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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry Electronic Supplementary Information Same data, different structures: diastereoisomers with substantially identical NMR data from nature Chuan-Xi Wang, a Guo-Dong Chen, a Chun-Chi Feng, a Rong-Rong e, a Sheng-Ying Qin, b Dan u, a e-ru Chen, a Xing-Zhong Liu, c Xin-Sheng Yao,* a and ao Gao* a a Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou 0, People s Republic of China b Clinical Experimental Center, First Affiliated ospital of Jinan University, Guangzhou 0, People s Republic of China c State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 000, People s Republic of China Corresponding author: Tel.: +8 8 ; fax: address: tghao@jnu.edu.cn; tyaoxs@jnu.edu.cn
2 Table of Contents. NMR data assignments/comparisons of Experimental section.... General experimental procedures.... Fungus materials and fermentation.... Extraction and isolation...0. Catalytic hydrogenation of fusarins G () and G ().... Preparation of (S) and (R) -MTPA esters ('a/'a and 'b/'b) of '/'.... zonolysis of fusarins G G ( )....7 Quantum chemical ECD calculations of....8 The in situ dimolybdenum CD method.... WST-8 cell viability assay.... D, D NMR spectra of The D, D NMR spectra of fusarin G ().... The D, D NMR spectra of fusarin G ().... The D, D NMR spectra of fusarin G ().... The D, D NMR spectra of fusarin G ().... The D, D NMR spectra of...0
3 . NMR data assignments/comparisons of Table S NMR data of in DMS-d (00 Mz for ; 00 Mz for C) Position C, mult. (J in z), -CSY MBC RESY., C.7, br d (7.),, 8.8, C.7, q (7.),,, 0.0, qc -., C.88, br s,,,,,,., qc - 8., C., br d (.), -,, 7, 8,,, 8, 7 7., qc , C.7, d (.) 7, 0,, 0,.0, C., dd (.,.7) 8, 0 7, 0, -7,, 0 0., C 7., br d (.7), 8,, 8,., qc - 8., qc - 8., qc -.8, C.0, s,, 7, 0, -, 8a, a,., qc - 8., br s,, 7 8b 7 7.0, qc , C.0, ddd (.,.0,.), a 8b, a, b,., ddd (.,., 7.), b 8a, a, b, 7.7, C.77, ddd (.0, 7.,.), a 8a, 8b, b,., ddd (.,.0,.0), b 8a, 8b, a, 7.0, qc -., C., s., C.7, br s,,, -, -7, 8.7, C., s, 7, 8, -,., C.80, br s 0 0,,, -.0, d (.), -7., br s, 7, 8,, -., br s, -., br s, 8
4 8 7 Table S NMR data of in DMS-d (00 Mz for ; 00 Mz for C) Position C, mult. (J in z), -CSY MBC RESY., C.7, br d (7.),, 8., C.7, q (7.),, 0.0, qc -., C.87, br s,,,,,,,., qc - 8., C., br d (.0), -,, 7, 8,,, 8, 7 7., qc , C.7, d (.) 7, 0,, 0,.0, C., dd (.,.7) 8, 0 7, 0,, 0 0., C 7., br d (.7), 8,, 8,.0, qc -.0, qc - 8., qc -.8, C.0, br s,, 7, 0, -, 8a, a,., qc - 8., brs,, 7 8b 7 7., qc , C.0, ddd (.,.0,.), a 8b, a, b,., ddd (.,., 7.), b 8a, a, b, 7.7, C.77, ddd (.0, 7.,.), a 8a, 8b, b,., ddd (.,.0,.0), b 8a, 8b, a, 7.0, qc -., C., s., C., br s,,, 8.7, C., s, 7, 8,, -,., C.80, br s 0 0,,, -.0, d (.0) -7., br s -.70, br s -.8, br s
5 8 7 Table S NMR data of in DMS-d (00 Mz for ; 00 Mz for C) Position C, mult. (J in z), -CSY MBC RESY., C., br d (7.),,.0, C.78, q (7.),, 0., qc -., C., br s,,,,,,,.7, qc , C.0, br d (.), -,, 7, 8,,, 8, 7 7., qc , C.8, d (.) 7, 0,, -, 0.7, C.8, dd (.,.7) 8, 0 7, 0, 0 0., C 7., br d (.7), 8,, 8,., qc - 8., qc - 8., qc -.8, C.0, br s,, 7, 0, -, 8a, a,., qc - 8., br s,, 7 8b 7 7., qc , C.0, ddd (.,.0,.), a 8b, a, b,., ddd (.,., 7.), b 8a, a, b, 7.7, C.7, ddd (.0, 7.,.), a 8a, 8b, b,., ddd (.,.0,.0), b 8a, 8b, a, 7., qc -., C., s., C.8, br s,,, -, -7., C., s, 7, 8,., C.80, br s 0 0,,, -.0, d (.) 8, -7.7, br s -., br s, -., br s
