Structurally Diverse Labdane Diterpenoids from <i>Leonurus japonicus</i> and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells.
Zhang, Xing-Jie; Zhong, Wei-Mao; Liu, Rui-Xue; Wang, Yong-Mei; Luo, Ting; Zou, Yan; Qin, Hua-Yan; Li, Xiao-Li; Zhang, Ruihan; Xiao, Wei-Lie; Journal of natural products 83 (2020) 2545–2558; doi:10.1021/acs.jnatprod.9b00597

data_1559095
_publ_section_title
;
 Structurally Diverse Labdane Diterpenoids from <i>Leonurus japonicus</i>
 and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2545
_journal_page_last               2558
_journal_paper_doi               10.1021/acs.jnatprod.9b00597
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H32 O6'
_chemical_formula_sum            'C22 H32 O6'
_chemical_formula_weight         392.47
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4086(2)
_cell_length_b                   11.8075(3)
_cell_length_c                   18.6030(4)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.33
_cell_measurement_theta_min      4.44
_cell_volume                     2066.65(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11610
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.321
_diffrn_reflns_theta_min         4.435
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.230
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.3924
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(8)
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0575P)^2^+0.8101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3778
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00597_si_001.cif
_cod_data_source_block           cu_xlm57_0m
_cod_depositor_comments
'Adding full bibliography for 1559094--1559095.cif.'
_cod_database_code               1559095
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.674
_shelx_estimated_absorpt_t_max   0.848
_shelx_res_checksum              94768
_shelx_hkl_checksum              21123