Biotransformation of β-Mangostin by an Endophytic Fungus of Garcinia mangostana to Furnish Xanthenes with an Unprecedented Heterocyclic Skeleton.
Arunrattiyakorn, Panarat; Kuno, Mayuso; Aree, Thammarat; Laphookhieo, Surat; Sriyatep, Teerayut; Kanzaki, Hiroshi; Garcia Chavez, Miguel Angel; Wang, Yan Alexander; Andersen, Raymond J.; Journal of natural products 81 (2018) 2244–2250; doi:10.1021/acs.jnatprod.8b00519

data_1553400
_publ_section_title
;
 Biotransformation of \b-Mangostin by an Endophytic Fungus of Garcinia
 mangostana to Furnish Xanthenes with an Unprecedented Heterocyclic
 Skeleton.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2244
_journal_page_last               2250
_journal_paper_doi               10.1021/acs.jnatprod.8b00519
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 O9'
_chemical_formula_sum            'C25 H28 O9'
_chemical_formula_weight         472.47
_chemical_name_common            '(-) Mangostafeejin A'
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.6878(3)
_cell_length_b                   11.6878(3)
_cell_length_c                   29.8747(8)
_cell_measurement_reflns_used    5880
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.39
_cell_measurement_theta_min      4.37
_cell_volume                     3534.27(16)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  PROSPECTOR
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15181
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.302
_diffrn_reflns_theta_min         4.368
_diffrn_source                   'microfocus I\mS'
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.753
_exptl_transmission_factor_min   0.638
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       0.0012(2)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                3142
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00519_si_004.cif
_cod_data_source_block           2a
_cod_original_cell_volume        3534.3(2)
_cod_database_code               1553400
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.630
_shelx_estimated_absorpt_t_max   0.905
_shelx_res_checksum              79612
_shelx_hkl_checksum              62421