neo-Clerodane Diterpenoids from Salvia polystachya Stimulate the Expression of Extracellular Matrix Components in Human Dermal Fibroblasts.
Bautista, Elihú; Ortiz-Pastrana, Naytzé; Pastor-Palacios, Guillermo; Montoya-Contreras, Angélica; Toscano, Rubén A; Morales-Jiménez, Jesús; Salazar-Olivo, Luis A; Ortega, Alfredo; Journal of natural products 80 (2017) 3003–3009; doi:10.1021/acs.jnatprod.7b00591

data_1548121
_publ_section_title
;
 neo-Clerodane Diterpenoids from Salvia polystachya Stimulate the
 Expression of Extracellular Matrix Components in Human Dermal
 Fibroblasts.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3003
_journal_page_last               3009
_journal_paper_doi               10.1021/acs.jnatprod.7b00591
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H22 O8'
_chemical_formula_sum            'C20 H22 O8'
_chemical_formula_weight         390.37
_chemical_name_common            'Polystachyne G/15-epi-polystachyne G'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   '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
_cell_angle_alpha                90
_cell_angle_beta                 118.237(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9433(12)
_cell_length_b                   7.8994(9)
_cell_length_c                   11.2708(17)
_cell_measurement_reflns_used    9005
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.54
_cell_measurement_theta_min      4.45
_cell_volume                     858.4(2)
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_collection       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Endevor \k-geometry diffractometer'
_diffrn_measurement_method       '\f and \w-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2394
_diffrn_reflns_av_unetI/netI     0.1328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22536
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_min         4.453
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  0.7322
_exptl_absorpt_correction_T_min  0.5844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Flack x determined using 458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1919
_refine_ls_R_factor_gt           0.1321
_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^)+(0.1163P)^2^+5.4985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3358
_refine_ls_wR_factor_ref         0.3676
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                1891
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00591_si_002.cif
_cod_data_source_block           Compound_1-2
_cod_depositor_comments
'Adding full bibliography for 1548120--1548122.cif.'
_cod_original_cell_volume        858.36(19)
_cod_database_code               1548121
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              51975
_shelx_hkl_checksum              85716