C-18 silica gel (40C60 m; Daiso Co

C-18 silica gel (40C60 m; Daiso Co., Tokyo, Japan), MCI gel CHP 20P (75C150 m, Mitsubishi Chemical Industries, Tokyo, Japan) and ATN1 Sephadex LH-20 (Amersham Pharmacia, Uppsala, Sweden) were utilized for column chromatography. of the total anthocyanins [6,7,8]; no comprehensive study has been carried out to explore the chemical constituents of This attracted our attention. In the course of continuous study, a new flavonoid glucoside, ruthenicunoid A, and eight known compounds were isolated and recognized. All the compounds were tested for his or her biological activity on SIRT1, a nicotinamide adenosine dinucleotide (NAD)-dependent deacetylase. Our attempts will become explained below. 2. Results and Discussion 2.1. Structure Elucidation of the Compounds The EtOH draw out of was suspended in water and partitioned with EtOAc. The EtOAc soluble part was submitted to a combination of chromatography to afford compounds 1989.2546 [M + Na]+ (calcd. for C43H50O25Na, 989.2539). The 1H NMR spectrum of 1 (Table 1) shows an AABB coupling system characteristic of a group of protons at = 8.5 Hz, H-2, 6) and 6.81 (2H, d, = 8.5 Hz, H-3, 5), four aromatic protons at = 1.8 Hz, H-3), = 1.8 Hz, H-5), = 1.8 Hz, H-2), and = 1.8 Hz, H-6), suggesting the presence of two 1,2,3,5-tetrasubstituted benzene rings. In addition, one methoxy group at = 15.9 Hz, H-7) and = 16.0 Hz, H-8) were observed. The 13C NMR and DEPT spectra of 1 1 (Table 1) show 43 carbon signals attributed to CPI 4203 two methyl (one oxygenated), three sp3 methylene, twenty-five methine (ten olefinic and fifteen aliphatic), and thirteen quaternary carbons (three carbonyls, ten sp2 including seven oxygenated). Inspection of these NMR data found that the partial signals resemble those of malvone [9,10], differing in that 5-OMe in malvone was replaced by 5-OH in 1. The HMBC correlation (Number 2) of CPI 4203 OCH3/C-3 and ROESY correlation of OCH3/H-2 (Number 2), in thought of the chemical shifts of C-4 (in ppm, in Hz, methanol-< 0.05, *** < 0.001 versus control (= 3). 3. Experimental Section 3.1. General Methods Optical rotations were recorded on a Horiba SEPA-300 polarimeter. UV spectrum was recorded on a Shimadzu UV-2401PC spectrometer (Shimadzu Corporation, Tokyo, Japan). GC analysis was performed using an Agilent 6890N gas chromatography instrument (Agilent Systems, Santa Clara, CA, USA). GC/MS analysis was performed using an Agilent 7890B GC System (Agilent Systems, Santa Clara, CA, USA) and a Asilent 5977 MSD inrun (Agilent Systems, Santa Clara, CA, USA). NMR spectra were recorded on a Bruker AV-400 (Bruker, Karlsruhe, Germany) or an AV-600 spectrometer (Bruker, Karlsruhe, Germany), with TMS as an internal standard. ESIMS, and HRESIMS were measured on an Agilent G6230TOF MS spectrometer (Agilent Systems, Santa Clara, CA, USA). C-18 silica gel (40C60 m; Daiso Co., Tokyo, Japan), MCI gel CHP 20P (75C150 m, Mitsubishi Chemical Industries, Tokyo, Japan) and Sephadex LH-20 (Amersham Pharmacia, Uppsala, Sweden) CPI 4203 were utilized for column chromatography. Semi-preparative HPLC was carried out using an Agilent 1200 liquid chromatograph having a YMC-Pack ODS-A column (250 mm 10 mm, i.d., 5 m) and Thermo Hypersil GOLD-C18 column (250 mm 21.2 mm, i.d., 5 m). 3.2. Flower Material The fruits of were collected from the market of herbal medicine in Yunnan province, Peoples Republic of China, in September 2016. The material was recognized by Mr. Bin Qiu at Yunnan Institute of Materia Medica, and a voucher specimen (CHYX-0605) is definitely deposited in the State Key Laboratory of Phytochemistry and Flower Resources in Western China, Kunming Institute of Botany, Chinese Academy of Sciences, Peoples Republic of China. 3.3. Extraction and Isolation The fruits of (5 kg) were powdered and soaked by 80%.