Dryopteris Fragrans Research Articles

Microwave-assisted ionic liquids pretreatment followed by hydro-distillation for the efficient extraction of essential oil from Dryopteris fragrans and evaluation of its antioxidant efficacy in sunflower oil storage

With strong dissolution abilities of ionic liquids to plant cell walls, an integrated microwave-assisted ionic liquids pretreatment followed by hydro-distillation method (MILP–MHD) was performed for the efficient extraction of essential oil from the rare Dryopteris fragrans. Under optimal conditions, this innovative MILP–MHD provided the remarkable superiority of much higher yield (0.91%) of D. fragrans essential oil (DEO) within much shorter extraction duration (14.2min) than those of the reported solvent-free microwave extraction technique (0.33% and 94min). Furthermore, the antioxidant efficacy of DEO in the stabilization of sunflower oil was determined and found to be comparable to the commonly-employed α-tocopherol (VE) but a little lower than the synthetic antioxidant butylated hydroxytoluene (BHT). Therefore, MILP–MHD is a potential and highly efficient technique for the extraction of valuable essential oils in flavor food industries and DEO can be explored as a potent natural antioxidant additive for edible oils or lipid foods storage.

Dryofragin, a phloroglucinol derivative, induces apoptosis in human breast cancer MCF-7 cells through ROS-mediated mitochondrial pathway

Dryofragin is a phloroglucinol derivative extracted from Dryopteris fragrans (L.) Schott. In this study, the anticancer activity of dryofragin on human breast cancer MCF-7 cells was investigated. Dryofragin inhibited the growth of MCF-7 cells in a time and concentration-dependent manner. The cell viability was measured using MTT assay. After treatment with dryofragin for 72, 48 and 24h, the IC50 values were 27.26, 37.51 and 76.10μM, respectively. Further analyses of DNA fragmentation and Annexin V-PI double-labeling indicated an induction of apoptosis. Dryofragin-treatment MCF-7 cells had a significantly accumulation of reactive oxygen species (ROS), as well as an increased percentage of cells with mitochondrial membrane potential (MMP) disruption. These phenomena were blocked by pretreatment for 2h of MCF-7 cells with the antioxidant compound N-acetyl-l-cysteine (NAC, 5mM). These results speak for the involvement of a ROS-mediated mitochondria-dependent pathway in dryofragin-induced apoptosis. Western blot results showed that dryofragin inhibited Bcl-2 and induced Bax expression which led to an activation of caspases-9 and -3 in the cytosol, and further cleavage of poly ADP-ribose polymerase (PARP) in the nucleus, then induced cell apoptosis. In conclusion, the present study provides evidence that dryofragin induces apoptosis in human breast cancer MCF-7 cells through a ROS-mediated mitochondrial pathway.

Solvent-free microwave extraction of essential oil from Dryopteris fragrans and evaluation of antioxidant activity

Solvent-free microwave extraction (SFME) of the essential oil from Dryopteris fragrans and its antioxidant activity were investigated. A central composite design combined with response surface methodology was applied to study the influences of extraction time, irradiation power and humidity (proportion of water pretreatment). A maximal extraction yield of 0.33% was achieved under optimal conditions of extraction time 34min, irradiation power 520W and humidity 51%. Sixteen compounds, representing 89.65% of the oil, were identified, of which the major ones, (1R,4S,11R)-4,6,6,11-tetramethyltricyclo[5.4.0.0(4,8)]undecan-1-ol (30.49%), 1R,4S,7S,11R-2,2,4,8-tetramethyltricyclo[5.3.1.0(4,11)]undec-8-ene (22.91%) and, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenemethanol (15.11%), accounted for 68.51% of the oil. The antioxidant activity of the essential oil was assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene/linoleic acid, and reducing power assay, the IC50 values were 0.19, 0.09 and 0.18mg/mL, respectively. All these results suggest that SFME represents an excellent alternative protocol for production of essential oils from plant materials.

Preparative separation of dryofragin and aspidin BB from Dryopteris fragrans extracts by macroporous resin column chromatography

A simple, efficient and environment-friendly chromatographic separation method was developed for preparative separation and enrichment of dryofragin and aspidin BB from Dryopteris fragrans. The adsorption properties of twelve macroporous adsorption resins were evaluated. The three selected resins were further screened depending on the separation performance of their packed columns, in which AB-8 resin showed better separation efficiency for dryofragin and aspidin BB. In order to maximize column efficiency, the operating parameters (flow rate, ethanol concentration and volume) of the resin column chromatography were optimized and compared with the conventional resin column adsorption. After preparative separation and enrichment on resin column chromatography, the contents of dryofragin and aspidin BB in the product were 8.39- and 5.99-fold increased with recovery yields of 91.22% and 75.64%, respectively. Moreover, the regenerated adsorbent exhibited excellent reusability within at least five cycles of adsorption/desorption. It suggested that multi-targets would be enriched effectively by resin column chromatography.

