The crystal structure of loganin penta-acetate monomethyl ether bromide

Lentz, P. J.; Rossmann, Michael G.

doi:10.1039/c2969001269a

Cited by 15 publications

(16 citation statements)

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“…Concerning the planar angles, the aromatic ring shows no large deformations, which was similar to the experimental data for previously analyzed indole alkaloids [26,29]. The planar angles were 118.78 ∘ (C9-C8-C13), 119.16 ∘ (C8-C9-C10), 121.06 ∘ (C9-C10-C11), 121.17 ∘ (C10-C11-C12), 117.62 ∘ (C11-C12-C13), and 122.18 ∘ (C8-C12-C13).…”

Section: Resultssupporting

confidence: 88%

“…The similarity between the modeled DFT structure ( Figure 2) (with 15S, 20S, and 21S configuration) and the experimental spectroscopic NMR data complements the conformational arrangement study of strictosidine. The 15S, 20S, and 21S configuration was reported in previous experimental Xray studies of strictosidine precursors [19,[28][29][30]. Finally, due to the consistency between the geometry calculated using the DFT B3LYP/6-31G(d) and B3LYP/6-31++G(2d,p) methods and the coupling constant values measured from the experimental 1 H spectrum, the conformation of the C21-O-C1 bridge (so far uncertain) was depicted with angles of 81.17 ∘ and lengths of 2.65Å between H21 and H1 ( Figure 2).…”

Section: Resultssupporting

confidence: 67%

“…Geometry Optimization. Because no crystallographic data for strictosidine are available, the geometry optimization data, which were calculated using the B3LYP/6-31G(d) and B3LYP/6-311++G(2d,p) basis set, were compared with the Xray data for similar structures [26][27][28][29]. Due to the similarity of the data obtained from both basis sets (Table 1), the discussion that follows is based on the B3LYP 6-31G(d) values but should also apply to B3LYP 6-311++G(2d,p).…”

Section: Resultsmentioning

confidence: 99%

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Structural, Vibrational, and Electronic Properties of the Glucoalkaloid Strictosidine: A Combined Experimental and Theoretical Study

Costa

Pinheiro

Oliveira

et al. 2016

Journal of Chemistry

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A detailed structural analysis and spectral behavior of the glucoalkaloid strictosidine, a precursor of all monoterpene indole alkaloids, are discussed. The experimental NMR, FTIR, and UV results were compared to the theoretical DFT spectra calculated by Becke using the three-parameter Lee-Yang-Parr (B3LYP) function with 6-31G(d) and 6-311++G(2d,p) basis sets. The theoretical geometry optimization data were compared with the X-ray data for precursors and similar structures in the associated literature. The similarity between the theoretical and experimental coupling constants values made it possible to affirm the values of dihedral angles and their configuration, reinforcing findings from previous stereochemical studies. Theoretical UV analysis agreed well with the measured experimental data, with bands assigned. Calculated HOMO/LUMO gaps show low excitation energy for strictosidine, justifying its stability and reaction kinetics. The molecular electrostatic potential map shows opposite potentials regions that form hydrogen bonds that stabilize the dimeric form, which were confirmed by excellent agreement of the dimeric form theoretical wavenumbers with the experimental IR spectrum. ESI-MS/MS data revealed patterns for the fragmentation of the protonated strictosidine molecule outlined by an NBO study.

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Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Structural, Vibrational, and Electronic Properties of the Glucoalkaloid Strictosidine: A Combined Experimental and Theoretical Study

Costa

Pinheiro

Oliveira

et al. 2016

Journal of Chemistry

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“…Loganin was first isolated from Strychnos nux vomica (Jones & Sheldrick, 1980). Its chemically deduced structure (Battersby, Hall, & Southgate, 1969;Brechbu¨hler-Bader, Coscia, Loew, Von Szczepanski, & Arigoni, 1968;Inouye, Yoshida, & Tobita, 1968) has been confirmed by total synthesis (Bu¨chi, Carlson, Powell, & Tietze, 1973) and by X-ray structure determination of a bromo derivative (Lentz & Rossmann, 1969). Sweroside was first isolated from Swertia japonica Makino in 1967 (Inouye et al, 1967) and was first seen in Gentiana genus in 1974 from G. Lutea L. (Bricout, 1974).…”

Section: Chemical Constituentsmentioning

confidence: 96%

Anti-inflammatory activity ofGentiana striataMaxim.

Cao

Shao

et al. 2012

Natural Product Research

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The anti-inflammatory activity and the mechanism of action of Gentiana striata Maxim. has been investigated. The most active phase, the ethyl acetate extract of Gentiana striata Maxim. (EGS), displayed potent inhibitory activity on feet oedema of rheumatoid arthritis (RA) inflicted rats. This anti-inflammatory activity might be partly based on the notable reduction of prostaglandin E2 (PGE₂) and nitric oxide (NO) levels. Six further compounds isolated from EGS have previously been reported as having anti-inflammatory activity.

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“…[8] However, the constitution of (8R)loganin was first determined in 1961 [9] and the absolute configuration in 1969 by an X-ray structural analysis. [10] Oxidation of the free hydroxyl group in (8S)-tetraacetylloganin (6) with pyridinium chlorochromate (PCC) in anhydrous dichloromethane furnishes (8S)-tetraacetyl-7-ketologanin (7) in good yield. Whereas the free iridoid glucoside (7a) has not as yet been detected in plants, the epimer (8R)-7-ketologanin has been isolated from the extracts of Lonicera coerulea [11] (Caprifoliaceae, German name: Blaue Heckenkirsche) and Strychnos nux-vomica (Loganiaceae).…”

Section: Introductionmentioning

confidence: 99%