Cyclopeptides from dianthus superbus

Youchu, Wang; Tan, Ning‐Hua; Zhou, Jun; Wu, Hou‐Ming

doi:10.1016/s0031-9422(97)00857-1

Cited by 41 publications

(32 citation statements)

References 4 publications

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“…13 Close to 100 cyclopeptides have been isolated from species of Caryophyllaceae composed almost exclusively of amino acid residues. 4 Like other members of this family, 14,15 gypsins A-D are all cyclic homodetic peptides. A comparison of gypsins A-D with cyclopeptides isolated from other Caryophyllaceae spp.…”

Section: Resultsmentioning

confidence: 99%

Gypsins A−D from Gypsophila arabica

et al. 2008

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Four new cyclopeptides, named gypsins A-D (1- 4), together with one known oleanane saponin, were isolated from the roots of Gypsophila arabica. The structures of cyclo(-Leu(1)-Pro(2)-Leu(3)-Trp(4)-Pro(5)-Gly(6)-) (1), cyclo(-Leu(1)-Pro(2)-Tyr(3)-Phe(4)-Pro(5)-Gly(6)-) (2), cyclo(-Ala(1)-Pro(2)-Tyr(3)-Leu(4)-Leu(5)-Pro (6)-Pro(7)-Ala(8)-) (3), and cyclo(-Leu(1)-Trp(2)-Pro(3)-Gly(4)-Gly(5)-Ser(6)-Ser(7)-) (4) were elucidated by 1D and 2D NMR spectroscopy including 1D-TOCSY, DQF-COSY, 2D-ROESY, HSQC, and HMBC experiments, as well as ESI tandem mass spectrometric fragmentation analysis and chemical evidence.

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Section: Resultsmentioning

confidence: 99%

Gypsins A−D from Gypsophila arabica

et al. 2008

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“…Mass spectra were obtained on a MS Agilent 1100 Series LC/MSD Trap mass spectrometer (ESI-MS) and a G1969A TOF MS (HR-ESI-MS), respectively. 1D-and 2D-NMR spectra were measured in pyridine-d 5 at 300 K on a Bruker ACF-500 NMR ( 1 H: 500 MHz, 13 C: 125 MHz) spectrometer, with tetramethylsilane (TMS) as an internal standard, in which coupling constants were given in Hz. Gas chromatography was done on Varian CP-3800 Gas Chromato-520…”

Section: Methodsmentioning

confidence: 99%

“…longicalycinus WILLIAMS led to the isolation of saponins, flavones, and cyclopeptides. [2][3][4][5] As part of our search for bioactive saponins from TCMs, we previously reported the structure elucidation of two new triterpenoid saponins. 6) In our continued research, further chemical investigation of this plant led to the isolation of three novel triterpenoid saponins.…”

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confidence: 99%

Three New Triterpenoid Saponins from <i>Dianthus superbus</i>

Luo

Chen

Kong

2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Dianthus superbus L. (Caryophyllaceae) is a small herb distributed in Shandong province and elsewhere in the northeast of China. This plant, known as "Qumai," is an important traditional Chinese medicine (TCM) used as a diuretic and an anti-inflammatory agent for the treatment of urinary infections, carbuncles, and carcinomas.1) Previous chemical investigation on this species and its variety D. superbus L. var. longicalycinus WILLIAMS led to the isolation of saponins, flavones, and cyclopeptides.2-5) As part of our search for bioactive saponins from TCMs, we previously reported the structure elucidation of two new triterpenoid saponins.6) In our continued research, further chemical investigation of this plant led to the isolation of three novel triterpenoid saponins. We now report the isolation and structural elucidation of three new saponins (1-3, see Fig. 1). Results and DiscussionCompound 1 23.7, 16.0, 17.4, 26.1, 12.7 and 122.7 (C-12) according to the heteronuclear single quantum coherence (HSQC) spectrum, respectively, and thereby were indicative of an olean-12-ene skeleton. In addition, the heteronuclear multiple bond correlation (HMBC) of H-24 (d H 1.57), H-3 (d H 4.65) with d C 180.5 showed that the carboxyl carbon at d C 180.5 was assigned to C-23, the other carboxyl carbon at d C 176.5 was attributed to C-28. In the nuclear Overhauser effect spectroscopy (NOESY) spectrum, observation of an NOE between H-3 and H-5a and the appearance of H-3 (d H 4.65) as a doublet (Jϭ12.0, 4.4 Hz) supported b-orientation of 3-OH. An NOE correlation between signals of an axial methyl at C-10 (H 3 -25) and a methyl at C-4 indicated that the COOH group was assigned to be a-oriented at C-4 (Fig. 2). Therefore, the aglycone was determined to be 3b-hydroxyolean-12-en-23,28-dioic acid, gypsogenic acid.7) The downfield 13 C-NMR chemical shift at d C 85.1 (C-3) and the upfield 13 C-NMR chemical shift at d C 176.5 (C-28) suggested that 1 was a bisdesmosidic saponin with glycosidic linkages at C-3 through an O-heterosidic bond and at C-28 through an ester bond.8) The sugar unit was confirmed to be glucose by co-TLC with standard sugars after hydrolysis, and the D-configuration was proved by GC-MS results of a derivatizated sample. The three sugar anomeric carbons were detected at d C 105.4, 105.1, and 95.6 in