Three drimane sesquiterpene glucoside from the aerial parts of Dryopteris fragrans (L.) schot

Sesquiterpene glucoside was isolated from the aqueous extract of the aerial parts of Dryopteris fragrans (L.) schot. Three new sesquiterpene glucoside xianglinmaojuesides A-C (1-3), 3beta,11-dihydroxy-drim-8 (12)-en-11-O-beta-D-glucopyranoside (1), 3beta,11-dihydroxy-drim-8(12)-en-3-O-beta-D-glucopyranoside (2), and 11,14-dihydroxy-drim-8(12)-en-11-O-beta-D-glucopyranoside (3) were finally obtained by reversed-phase HPLC and their structures were elucidated by HRESIMS and 1D, 2D NMR analyses.

A new phenolic glycoside from the aerial parts of Dryopteris fragrans

A new phenolic glycoside, 3,5-dimethyl-6-hydroxy-2-methoxy-4-O-D-glucopyranosyl-oxy-acetophenone (1), was isolated from the aerial parts of Dryopteris fragrans. The structure was elucidated on the basis of spectroscopic methods.

ChemInform Abstract: Ichthyotoxic Phloroglucinol Derivatives from Dryopteris fragrans and Their Antitumor Promoting Activity.

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Ichthyotoxic phloroglucinol derivatives from Dryopteris fragrans and their anti-tumor promoting activity.

Two new ichthyotoxic compounds, aspidin PB (8) and dryofragin (9), along with three known phloroglucinol derivatives (1-3) and five terpenoids, were isolated from the whole herbs of Dryopteris fragrans by toxicity-directed fractionation using Oryzias latipes (Japanese name; medaka). The structures of the new compounds were determined by spectroscopic methods including 2D NMR techniques. Amongst the isolates, aspidin PB (8), dryofragin (9), and 1-5 exhibited potent ichthyotoxic activity against medaka with a median tolerance limit (TLm after 24 h) of 1.2-4.3 microg/ml. These compounds which are toxic to fish also had a potent inhibitory effect on the activation of Epstein-Barr virus early-antigen (EBV-EA) induced by tetradecanoyl phorbol 13-acetate, which is an in vitro short-term assay for anti-tumor promoting agents. Aspidin BB (2) and albicanol (4), which exhibited strong inhibitory effects on the EBV-EA activation, significantly suppressed an in vivo two-stage carcinogenesis on mouse skin.

Dryofragin and Aspidin PB, Piscicidal Components from Dryopterisfragrans

The structures of dryofragin (5), a novel sesquiterpenoid connecting acylated filicinic acid, and a new aspidin analogue isolated as piscicidal components from the whole plant of Dryopteris fragrans have been elucidated by extensive spectroscopic analysis.

Chemotaxonomic investigations on Dryopteris fragrans

The phloroglucinol derivatives in four collections of Dryopteris fragrans var. remotiuscula Komarov from Finland, Ontario, and Newfoundland were investigated. The collections from two localities in Ontario gave different results, which indicate either chemical variability in the variety, or the possibility that var. remotiuscula in Ontario might be re-evaluated.

Dryopteris fragrans var. remotiuscula and Some Other Ferns from the Vicinity of Lake Sunapee, N. H.

Dryopteris fragrans var. remotiuscula and Some Other Ferns from the Vicinity of Lake Sunapee, N. H.

Porcupines and Ferns

Early in August, 1940, while at our summer home in the Catskills, I received a letter from a friend, asking me to collect some ferns she listed-Aspleniutm Rutamuraria, Onoclea Struthiopteris, Cryptogramma Stelleri, Polystichum Braunii, Cystopteris bulbifera, Woodsia glabella, and Lygodium palmatum, also Dryopteris fragrans -adding that the last had the fragrance of violets, but there was no use searching, as it grows only on the most inaccessible cliffs and was not known so far south. At

The Irresistible Charm of the Ferns

The general similarity of the four lists is shown by the fact that the four combined include only 40 species, which is only 6 less than the list for all New England and New York, north of Connecticut. The missing six are Dryopteris fragrans, D. Fzlix-mas and four coastal plain species, namely the two Woodwardias, Dryopteris simulata, and Lygodium. All the stations report Ophioglossum vulgatum. Of the seven Botrychiums named in Gray's Manual the Green Lakes and Willoughby have all except B. angustisegmentum. The other two localities lack B. Lunaria, and Dorset fails to report B. simplex. .It is hardly conceivable that it is not there.

An Interesting Specimen of the Fragrant Shield Fern

The following note attached by the writer to sheet number 7084 of Dr. Jennings' Ontario collection may be of sufficient interest to warrant its publication in the Fern Journal. The fern in question was collected August 19, 1914, on a steep diabase cliff on the south shore of north Ombabika peninsula, Lake Nipigon, Ontario. Dryopteris fragrans (L.) Schott. (7084). This is a very remarkable plant in that it has about 120 (counted as accurately as possible without destroying the planta few did drop off) dead fronds and 10 mature live fruiting fronds-130 in all at the time of its collection. The five other specimens of this species collected on the present expedition show 5, 7, 9, 4, and 6 green fronds respectively, an average of about seven green leaves to the plant including the first plant. Using this figure as the basis of the average annual leaf production, some of these dead fronds are at least 17 years old and the whole plant 18 years old. If it produced 10 fronds annually, they are 12 years old and the whole plant 13 years old. From these figures it seems perfectly reasonable to conclude that the oldest set of dead fronds is at least 15 years old. But this is not all. The rootstock is about 12 centi-