Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata
Li, Bin; Kuang, Yi; He, Jun-Bin; Tang, Rui; Xu, Lu-Lu; Leung, Chung-Hang; Ma, Dik-Lung; Qiao, Xue; Ye, Min; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00580

data_1556858
_publ_section_title
;
 Antcamphorols A--K, Cytotoxic and ROS Scavenging Triterpenoids from
 Antrodia camphorata
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00580
_journal_year                    2019
_chemical_formula_moiety         'C29 H44 O2'
_chemical_formula_sum            'C29 H44 O2'
_chemical_formula_weight         424.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0367(8)
_cell_length_b                   12.1537(7)
_cell_length_c                   18.4758(7)
_cell_measurement_reflns_used    4860
_cell_measurement_temperature    103.8
_cell_measurement_theta_max      70.7092
_cell_measurement_theta_min      3.6346
_cell_volume                     2478.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      103.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -26.00    0.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  121.0000 -103.0000 26

  2 omega  -25.00   27.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   97.0000    1.0000 52

  3 omega   12.00   85.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   60.0000 73

  4 omega   19.00   97.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -180.0000 78

  5 omega   32.00   61.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 29

  6 omega  -30.00   30.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 60

  7 omega   75.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -121.0000  103.0000 36

  8 omega  133.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   97.0000  107.0000 31

  9 omega  100.00  149.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 49

 10 omega   52.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -28.0000  171.0000 33

 11 omega   41.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 54

 12 omega   41.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 57

 13 omega   40.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -121.0000  172.0000 54

 14 omega   39.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 138

 15 omega  -10.00   15.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -150.0000 25

 16 omega   39.00   99.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000  -60.0000 60

 17 omega   38.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -28.0000  171.0000 25

 18 omega  137.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 19 omega   94.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 20 omega   85.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -97.0000    0.0000 25