6 8 7 Table S NMR data of in DMS-d (00 Mz for ; 00 Mz for C) Position C, mult. (J in z), -CSY MBC RESY., C., br d (7.),,.0, C.78, q (7.),, 0.0, qc -., C., br s,,,,,,,.7, qc , C.0, br d (.), -,, 7, 8,,, 8, 7 7., qc , C.8, d (.) 7, 0,, 0,, -.7, C., dd (.,.7) 8, 0 7, 0, -7, 0 0., C 7., br d (.7), 8,, 8,., qc - 8., qc - 8., qc -.8, C.0, br s,, 7, 0, -, 8a, a,., qc - 8., br s,, 7 8b 7 7., qc , C.0, ddd (.,.0,.), a 8b, a, b,., ddd (.,., 7.), b 8a, a, b, 7.7, C.7, ddd (.0, 7.,.), a 8a, 8b, b,., ddd (.,.0,.0), b 8a, 8b, a, 7., qc -., C., s.8, C.7, br s,,, -, -7., C., s, 7, 8,, 8., C.80, br s 0 0,,, -.0, d (.) 8, -7.7, br s, -., br s, -., br s
7 Fusarin G (): Yellowish oil; [α] D 7. (c.0, Me); UV (Me) λ max (log ε): 7 (.), 87 (.) nm; CD (c 0. 0 M, Me) λ max (Δε) (+.7), 8 (.7) 8 (+.); ESI-MS (positive) m/z 88. [M + Na] + ; RESI-TF-MS (positive): m/z 88.0 [M + Na] + (calcd for C N Na, 88.87); For the and C NMR data, see Table S. Fusarin G (): Yellowish oil; [α] D 8.8 (c.0, Me); UV (Me) λ max (log ε): 7 (.), 87 (.7) nm; CD (c M, Me) λ max (Δε) 8 ( 0.), 88 (.) 8 (+.); ESI-MS (positive) m/z 88. [M + Na] + ; RESI-TF-MS (positive): m/z [M + Na] + (calcd for C N Na, 88.87); For the and C NMR data, see Table S. Fusarin G (): Yellowish oil; [α] D 8. (c.0, Me); UV (Me) λ max (log ε): 7 (.), 87 (.) nm; CD (c 0. 0 M, Me) λ max (Δε) 8 (+.), 8 (.), (+.0); ESI-MS (positive) m/z 88. [M + Na] + ; RESI-TF-MS (positive): m/z 88.8 [M + Na] + (calcd for C N Na, 88.87); For the and C NMR data, see Table S. Fusarin G (): Yellowish oil; [α] D 0. (c.0, Me); UV (Me) λ max (log ε): 7 (.), 87 (.) nm; CD (c 0. 0 M, Me) λ max (Δε) (.), 87 (.0), (+.0); ESI-MS (positive) m/z 88. [M + Na] + ; RESI-TF-MS (positive): m/z 88.8 [M + Na] + (calcd for C N Na, 88.87); For the and C NMR data, see Table S. 7
8 Table S. The comparisons in chemical shifts between and, between and, between and. (00 Mz for ; 00 Mz for C; in DMS-d ; Δδ in ppm) Δδ (-) Δδ (-) Δδ (-) No. Δδ Δδ C Δδ Δδ C Δδ Δδ C / / / / / (a) 0.00/ / / / /0. 0. (b) /0. 0.0/0. 0.0/ / /0. 0.0/ / / / / /0.0 (c) /0. 0.0/0. 0.0/0. Figure S. The differences in chemical shifts (a): between and, (b): between and, (c): between and 8
9 . Experimental section. General experimental procedures ptical rotations were measured on a JASC P0 digital polarimeter, and UV data were recorded on a JASC V-0 UV/vis spectrometer. CD spectra were recorded on a JASC J-80 spectrophotometer using Me as the solvent. ESI-MS spectra were performed on a Finnigan LCQ Advantage MAX spectrometer and R-ESI MS spectra were obtained on Waters Synapt G mass spectrometer. and C NMR spectra were acquired with Bruker AV 00 and AV 00 spectrometers using solvent signals (DMS-d : δ.0/δ C., pyridine-d : δ 7./δ C.) as internal standards. Analytical PLC was performed on a Dionex PLC system equipped with an Ultimate 000 pump, an Ultimate 000 diode array detector (DAD), an Ultimate 000 Column Compartment, an Ultimate 000 autosampler (Dionex, USA) using a Phenomex Gemini C8 column (. 