In this study, we used the following instruments: Agilent-1260 High-Performance Liquid Chromatographer (Agilent, Santa Clara, CA, USA); DRX-500 AVANCE III-600MHz superconducting nuclear magnetic resonance imager (Bruker, Bremen, Germany); RID-20A differential refractive detector (Shimadzu, Kyoto, Japan); SB-600DTY ultrasonic Multi-frequency cleaning machine (Ningbo, China); Hve-50 autoclave; HCB-1300V medical ultra clean table (Haier, Qingdao, China). We used the following chemicals and materials: 11-α-d -galactopyranoside-bergenin, bergenin, (−)-gallocatechin, 11-O-galloybergenin, and 11-β-d -glucopyranosyl-bergenin (standard laboratory- and self-made products); UN1648 Acetonitrile (GR, Thermo Scientific, Waltham, MA, USA); Methanol (GR, BCR, USA); Phosphoric acid (GR, Tianjin Kemel, Tianjin, China); C-18 reversed-phase column packing ODS-A-HG (YMC, Kyoto, Japan); Sephadex LH-20 (Beijing Solarbio, Beijing, China); Semi-preparative column (250 mm × 10 mm, 5 μm, Shimadzu, Kyoto, Japan): Blank drug-sensitive paper (Jining Best Micro, Jining, China); Ceftazidime (Hangzhou Microbial Reagent, Hangzhou, China); Nystatin (Hefei BASF, Hefei, China).
Sephadex lh 20
Manufactured by Solarbio
Sourced in China, Japan
Sephadex LH-20 is a gel filtration material used for the purification and separation of a variety of compounds, including proteins, peptides, nucleic acids, and other small molecules. It is composed of cross-linked dextran beads and is typically used in column chromatography applications.
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Lab products found in correlation
Eclipse xdb c18 column, by Agilent Technologies (2 mentions)
341 polarimeter, by PerkinElmer (1 mentions)
Lc ltq orbitrap xl spectrometer, by Thermo Fisher Scientific (1 mentions)
J 810 spectrometer, by Jasco (1 mentions)
Apex duo diffractometer, by Bruker (1 mentions)
Cary 50 instrument, by Agilent Technologies (1 mentions)
Am 400 spectrometer, by Bruker (1 mentions)
Epigallocatechin, by Merck Group (1 mentions)
Orlistat, by Maclin Biochemical Technology (1 mentions)
Acarbose, by Maclin Biochemical Technology (1 mentions)
Ascorbic acid, by Maclin Biochemical Technology (1 mentions)
2 2 diphenyl 1 picrylhydrazyl (dpph), by Merck Group (1 mentions)
Catechin, by Merck Group (1 mentions)
Epicatechin, by Merck Group (1 mentions)
Chloramphenicol, by Solarbio (1 mentions)
Primescript rt kit, by Takara Bio (1 mentions)
Transzol up plus rna kit, by Transonic Systems (1 mentions)
Crystal violet, by Sangon (1 mentions)
Coomassie brilliant blue r 250, by Solarbio (1 mentions)
Agilent 1260, by Agilent Technologies (1 mentions)
6 protocols using sephadex lh 20
1
Isolation and Characterization of Bergenin Derivatives
2
Phytochemical Characterization of Natural Compounds
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TLC was accomplished by silica gel 60 F254+365 (Qingdao Ocean Chemical Co., Ltd., China). Silica gel (80–120 and 200–300 mesh; Qingdao Ocean Chemical Co., Ltd., China), RP‐C18 silica gel (spherical, 20–45 μm, Santai Technologies, Inc., China), and Sephadex LH‐20 (Beijing Solarbio Science & Technology Co., Ltd., China) were utilized for column chromatography. HPLC was completed on an Essentia Prep LC‐16P with a UV detector via an RP‐C18 column (5 μm, 10×250 mm, YMC‐Pack, ODS‐A). Thermo Fisher LC‐LTQ‐Orbitrap XL spectrometer was used to collect the HRESIMS data. Bruker AM‐400 spectrometer was employed to obtain NMR data as well as taking the solvent peaks (CH3OH‐d4: δH 3.31, δC 49.10; DMSO‐d6: δH 2.50, δC 39.51) as internal references of the 1H and 13C NMR chemical shifts. JASCO J‐810 spectrometer was taken to carry out the ECD spectra measurement. Infrared spectra data were collected via Bruker Vertex 70 equipment. Ultraviolet spectra were analyzed by a Varian Cary 50 instrument. The single‐crystal X‐ray diffraction data were gathered by a Bruker APEX DUO diffractometer under the graphite‐monochromated Cu Kα radiation. The optical rotation measurement was fulfilled by a Perkin‐Elmer 341 polarimeter.
3
Extraction and Analysis of Wild Rice Phytochemicals
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Wild rice Z. latifolia was collected from Jiangling County, Jingzhou City, Hubei Province, China (30°13′10″ N; 112°34′5″ E), in September 2017. The sample was obtained by manually harvesting mature plant tassels, drying and then dehulling them to obtain the seeds. The seeds were ground to a fine powder in a mechanical grinder and then sieved through a 0.45 mm sifter.
