Bioassay-Guided Isolation of an Abetiane-Type Diterpenoid from <i>Prunella vulgaris</i> That Protects against Concanavalin A-Induced Autoimmune Hepatitis.
Cao, Yunfang; Tan, Xiaosheng; Al Chnani, Ali Adhab; Li, Pengkun; Shi, Zhengyi; Feng, Hao; Sun, Lingjuan; Xia, Qiangbing; Yang, Xi; Duan, Yulin; Guo, Yi; Chen, Gang; Qi, Changxing; Zhang, Yonghui; Journal of natural products 84 (2021) 2189–2199; doi:10.1021/acs.jnatprod.1c00247

data_1564531
_publ_section_title
;
 Bioassay-Guided Isolation of an Abetiane-Type Diterpenoid from
 <i>Prunella vulgaris</i> That Protects against Concanavalin A-Induced
 Autoimmune Hepatitis.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2189
_journal_page_last               2199
_journal_paper_doi               10.1021/acs.jnatprod.1c00247
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C21 H28 O6'
_chemical_formula_weight         376.43
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                84.282(2)
_cell_angle_beta                 68.4130(10)
_cell_angle_gamma                89.8290(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8662(4)
_cell_length_b                   10.0457(5)
_cell_length_c                   12.0334(7)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      79.13
_cell_measurement_theta_min      3.97
_cell_volume                     990.99(9)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      154(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25881
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.421
_diffrn_reflns_theta_min         3.973
_exptl_absorpt_coefficient_mu    0.753
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 3124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7561
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0354
_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          0.1036
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.780
_reflns_number_gt                7391
_reflns_number_total             7561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00247_si_002.cif
_cod_data_source_block           cyf193
_cod_database_code               1564531
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              12782
_shelx_hkl_checksum              24871