0 mm, μm). Semi-preparative PLC was carried out on a Dionex PLC system equipped with an Ultimate 000 pump, and an Ultimate 000 RS variable wavelength Detector (Dionex, USA) using a Phenomex Gemini C8 column (0.0 0 mm, μm). The medium-pressure liquid chromatography (MPLC) system was equipped with a dual pump gradient system, an UV preparative detector, and a Dr Flash II fraction collector system (Shanghai Lisui E-Tech Co., Ltd.). Column chromatography (CC) was carried out on DS (0 μm, YMC). TLC was performed on precoated silica gel plates (SGF, 0. mm, Yantai Chemical Industry Research Institute, China).. Fungus materials and fermentation The strain of Mucor sp. was isolated from soil collected in Sinkiang province, People s Republic of China. The isolate was identified by one of the authors (X. Z. Liu) and assigned the accession number XJ070- in the culture collection at the Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University. The fungal strain was identified as Mucor sp. based on its morphological characteristics and analysis of the internal transcribed spacer (ITS) sequence. In brief, the ITS region of the fungal strain was amplified by PCR and sequenced. A blast search of the ITS sequence (Gene bank accession number: KP7780) showed a % sequence identity with Mucor hiemalis (Gene bank accession number: KF.). The detailed identification method for the ITS sequence analysis is described below. Fresh fungal mycelia (about 0 mg) were obtained by centrifuging ml of fresh culture in a. ml microcentrifuge tube. 00 µl of preheated (0 C) CTAB extraction buffer (% CTAB (w/v), 00 mm Tris-Cl,. M NaCl, mm EDTA, p 8.0) and 0. g sterilized quartz sand (Sangon Biotech Co., Ltd, Shanghai, China) were added, and the fungal mycelia were ground using a glass pestle. 00 µl of preheated (0 C) CTAB extraction buffer was added, and incubated at 0 C for 0 min with occasional gentle swirling. After that, 00 µl of phenolchloroform (:, v/v) was added and mixed thoroughly to form an emulsion. The mixture was centrifuged at 0,000 rpm for 0 min at room temperature. The aqueous phase (00 µl) was removed, placed into a fresh. ml tube and extracted with 00 µl chloroform. The mixture was centrifuged at 0,000 rpm for 0 min at room temperature and the aqueous phase (00 µl) was transferred into a new. ml tube. Isopropanol (00 µl) was added and the genomic DNA in the aqueous phase was precipitated by centrifuging at 0,000 rpm for 0 min. The DNA pellet was washed with 70% ethanol twice, dried, and suspended in 0 µl. The primer pairs ITS ('- TCCGTAGGTGAACCTGCGG-') and ITS ('-TCCTCCGCTTATTGATATGC-') were used for amplification of the ITS fragment, which was performed using a TaKaRa PCR Amplification Kit (Takara, Dalian, China). After PCR, µl of the reaction mixture was loaded onto an agarose gel (% agarose) and subjected to electrophoresis. After the band containing the PCR products (approximate size 0 bp for the partial ITS gene) was confirmed, the PCR products were then submitted for sequencing (Sangon Biotech, Shanghai, China) with the corresponding primers. The sequence data have been submitted to GenBank.
