[11]-Chaetoglobosins from Pseudeurotium bakeri Induce G2/M Cell Cycle Arrest and Apoptosis in Human Cancer Cells
Duan, Fang-Fang; Liu, Lin; Gao, Ying; Peng, Xiao-Gang; Meng, Xiang-Gao; Ruan, Han-Li; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.0c01335

data_1563743
_publ_section_title
;
 [11]-Chaetoglobosins from Pseudeurotium bakeri Induce G2/M Cell Cycle
 Arrest and Apoptosis in Human Cancer Cells
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01335
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H36 N2 O3, C H4 O'
_chemical_formula_sum            'C30 H40 N2 O4'
_chemical_formula_weight         492.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8192(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5437(2)
_cell_length_b                   9.9455(2)
_cell_length_c                   11.8095(2)
_cell_measurement_reflns_used    19097
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.4720
_cell_measurement_theta_min      3.8320
_cell_volume                     1322.03(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -11.00  23.00   0.50    0.50    --    0.00  38.00 -30.00   68
  2  \w    -32.00  17.00   0.50    0.50    --    0.00 -38.00  60.00   98
  3  \w    -18.00  28.00   0.50    0.50    --    0.00 -77.00-180.00   92
  4  \w    -21.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  104
  5  \w    -14.00  74.00   0.50    0.50    --    0.00  38.00  90.00  176
  6  \w    -21.00  87.00   0.50    0.50    --    0.00  57.00 -90.00  216
  7  \w    -16.00  62.00   0.50    0.50    --    0.00  19.00-150.00  156
  8  \w     30.00  80.00   0.50    0.50    --    0.00  38.00 -30.00  100
  9  \w    -20.00  41.00   0.50    0.50    --    0.00  57.00-150.00  122
 10  \w     49.00  89.00   0.50    0.50    --    0.00  57.00-150.00   80
 11  \w    140.00 175.00   0.50    0.50    --   94.60  52.00 143.14   70
 12  \w     66.00  92.00   0.50    0.50    --   94.60  74.00 -71.83   52
 13  \w     69.00 174.00   0.50    0.50    --   94.60  68.00-176.19  210
 14  \w     69.00  95.00   0.50    0.50    --   94.60  68.00  60.68   52
 15  \w    135.00 161.00   0.50    0.50    --   94.60  75.00-166.56   52
 16  \w     73.00 116.00   0.50    0.50    --   94.60  52.00 143.14   86
 17  \w    139.00 177.00   0.50    0.50    --   94.60  59.00 -67.14   76
 18  \w     66.00  92.00   0.50    0.50    --   94.60  75.00-166.56   52
 19  \w     68.00 166.00   0.50    0.50    --   94.60  70.00  75.42  196
 20  \w    134.00 159.00   0.50    0.50    --   94.60  71.00 155.76   50
 21  \w     66.00  99.00   0.50    0.50    --   94.60  74.00 -12.22   66
 22  \w    124.00 181.00   0.50    0.50    --   94.60  74.00 -12.22  114
 23  \w     67.00 180.00   0.50    0.50    --   94.60  72.00 -22.28  226
 24  \w     68.00  93.00   0.50    0.50    --   94.60  70.00  49.50   50
 25  \w    103.00 184.00   0.50    0.50    --   94.60  70.00  49.50  162
 26  \w      5.00  76.00   0.50    0.50    --   94.60 -82.00  90.00  142
 27  \w      6.00  68.00   0.50    0.50    --   94.60 -82.00 150.00  124
 28  \w     74.00 122.00   0.50    0.50    --   94.60 -82.00 150.00   96
 29  \w    158.00 183.00   0.50    0.50    --   94.60  66.00 150.22   50
 30  \w    156.00 182.00   0.50    0.50    --   94.60  63.00 -42.71   52
 31  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 155.76   52
 32  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 33  \w    135.00 183.00   0.50    0.50    --   94.60  74.00-128.94   96
 34  \w     69.00  95.00   0.50    0.50    --   94.60  66.00 150.22   52
 35  \w     64.00 125.00   0.50    0.50    --   94.60 -82.00  60.00  122
 36  \w     71.00 135.00   0.50    0.50    --   94.60  61.00 -30.00  128
 37  \w      7.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  238
 38  \w     72.00  97.00   0.50    0.50    --   94.60  61.00 120.00   50
 39  \w     77.00 119.00   0.50    0.50    --   94.60  45.00  60.00   84
 40  \w     71.00 129.00   0.50    0.50    --   94.60  61.00-180.00  116
 41  \w     67.00 122.00   0.50    0.50    --   94.60  74.00-128.94  110
 42  \w     71.00 124.00   0.50    0.50    --   94.60  61.00 -90.00  106
 43  \w     69.00  95.00   0.50    0.50    --   94.60  66.00  91.47   52
 44  \w     80.00 112.00   0.50    0.50    --   94.60  45.00  30.00   64
 45  \w     71.00 140.00   0.50    0.50    --   94.60  61.00 150.00  138
 46  \w     67.00 136.00   0.50    0.50    --   94.60  71.00  93.09  138
 47  \w     69.00  94.00   0.50    0.50    --   94.60  70.00-131.46   50
 48  \w     70.00 115.00   0.50    0.50    --   94.60  63.00 -42.71   90
 49  \w     44.00  77.00   0.50    0.50    --   94.60 -82.00 -60.00   66
 50  \w     82.00 124.00   0.50    0.50    --   94.60 -82.00 -60.00   84
 51  \w     13.00  73.00   0.50    0.50    --   94.60 -82.00 -30.00  120
 52  \w     95.00 121.00   0.50    0.50    --   94.60 -82.00 -30.00   52
 53  \w     71.00 135.00   0.50    0.50    --   94.60  59.00 -67.14  128
 54  \w     92.00 122.00   0.50    0.50    --   94.60 -82.00  90.00   60
 55  \w     72.00  98.00   0.50    0.50    --   94.60  56.00-129.39   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0849791000
_diffrn_orient_matrix_UB_12      -0.0214999000
_diffrn_orient_matrix_UB_13      0.1191521000
_diffrn_orient_matrix_UB_21      0.1023543000
_diffrn_orient_matrix_UB_22      0.0617831000
_diffrn_orient_matrix_UB_23      -0.0469579000
_diffrn_orient_matrix_UB_31      -0.0320820000
_diffrn_orient_matrix_UB_32      0.1404023000
_diffrn_orient_matrix_UB_33      0.0388275000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27413
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.933
_diffrn_reflns_theta_min         3.839
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.2613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                5023
_reflns_number_total             5210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01335_si_005.cif
_cod_data_source_block           20200109_pss-1
_cod_database_code               1563743
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.738
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C5'(H5'), C6'(H6'), C7'(H7'), C8'(H8'), C13(H13), C14(H14),
 N1'(H1'), N2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O4(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.689
_oxdiff_exptl_absorpt_empirical_full_min 0.505