Isoarnottinin 4'-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity

Coumarins are a well-known group of natural products distributed in the plant kingdom especially in the family Apiaceae with various biological activities. Isoarnottinin 4'-glucoside is a simple glycosylated coumarin found previously in a few genera of Apiaceae, and its biological activities have not been previously described in details. In the present paper, the compound was isolated from Prangos uloptera (Apiaceae) leaves using HPLC techniques. Antimicrobial, phytotoxic and cytotoxic activities of the compound were evaluated by disk diffusion, lettuce assay and MTT method. Our results indicated that the compound has high antibacterial effect against Erwinia carotovora, a common plant pathogen with MIC value of 100 microg/mL. The compound also exhibited significant phytotoxic activity against lettuce and modest cytotoxic activity against HeLa cell line with IC50 of 0 .84 mg/mL. It could be concluded that isoamottinin 4'-glucoside may play phytoalexin or allelopathic role for plant and may be a candidate for an antibacterial agent or a bioherbicide.     

Coumarins and gamma-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release

The n-hexane and ethyl acetate extracts of the stems and the ethyl acetate extracts of roots from Prangos pabularia afforded an gamma-pyrone derivative and furanocoumarin derivatives with three glucose and gamma-pyrone (pabularin A, B and C), along with 26 previously known compounds (18 coumarins, six terpenoids and two glycosides). Their structures were established on the basis of spectroscopic studies. Of these, 16 coumarin derivatives isolated from P. pabularia were tested for antibacterial activity and inhibition of cytokine release.     

A comparative analysis of complete plastid genomes from Prangos fedtschenkoi and Prangos lipskyi (Apiaceae)

Prangos fedtschenkoi (Regel & Schmalh.) Korovin and P. lipskyi Korovin (Apiaceae) are rare plant species endemic to mountainous regions of Middle Asia. Both are edificators of biotic communities and valuable resource plants. The results of recent phylogenetic analyses place them in Prangos subgen. Koelzella (M. Hiroe) Lyskov & Pimenov and suggest they may possibly represent sister species. To aid in development of molecular markers useful for intraspecific phylogeographic and population‐level genetic studies of these ecologically and economically important plants, we determined their complete plastid genome sequences and compared the results obtained to several previously published plastomes of Apiaceae. The plastomes of P. fedtschenkoi and P. lipskyi are typical of Apiaceae and most other higher plant plastid DNAs in their sizes (153,626 and 154,143 bp, respectively), structural organization, gene arrangement, and gene content (with 113 unique genes). A total of 49 and 48 short sequence repeat (SSR) loci of 10 bp or longer were detected in P. fedtschenkoi and P. lipskyi plastomes, respectively, representing 42–43 mononucleotides and 6 AT dinucleotides. Seven tandem repeats of 30 bp or longer with a sequence identity ≥90% were identified in each plastome. Further comparisons revealed 319 polymorphic sites between the plastomes (IR, 21; LSC, 234; SSC, 64), representing 43.8% transitions (Ts), 56.1% transversions (Tv), and a Ts/Tv ratio of 0.78. Within genic regions, two indel events were observed in rpoA (6 and 51 bp) and ycf1 (3 and 12 bp), and one in ndhF (6 bp). The most variable intergenic spacer region was that of accD/psaI, with 21.1% nucleotide divergence. Each Prangos species possessed one of two separate inversions (either 5 bp in ndhB intron or 9 bp in petB intron), and these were predicted to form hairpin structures with flanking repeat sequences of 18 and 19 bp, respectively. Both species have also incorporated novel DNA in the LSC region adjacent to the LSC/IRa junction, and BLAST searches revealed it had a 100 bp match (86% sequence identity) to noncoding mitochondrial DNA. Prangos‐specific primers were developed for the variable accD/psaI intergenic spacer and preliminary PCR‐surveys suggest that this region will be useful for future phylogeographic and population‐level studies.     

Terpenoids and gamma-pyrone derivatives from Prangos tschimganica

The methanol extract of the dried aerial parts of Prangos tschimganica afforded seven monoterpenoids and four gamma-pyrone derivatives. Their structures were established on the basis of chemical and spectroscopic evidence.     

Coumarins from Musineon divaricatum

A chemical investigation of Musineon divaricatum has resulted in the isolation of 19 coumarins, five of which are novel compounds; 18 are khellactone derivatives. The coumarins were isolated from the crude extracts by a combination of adsorption chromatography, gel permeation and HPLC; the more successful HPLC separations utilized a nitrile bonded phase column. The structures were determined by ¹H NMR and mass spectral studies and by comparisons with literature data. The relative configuration for the entire series was secured from ¹H NMR data, while the absolute configuration could be assigned with any certainty only in the cases of two of the compounds.     

Coumarins from Seseli bocconi

A new khellactone, bocconin, in addition to known compounds, have been isolated from Seseli bocconi subsp. bocconi and subsp. praecox Gamisans. Their structures were elucidated on the basis of spectral analyses and hydrolytic studies.     

Coumarins from Amyris balsamifera

Two new coumarins have been isolated from the aerial parts of Amyris balsamifera. On the basis of spectral and chemical data, these have been identified as (R)-(+)-6-(2′-hydroxy-3′-methyl-3′-butenyl)-7-methoxycoumarin and balsamiferone, 7-hydroxy-3,6-bis (3′-methyl-2′-butenyl)-coumarin.     

Coumarins from two Coleonema species

The aerial parts of Coleonema aspalathoides yielded a single coumarin, 7-(3,3-dimethylallyloxy)-coumarin. Coleonema calycinum afforded 11 coumarins including three novel compounds identified on the basis of spectral data as 7-(2-hydroxy-3-methylbut-3-enoxy)-coumarin,7-(E-3-methoxycarbonylbut-2-enoxy)-coumarin and 7-methoxy-8-(2,3-dihydroxy-3-methylbutoxy)-coumarin.     

Coumarins from Malaysian Micromelum minutum

In a continuation of our study of the Rutaceae, detailed chemical investigation on Micromelum minutum (Rutaceae) collected from Sepilok, Sabah, Malaysia gave four new coumarins. The structures of the coumarins have been fully characterised by spectroscopic methods as 3",4"-dihydrocapnolactone 1, 2',3'-epoxyisocapnolactone 2, 8-hydroxyisocapnolactone-2',3'-diol 3 and 8-hydroxy-3",4"-dihydrocapnolactone-2',3'-diol 4.     

Coumarins from the heartwoods of Mansonia gagei Drumm

Three coumarins and three known mansonones were isolated from the heartwood of Mansonia gagei Drumm. The structures of the three coumarins were elucidated as 3,8-dimethyl-5-isopropyl-6-methoxycoumarin (mansonrin A) 3,8-dimethyl-5-isopropyl-6-hydroxycoumarin (mansorin B) and 2,3-dihydro-3,6,9-trimethyl naphtho[1,8-bc]pyran-7-oxa-8-one (mansorin C) by analyses of physical properties and spectroscopic data. The cytotoxicity of the isolated compounds against brine shrimp Artemia salina Linn. was also evaluated.