10 The fungal strain was cultured on slants of potato dextrose agar (PDA) at C for days. Agar plugs were used to inoculate four Erlenmeyer flasks (0 ml), each containing 00 ml of potato dextrose broth (PDB). The four flasks of the inoculated media were incubated at C on a rotary shaker at 0 rpm for five days to prepare the seed culture. Fermentation was carried out in twenty Erlenmeyer flasks (00 ml), each containing 70 g of rice. Distilled (0 ml) was added to each flask, and the rice was soaked overnight before autoclaving at C for 0 min. After cooling to room temperature, each flask was inoculated with.0 ml of the spore inoculum and incubated at C for 0 days.. Extraction and isolation The fermented material was extracted twice with EtAc, and the organic solvent was removed under reduced pressure to yield the crude extract (. g). The crude extract was dissolved in 0% v/v aqueous Me (00 ml) and partitioned against the same volume of cyclohexane to afford a cyclohexane fraction (C,. g) and an aqueous Me fraction (W,.7 g). The aqueous Me fraction (W,.7 g) was separated by DS CC ( 8 cm) with elution by Me (0:70, 0:0, 70:0, 0:0 and 00:0, v/v, each 800 ml) to afford fractions (W W). Fraction W (. g) was further separated by MPLC with gradient elution by Me- (% 00%, v/v) to afford fourteen subfractions (Wa to Wn). Subfraction Wi (0. mg) was purified by semi-preparative PLC, using Me (0:0, v/v) at a flow rate of. ml/min to yield (t R :.min,. mg). Subfraction Wg (. mg) was purified by semi-preparative PLC, using Me (0:0, v/v) at a flow rate of. ml/min to yield (t R :. min,.0 mg). Subfraction We (.8 mg) was purified by semi-preparative PLC, using Me (0:0, v/v) at a flow rate of. ml/min to yield (t R :.0 min,.8 mg) and (t R :.8 min, 0. mg). - were analysis by PLC method under the same condition (Figure S). Figure S. The PLC chromatogram for (Phenomex Gemini C8, μm, 0 0 mm; Me/ 0:0; flow rate. ml/min; nm). 0
11 . Catalytic hydrogenation of fusarins G () and G () ; 0%Pd/C methanol, r.t. ' (R)-MTPA chloride (S)-MTPA chloride MTPA 'a: (S)-MTPA ester of ' 'b: (R)-MTPA ester of ' ; 0%Pd/C methanol, r.t. ' (R)-MTPA chloride (S)-MTPA chloride MTPA 'a: (S)-MTPA ester of ' 'b: (R)-MTPA ester of ' Scheme S. Application of a modified Mosher's method after catalytic hydrogenation for determination of the absolute configuration of C- in and ( δ (δ S δ R ) values (in ppm) obtained for (S)- and (R)-MTPA esters ('a and 'b, 'a and 'b)) Fusarin G () ( mg, mmol) was dissolved in Me ( ml) and reduced with 0% Pd/C ( mg) under a atmosphere for h at room temperature. The mixture was filtered, and the filtrate was evaporated and separated by semi-preparative PLC (Phenomex Gemini C 8, μm, 0 0 mm; gradient of % to 0% Me/ in 0 min; flow rate. ml/min; nm) to give ' ( mg). Fusarin G () ( mg, mmol) was dissolved in Me ( ml) and reduced with 0% Pd/C ( mg) under a atmosphere for h at room temperature. The mixture was filtered, and the filtrate was evaporated and separated by semi-preparative PLC (Phenomex Gemini C 8, μm, 0 0 