304
J. C. Pardo-Novoa and C. M. Cerda-García-Rojas
in understanding the chemical reactivity of these organic natural products, as well
as in later stages of their research, in explaining their biological properties in terms
of molecular interactions with more complex structures, such as the proteins of a
biological system. The availability of these new techniques of structure elucidation
rapidly produces the generation of large amounts of data in ever shorter times, with
increasingly finer precision, with data stored in large information repositories. In
future, this will allow the generation of faster and automated scenarios, including
artificial intelligence systems, with the aim of solving more complex compound
structural problems or the discovery of new molecular phenomena.
Acknowledgements We are grateful to Conacyt-Mexico for financial support through grant CB
241053 and for a postdoctoral fellowship awarded to J.C.P.N. The authors wish to thank Dr. J.
Martín Torres-Valencia, Universidad Autónoma del Estado de Hidalgo, Pachuca, Hidalgo, Mexico
for kindly providing the plant photographs.
References
1. Radulovi´ c NS, Mladenovi´ c MZ, Stojanovi´ c NM, Randjelovi´ c PJ, Blagojevi´ c PD (2019) Structural elucidation of presilphiperfolane-7α,8α-diol, a bioactive sesquiterpenoid from Pulicaria vulgaris: a combined approach of solvent-induced chemical shifts, GIAO calculation
of chemical shifts, and full spin analysis. J Nat Prod 82:1874
2. MestreNova NMR Predict Desktop 9.0.0, Mestrelab Research. https://mestrelab.com/sof
tware/mnova-nmrpredict-desktop/
3. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G,
Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov
AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa
J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta
JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R,
Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega
N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts
R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL,
Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels
AD, Farkas ¨
O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian
Inc., Wallingford, CT, USA
4. Benteldjoune M, Chini MG, Iannuzzi AM, Kabouche A, Kabouche Z, D’Ambola M,
Marzocco S, Autore G, Bifulco G, De Tommasi N (2019) Guaianolides from Ormenis mixta:
structural insights and evaluation of their anti-inflammatory profile. Planta Med 85:947
5. Bagno A, Rastrelli F, Saielli G (2006) Toward the complete prediction of the 1 H and 13 C NMR
spectra of complex organic molecules by DFT methods: application to natural substances.
Chem Eur J 12:5514
6. Dracinsky M, Budesinsky M, Warzajtis B, Rychlewska U (2012) Solution and solid-state
effects on NMR chemical shifts in sesquiterpene lactones: NMR, X-ray, and theoretical
methods. J Phys Chem A 116:680
7. Pickard CJ, Mauri F (2001) All-electron magnetic response with pseudopotentials: NMR
chemical shifts. Phys Rev B 63:245101
8. Fattorusso E, Luciano P, Romano A, Taglialatela-Scafati O, Appendino G, Borriello M,
Fattorusso C (2008) Stereostructure assignment of medium-sized rings through an NMRcomputational combined approach. Application to the new germacranes ketopelenolides C
and D. J Nat Prod 71:1988
J. C. Pardo-Novoa and C. M. Cerda-García-Rojas
in understanding the chemical reactivity of these organic natural products, as well
as in later stages of their research, in explaining their biological properties in terms
of molecular interactions with more complex structures, such as the proteins of a
biological system. The availability of these new techniques of structure elucidation
rapidly produces the generation of large amounts of data in ever shorter times, with
increasingly finer precision, with data stored in large information repositories. In
future, this will allow the generation of faster and automated scenarios, including
artificial intelligence systems, with the aim of solving more complex compound
structural problems or the discovery of new molecular phenomena.
Acknowledgements We are grateful to Conacyt-Mexico for financial support through grant CB
241053 and for a postdoctoral fellowship awarded to J.C.P.N. The authors wish to thank Dr. J.
Martín Torres-Valencia, Universidad Autónoma del Estado de Hidalgo, Pachuca, Hidalgo, Mexico
for kindly providing the plant photographs.
References
1. Radulovi´ c NS, Mladenovi´ c MZ, Stojanovi´ c NM, Randjelovi´ c PJ, Blagojevi´ c PD (2019) Structural elucidation of presilphiperfolane-7α,8α-diol, a bioactive sesquiterpenoid from Pulicaria vulgaris: a combined approach of solvent-induced chemical shifts, GIAO calculation
of chemical shifts, and full spin analysis. J Nat Prod 82:1874
2. MestreNova NMR Predict Desktop 9.0.0, Mestrelab Research. https://mestrelab.com/sof
tware/mnova-nmrpredict-desktop/
3. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G,
Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov
AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa
J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta
JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R,
Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega
N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts
R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL,
Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels
AD, Farkas ¨
O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian
Inc., Wallingford, CT, USA
4. Benteldjoune M, Chini MG, Iannuzzi AM, Kabouche A, Kabouche Z, D’Ambola M,
Marzocco S, Autore G, Bifulco G, De Tommasi N (2019) Guaianolides from Ormenis mixta:
structural insights and evaluation of their anti-inflammatory profile. Planta Med 85:947
5. Bagno A, Rastrelli F, Saielli G (2006) Toward the complete prediction of the 1 H and 13 C NMR
spectra of complex organic molecules by DFT methods: application to natural substances.
Chem Eur J 12:5514
6. Dracinsky M, Budesinsky M, Warzajtis B, Rychlewska U (2012) Solution and solid-state
effects on NMR chemical shifts in sesquiterpene lactones: NMR, X-ray, and theoretical
methods. J Phys Chem A 116:680
7. Pickard CJ, Mauri F (2001) All-electron magnetic response with pseudopotentials: NMR
chemical shifts. Phys Rev B 63:245101
8. Fattorusso E, Luciano P, Romano A, Taglialatela-Scafati O, Appendino G, Borriello M,
Fattorusso C (2008) Stereostructure assignment of medium-sized rings through an NMRcomputational combined approach. Application to the new germacranes ketopelenolides C
and D. J Nat Prod 71:1988