New Techniques of Structure Elucidation for Sesquiterpenes
305
9. Wang J, Ren Q, Zhang YY, Guo R, Lin B, Huang XX, Song SJ (2019) Assignment of the
stereostructures of sesquiterpenoids from the roots of Daphne genkwa via quantum chemical
calculations. Fitoterapia 138:104352
10. Grimblat N, Zanardi MM, Sarotti AM (2015) Beyond DP4: an improved probability for the
stereochemical assignment of isomeric compounds using quantum chemical calculations of
NMR shifts. J Org Chem 80:12526
11. Xia GY, Wang LY, Zhang JF, Wu YZ, Ge GB, Wang YN, Lin PC, Lin S (2020) Three new
polyoxygenated bergamotanes from the endophytic fungus Penicillium purpurogenum IMM
003 and their inhibitory activity against pancreatic lipase. Chin J Nat Med 18:75
12. Pierens GK (2014) 1 H and 13 C NMR scaling factors for the calculation of chemical shifts in
commonly used solvents using density functional theory. J Comput Chem 35:1388
13. Ferreira de Albuquerque AC, Ribeiro DJ, de Amorim MB (2016) Structural determination of
complex natural products by quantum mechanical calculations of 13 C NMR chemical shifts:
development of a parameterized protocol for terpenes. J Mol Model 22:183
14. Galasso V, Kovac B, Modelli A (2007) A theoretical and experimental study on the molecular
and electronic structures of artemisinin and related drug molecules. Chem Phys 335:141
15. Kutateladze AG, Reddy DS (2017) High-throughput in silico structure validation and revision
of halogenated natural products is enabled by parametric corrections to DFT-computed 13 C
NMR chemical shifts and spin–spin coupling constants. J Org Chem 82:3368
16. Schmiedel VM, Hong YJ, Lentz D, Tantillo DJ, Christmann M (2018) Synthesis and structure
revision of dichrocephones A and B. Angew Chem Int Ed 57:2419
17. Nguyen QNN, Tantillo DJ (2016) Using quantum chemical computations of NMR chemical
shifts to assign relative configurations of terpenes from an engineered Streptomyces host. J
Antibiot 69:534
18. Grimblat N, Gavín JA, Hernández Daranas A, Sarotti AM (2019) Combining the power of
J coupling and DP4 analysis on stereochemical assignments: the J-DP4 methods. Org Lett
21:4003
19. Fattorusso C, Stendardo E, Appendino G, Fattorusso E, Luciano P, Romano A, TaglialatelaScafati O (2007) Artarborol, a nor-caryophyllane sesquiterpene alcohol from Artemisia
arborescens. Stereostructure assignment through concurrence of NMR data and computational
analysis. Org Lett 9:2377
20. Junior FMDS, Velozo LSM, de Carvalho EM, Marques AM, Borges RM, Trindade APF,
dos Santos MIS, de Albuquerque ACF, Costa FLP, Kaplan MAC, de Amorim MB (2013) 3Ishwarone, a rare ishwarane sesquiterpene from Peperomia scandens Ruiz & Pavon: structural
elucidation through a joint experimental and theoretical study. Molecules 18:13520