mm; gradient of % to 0% Me/ in 0 min; flow rate. ml/min; nm) to give ' ( mg). ': Amorphous powder; NMR (pyridine-d, 00 Mz) δ 0.8 (, t, J = 7. z, -),.8 (, m, a-),. (, m, b-),. (, dt, J =., 7. z, -),. (, br d, J =. z, -),. (, br s, -),.0-.7 (, overlapped, -8, -, -0),. (, m, -),. (, br s, -),. (, m, -8),. (, m, a-),. (, m, b-),. (, s, -),.0 (, br s, -),.0 (, s, -),. (, d, J =.8 z, -), 0. (, br s, exchangeable hydrogen),.0 (, br s, exchangeable hydrogen),.0 (, br s, -),. (, br s, exchangeable hydrogen),.0 (, br s, exchangeable hydrogen). ESI-MS m/z. [M + Na] +, m/z 70.7 [M - ] -. ': Amorphous powder; NMR (pyridine-d, 00 Mz) δ 0.8 (, t, J = 7. z, -),.8 (, m, a-),. (, m, b-),. (, dt, J =., 7. z, -),. (, br d, J =. z, -),. (, br s, -),.0-.7 (, overlapped, -8, -, -0),. (, m, -),. (, br s, -),. (, m, -8),. (, m, a-),. (, m, b-),. (, s, -),.0 (, br s, -),. (, s, -),. (, d, J =. z, -), 0. (, br s, exchangeable hydrogen),.0 (, br s, exchangeable hydrogen),. (, br s, -),. (, br s, exchangeable hydrogen),.0 (, br s, exchangeable hydrogen). ESI-MS m/z. [M + Na] +, m/z 70.8 [M - ] -.. Preparation of (S) and (R) -MTPA esters ('a/'a and 'b/'b) of '/' A solution of '/' (0. mg) in pyridine-d (0. ml) was treated with (R)-MTPA chloride ( μl) under an atmosphere of nitrogen in an NMR tube. The mixture was placed at room temperature for h to obtain the (S)- MTPA ester ('a/'a). The same procedure was used to prepare the (R)-MTPA ester ('b/'b) with (S)-MTPA chloride. The key δ values ( δ - : +0.0; δ - : +0.; δ - : -0.07) of the (S)- and (R)-MTPA esters of ' ('a and 'b) indicated the R configuration for C- in.
12 The key δ values ( δ - : ; δ - : -0.; δ - : +0.0) of the (S)- and (R)-MTPA esters of ' ('a and 'b) indicated the S configuration for C- in.. zonolysis of fusarins G G ( ) A solution of (.0 mg) in CCl /C (:, ml) was treated with at 78 C for 0 min. After excess was removed by a stream of N, the reaction mixture was treated with dimethyl sulfide at room temperature for hours. The residue, after evaporation, was separated by semi-preparative PLC (Phenomex Gemini C8, μm, 0 0 mm; Me/ :; flow rate. ml/min; nm) to afford (mg). The same procedure was used for -. The products of - after the ozonolysis reaction was identified as by the retention times, NMR data, and ECD spectra. ; -78 C Dimethyl sulfide; r.t (R, 7S) (S, 7S) (S, 7R) (R, 7R) 8 Scheme S. was obtained from by the ozonolysis reaction respectively : Yellowish oil; [α] D. (c 0., Me); UV (Me) λ max (log ε): (.) nm; CD (c.7 0 M, Me) λ max (Δε) (+.77), 8 ( 0.7), 7 (+0.0), 07 ( 0.0); ESI-MS (positive) m/z. [M + Na] + ; ESI-MS (negative) m/z 7. [M - ] - ; RESI-TF-MS (positive): m/z.08 [M + Na] + (calcd for C N Na,.08); For the and C NMR data, see Table S. Table S NMR data of in DMS-d (00 Mz for ; 0 Mz for C) Position C, mult. (J in z), -CSY MBC., C., s,., qc - 7.8, qc - 8.8, qc -., C., s,,, 8, 0., qc , s 8 70., qc - 8., C.07, m 0a, 0b, , C.8, ddd (.0, 7.,.7), a, 0b., ddd (.0, 7.,.0), b, 0a - * -.8, br s - * -.8, br s * Assignments can be exchanged with each other.
