[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_1563746
_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         'C31 H36 N2 O6, 3(C H4 O)'
_chemical_formula_sum            'C34 H48 N2 O9'
_chemical_formula_weight         628.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.13141(4)
_cell_length_b                   15.63357(6)
_cell_length_c                   30.34804(13)
_cell_measurement_reflns_used    55525
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6310
_cell_measurement_theta_min      3.2190
_cell_volume                     3383.48(3)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -22.00  88.00   0.50    0.50    --    0.00  57.00  60.00  220
  2  \w     26.00  57.00   0.50    0.50    --    0.00  19.00-150.00   62
  3  \w    -89.00 -34.00   0.50    0.50    --    0.00 -38.00-180.00  110
  4  \w    -20.00   5.00   0.50    0.50    --    0.00  57.00-180.00   50
  5  \w     30.00  89.00   0.50    0.50    --    0.00  38.00 120.00  118
  6  \w    -25.00  42.00   0.50    0.50    --    0.00  70.00 -25.44  134
  7  \w    -14.00  17.00   0.50    0.50    --    0.00  19.00-150.00   62
  8  \w    -17.00  15.00   0.50    0.50    --    0.00  38.00 120.00   64
  9  \w     47.00  82.00   0.50    0.50    --    0.00  70.00 -25.44   70
 10  \w     31.00  83.00   0.50    0.50    --    0.00  57.00-180.00  104
 11  \w    -18.00  16.00   0.50    0.50    --    0.00 -38.00-180.00   68
 12  \w    -22.00  44.00   0.50    0.50    --    0.00  57.00 -90.00  132
 13  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  41.33   50
 14  \w    157.00 184.00   0.50    0.50    --   94.60  60.00  49.74   54
 15  \w     71.00 183.00   0.50    0.50    --   94.60  59.00  76.06  224
 16  \w    121.00 149.00   0.50    0.50    --   94.60  60.00  49.74   56
 17  \w     71.00  96.00   0.50    0.50    --   94.60  60.00  49.74   50
 18  \w     74.00 107.00   0.50    0.50    --   94.60  49.00  29.58   66
 19  \w     72.00  97.00   0.50    0.50    --   94.60  56.00  26.92   50
 20  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 -41.05   50
 21  \w    158.00 184.00   0.50    0.50    --   94.60  75.00 -60.61   52
 22  \w     71.00  98.00   0.50    0.50    --   94.60  61.00-168.29   54
 23  \w     70.00  96.00   0.50    0.50    --   94.60  64.00-136.07   52
 24  \w     71.00 184.00   0.50    0.50    --   94.60  61.00-136.90  226
 25  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 138.57   52
 26  \w    156.00 182.00   0.50    0.50    --   94.60  72.00 138.57   52
 27  \w     66.00 118.00   0.50    0.50    --   94.60  75.00 127.81  104
 28  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-130.93   52
 29  \w    121.00 147.00   0.50    0.50    --   94.60  72.00-130.93   52
 30  \w     67.00  97.00   0.50    0.50    --   94.60  71.00 121.14   60
 31  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 -60.61   50
 32  \w     71.00 184.00   0.50    0.50    --   94.60  61.00 109.85  226
 33  \w    148.00 174.00   0.50    0.50    --   94.60  72.00 -73.44   52
 34  \w     66.00  91.00   0.50    0.50    --   94.60  75.00-172.76   50
 35  \w    147.00 172.00   0.50    0.50    --   94.60  72.00  73.96   50
 36  \w     67.00  92.00   0.50    0.50    --   94.60  72.00  73.96   50
 37  \w    153.00 179.00   0.50    0.50    --   94.60  65.00-113.69   52
 38  \w     66.00  92.00   0.50    0.50    --   94.60  75.00 -33.37   52
 39  \w     67.00  92.00   0.50    0.50    --   94.60  72.00  -5.79   50
 40  \w    152.00 178.00   0.50    0.50    --   94.60  72.00  -5.79   52
 41  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00 -30.00  242
 42  \w      6.00 120.00   0.50    0.50    --   94.60 -82.00 150.00  228
 43  \w     68.00  93.00   0.50    0.50    --   94.60  70.00 -86.58   50
 44  \w    100.00 126.00   0.50    0.50    --   94.60 -82.00-180.00   52