21. Subramaniam G, Karimi S, Phillips D (2006) Solution conformation of longifolene and its
precursor by NMR and ab initio calculations. Magn Reson Chem 44:1118
22. Koshino H, Satoh H, Yamada T, Esumi Y (2006) Structural revision of peribysins C and D.
Tetrahedron Lett 47:4623
23. Bifulco G, Dambruoso P, Gomez-Paloma L, Riccio R (2007) Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods. Chem Rev
107:3744
24. Forsyth DA, Sebag AB (1997) Computed 13 C NMR chemical shifts via empirically scaled
GIAO shieldings and molecular mechanics geometries. Conformation and configuration from
13 C shifts. J Am Chem Soc 119:9483
25. Karplus M (1959) Contact electron-spin coupling of nuclear magnetic moments. J Chem Phys
30:11
26. Haasnoot CAG, de Leeuw FAAM, Altona C (1980) The relationship between proton-proton
NMR coupling constants and substituent electronegativities–I: an empirical generalization of
the Karplus equation. Tetrahedron 36:2783
27. Rusakova IL, Krivdin LB (2015) Karplus dependence of spin–spin coupling constants revisited theoretically. Part 1: second-order double perturbation theory. Phys Chem Chem Phys
15:18195
305
9. Wang J, Ren Q, Zhang YY, Guo R, Lin B, Huang XX, Song SJ (2019) Assignment of the
stereostructures of sesquiterpenoids from the roots of Daphne genkwa via quantum chemical
calculations. Fitoterapia 138:104352
10. Grimblat N, Zanardi MM, Sarotti AM (2015) Beyond DP4: an improved probability for the
stereochemical assignment of isomeric compounds using quantum chemical calculations of
NMR shifts. J Org Chem 80:12526
11. Xia GY, Wang LY, Zhang JF, Wu YZ, Ge GB, Wang YN, Lin PC, Lin S (2020) Three new
polyoxygenated bergamotanes from the endophytic fungus Penicillium purpurogenum IMM
003 and their inhibitory activity against pancreatic lipase. Chin J Nat Med 18:75
12. Pierens GK (2014) 1 H and 13 C NMR scaling factors for the calculation of chemical shifts in
commonly used solvents using density functional theory. J Comput Chem 35:1388
13. Ferreira de Albuquerque AC, Ribeiro DJ, de Amorim MB (2016) Structural determination of
complex natural products by quantum mechanical calculations of 13 C NMR chemical shifts:
development of a parameterized protocol for terpenes. J Mol Model 22:183
14. Galasso V, Kovac B, Modelli A (2007) A theoretical and experimental study on the molecular
and electronic structures of artemisinin and related drug molecules. Chem Phys 335:141
15. Kutateladze AG, Reddy DS (2017) High-throughput in silico structure validation and revision
of halogenated natural products is enabled by parametric corrections to DFT-computed 13 C
NMR chemical shifts and spin–spin coupling constants. J Org Chem 82:3368
16. Schmiedel VM, Hong YJ, Lentz D, Tantillo DJ, Christmann M (2018) Synthesis and structure
revision of dichrocephones A and B. Angew Chem Int Ed 57:2419
17. Nguyen QNN, Tantillo DJ (2016) Using quantum chemical computations of NMR chemical
shifts to assign relative configurations of terpenes from an engineered Streptomyces host. J
Antibiot 69:534
18. Grimblat N, Gavín JA, Hernández Daranas A, Sarotti AM (2019) Combining the power of
J coupling and DP4 analysis on stereochemical assignments: the J-DP4 methods. Org Lett
21:4003
19. Fattorusso C, Stendardo E, Appendino G, Fattorusso E, Luciano P, Romano A, TaglialatelaScafati O (2007) Artarborol, a nor-caryophyllane sesquiterpene alcohol from Artemisia
arborescens. Stereostructure assignment through concurrence of NMR data and computational
analysis. Org Lett 9:2377
20. Junior FMDS, Velozo LSM, de Carvalho EM, Marques AM, Borges RM, Trindade APF,
dos Santos MIS, de Albuquerque ACF, Costa FLP, Kaplan MAC, de Amorim MB (2013) 3Ishwarone, a rare ishwarane sesquiterpene from Peperomia scandens Ruiz & Pavon: structural
elucidation through a joint experimental and theoretical study. Molecules 18:13520
21. Subramaniam G, Karimi S, Phillips D (2006) Solution conformation of longifolene and its
precursor by NMR and ab initio calculations. Magn Reson Chem 44:1118
22. Koshino H, Satoh H, Yamada T, Esumi Y (2006) Structural revision of peribysins C and D.
Tetrahedron Lett 47:4623
23. Bifulco G, Dambruoso P, Gomez-Paloma L, Riccio R (2007) Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods. Chem Rev
107:3744
24. Forsyth DA, Sebag AB (1997) Computed 13 C NMR chemical shifts via empirically scaled
GIAO shieldings and molecular mechanics geometries. Conformation and configuration from
13 C shifts. J Am Chem Soc 119:9483
25. Karplus M (1959) Contact electron-spin coupling of nuclear magnetic moments. J Chem Phys
30:11
26. Haasnoot CAG, de Leeuw FAAM, Altona C (1980) The relationship between proton-proton
NMR coupling constants and substituent electronegativities–I: an empirical generalization of
the Karplus equation. Tetrahedron 36:2783
27. Rusakova IL, Krivdin LB (2015) Karplus dependence of spin–spin coupling constants revisited theoretically. Part 1: second-order double perturbation theory. Phys Chem Chem Phys
15:18195