13 .7 Quantum chemical ECD calculations of The molecular structures of (R, R, S)- and (S, S, R)- were converted into SMILES code before their initial D structures were generated with CRINA version.. For each molecule, the initial D structure was minimized with the MMFFS force field implemented in CNFLEX version 7.0 with the default parameters before its conformation space was sampled. The conformer databases were generated using CNFLEX version 7.0, with an energy window for acceptable conformers (ewindow) of kcal mol - above the ground state using the modified version of the MMFF force-field mentioned above, a maximum number of conformations per molecule (maxconfs) of 00 and an RMSD cutoff (rmsd) of 0.Å. This resulted in only one conformer. Then the conformer was optimized with the F/-G (d) method in Gaussian 0 (). Further optimization at the BP8/- G (d) level produced the dihedral angles. The optimized conformer was used for the ECD calculations, which were performed with Gaussian 0 (BP8/-++G (d, p)). The solvent effects were taken into account by the polarizable-conductor calculation model (CPCM, methanol as the solvent). Figure S. Experimental ECD spectrum of and calculated CD spectra of (R, R, S)- and (S, S, R)- (UV correction = 0 nm, band width σ = 0. ev) References: () Frisch, M. J.; Trucks, G. W.; Schlegel,. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji,.; Caricato, M.; Li, X.; ratchian,. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; ada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; asegawa, J.; Ishida, M.; Nakajima, T.; onda, Y.; Kitao,.; Nakai,.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; gliaro, F.; Bearpark, M.; eyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev,.; Austin, A. J.; Cammi, R.; Pomelli, C.; chterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; rtiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 0, Revision C; Gaussian, Inc., Wallingford CT, 0.
14 .8 The in situ dimolybdenum CD method PLC grade DMS was dried with Å molecular sieves. Following a previously published procedure (), a mixture of :. diol-mo (Ac) for (or ) was subjected to CD measurement at a concentration of 0. mg/ml. The first CD spectrum was recorded immediately after mixing, and its time evolution was monitored until stationary (about 0 min after mixing). The inherent CD was subtracted. The observed signs of the diagnostic bands at around 0 nm in the induced CD spectrum were correlated to the absolute configuration of C- and C-7. C C [Mo + ] C 8 C 8 [Mo + ] C C (a) (b) Figure S. (a) The CD spectra of and in DMS containing Mo (Ac) with the inherent CD spectra subtracted; (b) Conformations of the Mo + complexes of and. Reference: () Snatzke, G. Circular Dichroism and Absolute Conformation: Application of Qualitative M Theory to Chiroptical Phenomena. Angew. Chem., Int. Ed. 7, 8: 77; Angew. Chem. 7, : 80.. WST-8 cell viability assay Cell viability was measured using a cell count kit 8 (CCK-8) assay (Dojindo Laboratories, Kumamoto, Japan) which is based on the conversion of a water-soluble tetrazolium salt, -(-methoxy--nitrophenyl)--(- nitrophenyl)--(,-disulfophenyl)--tetrazolium, monosodium salt (WST-8), to a water-soluble formazan dye upon reduction by dehydrogenases in the presence of an electron carrier (). In brief, 0 cells were cultured in flat-bottomed well plates with a final volume of 00 μl/well of culture medium. After h, the cells were treated with different concentrations (.- mm) of each compounds (fusarins G-G) or DMS for 8 h. CCK- 8 solution (0 μl) was added to each well, followed by incubation for h at 7 C. Then, the plate was shaked thoroughly for min. The absorbance of samples at 0 nm was measured using a microtiter plate reader (Sunrise Remote/Touch screen, Columbusplus, Austria). The growth rates as stimulated by the compounds were calculated by the following formula: [(A compound -A DMS )/A DMS ] 00%. Fusarins G G ( ) showed no effect on the proliferation of the epg cell line, but stimulated the growth of the L cell line after exposure at.- mm (Figure S).
