Conformational, configurational, and supramolecular studies of podocephalol acetate from Lasianthaea aurea
Although podocephalol (1) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the essential oils of several vegetal species, its absolute configuration (AC) and conformational preferences remained to be established. The structures of ar‐himac...
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| Published in | Chirality (New York, N.Y.) Vol. 31; no. 11; pp. 923 - 933 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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01.11.2019
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| Abstract | Although podocephalol (1) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the essential oils of several vegetal species, its absolute configuration (AC) and conformational preferences remained to be established. The structures of ar‐himachalene 1, now isolated from Lasianthaea aurea, and its derived acetate 2, were herein confirmed by extensive 1D and 2D nuclear magnetic resonance (NMR) studies, while the conformational preferences of the cycloheptene was established by density functional theory (DFT) calculations, which in combination with vibrational circular dichroism measurements provided the (R) absolute configuration of the molecules. The structure and AC were further verified through the Flack and Hooft parameters calculations derived from single crystal X‐ray diffraction data of 2. In addition, careful evaluation of the crystal data allowed observing supramolecular layers cell package, an uncommon property in natural terpenes that might have potential applications. A transmission electron microscopy analysis of crystal of 2 was also possible, providing its physical characteristics at the micrometric scale. |
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| AbstractList | Abstract
Although podocephalol (
1
) and its derived acetate
2
were found in
Lasianthaea podocephala
four decades ago, and
1
was later detected in the essential oils of several vegetal species, its absolute configuration (AC) and conformational preferences remained to be established. The structures of
ar
‐himachalene
1
, now isolated from
Lasianthaea aurea
, and its derived acetate
2
, were herein confirmed by extensive 1D and 2D nuclear magnetic resonance (NMR) studies, while the conformational preferences of the cycloheptene was established by density functional theory (DFT) calculations, which in combination with vibrational circular dichroism measurements provided the (
R
) absolute configuration of the molecules. The structure and AC were further verified through the Flack and Hooft parameters calculations derived from single crystal X‐ray diffraction data of
2
. In addition, careful evaluation of the crystal data allowed observing supramolecular layers cell package, an uncommon property in natural terpenes that might have potential applications. A transmission electron microscopy analysis of crystal of
2
was also possible, providing its physical characteristics at the micrometric scale. Although podocephalol (1) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the essential oils of several vegetal species, its absolute configuration (AC) and conformational preferences remained to be established. The structures of ar‐himachalene 1, now isolated from Lasianthaea aurea, and its derived acetate 2, were herein confirmed by extensive 1D and 2D nuclear magnetic resonance (NMR) studies, while the conformational preferences of the cycloheptene was established by density functional theory (DFT) calculations, which in combination with vibrational circular dichroism measurements provided the (R) absolute configuration of the molecules. The structure and AC were further verified through the Flack and Hooft parameters calculations derived from single crystal X‐ray diffraction data of 2. In addition, careful evaluation of the crystal data allowed observing supramolecular layers cell package, an uncommon property in natural terpenes that might have potential applications. A transmission electron microscopy analysis of crystal of 2 was also possible, providing its physical characteristics at the micrometric scale. |
| Author | Villagómez‐Guzmán, Ana K. Gómez‐Hurtado, Mario A. Cerda‐García‐Rojas, Carlos M. Cruz‐Corona, Rosalba Joseph‐Nathan, Pedro Rodríguez‐García, Gabriela Talavera‐Alemán, Armando Río, Rosa E. |
| Author_xml | – sequence: 1 givenname: Gabriela orcidid: 0000-0002-9840-9968 surname: Rodríguez‐García fullname: Rodríguez‐García, Gabriela organization: Universidad Michoacana de San Nicolás de Hidalgo – sequence: 2 givenname: Ana K. orcidid: 0000-0002-9309-5971 surname: Villagómez‐Guzmán fullname: Villagómez‐Guzmán, Ana K. organization: Universidad Michoacana de San Nicolás de Hidalgo – sequence: 3 givenname: Armando orcidid: 0000-0002-0020-2441 surname: Talavera‐Alemán fullname: Talavera‐Alemán, Armando organization: Universidad Michoacana de San Nicolás de Hidalgo – sequence: 4 givenname: Rosalba surname: Cruz‐Corona fullname: Cruz‐Corona, Rosalba organization: Universidad Michoacana de San Nicolás de Hidalgo – sequence: 5 givenname: Mario A. orcidid: 0000-0002-2386-4819 surname: Gómez‐Hurtado fullname: Gómez‐Hurtado, Mario A. organization: Universidad Michoacana de San Nicolás de Hidalgo – sequence: 6 givenname: Carlos M. orcidid: 0000-0002-5590-7908 surname: Cerda‐García‐Rojas fullname: Cerda‐García‐Rojas, Carlos M. email: ccerda@cinvestav.mx organization: Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional – sequence: 7 givenname: Pedro orcidid: 0000-0003-3347-3990 surname: Joseph‐Nathan fullname: Joseph‐Nathan, Pedro organization: Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional – sequence: 8 givenname: Rosa E. orcidid: 0000-0001-8932-552X surname: Río fullname: Río, Rosa E. email: ndelrio@umich.mx organization: Universidad Michoacana de San Nicolás de Hidalgo |
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| Keywords | podocephalol TEM analysis Lasianthaea Asteraceae vibrational circular dichroism supramolecular analysis absolute configuration ar-himachalene |
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| Snippet | Although podocephalol (1) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the essential oils of... Abstract Although podocephalol ( 1 ) and its derived acetate 2 were found in Lasianthaea podocephala four decades ago, and 1 was later detected in the... |
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| SubjectTerms | Absolute configuration Acetates - chemistry Acetic acid ar‐himachalene Asteraceae Asteraceae - chemistry Circular dichroism Configurations Density functional theory Dichroism Essential oils Lasianthaea Mathematical analysis Models, Molecular Molecular Conformation Molecular structure NMR Nuclear magnetic resonance Physical characteristics Physical properties podocephalol Single crystals Stereoisomerism supramolecular analysis TEM analysis Terpenes Transmission electron microscopy vibrational circular dichroism |
| Title | Conformational, configurational, and supramolecular studies of podocephalol acetate from Lasianthaea aurea |
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