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1 Supporting Information Penibruguieramine A, a Novel Pyrrolizidine Alkaloid from the Endophytic Fungus Penicillium sp. GD6 Associated with Chinese Mangrove Bruguiera gymnorrhiza Zhen-Fang Zhou, Tibor Kurtán, Xiao-Hong Yang, Attila Mándi, Mei-Yu Geng, Bo-Ping Ye,, Orazio Taglialatela-Scafati,, and Yue-Wei Guo, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Acadeny of Science, Zu Chong Zhi Road, 555, Shanghai , People s Republic of China Department of Organic Chemistry, University of Debrecen, P.O. Box 20, 4010 Debrecen, Hungary School of Life Science & Technology, China Pharmaceutical University, Nanjing , Jiangsu, People s Republic of China Dipartimento di Farmacia, Università di Napoli Federico II, Via D. Montesano, 49, Napoli, Italy * Corresponding author: yebp@cpu.edu.cn (B.-P. Y.); scatagli@unina.it (O. T.-S.). ywguo@mail.shcnc.ac.cn (Y.-W. G.). S1
2 S1. Experimental Section General Experimental Procedures Fungal Material and Fermentation Extraction and Isolation Bioassay procedures Computational section for compound 1 References S2. 1 H NMR spectrum (500 MHz) of penibruguieramine A (1) in CDCl 3. S3. 13 C NMR spectrum (125 MHz) of penibruguieramine A (1) in CDCl 3. S4. HSQC spectrum (500 MHz) of penibruguieramine A (1) in CDCl 3. S5. 1 H- 1 H COSY spectrum (500 MHz) of penibruguieramine A (1) in CDCl 3. S6. HMBC spectrum (500 MHz) of penibruguieramine A (1) in CDCl 3. S7. ROESY spectrum (600 MHz) of penibruguieramine A (1) in CDCl 3. S8. HR-ESIMS spectrum of penibruguieramine A (1). S9. IR spectrum of penibruguieramine A (1). S2
3 S1. Experimantal Senction General Experimental Procedures. Commercial silica gel (Qing Dao Hai Yang Chemical Group Co., mesh), C18 reversed-phase silica gel ( mesh, Merck); MCI gel (CHP20P, μm, Mitsubishi Chemical Industries Ltd.) and Sephadex LH-20 gel (Amersham Biosciences) were used for column chromatography. Pre-coated silica gel GF 254 plates (Qing Dao Hai Yang Chemical Group Co. Ltd. Qingdao, People s Republic of China) were used for analytical thin-layer chromatography (TLC). Optical rotations were determined on a Perkin-Elmer 341 polarimeter. IR spectra were recorded on a Perkin-Elmer 577 spectrometer with KBr disks. CD spectra were measured on a JASCO J-810 instrument. NMR spectra were acquired on Bruker Avance III 500, and Varian INOVA 600 spectrometers. Chemical shifts are reported with the residual CHCl 3 (δ H 7.26 ppm) as the internal standard for 1 H NMR spectrometry, and CDCl 3 (δ C 77.0 ppm) for 13 C NMR spectrometry. ESIMS and HRESIMS were obtained on an Esquire 3000plus (Bruker Daltonics) and a Waters-Micromass Q-TOF Ultima Global electrospray mass spectrometer, respectively. All solvents used were of analytical grade (Shanghai Chemical Reagents Company, Ltd.). Fungal Material and Fermentation. The fungal strain GD6 was isolated from the stem bark of Bruguiera gymnorrhiza collected from Techeng island of Zhanjiang, China in April 10, It was initially identified as Penicillium species based on its morphological characters and the internal transcribed spacer (ITS) sequence (Accession number in GenBank is KF604117). The frozen samples of this fungus are maintained in the School of Life Science & Technology in China Pharmaceutical University (Sample GD6). Fungal spores were inoculated into 25 ml potato-dextrose media and grown at 28 C for one week with shaking (160 rpm). The cellular material was transferred into a sterile 50 Erlenmeyer flask (1 L, containing of 200 ml potato-dextrose media) and mixed by S3
4 vortexing for 5 min to create a uniform fungal cells/spores suspension. Aliquotes of the fungal suspension were inoculated into 50 Erlenmeyer flasks (1 L) containing 300 ml autoclaved media (20.0 g/l glucose, 5.0 g/l peptone, 3.0 g/l malt extract, 3.0 g/l yeast extract, g/l NaCl, and ph 7.0). Culture vessels were maintained on the bench-top at room temperature for 25 days. Extraction and Isolation. The whole cultures (300mL 100 flasks) were filtered through a four-layer cheesecloth to separate mycelia from broth. The broth was extracted with EtOAc to give an evaporated extract (11.27 g). The dried mycelia were homogenized and extracted with a mixture of CHCl 3 and MeOH (1:1, v/v), and the evaporated extract was partitioned between EtOAc and H 2 O to yield an EtOAc-soluble extract (9.89 g). These two parts were combined for further separation based on their identical TLC profiles. The total EtOAc-soluble fraction was subjected to MCI column chromatography with a solvent system consisting of % methanol water to afford 9 fractions (Fractions 1 9) based on TLC analysis. Fraction 7 was first eluted with a gradient petroleum ether-etoac (7:3 to 1:1) and was further purified by CC on C-18 reversed-phase silica gel (methanol/water, 7:3) to give compound 1 (1.5 mg). Fraction 8 was chromatographed on silica gel with petroleum ether-acetone (7:3 and 1:1) to yield compound 2 (8.6 mg) and the subfraction 8a, which was purified by Sephadex LH-20 (CHCl 3 /MeOH, 1:1) to give compound 3 (4.7 mg). Fraction 9 was first separated by C-18 reversed-phase silica gel column with a gradient methanol-water (1:1 to 1:0) and further purified by Sephadex LH-20 (CHCl 3 /MeOH, 1:1) to afford compound 4 (1.4 mg). Bioassay procedures. The cytotoxicities of compounds 1-4 against human lung adenocarcinoma A-549 and Human promyelocytic leukemia cells HL-60 cell lines were evaluated by using the SRB 1 and MTT 2 methods, respectively, according to the protocols described in previous literature. Doxorubicin was used as the positive control, with IC 50 values of μm for the A-549 cell line and for the HL-60 cell line, respectively. Computational section for compound 1. Mixed torsional/low mode conformational searches were carried out by means of the Macromodel software using Merck S4
