1H- and 13C-NMR spectral data were recorded in CDCl3 on a Bruker DRX 300 spectrometer (Karlsruhe, Germany) at 600 and 150 MHz, respectively, and chemical shifts were presented as δ (ppm). UV spectra were obtained in methanol using a UVICON 933/934 spectrophotometer (Kontron Instrument, Milan, Italy), and mass spectra were obtained via direct infusion or liquid chromatographic introduction into a Finnigan LCQ Advantage MAX ion trap mass spectrometer equipped with a Finnigan Surveyor Modular HPLC system (Thermo Electron Co., Waltham, MA, USA). Silica gel 60 RP-18 (40–63 μm, Merck, Darmstadt, Germany) was used for column chromatography. Pre-coated silica gel plates (silica gel 60 F254, 0.25 and 0.5 mm thickness, Merck) were used for analytical thin-layer chromatography (TLC). Hitachi L-6200 HPLC (Hitachi, Tokyo, Japan) was used to isolate the active compounds (Shiseido Capcell Pak C18 UG120, 250 × 10 mm, 10 μm, Japan).
Silica gel 60 rp 18
Manufactured by Merck Group
Sourced in Germany
Silica gel 60 RP-18 is a type of chromatographic packing material used in reversed-phase liquid chromatography (RPLC). It consists of silica particles with chemically bonded octadecyl (C18) functional groups, which provide non-polar interaction with analytes. This material is commonly used for the separation and purification of a wide range of organic compounds, including pharmaceuticals, natural products, and environmental pollutants.
Automatically generated - may contain errors
Lab products found in correlation
Acid phosphatase, by Merck Group (2 mentions)
Sciex x500r mass spectrometer, by AB Sciex (2 mentions)
Vnmrs 500 nmr spectrometer, by Agilent Technologies (2 mentions)
Ft ir 4100 spectrometer, by Jasco (2 mentions)
P 1010 polarimeter, by Jasco (2 mentions)
Lcq advantage max, by Thermo Fisher Scientific (1 mentions)
Drx 300 spectrometer, by Bruker (1 mentions)
Silica gel 60 f254, by Merck Group (1 mentions)
Capcell pak c18 ug120, by Shiseido (1 mentions)
Fla 7000, by Fujifilm (1 mentions)
341 polarimeter, by PerkinElmer (1 mentions)
Cd3od, by Cambridge Isotopes (1 mentions)
Luna rp18 column, by Phenomenex (1 mentions)
Acetone d6, by Cambridge Isotopes (1 mentions)
Lc 6ad pump, by Phenomenex (1 mentions)
Pyridine d5, by Cambridge Isotopes (1 mentions)
Ultrotof q instrument, by Bruker (1 mentions)
Sephadex lh 20, by Cytiva (1 mentions)
Dpx 300 spectrometer, by Bruker (1 mentions)
Silica gel 60, by Merck Group (1 mentions)
6 protocols using silica gel 60 rp 18
1
Comprehensive spectroscopic analysis protocol
2
Polyisoprene Chain Length Analysis
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Analysis of chain length for polyisoprenes extracted by 1-butanol was performed as previously described16 . The extracts were hydrolyzed with acid phosphatase (Sigma) to produce alcohols, which were then extracted with pentane for analysis by reversed-phase TLC with HPTLC Silica Gel 60 RP-18 (Merck) and an acetone/water (39:1, v/v) solvent system. The [14C]IPP polymers spread on the TLC plate were detected with a FLA7000 instrument (Fujifilm). The chain length of the reaction products was estimated with the use of carbon number–defined Z,E-mixed polyprenols (C55, C60, C85, and C90) as authentic standards, as described previously16 .
