Fr-4-19 (1.8 g) was applied to the SEC and got three subfractions. Fr-4-6 (250 mg) was applied on SEC (hexanes: acetone: methanol, 3:1:6, 3× 100 cm) and yielded compound 1 (156 mg). Based on TLC analysis fraction 4 (45.5 g) was applied on a flash silica gel (40–63 μm 7 × 45 cm) using hexanes: EtOAc (5 → 100%) EtOAc: MeOH (85:15) and MeOH to yield Fr-4-1 to Fr-4-25 subfractions.
#DAPHNE AFTER SHOOTS FREE#
Fraction eluted by MeOH: H 2O (60:40, 163 g) free from fats and sugars was selected, coated on Celite and applied on flash silica gel (40–63 μm 10 × 13 cm) using CHCl 3 (3 L, Fr. It was then applied on VLC in a sintered glass filter funnel (10*7 cm) containing reversed-phase RP 18 using MeOH: H 2O (30:70, 2 L 60:40, 6 L 100:0, 2 L) as a solvent. The extract was filtered, concentrated in a rotary evaporator at 40 ☌, and yielded a gummy material (205 g). The shade dried shoots were crushed to a fine powder (2180 g) and extracted in a percolator using chloroform: methanol (2:1) with a flow rate of 3 mL/min for 10 days. (China) or Sigma-Aldrich (USA) otherwise it is mentioned in the text. Methanol (MeOH), chloroform (CHCl 3), hexanes, ethyl acetate (EtOAc), acetone (Me 2CO), and all other solvents or reagent were purchased from Fisher Scientific International, Inc. Spots were detected using UV light cabinet and visualized by 1% vanillin in 5% sulfuric acid solution-processed by hair dryer heating. Flash silica gel (40–63 μm Fisher Scientific, Fair Lawn, NJ, USA), and Sephadex LH-20 (Sigma-Aldrich) were used for gravity column chromatographies (CC) and size exclusion chromatographies (SEC). Electronic circular dichroism data was taken by Olis DSM 20 CD digital spectrophotometer (Bogart, GA, USA).
#DAPHNE AFTER SHOOTS SERIES#
High-resolution mass spectra were acquired on an Agilent 1100 SL series mass spectrometer (Agilent Technologies Inc., Wilmington, DE, USA). NMR spectra were taken at 25 ☌ on AVANCE DRX-400 and 500 NMR spectrometers (Bruker, Ettlingen, Germany). IR spectrum was obtained by Rayleigh WQF-510 FTIR spectrometer (China) on NaCl pellets. The specific rotation was recorded by AutoPol IV polarimeter (Rudolph, Hackettstown, NJ, USA). Previous phytochemical research on the leaves of this plant, as well as anticancer biological studies of this plant, made us interested in a selection of other parts of the plant (shoots) for further phytochemical investigation with the aim of the discovery of new anticancer structures Figs Figs1, 1, ,2 2 and and3 3. The last two flavonoids showed good antioxidant, whereas mucronin A and mucronin B showed antituberculosis activities. mucronata grows in Pakistan, which include daphnecin, aquillochin, mucronin A, and mucronin B, cinnamic acid, 7,8-dimethoxycoumarin, 7,8-dihdroxycoumarin, umbelliferone, cumarin, daphnin, lupeol, β-amyrin, betulin, 3-O-β-glucostigmasterol, 5-hydroxy-3,6,7,4′-tetramethoxyflavone, 5,7,3′,4′-tetrahydroxyflavone, and 5,3′,4′-trihydroxyflavone-7-O-β-D-glucopyranoside. During the last decade, various compounds were reported from D. Recently it has shown antituberculosis and anticancer activities against different cancer cell lines. It is used in ethnomedicine for musculoskeletal disorders, rheumatoid, and wound healing.
Daphne mucronata Royle (common name Kheweshk) is a wild shrub that grows in different parts of Iran. Daphne fruits are not edible and reported to be toxic. Flowers are hermaphrodite in a cluster or umbrella form, pink and fragrant, and fruits are fleshy, ovoid, or almost spherical. The Daphne species are characterized as shrub either straight or recumbent with clustered or scattered alternate and leathery leaves. Thymelaeaceae is one of the large plant families with 44 genera and 500 species, including Daphne genus. Natural products have been used as medicine for several centuries, and herbal medicine has been increasingly used as a pain reliever and for curing various diseases.
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