Cyclopeptides from dianthus superbus
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 m⧹z 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.
References (8)
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2023, Phytochemistry LettersStructure-activity relationship studies of Longicalcynin A analogues, as anticancer cyclopeptides
2020, Chemico-Biological InteractionsCitation Excerpt :On the other hand, cyclization of peptides, in addition to increasing biological stability, can fix peptides conformation and improve their interaction with biological active site, and therefore, give better pharmacological activity [12]. Anticancer activity of naturally originated cyclopeptides has attracted many researchers to look for various analogues in order to increase activity while reduce some of the side effects of these peptides on biological application [15–17]. From a Chinese medicinal plant, Dianthus superbus, initially two and then four cyclohexapeptides were isolated called as Dianthin A-F [16,17].
Two new quinolone alkaloids from Dianthus superbus var. superbus
2019, Tetrahedron LettersInhibitory effects of Dianthi Herba ethanolic extract on inflammatory and nociceptive responses in murine macrophages and mouse models of abdominal writhing and ear edema
2018, Journal of EthnopharmacologyCitation Excerpt :Dianthi Herba, consisting of the aerial parts of both species, is frequently used as a diuretic and anti-inflammatory therapy in traditional East Asian medicine (Jiangsu New Medical College, 1977; López-Expósito et al., 2011; The State Pharmacopoeia Commission of The People’s Republic of China, 2005). Specifically, Dianthi Herba is frequently used to treat urinary inflammation-related diseases including urinary infection, gonorrhea, carbuncles, and carcinoma (Oshima et al., 1984; Raman and Park, 2015; Wang et al., 1998; WHO, 1998). Previous studies illustrated that it exerts apoptotic effects in human oral cancer and HepG2 human hepatocellular carcinoma cells (Nho et al., 2012; Shin et al., 2013).
Activation of apoptosis by ethyl acetate fraction of ethanol extract of Dianthus superbus in HepG2 cell line
2012, Cancer EpidemiologyCitation Excerpt :Powell et al. reported that aqueous extract of herba Scutellaria barbatae could induce apoptosis of ovarian cancer cell lines [11]. Dianthus superbus L., which is widely distributed in China, is commonly used as a traditional Chinese medicine, as a diuretic and anti-inflammatory agent, in the treatment of urinary infections, carbuncles and carcinoma of the oesophagus [12]. We have recently reported antioxidant and cytotoxic activities of various fractions of ethanol extract of D. superbus.