(+)-Catechin (C), (−)-epicatechin (EC), and (−)-epigallocatechin (EGC), DPPH (2,2-diphenyl-1-picrylhydrazyl), α-glucosidase (type I, from Saccharomyces cerevisiae), and pancreatic lipase (type II, from porcine pancreas) were purchased from Sigma-Aldrich Chemical Co., (St. Louis, MO, USA). Ascorbic acid, acarbose, and orlistat were obtained from Macklin Biochemical Co., Ltd. (Shanghai, China). Phloroglucinol was from Aladdin Reagents Co., Ltd. (Shanghai, China). HPLC and LC–MS grade solvents were bought from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China). The D101 macroporous resin and Sephadex LH-20 were from Solarbio Science & Technology Co., Ltd. (Beijing, China) and GE Healthcare Bio-Sciences AB (Uppsala, Sweden), respectively. Precoated silica gel plates (GF254, Qingdao Marine Chemical Co., Ltd., Qingdao, China) were used for thin layer chromatography (TLC) analysis, and spots were visualized by spraying with anisaldehyde-sulfuric acid agent.
(+)-Catechin (C), (−)-epicatechin (EC), and (−)-epigallocatechin (EGC), DPPH (2,2-diphenyl-1-picrylhydrazyl), α-glucosidase (type I, from Saccharomyces cerevisiae), and pancreatic lipase (type II, from porcine pancreas) were purchased from Sigma-Aldrich Chemical Co., (St. Louis, MO, USA). Ascorbic acid, acarbose, and orlistat were obtained from Macklin Biochemical Co., Ltd. (Shanghai, China). Phloroglucinol was from Aladdin Reagents Co., Ltd. (Shanghai, China). HPLC and LC–MS grade solvents were bought from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China). The D101 macroporous resin and Sephadex LH-20 were from Solarbio Science & Technology Co., Ltd. (Beijing, China) and GE Healthcare Bio-Sciences AB (Uppsala, Sweden), respectively. Precoated silica gel plates (GF254, Qingdao Marine Chemical Co., Ltd., Qingdao, China) were used for thin layer chromatography (TLC) analysis, and spots were visualized by spraying with anisaldehyde-sulfuric acid agent.
4
Extraction and Characterization of A. membranaceus
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The stems and leaves of A. membranaceus were collected from Fangshan City, China, in July–August 2021. The plant's name was confirmed in a website (http://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:478611-1 ). All the plant material collected was washed clean with tap water, air-dried at room temperature, and ground into a powder with a pulverizer. Beef extract peptone agar, beef extract peptone, chloramphenicol, Coomassie Brilliant Blue R-250, and Sephadex LH-20 were purchased from Solarbio (Beijing, China). A micro alkali proteinase assay kit was purchased from Elabscience (Wuhan, China). Crystal violet was purchased from Sangon Biotech (Shanghai, China). The TransZol Up Plus RNA Kit was purchased from Trans (Beijing, China). The PrimeScript™ RT Kit was purchased from Takara Bio (Dalian, China). All other chemicals and solvents used were of analytical grade. Isoliquiritigenin (Cat No. SI8220), biochanin A (Cat No. SB8240), and isorhamnetin (Cat No. SI8280) were purchased from Solarbio (Beijing, China), and the purity of the three standards was ≥98% by high-performance liquid chromatography (HPLC).
5
Isolating Antibacterial Compounds from A. alternata
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To obtain specific antibacterial substances from the crude extract produced by A. alternata FB1, MRSA was mainly used as the indicator bacterium to trace the antibacterial components. The methanol-dissolved extract was filtered through a 0.22 µm nylon membrane, and the crude extract was separated by molecular sieve, with the molecular sieve filler consisting of the Sephadex LH-20 (Solarbio, China). The mobile phase was anhydrous methanol, and 1.5 mL was collected every minute. The components separated by molecular sieve were tested for bacteriostasis, and the active parts were collected and concentrated. The concentrated active substances were purified by RP-HPLC (Agilent 1260, USA), using Eclipse XDB-C18 column (5 µm; 4.6 × 250 mm; Agilent, USA). The column was eluted at a flow rate of 2 mL/min with mobile phase A and mobile phase B under the following conditions: 0–5 min, 0% mobile phase B to 80% mobile phase B, and 5–20 min, 80% mobile phase B to 100% mobile phase B, wherein mobile phase A was composed of water and methanol (90:10, vol/vol) and mobile phase B was 100% methanol. The elution was monitored using a UV detector set at 260 nm. The inhibitory activity against the indicator bacteria was detected.
6
Comprehensive Analytical Techniques for Natural Products
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Optical rotations were acquired on a JASCOP-1020 polarimeter. ECD data were measured on a Chirascan spectropolarimeter. IR spectra were measured on PerkinElmer infrared spectrophotometer. 1D and 2D NMR spectra were recorded on Bruker Avance 400 or 600 DRX spectrometers in acetone-d6, methanol-d4, DMSO-d6 and chloroform-d. Column chromatography (CC) was performed on silica gel (200– 300 mesh; Qingdao Marine Chemical Plant Branch., China), RP-C18 (ODS-A, 50 μm, YMC, Kyoto, Japan), or Sephadex LH-20 (100–200 mesh; Beijing Solarbio Technology Co., Ltd., China). Plates precoated with silica gel GF254 (Rushan, Shandong Sun Desiccant Co., Ltd.) were used for thin layer chromatography (TLC). An Agilent HPLC series 1260 and Shimadzu LC-20AR were used for analysis and isolation. For analysis, an Agilent Eclipse XDB-C18 column (4.6 × 150 mm, 5 μm) was used. The isolation was achieved on an Agilent semi-preparative Eclipse XDB-C18 column (9.4 × 250 mm, 5 μm). HPLC-MS data were acquired on an Agilent 1260 Series system coupled with an Agilent Accurate-Mass-Q-TOF MS 6520 system equipped with an Electrospray ionization (ESI) source.
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