5 Molecular Force Field (MMFF) with implicit solvent model for chloroform applying a 21 kj/mol energy window. The resultant 1113 conformers were reclustered for the heavy atoms and OH hydrogens disregarding the orientation of the alkenyl side-chain. Geometry reoptimizations of 31 conformers [B3LYP/6-31G(d) level in vacuo and B3LYP/TZVP level with PCM solvent model for CH 3 CN] and TDDFT calculations were performed with Gaussian 09 4 using various functionals (B3LYP, BH&HLYP, PBE0) and TZVP basis set. ECD spectra were generated as the sum of Gaussians 5 with 3000 cm 1 half-height width (corresponding to ca. 15 nm at 220 nm), using dipole-velocity computed rotational strengths. Boltzmann distributions were estimated from the ZPVE corrected B3LYP/6-31G(d) energies in the gas phase calculations and from the B3LYP/TZVP energies in the solvent model calculations. The MOLEKEL 6 software package was used for visualization of the results. Figure S1. Low-energy conformers ( 1%) of (1S,2R,8R)-1 calculated at B3LYP/6-31G(d) level of theory in vacuo. S5
6 Figure S2. Low-energy conformers ( 1%) of (1S,2R,8R)-1 calculated at B3LYP/TZVP level with PCM solvent model for CH 3 CN. S6
7 Table 1. Cartesian coordinates for the low-energy reoptimized MMFF conformers calculated at B3LYP/6-31G(d) level of theory in vacuo. Conformer A 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H S7
8 35 H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer B 1 C C C N C C C C C C O C C C C C C C O O H H S8
9 23 H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer C 1 C C C N C C C C C C S9
10 11 O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. S10
11 Conformer D 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H S11
12 39 H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer E 1 C C C N C C C C C C O C C C C C C C O O H H H H H H S12
13 27 H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer F 1 C C C N C C C C C C O C C C S13
14 15 C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer G 1 C C S14
15 3 C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H S15
16 43 H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer H 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H S16
17 31 H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer I 1 C C C N C C C C C C O C C C C C C C S17
18 19 O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer J 1 C C C N C C S18
19 7 C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H S19
20 47 H B3LYP Energy = a.u.; E+ZPVE = a.u. Conformer K 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H S20
21 35 H H H H H H H H H H H H H B3LYP Energy = a.u.; E+ZPVE = a.u. Table SX. Cartesian coordinates for the low-energy reoptimized MMFF conformers calculated at B3LYP/TZVP level of theory with PCM solvent model for MeCN. Conformer A 1 C C C N C C C C C C O C C C C C C C O S21
22 20 O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer B 1 C C C N C C C S22
23 8 C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H S23
24 B3LYP Energy = a.u. Conformer C 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H S24
25 36 H H H H H H H H H H H H B3LYP Energy = a.u. Conformer D 1 C C C N C C C C C C O C C C C C C C O O H H H S25
26 24 H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer E 1 C C C N C C C C C C O S26
27 12 C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer F S27
28 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H S28
29 40 H H H H H H H H B3LYP Energy = a.u. Conformer G 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H S29
30 28 H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer H 1 C C C N C C C C C C O C C C C S30
31 16 C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer I 1 C C C S31
32 4 N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H S32
33 44 H H H H B3LYP Energy = a.u. Conformer J 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H S33
34 32 H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer K 1 C C C N C C C C C C O C C C C C C C O S34
35 20 O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer L 1 C C C N C C C S35
36 8 C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H S36
37 B3LYP Energy = a.u. Conformer M 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H S37
38 36 H H H H H H H H H H H H B3LYP Energy = a.u. Conformer N 1 C C C N C C C C C C O C C C C C C C O O H H H S38
39 24 H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer O 1 C C C N C C C C C C O S39
40 12 C C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H B3LYP Energy = a.u. Conformer P S40
41 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H H H H H H H H H H H H H S41
42 40 H H H H H H H H B3LYP Energy = a.u. Conformer Q 1 C C C N C C C C C C O C C C C C C C O O H H H H H H H S42
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