ABSTRACT
OBJECTIVE@#To study the chemical constituents of the roots of Angelica dahurica, a well-known Chinese herbal medicine named Baizhi in Chinese.@*METHODS@#Compounds were separated by various chromatographies, and the structures of new compounds were elucidated based on the analysis of their spectroscopic and spectrometric data (1D, 2D NMR, HRESI MS, IR, and UV). The absolute configurations of new compounds were determined by the calculated electronic circular dichroism and chemical derivatization. The inhibitory activities of all isolates against nitric oxide (NO) production were evaluated using lipopolysaccharide-activated RAW 264.7 macrophage cells.@*RESULTS@#Seven new 3,4-dihydro-furanocoumarin derivatives ( 1a/ 1b, 2a/ 2b, 3a/ 3b, 4) together with a known furanocoumarin ( 5) were isolated from the roots of A. dahurica. The new compounds included three pairs of enantiomers, (4S, 2''R)-angelicadin A ( 1a)/(4R, 2''S)-angelicadin A ( 1b), (4S, 2''S)-angelicadin A ( 2a)/(4R, 2''R)-angelicadin A ( 2b), and (4S, 2''S)-secoangelicadin A ( 3a)/(4R, 2''R)-secoangelicadin A ( 3b), together with (4R, 2''R)-secoangelicadin A methyl ester ( 4). The known xanthotoxol ( 5) inhibited the NO production with the half-maximal inhibitory concentration (IC50) value of (32.8 ± 0.8) µmol/L, but all the new compounds showed no inhibitory activities at the concentration of 100 µmol/L.@*CONCLUSION@#This is the first report of the discovery of 3,4-dihydro-furanocoumarins from A. dahurica. The results are not only meaningful for the understanding of the chemical constituents of A. dahurica, but also enrich the reservoir of natural products.
ABSTRACT
The endangered medicinal plant Glehnia littoralis is one of the important natural source of furanocoumarin, which has been used as mucolytic, antitussive, antitumour and antibacterial. However, the genetic information of furanocoumarin biosynthesis in G. littoralis is scarce at present. The objective of this study was to mine the putative candidate genes involved in the biosynthesis pathway of furanocoumarin and provide references for gene identification, and functional genomics of G. littoralis. We carried out the transcriptome analysis of leaves and roots in G. littoralis, which provided a dataset for gene mining. Psoralen, imperatorin and isoimperatorin were detected in G. littoralis by high performance liquid chromatography analysis. Candidate key genes were mined based on the annotations and local BLAST with homologous sequences using BioEdit software. The relative expression of genes was analysed using quantitative real-time polymerase chain reaction. Further, the CYP450 genes were mined using phylogenetic analyses using MEGA 6.0 software. A total of 156,949 unigenes were generated, of which 9021 were differentially-expressed between leaves and roots. A total of 82 unigenes encoding eight enzymes in furanocoumarin biosynthetic pathway were first obtained. Seven genes that encoded key enzymes in the downstream furanocoumarin biosynthetic pathway and expressed more in roots than leaves were screened. Twenty-six candidate CYP450 unigenes expressed abundantly in roots and were chiefly concentrated in CYP71, CYP85 and CYP72 clans. Finally, we filtered 102 differentially expressed transcription factors (TFs) unigenes. The transcriptome of G. littoralis was characterized which would help to elucidate the furanocoumarin biosynthetic pathway in G. littoralis and provide an invaluable resource for further study of furanocoumarin.
