Asaroidoxazines from the Roots of Asarum asaroides Induce Apoptosis in Human Neuroblastoma Cells
Ohta, Shinji; Oshimo, Shiori; Ohta, Emi; Nehira, Tatsuo; Ômura, Hisashi; Uy, Mylene M.; Ishihara, Yasuhiro; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00574

data_1559130
_publ_section_title
;
 Asaroidoxazines from the Roots of Asarum asaroides Induce Apoptosis in
 Human Neuroblastoma Cells
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00574
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H20 N2 O8 S'
_chemical_formula_weight         460.45
_chemical_melting_point          206
_chemical_name_common            'Asaroidoxazine A'
_chemical_name_systematic
;
(S)-2-((9,12-dimethoxy-5-oxo-5,8-dihydro-[1,3]dioxolo[4',5':3,4]phenanthro[10,1-cd][1,2]oxazin-8-yl)thio)acetamide
;
_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   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.2580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0144(4)
_cell_length_b                   11.1979(9)
_cell_length_c                   18.4427(14)
_cell_measurement_reflns_used    6300
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      1.10
_cell_volume                     1035.32(14)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6300
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.955
_diffrn_reflns_theta_min         1.104
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                4281
_reflns_number_total             4615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00574_si_002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559130
_shelxl_version_number           2014-3
_shelx_res_checksum              18047
_shelx_hkl_checksum              40018