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“…Arenaria oreophila (whole plants) Arenariphilin A (60) cyclo(Thr-Gly) [136] Arenariphilin B (61) cyclo(Ser1-Gly-Ser2-Ile-Phe1-Phe2) [136] Brachystemma calycinum Brachystemin A cyclo(Pro1-Phe-Leu-Ala1-ThrPro2-Ala2-Gly) [20] Dianthus superbus Dianthin A cyclo(Ala-Tyr-Asn-Phe-GlyLeu) [137] Dianthin B cyclo(Ile-Phe2-Phe1-Pro2-GlyPro1) [137] Dianthin C (68) [138] Dianthin D (70) [138] Dianthin E (69) Cytotoxic [138] Dianthin F (66) Cytotoxic [138] Drymaria diandra…”

Section: Family (Species) Constituents Structures Bioactivity Referencesmentioning

confidence: 99%

“…For example, RA-VII was converted into its thioamide (135), which was, then, converted to its oxazole derivative (138); acid hydrolysis of the oxazole (138) gave [D-Ala4]RA-VII (136). Acid hydrolysis of the oxazoles under mild conditions also afforded [D-Ala2]RA-VII (137) and [L-Ala1]RA-VII, respectively Their structures (Fig. (45)) were established by X-ray crystallography.…”

Section: Bioactive Rubiaceae-cyclopeptidesmentioning

confidence: 99%

Naturally-Occurring Cyclopeptides: Structures and Bioactivity

Pomilio¹,

Battista²,

Vitale

2006

COC

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Cyclic peptides are a special bioactive group of compounds with interesting pharmacological and biochemical properties. Different natural sources are mentioned in this paper, but interest is focused on those cyclopeptides isolated from higher plants and higher fungi. Cyclopeptides occur in higher plant species, which belong to the following families: Annonaceae, Araliaceae, Asteraceae, Caryophyllaceae, Euphorbiaceae, Fabaceae, Labiatae, Linaceae, Olacaceae, Rhamnaceae, Rubiaceae, Rutaceae, Schizandraceae, Solanaceae, and Violaceae. Basidiomycetes is the group of higher fungi, which has shown to be rich in cyclopeptides, e.g., Amanita, Conocybe, Lepiota, Galerina, and Omphalotus species. Usually these compounds are associated to a toxic response in mammals, as well as to cytotoxic, insecticidal, antimalarial, estrogenic, sedative, nematicidal, antimicrobial, immunosuppressive, and enzyme-inhibitory activities. Structures are elucidated by chemical methods and spectroscopic techniques. Configurational and conformational analyses of some bioactive cyclopeptides are discussed. Conformational studies of the natural cyclopeptides and their derivatives are related to the stereochemical requirements for these bioactive compounds.

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Cyclopeptides from dianthus superbus

Cited by 41 publications

References 4 publications

Gypsins A−D from Gypsophila arabica

Gypsins A−D from Gypsophila arabica

Three New Triterpenoid Saponins from <i>Dianthus superbus</i>

Naturally-Occurring Cyclopeptides: Structures and Bioactivity

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