Ž .Fitoterapia 71 2000 610]612

Phytochemical communication

Condensed tannins from Myrica gale

Suzana C. Santosa,U, Peter G. Watermanb

aInstituto de Quımica, Uni ersidade Federal de Goias, Caixa Postal 131, CEP 74001-970,´ ´Goiania, Goias, Brazilˆ ´

bCentre for Phytochemistry, Southern Cross Uni ersity, P.O. Box 157, Lismore, NSW 2480,Australia

Received 7 March 2000; accepted 2 April 2000

Abstract

From the aerial parts of the Myrica gale catechin, epicatechin, gallocatechin, epigallocate-Ž . Ž .chin, epigallocatechin-3-O-gallate, gallocatechin- 4a-8 -epicatechin, gallocatechin- 4a-8 -ep-

Ž . Ž . Ž .igallocatechin, and gallocatechin- 4a-8 -gallocatechin- 4a-8 -gallocatechin 1 , were isolated.The 1H- and 13C-NMR data of the peracetate derivative of the trimer are reported. Q 2000Elsevier Science B.V. All rights reserved.

Keywords: Myrica gale; Condensed tannins

Ž .Plant. Myrica gale L. Myricaceae , aerial parts were collected from Queen’s ViewŽ .Park, Scotland central region in September 1992. A voucher specimen was

deposited at the Phytochemistry Research Laboratories, University of Strathclyde,Glasgow, UK.

Uses in traditional medicine and other reported activities. The leaf oil is used asw x w xan insect repellent 1 , and a leaf extract as an antiviral agent 2 . Dihydrochalcones

w xshowed bacteriostatic and fungistatic activities 3 ; diarylheptanoids showed antioxi-w xdant activity 4,5 .

U Corresponding author. Fax: q55-62-821-1008.Ž .E-mail address: suzana@quimica.ufg.br S.C. Santos .

0367-326Xr00r$ - see front matter Q 2000 Elsevier Science B.V. All rights reserved.Ž .PII: S 0 3 6 7 - 3 2 6 X 0 0 0 0 1 9 8 - 2

( )S.C. Santos, P.G. Waterman r Fitoterapia 71 2000 610]612 611

w x w xPreviously isolated constituents. Diarylheptanoids 6 , chalcones 7 , dihydrochal-w x w xcones 7,8 , flavanones, and flavonol glycosides 9 .

w x Ž .New-isolated constituents. Five monomers } catechin 10 0.87% , epicatechinw x Ž . w x Ž . w x Ž .10 0.43 , gallocatechin 10 2.17 , epigallocatechin 10 0.33 and epigallocate-

w x Ž . Ž . w xchin-3-O-gallate 11 0.15 ; two dimers } gallocatechin- 4a-8 -epicatechin 10Ž . Ž . w x Ž .0.07 and gallocatechin- 4a-8 -epigallocatechin 12 0.08 ; and the trimer gallocat-

Ž . Ž . Ž . w x Ž .echin- 4a-8 -gallocatechin- 4a-8 -gallocatechin 1 13 0.10 . The last three com-pounds were isolated and characterised as their peracetate derivatives.

( ) ( )Gallocatechin- 4a-8 -gallocatechin- 4a-8 -gallocatechin peracetate. A brown powder;1 Ž . ŽH-NMR 400 MHz, CDCl : d 1.29]2.36 s, 3 = aliphatic and 15 = phenolic3

. Ž . Ž . Ž .OAc , 2.11]2.58 2H, m, H-4I , 4.20 d, J 9 Hz, H-4C , 4.57 d, J 8.5 Hz, H-4F ,Ž . Ž . Ž . Ž .4.68 d, J 10 Hz, H-2C , 4.78 d, J 10 Hz, H-2F , 5.20 m, H-3I , 5.24 bs, H-2I ,Ž . Ž . Ž .5.39 dd, J 8.5, J 10 Hz, H-3F , 5.57 t, J 9.3 Hz, H-3C , 6.35 d, J 2.3 Hz, H-6A ,1 2Ž . Ž . Ž .6.54 d, J 2.3 Hz, H-8A , 6.58 s, H-6D , 6.66 4H, s, H-29 and H-69B and H , 6.68

Ž . Ž . 13 Ž .s, H-6G , 6.96 2H, s, H-29 and H-69E ; C-NMR 100 MHz, CDCl : d 20.3]21.33Ž . Ž . Ž . Ž . Ž . Ž .18 = CH CO] , 29.6 C-4I , 36.9 C-4F , 37.1 C-4C , 66.8 C-3I , 70.8 C-3C , 72.13Ž . Ž . Ž . Ž . Ž . Ž .C-3F , 77.3 C-2I , 78.8 C-2C , 79.6 C-2F , 108.3 C-8A , 108.6 C-6G , 109.8Ž . Ž . Ž . Ž . Ž . Ž .C-6A , 109.9 C-10G , 110.7 C-6D , 116.7 C-8G , 117.2 C-10A , 117.3 C-10D ,

Ž . Ž . Ž . Ž .118.7 C-8D , 119.4 4C, C-29 and C-69B and H , 119.6 C-29E , 124.5 C-69E , 134.3Ž . Ž . Ž . Ž . Ž .C-49B , 134.7 C-49E , 135.0 2C, C-19B and C-49H , 135.1 C-19E , 137.0 C-19H ,

Ž . Ž . Ž .143.2 4C, C-39 and C-59B and H , 143.4 2C, C-39 and C-59E , 147.3 C-7G , 147.5

( )S.C. Santos, P.G. Waterman r Fitoterapia 71 2000 610]612612

Ž . Ž . Ž . Ž . Ž . Ž .C-7D , 147.6 C-5D , 148.2 C-5G , 149.5 C-5A , 150.2 C-7A , 151.3 C-9G , 154.5Ž . Ž . Ž . Ž .C-9D , 156.5 C-9A , 166.4]171.7 18 = CH CO] ; CD spectrum MeOH : 2103wŽ . x wŽ . x wŽ . xu y 196 647 nm, 234 u y 115 416 nm, 278 u y 37 390 nm; FAB-MS mrz:

wŽ .q x q Ž . Ž .1671 M q H 25% ; M corresponding to C H O , 1567 80 , 1525 100 .81 75 39

Acknowledgements

The authors would like to acknowledge CAPES Brazilian agency for financialsupport.

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