 45  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -90.00   50
 46  \w    139.00 165.00   0.50    0.50    --   94.60  61.00 -90.00   52
 47  \w     71.00 130.00   0.50    0.50    --   94.60  62.00  99.44  118
 48  \w     70.00 117.00   0.50    0.50    --   94.60  65.00-113.69   94
 49  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -73.44   50
 50  \w      8.00  80.00   0.50    0.50    --   94.60 -77.00  30.00  144
 51  \w     91.00 120.00   0.50    0.50    --   94.60 -77.00  30.00   58
 52  \w     73.00  99.00   0.50    0.50    --   94.60  54.00 -88.70   52
 53  \w     67.00 104.00   0.50    0.50    --   94.60  71.00 149.29   74
 54  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 109.34   50
 55  \w     72.00  97.00   0.50    0.50    --   94.60  61.00   0.00   50
 56  \w     72.00 133.00   0.50    0.50    --   94.60  61.00-150.00  122
 57  \w    154.00 179.00   0.50    0.50    --   94.60  61.00-150.00   50
 58  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -79.19   50
 59  \w    103.00 136.00   0.50    0.50    --   94.60  61.00 -79.19   66
 60  \w    144.00 169.00   0.50    0.50    --   94.60  61.00 -79.19   50
 61  \w     74.00 175.00   0.50    0.50    --   94.60  54.00  -2.09  202
 62  \w    108.00 184.00   0.50    0.50    --   94.60  73.00  11.99  152
 63  \w     71.00  97.00   0.50    0.50    --   94.60  61.00-120.00   52
 64  \w     71.00  97.00   0.50    0.50    --   94.60  61.00-180.00   52
 65  \w     67.00  93.00   0.50    0.50    --   94.60  73.00  11.99   52
 66  \w     75.00 171.00   0.50    0.50    --   94.60  47.00 -50.81  192
 67  \w     72.00  98.00   0.50    0.50    --   94.60  57.00 -26.33   52
 68  \w     68.00  93.00   0.50    0.50    --   94.60  69.00 -57.86   50
 69  \w    147.00 172.00   0.50    0.50    --   94.60  61.00  41.33   50
 70  \w     77.00 171.00   0.50    0.50    --   94.60  39.00-160.96  188
 71  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  60.00   50
 72  \w     13.00 119.00   0.50    0.50    --   94.60 -82.00-150.00  212
 73  \w      5.00 117.00   0.50    0.50    --   94.60 -82.00   0.00  224
 74  \w     86.00 111.00   0.50    0.50    --   94.60 -82.00  90.00   50
 75  \w    152.00 177.00   0.50    0.50    --   94.60  56.00  26.92   50
;
_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      -0.0374111000
_diffrn_orient_matrix_UB_12      0.0375750000
_diffrn_orient_matrix_UB_13      0.0461039000
_diffrn_orient_matrix_UB_21      0.0246030000
_diffrn_orient_matrix_UB_22      -0.0894851000
_diffrn_orient_matrix_UB_23      0.0204393000
_diffrn_orient_matrix_UB_31      0.2113403000
_diffrn_orient_matrix_UB_32      0.0170495000
_diffrn_orient_matrix_UB_33      0.0057864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            87098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.081
_diffrn_reflns_theta_min         2.912
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65364
_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    1.234
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0401P)^2^+1.8219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                6740
_reflns_number_total             6833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01335_si_008.cif
_cod_data_source_block           exp_42
_cod_original_cell_volume        3383.49(3)
_cod_database_code               1563746
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.712
_reflns_odcompleteness_completeness 99.97
_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), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C13(H13), C14(H14),
 N1'(H1'A), N2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C27(H27A,H27B,
 H27C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O7(H7A), O8(H8A), O9(H9)
;
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.500