Elsevier

Phytochemistry

Volume 49, Issue 5, 5 November 1998, Pages 1453-1456
Phytochemistry

Cyclopeptides from dianthus superbus

https://doi.org/10.1016/S0031-9422(97)00857-1Get rights and content

Abstract

Two new cyclic hexapeptides, dianthin A(1) and B(2), were isolated from the whole plants of Dianthus superbus. Their structures were established as cyclo-(Ala-Tyr-Asn-Phe-Gly-Leu) and cyclo-(Ile-Phe2-Phe1-Pro2-Gly-Pro1) by IR, UV 2D NMR and FABMS spectra.

Introduction

Dithanus superbus L. (Caryophyllaceae), which is widely distributed in China, is commonly used as a traditional Chinese medicine for a diuretic and anti-inflammatory agent in the treatment of urinary infections, carbuncles and carcinoma of the oesophagus [1]. Since little chemical research has been published on it 2, 3, 4and in a series of investigations on Caryophyllaceae cyclopeptides 5, 6, 7, in this paper we describe the isolation and structural determination of two new cyclopeptides named dianthin A(1) and dianthin B(2) from whole plants.

Section snippets

Results and discussion

Two new cycle hexapeptides, dianthin A(1) and dianthin B(2), were isolated from the ethyl acetate fraction of the ethanol extract of Dianthus superbus whole plants by column chromatography as described in the Experimental.

Dianthin A(1), cubic crystals, was negative to ninhydrin reagent but positive after hydrolysis with 6 M HCl. Its molecular formula was assigned as C33H43N7O8 (NMR and HR-FABMS) ([M+1]+ at mz 666.3223, ∇ 2.8 mDa). The IR spectrum exhibited intense N-H and CO absorptions at

General

Mp (uncorr.) were determined on a Koffler apparatus; the optical rotations were measured with a Horiba Sepa-300 polarimeter; IR spectra were recorded on a Perkin-Elmer 577 instrument; UV spectra were recorded on a Shimadzu UV-210A spectrometer; NMR spectra were measured on Varian INOVA-600 and Bruker AM-400 instruments; FABMS spectra were recorded on a VG Auto Spec-3000 spectrometer.

Plant material

The whole plants of Dianthus superbus L. were bought from Yunnan Province Drug Company in April 1995.

Extraction and isolation

The whole

Acknowledgements

—We wish to thank Mrs Hui-Ling Liang, Mrs Yu Wu (Kunming Institute of Botany, Chinese Academy of Sciences) and Miss Jing-Fei Xu, Dr Fa-Hu He (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences) for measuring the FABMS and NMR spectra. The work was supported by grants from the National Natural Science Foundation of China.

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