15 Figure S. (a) Percentage of stimulated growth of epg cells after exposure to.- mm ; (b) Percentage of stimulated growth of L cells after exposure to.- mm Reference: () Ishiyama, M.; Tominaga,.; Shiga, M.; Sasamoto, K.; hkura, Y.; Ueno, K. A combined assay of cell viability and in vitro cytotoxicity with a highly water-soluble tetrazolium salt, neutral red and crystal violet. Biol. Pharm. Bull., : 8.
16 . D, D NMR spectra of -. The D, D NMR spectra of fusarin G () Figure S. NMR spectrum of fusarin G () (00 Mz, in DMS-d ) Figure S7. C NMR spectrum of fusarin G () (00 Mz, in DMS-d )
17 8 7 7 Figure S8. DEPT spectrum of fusarin G () (00 Mz, in DMS-d ) Figure S. SQC spectrum of fusarin G () (DMS-d ) 7
18 7 8 Figure S0., -CSY spectrum of fusarin G () (DMS-d ) 7 8 Figure S. MBC spectrum of fusarin G () (DMS-d ) 8
19 7 8 Figure S. RESY spectrum of fusarin G () (DMS-d ). The D, D NMR spectra of fusarin G () Figure S. NMR spectrum of fusarin G () (00 Mz, in DMS-d )
20 8 7 7 Figure S. C NMR spectrum of fusarin G () (00 Mz, in DMS-d ) Figure S. DEPT spectrum of fusarin G () (00 Mz, in DMS-d )
21 8 7 7 Figure S. SQC spectrum of fusarin G () (DMS-d ) 7 8 Figure S7., -CSY spectrum of fusarin G () (DMS-d )
22 7 8 Figure S8. MBC spectrum of fusarin G () (DMS-d ) 7 8 Figure S. RESY spectrum of fusarin G () (DMS-d )
23 . The D, D NMR spectra of fusarin G () 8 7 Figure S. NMR spectrum of fusarin G () (00 Mz, in DMS-d ) Figure S. C NMR spectrum of fusarin G () (00 Mz, in DMS-d )
24 8 7 7 Figure S. DEPT spectrum of fusarin G () (00 Mz, in DMS-d ) Figure S. SQC spectrum of fusarin G () (DMS-d )
25 7 8 Figure S., -CSY spectrum of fusarin G () (DMS-d ) 7 8 Figure S. MBC spectrum of fusarin G () (DMS-d )
26 7 8 Figure S. RESY spectrum of fusarin G () (DMS-d ). The D, D NMR spectra of fusarin G () Figure S7. NMR spectrum of fusarin G () (00 Mz, in DMS-d )
27 8 7 Figure S8. C NMR spectrum of fusarin G () (00 Mz, in DMS-d ) 8 7 Figure S. DEPT spectrum of fusarin G () (00 Mz, in DMS-d ) 7
28 8 7 Figure S0. SQC spectrum of fusarin G () (DMS-d ) 7 8 Figure S., -CSY spectrum of fusarin G () (DMS-d ) 8
29 7 8 Figure S. MBC spectrum of fusarin G () (DMS-d ) 7 8 Figure S. RESY spectrum of fusarin G () (DMS-d )
30 . The D, D NMR spectra of Figure S. NMR spectrum of (00 Mz, in DMS-d ) Figure S. C NMR spectrum of (0 Mz, in DMS-d ) 0
31 0 7 8 Figure S. DEPT spectrum of (0 Mz, in DMS-d ) Figure S7. SQC spectrum of (DMS-d )
32 0 7 8 Figure S8., -CSY spectrum of (DMS-d ) Figure S. MBC spectrum of (DMS-d )
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