ABSTRACT
Changium smyrnioides is an endangered and endemic medicinal herb in China which contains rich furanocoumarins. Bergaptol, bergapten and xanthotoxin are natural furanocoumarins in Ch. smyrnioides, among which bergaptol is mainly contained in in vitro cultures while the latter ones distribute in all organs and cultures of the plant. In this study, methyl jasmonate was used to elicit furanocoumarins in both cultivated plant and suspension cells. The accumulations of biomass and 3 furanocoumarins as well as the activity of cell, phenylalanine ammonia-lyase and antioxidase were detected. The results showed that methyl jasmonate induced the biosynthesis of furanocoumarins markedly and suspension cells from petiole produced more furanocoumarins than those from leaf. In the case of suspension cells, the concentration at 100 μmol•L⁻¹ triggered the highest yield of furanocoumarins and the 10th day of the culture period was the proper time for treatment. After 4 days the yields of bergaptol, bergapten and xanthotoxin in suspension cells from petiole were enhanced to 2.83,14.04,0.62 mg•L⁻¹ respectively. The biomass and viability of treated suspension cells decreased. At the same time, the activity of antioxidase increased, which indicated that methyl jasmonate induced cell defense. In both in vivo and in vitro conditions, cells from petiole seemed to be more sensitive to methyl jasmonate treatment compared to those from leaf. Bergaptol and xanthotoxin mainly accumulated in medium and cell respectively. Bergapten was detected in both cell and medium. The elicitation treatment only enormously affected the yields but did not significantly involve the distributions of 3 furanocoumarins. This is the first systematic study focusing on the elicitation effects of methyl jasmonate and a series of changes which lead to the increase of furanocoumarins in Ch. smyrnioides cell suspension cultures. Methyl jasmonate appears to be an effective elicitor in the research and further efforts should be made to reveal the mechanism in detail.
ABSTRACT
OBJECTIVE: To determine simultaneously the contents of xanthotoxin, bergaptol, and bergapten in cultivated Changium smyrnioides Wollf and its in vitro cultures by HPLC. METHODS: Agilent-C18column (4.6 mm × 250 mm, 5 μm) was used for chromatographic separation and PAD was applied as detector. The flow rate was 1.0 mL·min-1 with a mobile phase of methanol-water in gradient elution mode. The detection wavelength was set at 314 nm while the injection volume was 10 μL. RESULTS: The linear regression equations of xanthotoxin, bergaptol, and bergapten were Y = 17 057ρ-87.689 (r = 1.000 0), Y = 23 828ρ-380.44 (r = 0.999 9) and Y = 37 123ρ-441. 16(r = 0.999 9), respectively. The contents of xanthotoxin and bergapten in cultivated and regenerated specimens were obviously higher than those in calli and suspension cells, while bergaptol was only detected in the latter two samples. A larger amount of furanocoumarins accumulated in the cells from leaves and petioles. CONCLUSION: The established method is simple and effective with high sensitivity and good repeatability. It can be adopted in studies on the utilization of Changium smyrnioides, especially the regulation and induction of furanocoumarins.
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The first study on chemical constituents and biological activities of Clausena lansium (Lour.) Skeels (Rutaceae) growing in Vietnam has been done. Phytochemical investigation of n-hexane extract led to the isolation of five compounds: dihydroindicolactone (1), 8-geranyloxy psoralen (2), imperatorin (3), heraclenol (4) and indicolactone (5), in which this is the first report on the presence of dihydroindicolactone (1). Their structures were elucidated based on LC/MS/NMR hyphenated techniques as well as comparison with those of literature data. The n-hexane extract and its subfractions, ethanol 95% extract and several isolated compounds were evaluated for antifungal activity.
Subject(s)
Clausena , Ethanol , Ficusin , VietnamABSTRACT
Phytochemical studies on the aerial parts of Prangos uloptera, an endemic Iranian species of the genus Prangos, yielded five coumarins, xanthotoxin (1), prangenin (2), scopoletin (3), deltoin (4) and prangolarin (5). The structures of these coumarins were elucidated by spectroscopic means, and the antioxidant potential of 1-5 was evaluated by the DPPH assay. The chemotaxonomic significance of 1-5 is also discussed.
Os estudos fitoquímicos das partes aéreas de Prangos uloptera, uma espécie do gênero Prangos endêmica do Irã, forneceram cinco cumarinas, xantotoxina (1), prangenina (2), escopoletina (3), deltoína (4) e prangolarina (5). As estruturas destas cumarinas foram elucidas através de métodos espectroscópicos e o potencial antioxidante de 1-5 foi avaliado pelo ensaio de DPPH. O significado quimiotaxonômico de 1-5 também é discutido.