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_1557825
_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         'C27 H32.77 O8'
_chemical_formula_sum            'C27 H33 O8'
_chemical_formula_weight         485.53
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.7250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.32150(10)
_cell_length_b                   10.26040(10)
_cell_length_c                   14.32600(10)
_cell_measurement_reflns_used    10144
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4250
_cell_measurement_theta_min      4.2920
_cell_volume                     1205.60(2)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_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    -72.00 -47.00   1.00    1.00    --  -40.98 -57.00-150.00   25
  2  \w   -116.00  -8.00   1.00    1.00    --  -40.98 -77.00-150.00  108
  3  \w   -113.00 -75.00   1.00    1.00    --  -40.98 -57.00 -90.00   38
  4  \w    -64.00  22.00   1.00    1.00    --  -40.98  37.00   0.00   86
  5  \w    -60.00 -18.00   1.00    1.00    --  -40.98 -37.00 -90.00   42
  6  \w    -72.00 -34.00   1.00    1.00    --  -40.98 -57.00 -90.00   38
  7  \w      1.00  81.00   1.00    1.00    --   40.98 -99.00  60.00   80
  8  \w      9.00  34.00   1.00    1.00    --   40.98  77.00-150.00   25
  9  \w     31.00  57.00   1.00    1.00    --   40.98  37.00 -60.00   26
 10  \w     75.00 102.00   1.00    1.00    --  106.95  77.00 -60.00   27
 11  \w     78.00 105.00   1.00    1.00    --  106.95  61.00 -30.00   27
 12  \w     74.00 100.00   1.00    1.00    --  106.95  77.00 -90.00   26
 13  \w    153.00 178.00   1.00    1.00    --  106.95  61.00 -30.00   25
 14  \w     24.00  68.00   1.00    1.00    --  106.95 -94.00-120.00   44
 15  \w     95.00 162.00   1.00    1.00    --  106.95 125.00  30.00   67
 16  \w     81.00 176.00   1.00    1.00    --  106.95  45.00 -90.00   95
 17  \w     36.00  82.00   1.00    1.00    --  106.95 -61.00  90.00   46
 18  \w     79.00 104.00   1.00    1.00    --  106.95  61.00 -90.00   25
 19  \w     75.00 100.00   1.00    1.00    --  106.95  77.00-150.00   25
 20  \w    106.00 140.00   1.00    1.00    --  106.95  61.00-120.00   34
 21  \w     78.00 105.00   1.00    1.00    --  106.95  61.00 -60.00   27
 22  \w     78.00 112.00   1.00    1.00    --  106.95  61.00-180.00   34
 23  \w     78.00 104.00   1.00    1.00    --  106.95  61.00-150.00   26
 24  \w     74.00 100.00   1.00    1.00    --  106.95  77.00-120.00   26
 25  \w     78.00 104.00   1.00    1.00    --  106.95  61.00-120.00   26
 26  \w     77.00 103.00   1.00    1.00    --  106.95  77.00 -30.00   26
 27  \w     81.00 107.00   1.00    1.00    --  106.95  45.00-120.00   26
 28  \w     82.00 114.00   1.00    1.00    --  106.95  45.00 -60.00   32
 29  \w    141.00 167.00   1.00    1.00    --  106.95  45.00 -60.00   26
 30  \w     81.00 136.00   1.00    1.00    --  106.95  45.00 -30.00   55
 31  \w     72.00 109.00   1.00    1.00    --  106.95 -94.00-120.00   37
 32  \w     94.00 174.00   1.00    1.00    --  106.95 125.00 -60.00   80
 33  \w     74.00 177.00   1.00    1.00    --  106.95  77.00-180.00  103
 34  \w    -75.00 -49.00   1.00    1.00    --  -41.23 -37.00 -90.00   26
 35  \w    -57.00 -29.00   1.00    1.00    --  -41.23 -77.00  30.00   28
 36  \w     78.00 104.00   1.00    1.00    --  106.95  61.00 -90.00   26
 37  \w     82.00 108.00   1.00    1.00    --  106.95  45.00   0.00   26
 38  \w     75.00 101.00   1.00    1.00    --  106.95  77.00 -30.00   26
 39  \w    111.00 136.00   1.00    1.00    --  106.95 -61.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1453554000
_diffrn_orient_matrix_UB_12      -0.0005723000
_diffrn_orient_matrix_UB_13      -0.0824390000
_diffrn_orient_matrix_UB_21      -0.1177679000
_diffrn_orient_matrix_UB_22      -0.0208435000
_diffrn_orient_matrix_UB_23      0.0708502000
_diffrn_orient_matrix_UB_31      -0.0170773000
_diffrn_orient_matrix_UB_32      0.1486606000
_diffrn_orient_matrix_UB_33      0.0095948000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11208
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.553
_diffrn_reflns_theta_min         5.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59982
_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_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0687P)^2^+0.2450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                4420
_reflns_number_total             4443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00244_si_005.cif
_cod_data_source_block           5
_cod_database_code               1557825
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     block
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2. Others
 Sof(O4)=Sof(H4A)=1-FVAR(1)
 Sof(H21)=Sof(O5)=Sof(H5A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C17(H17), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15), C21(H21)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5A)
;
_shelx_res_checksum              66747
_shelx_hkl_checksum              82946
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.271
_oxdiff_exptl_absorpt_empirical_full_min 0.561