Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses
Ebada, Sherif S.; Al-Jawabri, Nariman A.; Youssef, Fadia S.; El-Kashef, Dina H.; Knedel, Tim-Oliver; Albohy, Amgad; Korinek, Michal; Hwang, Tsong-Long; Chen, Bing-Hung; Lin, Guan-Hua; Lin, Chia-Yi; Aldalaien, Sa'ed M.; Disi, Ahmad M.; Janiak, Christoph; Proksch, Peter; RSC Advances 10 (2020) 38128–38141; doi:10.1039/D0RA04876C

data_7241674
_publ_section_title
;
 Anti-inflammatory, antiallergic and COVID-19 protease inhibitory
 activities of phytochemicals from the Jordanian hawksbeard:
 identification, structure--activity relationships, molecular modeling and
 impact on its folk medicinal uses
;
_journal_issue                   62
_journal_name_full               'RSC Advances'
_journal_page_first              38128
_journal_page_last               38141
_journal_paper_doi               10.1039/D0RA04876C
_journal_volume                  10
_journal_year                    2020
_chemical_compound_source
'plant Crepis sancta, family Asteraceae, collected Southern Jordan'
_chemical_formula_moiety         'C19 H18 O8'
_chemical_formula_sum            'C19 H18 O8'
_chemical_formula_weight         374.33
_chemical_name_common            chrysosplentin
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-04-03 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.789(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2577(3)
_cell_length_b                   17.3639(8)
_cell_length_c                   13.3620(6)
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    136(2)
_cell_measurement_theta_max      22.863
_cell_measurement_theta_min      2.802
_cell_volume                     1675.32(13)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 4.5.3 (Crystal Impact, 2018)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_diffrn_ambient_temperature      136(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans, \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         1.532
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         6958
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0438P)^2^+0.1359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5346
_reflns_number_total             6958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra04876c2.cif
_cod_data_source_block           mo_tok_dina_csv5_mo2_0ma_a_pl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7241674
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              34001