Chemical constituents from bulbs of allium ascalonicuml

SCIENTIFIC RESEARCH Journal o f MedicinalMaterials, 2022, Vol 27, No (pp - ) ìỉs m i Vu Thi Diep1, Nguyên Thi Thu1, Nguyên Tra My1, Hoang Dieu Huong1, Nguyên Thi Hang1, Ha Van Oanh2, Nguyên Minh Khoi1, Do Thi Ha1’*, Pham Thi My Dung3, Hoang Viet Dung3 1National Instỉtute o f Medicinal Materials (NIMM), Hanoỉ, Vietnam; 2Hanoi University o f Pharmacy, Vỉetnam; 3Vỉetnam Milìtary Medicaỉ University *Corresponding author: hado.ninuns@gmail.com (Received January 14*, 2022) Summary Chemical Constituents from Bulbs of Aỉlium ascalonicum L Nine compounds (1 - 9) were isolated from bulbs o f Allium ascalonicum Theừ Chemical structures were identiíĩcd using spectroscopic methods (NMR and MS) and comparison with literature data These compounds are protocatechuic acid (1), /raní-lV-coumaroyltyramin (2), 5,7-dihydroxy-2-heptacosanyl-benzopyran-4-one (3), quercetin (4), quercetin 4'glucopyranoside (5), isorhamnetin (6), isorhamnetin 4'-glucopyranoside (7), (22/?,255)-spirost-5-en-l/?,3/?-diol 1-O-ịi-Dgalactopyranoside (8), and (221?,25S)-spirost-5-en-l/ỉ,3/?-diol 1-ỡ-[a-L-rhamnopyranosyl-( 1—>2)-a-L-arabinopyranoside] (9) This is the first report about the presence of compounds ,3 ,8 , and from A ascalonicum Keywords: Allium ascaỉonicum L., Flavonoid, Phenolic, Pyrimỉdine, Saponin Introductỉon Shallot (Ảỉỉium ascalonicum L.), a member of the Liliaceae family, has been used as a spice, food, and folk medicine throughout history It possesses a wide range of medicinal properties, including digestive stimulant, anti-inílammatory [ ], antibacterial, antihuigal [2 ], and anticancer effects [3], etc In Vietnamese folk medicine, this plant has been used to treat typhoid, fever, colds, headaches, bloating and poisoning, blurred Vision, deaf ears, and breast swelling [4] There are many different varieties of A ascalonicum L., which depend on where its cultivation is Ly Son onions (Hanh Ly Son) are grovvn in Ly Son Island, Quang Ngai province, which has special soil and climate conditions that make Ly Son onion purple color and special ílavor Until now, not many studies on the Chemical compositions and biological effects o f Ly Son onion have been conducted Previous studies indicated that A ascaỉonỉcum contains essential oils [5], ílavonoids [6 ],[7], triterpenoids [8 ], and saponins [6 ],[9] Several studies on Ly Son onion have demonstrated that it exhibited antioxidant eíĩects [ ] and it improved behavior in autistic children [11] The objective o f the present study is to investigate the Chemical composition of Ly Son onion Materials and methods 2.1 Plant material Fresh bulbs of Alỉium ascalonicum L were collected in Ly Son, Quang Ngai, Vietnam in September 2020 and were identiíled by MSc Nguyên Van Hieu and MSc Lai Viet Hung (Department o f Medicinal Resource - National Institute o f Medicinal Materials) The voucher specimen (DL-40221) was deposited at the Herbarium of NIMM 2.2 General experimental procedures NMR spectra were recorded on Bruker AM 500 or 600 FT-NMR spectrometer (Karlsruhe, Germany) using TMS as the intemal Standard MS data were analyzed with an LC-MS/MS System (Shimadzu, Japan) Silica gel (Merck, 0.040 - 0.063 mm particle size), RP-C 18 (Merck, 30 - 50 pm particle size) were used for column chromatography (CC) Thin-layer chromatography (TLC) was carried out with silica gel 60F254 (Merck, silica gel, 0.25 mm) and RP-18F254 (Merck, 0.25 mm) plates Spots were detected with u v light 254 and 365 nm or by spraying with 10% sulíuric acid in 96% ethanol (EtOH) and then heating 2.3 Extractỉon and isolation The chopped bulbs (3.5 kg, dry weight) were macerated with 90% ethanol at room temperature times X 24 h After removal o f the solvent, the ethanol extract (595.37 g) was suspended with water and successively separated with organic solvents to get M-hexane (25.01 g), ethyl acetate (36.4 g), and aqueous (450.1 g) exứacts The n-hexane extract (23.0 g) was separated by silica gel cc and eluted by a gradient o f nhexane (Hx)-ethyl acetate (EtOAc) (100:0 0:100, v/v) to obtain íractions (H1-H7) Journal o f MedicinalMaterials, 2022, Vol 27, No Fraction H3 (2.36 g) was chromatographed on silica geỉ c c eluting with Hx-EtOAc (30:1, v/v) to yield compound (20 mg) The EtOAc extract (33.16 g) was íractionated by siỉica geỉ c c and eluted by a gradient of dichloromethane-methanol (DCM-MeOH, 100:1 to 2:1, v/v) to give 11 íractions (E l-E ll) Fraction E4 (3.91 g) was chromatographed on silica gel c c with gradient solvents o f DCMMeOH (50:1, v/v) to DCM-MeOH (0:100, v/v) to yield compound (20 mg) Fraction E (3.24 g) was chromatographed on silỉca gel c c eluting with DCM-acetone (40:1 - 0:100, v/v) to give fractions (E6.1-E6.5) Fraction E6.1 (0.85 g) was washed using DCM-MeOH (80:1, v/v) to yield compound (100 mg) Fraction E6.2 (0.29 g) was applied to RP-18 c c using MeOH-H (1:1, v/v) to yield compounds ( mg) and ( mg) Fraction E (1.27 g) was puriíied by RP-18 c c and eluted with MeOH-IỈ (1:2, v/v) to obtain compound (10 mg) Fraction E9 (2.81 g) was separated by RP-18 c c eluting with MeOHH 2O (1:2, v/v) to give fractions (E9.1-E9.7) Fraction E9.2 (0.63 g) was applied to siỉica gel c c and eluted with EtOAc-MeOH (20:1, v/v) to give compound ( mg) Compounds (10 mg) and (6.2 mg) were purified from fraction E9.6 (0.43 g) by silica gel c c eluting with EtOAc-MeOH-HCOOH (25:1:1, v/v/v) Protocatechuic acid (1): White powder, ESIMS: m/z 153.1 [M -H ]; 'H -N M R (600 MHz, CD OD), ổtì (ppm): 7.46 (1H, d, J = 1.8 Hz, H2), 6.82 (1H, d, J = 8.4 Hz, H-5), and 7.45 (1H, dd, J = 1.8, 8.4 Hz, H- ); 13C-NM R (150 MHz, CD 3OD), ỏc (ppm): 123.9 (C-l), 115.8 (C-2), 146.1 (C-3), 151.5 (C-4), 117.7 (C-5), 123.9 (C6 ), and 170.2 (C-7) 7V