3
Spectroscopic Characterization of Natural Compounds
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HRESIMS data were acquired with electrospray ionization in negative ion mode on an UltrOTOF-Q instrument (Bruker Daltonics, Billerica, MA, USA). NMR spectroscopic data were recorded at room temperature in CDCl3, acetone-d6, CD3OD, and/or pyridine-d5 (Cambridge Isotope Laboratories, Andover, MA, USA) on a Bruker DPX-300 spectrometer (Bruker, Karlhue, Germany) operating at 300.13 MHz (1H)/75.47 MHz (13C). Standard pulse sequences were used for homo- and heteronuclear correlation experiments. Optical rotation was determined on a Perkin Elmer 341 polarimeter (λ = 589 nm, PerkinElmer Inc., Waltham, MA, USA). Column chromatography procedures were performed on silica gel 60 (70–230 mesh, Merck, Darmstadt, Germany), silica gel 60 RP-18 (230–400 mesh, Merck, Darmstadt, Germany) and Sephadex LH-20 (Amersham Biosciences, Buckinghamshire, UK). Reversed-phase semipreparative HPLC separations were carried out with a Shimadzu (Shimadzu, Kyoto, Japan) LC-6AD pump using a Phenomenex Luna RP-18 column (5 µm, 21.6 × 250 mm) at flow rates of 12 or 14 mL/min, with monitoring at 210, 230 or 254 nm.
4
Chain Length Analysis of Polyisoprenes
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Analysis of chain length for polyisoprenes extracted by 1-butanol was performed as previously described [8] . The extracts were hydrolyzed with acid phosphatase (Sigma) to produce alcohols, which were then extracted with pentane [18] for analysis by reversed-phase thin-layer chromatography (TLC) with HPTLC Silica gel 60 RP-18 (Merck) and an acetone/water (39:1, v/v) solvent system. The [ 14 C]IPP polymers spread on the TLC plate were detected with a BAS1000 Mac Bioimage Analyzer (Fujifilm). The chain length of the reaction products was estimated with the use of carbon number-defined Z,E-mixed polyprenols (C 55 , C 60 , C 85 , and C 90 ) as authentic standards, as described previously [8] .
5
Phorbas sp. Metabolite Isolation and Characterization
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A specimen of Phorbas sp. (voucher number 07G-26) was collected by hand from Gageo Island, South Korea, in 2007. Optical rotations were measured on a JASCO P-1010 polarimeter (Jasco, Easton, MD, USA). IR spectra were recorded using a JASCO FT/IR 4100 spectrometer (Jasco, Easton, MD, USA), and ultraviolet (UV) spectra using a Varian Cary 50 UV-Visible spectrophotometer (Agilent, Santa Clara, CA, USA). High-resolution (HR)-electrospray ionization (ESI) mass spectra were obtained using a SCIEX X500R mass spectrometer (Sciex, Framingham, MA, USA). The NMR spectra were recorded on a Varian VNMRS 500 NMR spectrometer (Varian, Palo Alto, CA, USA) operating at 500 (1H) or 125 MHz (13C), respectively, with chemical shifts given in ppm using a methanol-d4 solution concerning residual solvent peaks at 3.30 and 49.0 ppm. Semi-preparative liquid chromatography was performed using an Agilent 1200 pump (Agilent, Santa Clara, CA, USA) and an RI detector. Vacuum column chromatography was performed using RP-18 silica gel 60 (Merck, Darmstadt, Germany).
6
Structural Characterization of Natural Compounds
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The optical rotation values were measured using a JASCO P-1010 polarimeter (Jasco, Easton, MD, USA). IR spectra were recorded on a JASCO FT/IR 4100 spectrometer (Jasco, Easton, MD, USA), and ultraviolet (UV) spectra were recorded using a Varian Cary 50 UV-visible spectrophotometer (Agilent, Santa Clara, CA, USA). High-resolution (HR)-electrospray ionization (ESI) mass spectra were measured using a SCIEX X500R mass spectrometer (Sciex, Framingham, MA, USA). Nuclear magnetic resonance (NMR) spectra were recorded on a Varian VNMRS 500 NMR spectrometer (Varian, Palo Alto, CA, USA), operating at 500 MHz (1H) and 125 MHz (13C), with chemical shifts of the proton and carbon spectra measured in methanol-d4 solution, were reported in reference to residual solvent peaks at 3.30 ppm and 49.0 ppm, respectively. Semi-preparative liquid chromatography (SemiPrep-LC) was performed using a Waters 515 pump (Agilent, Santa Clara, CA, USA) equipped with an RI detector. Column chromatography was performed using an RP-18 silica gel 60 (Merck, Darmstadt, Germany) and Sephadex LH-20 (Pharmacia, Uppsala, Sweden).
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