0Ž .Glc-5 3.35 m 75.6Ž .Glc-6 3.85 m 61.8

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