New diterpene from Hedychium villosum

Ž .Fitoterapia 72 2001 837�838

Phytochemical communication

New diterpene from Hedychium �illosum

Peng Xiao, Cuirong Sun, Muhammad Zahid,Omar Ishrud, Yuanjiang Pan�

Department of Chemistry, Zhejiang Uni�ersity, Hangzhou 310027, PR China

Received 26 March 2001; accepted in revised form 21 April 2001

Abstract

The stems of Hedychium �illosum yielded the new diterpenoid 1, named villosin, alongwith coronarin E and �-sitosterol. Their structures were elucidated by spectroscopic meth-ods including mono- and bi-dimensional NMR. � 2001 Elsevier Science B.V. All rightsreserved.

Keywords: Hedychium �illosum; Diterpenoids; Sterols

Ž . Ž .Plant. Hedychium �illosum Wall. Zingiberaceae stems 4 kg were collected inMay 1996, in the Xishuangbanna region, Yunnan province, China and air-dried at40�C. Samples were identified by Dr Qin Zhao, Kunming Institute of Botany,Yunnan, PRChina, where a voucher specimen has been deposited.

Uses in traditional medicine. In China, stems are used as a remedy for cough and� �apoplexy 1 .

Previously isolated constituents. No report.

( ) Ž . � � Ž .New-isolated constituents. Villosin 1 yield: 15.3 mg , coronarin E 2,3 9.8 mgŽ .and �-sitosterol 30.7 mg .

� Corresponding author. Tel.: �86-571-8795-1264; fax: �86-571-8795-1264.Ž .E-mail address: panyuanjiang@css.zju.edu.cn Y. Pan .

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 0 7 - 0

( )P. Xiao et al. � Fitoterapia 72 2001 837�838838

( ( ) ) ( ) Ž .Villosin labda-8 17 ,11,13-trien-16-oic-lactone 1 . Colorless crystals Et O , mp2108.4�108.8�C; C H O ; ESIMS: m�z 301 positive, and m�z 299 negative;20 28 2

Ž �. Ž .EIMS: m�z 300 M , 285, 257, 137 and 83; IR bands KBr : 3080, 1645, 1510, 895�1 1 Ž . Žand 870 cm ; H-NMR 500 MHz, CDCl : � 1.03 1H, ddd, J 4.1, 12.6, 9.4 Hz,3

. Ž . Ž .H-1 ax , 1.45 1H, m, H-1 eq , 1.60 1H, dddd, J 4.1, 4.3, 12.6, 13.5 Hz, H-2 ax , 1.42Ž . Ž . Ž .1H, m, H-2 eq , 1.21 1H, ddd, J 4.3, 13.5, 9.8 Hz, H-3 ax , 1.39 1H, m, H-3 eq ,

Ž . Ž1.12 1H, dd, J 2.5, 12.5 Hz, H-5 , 1.38 1H, dddd, J 4.3, 12.2, 12.5, 13.5 Hz, H-6. Ž . Ž . Žax , 1.73 1H, m, H-6 eq , 2.10 1H, ddd, J 5.0, 12.9, 13.0 Hz, H-7 ax , 1.38 1H,

. Ž . Žddd, J 2.4, 4.3, 12.9 Hz, H-7 eq , 2.41 1H, d, J 10.1, H-9 , 6.92 1H, dd, J 15.78,. Ž . Ž . Ž .10.11 Hz, H-11 , 6.18 1H, d, J 15.81, H-12 , 7.16 1H, s, H-14 , 4.81 2H, s, H-15 ,

Ž . Ž . Ž .4.51 1H, d, J 1.38, H-17a , 4.76 1H, d, J 1.36, H-17b , 0.89 3H, s, H-18 , 0.87Ž . Ž . 13 Ž . Ž .3H, s, H-19 , 0.84 3H, s, H-20 ; C-NMR 125 MHz, CDCl : 41.05 C-1 , 19.343Ž . Ž . Ž . Ž . Ž . Ž . Ž .C-2 , 42.51 C-3 , 29.98 C-4 , 54.98 C-5 , 23.58 C-6 , 36.75 C-7 , 149.69 C-8 ,

Ž . Ž . Ž . Ž . Ž . Ž .62.44 C-9 , 39.53 C-10 , 137.10 C-11 , 120.62 C-12 , 129.62 C-13 , 142.21 C-14 ,Ž . Ž . Ž . Ž . Ž . Ž .69.61 C-15 , 172.31 C-16 , 108.41 C-17 , 33.81 C-18 , 22.18 C-19 , 15.29 C-20 .

Acknowledgements

This project is supported by NSFC and the Natural Science Foundation ofZhejiang province, PR China.

References

� �1 The dictionary of Chinese traditional remedies, 1979, p. 89� �2 Zhao Q, Hao XJ, Chen YZ, Zou C. Acta Pharm Sin 1995;30:119.� �3 Zhao Q, Hao XJ, Chen YZ, Zou C. Chem J Chin Univ 1995;16:64.