Unprecedented Quassinoids from Eurycoma longifolia: Biogenetic Evidence and Antifeedant Effects
Yang, Wei-Qun; Shao, Xue-Hua; Deng, Fang; Hu, Li-Jun; Xiong, Yu; Huang, Xiao-Jun; Fan, Chun-Lin; Jiang, Ren-Wang; Ye, Wen-Cai; Wang, Ying; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00244

data_1557822
_publ_section_title
;
 Unprecedented Quassinoids from Eurycoma longifolia: Biogenetic Evidence
 and Antifeedant Effects
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00244
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H36 O8, H2 O'
_chemical_formula_sum            'C28 H38 O9'
_chemical_formula_weight         518.58
_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
_audit_creation_date             2020-01-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6408(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2781(2)
_cell_length_b                   9.82934(16)
_cell_length_c                   11.8906(2)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4360
_cell_measurement_theta_min      4.0000
_cell_volume                     1286.20(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00-180.00   99
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00 -90.00   99
  3  \w    -74.00  35.00   1.00    1.00    --  -41.11  77.00-180.00  109
  4  \w     17.00 116.00   1.00    1.00    --   41.11  37.00 -30.00   99
  5  \w     13.00 113.00   1.00    1.00    --   41.11  57.00  60.00  100
  6  \w     23.00  97.00   1.00    1.00    --   41.11-125.00   0.00   74
  7  \w     81.00 178.00   1.00    5.63    --  106.95  45.00 -90.00   97
  8  \w     74.00 178.00   1.00    5.63    --  106.95  77.00-180.00  104
  9  \w     74.00 178.00   1.00    5.63    --  106.95  77.00 -90.00  104
 10  \w     94.00 178.00   1.00    5.63    --  106.95 125.00 120.00   84
 11  \w     94.00 178.00   1.00    5.63    --  106.95 125.00  60.00   84
 12  \w     78.00 178.00   1.00    5.63    --  106.95  61.00-150.00  100
 13  \w     79.00 178.00   1.00    5.63    --  106.95  30.00-120.00   99
 14  \w     74.00 178.00   1.00    5.63    --  106.95  77.00-120.00  104
 15  \w     78.00 178.00   1.00    5.63    --  106.95  61.00-120.00  100
 16  \w     24.00 109.00   1.00    5.63    --  106.95 -94.00  60.00   85
 17  \w     78.00 178.00   1.00    5.63    --  106.95  61.00 -90.00  100
 18  \w     78.00 153.00   1.00    5.63    --  106.95  61.00 -60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11862
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        63.983
_diffrn_reflns_theta_max         63.983
_diffrn_reflns_theta_min         3.810
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0609P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3996
_reflns_number_total             4142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00244_si_003.cif
_cod_data_source_block           p20-9-el9
_cod_original_cell_volume        1286.19(4)
_cod_database_code               1557822
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C11(H11), C17(H17), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              85513
_shelx_hkl_checksum              65085
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;