 21 omega  108.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 43
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1143763000
_diffrn_orient_matrix_UB_12      0.0715145000
_diffrn_orient_matrix_UB_13      -0.0090966000
_diffrn_orient_matrix_UB_21      0.0785318000
_diffrn_orient_matrix_UB_22      0.0954245000
_diffrn_orient_matrix_UB_23      -0.0285769000
_diffrn_orient_matrix_UB_31      -0.0153204000
_diffrn_orient_matrix_UB_32      -0.0429666000
_diffrn_orient_matrix_UB_33      -0.0778125000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10755
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.856
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_coef       0.0020(7)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         4682
_refine_ls_number_restraints     411
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.1064
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0862P)^2^+5.9719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2631
_refine_ls_wR_factor_ref         0.2645
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                4450
_reflns_number_total             4682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00580_si_003.cif
_cod_data_source_block           exp_4148
_cod_database_code               1556858
_chemical_oxdiff_formula         C5
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Sof: H20B(0.231) H22E(0.231) H22F(0.231) H23E(0.231) H23F(0.231)
 H25B(0.231) H26G(0.231) H26H(0.231) H26I(0.231) H27G(0.231) H27H(0.231)
 H27I(0.231) H28E(0.231) H28F(0.231) C22B(0.231) C23B(0.231) C24B(0.231)
 C25B(0.231) C26B(0.231) C27B(0.231) C28B(0.231)
 Fixed Uiso: H1A(0.044) H1B(0.044) H2(0.088) H2A(0.056) H2B(0.056) H4(0.051)
 H5(0.04) H6A(0.047) H6B(0.047) H7(0.042) H11(0.041) H12(0.046) H14(0.039)
 H15A(0.054) H15B(0.054) H16A(0.07) H16B(0.07) H17(0.055) H18A(0.062)
 H18B(0.062) H18C(0.062) H19A(0.077) H19B(0.077) H19C(0.077) H20(0.084)
 H20A(0.084) H20B(0.084) H21A(0.115) H21B(0.115) H21C(0.115) H22A(0.065)
 H22B(0.065) H22C(0.038) H22D(0.038) H22E(0.038) H22F(0.038) H23A(0.044)
 H23B(0.044) H23C(0.05) H23D(0.05) H23E(0.042) H23F(0.042) H25(0.033)
 H25A(0.05) H25B(0.035) H26A(0.087) H26B(0.087) H26C(0.087) H26D(0.083)
 H26E(0.083) H26F(0.083) H26G(0.074) H26H(0.074) H26I(0.074) H27A(0.082)
 H27B(0.082) H27C(0.082) H27D(0.079) H27E(0.079) H27F(0.079) H27G(0.074)
 H27H(0.074) H27I(0.074) H28A(0.056) H28B(0.056) H28C(0.078) H28D(0.078)
 H28E(0.06) H28F(0.06) H29A(0.091) H29B(0.091) H29C(0.091)
 Fixed X: H1A(0.2488) H1B(0.1118) H2(0.091) H2A(0.0813) H2B(0.1999) H4(0.1201)
 H5(0.2921) H6A(0.0971) H6B(0.2381) H7(0.164) H11(0.1302) H12(0.2072)
 H14(0.2415) H15A(0.2017) H15B(0.059) H16A(0.1806) H16B(0.0371) H17(0.1743)
 H18A(-0.0359) H18B(-0.0232) H18C(-0.0593) H19A(-0.0671) H19B(-0.108) H19C(-
 0.0905) H20(-0.0731) H20A(-0.0731) H20B(-0.0699) H21A(0.051) H21B(-0.0807)
 H21C(-0.0609) H22A(-0.0014) H22B(-0.0736) H22C(0.1162) H22D(0.1379)
 H22E(0.1273) H22F(0.1421) H23A(0.1887) H23B(0.1128) H23C(-0.0709) H23D(-
 0.0647) H23E(-0.0329) H23F(-0.0693) H25(-0.021) H25A(0.1957) H25B(0.1994)
 H26A(0.2162) H26B(0.0989) H26C(0.118) H26D(0.0215) H26E(0.1071) H26F(-0.0116)
 H26G(0.0916) H26H(0.0358) H26I(-0.0268) H27A(0.1241) H27B(-0.0183)
 H27C(0.0324) H27D(0.1146) H27E(0.2189) H27F(0.2392) H27G(0.1167) H27H(0.2525)
 H27I(0.1882) H28A(0.2308) H28B(0.1982) H28C(-0.0261) H28D(0.067) H28E(0.0171)
 H28F(0.0979) H29A(0.3659) H29B(0.2874) H29C(0.2488)
 Fixed Y: H1A(0.0572) H1B(0.0141) H2(-0.0394) H2A(0.0792) H2B(0.0027)
 H4(0.2943) H5(0.2592) H6A(0.4142) H6B(0.4428) H7(0.4519) H11(0.0241)
 H12(0.0801) H14(0.2648) H15A(0.4418) H15B(0.4294) H16A(0.3684) H16B(0.3839)
 H17(0.1891) H18A(0.2739) H18B(0.2095) H18C(0.1441) H19A(0.2258) H19B(0.1522)
 H19C(0.2821) H20(0.2148) H20A(0.2281) H20B(0.233) H21A(0.021) H21B(0.0468)
 H21C(0.0404) H22A(0.3184) H22B(0.2124) H22C(0.2968) H22D(0.1712) H22E(0.2549)
 H22F(0.1242) H23A(0.2126) H23B(0.1154) H23C(0.1768) H23D(0.3075) H23E(0.0937)
 H23F(0.221) H25(0.1768) H25A(0.1423) H25B(0.3043) H26A(0.1131) H26B(0.0696)
 H26C(0.0394) H26D(0.0371) H26E(-0.0138) H26F(0.054) H26G(0.4665) H26H(0.3976)
 H26I(0.3929) H27A(0.3149) H27B(0.3243) H27C(0.2295) H27D(0.1869) H27E(0.0997)
 H27F(0.2274) H27G(0.2825) H27H(0.2742) H27I(0.3917) H28A(0.3714) H28B(0.3771)
 H28C(0.3905) H28D(0.3453) H28E(0.0424) H28F(0.1092) H29A(0.3657) H29B(0.3638)
 H29C(0.4426)
 Fixed Z: H1A(0.3313) H1B(0.331) H2(0.059) H2A(0.4512) H2B(0.4511) H4(0.447)
 H5(0.3322) H6A(0.337) H6B(0.3291) H7(0.2094) H11(0.2184) H12(0.092)
 H14(0.1048) H15A(0.0765) H15B(0.0932) H16A(-0.0341) H16B(-0.0238) H17(-0.0133)
 H18A(0.3099) H18B(0.3851) H18C(0.313) H19A(0.1553) H19B(0.0878) H19C(0.0782)
 H20(-0.0359) H20A(-0.0515) H20B(-0.0597) H21A(-0.0661) H21B(-0.0982) H21C(-
 0.0125) H22A(-0.1311) H22B(-0.1604) H22C(-0.1187) H22D(-0.1418) H22E(-0.134)
 H22F(-0.1278) H23A(-0.1428) H23B(-0.1801) H23C(-0.1952) H23D(-0.1855) H23E(-
 0.1989) H23F(-0.1956) H25(-0.2935) H25A(-0.2581) H25B(-0.2466) H26A(-0.3359)
 H26B(-0.378) H26C(-0.2945) H26D(-0.2429) H26E(-0.3044) H26F(-0.3265) H26G(-
 0.2736) H26H(-0.2078) H26I(-0.2859) H27A(-0.3799) H27B(-0.3646) H27C(-0.4166)
 H27D(-0.4009) H27E(-0.3827) H27F(-0.3654) H27G(-0.3893) H27H(-0.3593) H27I(-
 0.3665) H28A(-0.2101) H28B(-0.297) H28C(-0.2875) H28D(-0.3504) H28E(-0.2993)
 H28F(-0.3599) H29A(0.4429) H29B(0.5157) H29C(0.4502)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.842
_shelx_shelxl_version_number     2014/7