Carbon-13 and Proton NMR Shift Assignments and Physical Constants of Norditerpenoid Alkaloids

Pelletier, S. William; Joshi, B. S.

doi:10.1007/978-1-4612-3006-9_3

Cited by 38 publications

(23 citation statements)

References 114 publications

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“…The 1 H-doublet signal at δ H 5.16 ( J = 5.1 Hz) was assigned to H-14 β , resulting in location of the benzoyl group at C-14 [ 28 , 29 ]. Four methoxyl groups were attributed to C-1, C-6, C-16, and C-18 based on the cross-peaks between 1-OCH 3 ( δ H 3.23, s) and C-1 ( δ C 83.5, d), 6-OCH 3 ( δ H 3.27, s) and C-6 ( δ C 84.1, d), 16-OCH 3 ( δ H 3.61, s) and C-16 ( δ C 89.2, d), 18-OCH 3 ( δ H 3.28, s) and C-18 ( δ C 76.2, t) in its HMBC spectrum ( Figure 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…The one-proton double signal ( J = 5.16 Hz) at δ H 5.41 was attributed to H-14 β , implying the appearance of a benzoyl group at C-14 position [ 28 , 29 ]. The location of four methoxyl groups were based on the long-range correlations between 1-OCH 3 ( δ H 3.24) and C-1 ( δ C 83.6 d), 6-OCH 3 ( δ H 3.24) and C-6 ( δ C 84.1 d), 16-OCH 3 ( δ H 3.80) and C-16 ( δ C 86.1 d),18-OCH 3 ( δ H 3.29) and C-18 ( δ C 76.8 t) in HMBC spectrum ( Figure 3 ).…”

Section: Resultsmentioning

confidence: 99%

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Attenuated Structural Transformation of Aconitine during Sand Frying Process and Antiarrhythmic Effect of Its Converted Products

Wang

Pei

Yan

2021

Evidence-Based Complementary and Alternative Medicine

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The transformation pathways of diterpenoid alkaloids have been clarified in the boiling and steaming process. Aconitine, a famous diterpenoid alkaloid, is successively transformed into benzoylaconine and aconine during the processes of boiling and steaming, but the transformation pathway remains to be determined in the sand frying process. The present study aims at investigating the transformation pathways of aconitine in the process of sand frying, as well as assessing the cardiotoxicity and antiarrhythmic activity of aconitine and its converted products. The parameters of temperature and time for the structural transformation of aconitine were confirmed by HPLC. The converted products were further separated and identified by column chromatography, NMR, and HR-ESI-MS. Furthermore, by observing the lead II electrocardiogram (ECG) changes in rats under an equivalent dose, the cardiotoxicity of aconitine and its converted products were compared. Ultimately, the antiarrhythmic effect of the converted products was investigated by employing the model of aconitine-induced arrhythmia. Consequently, the structure of aconitine was converted when processed at 120°C–200°C for 1–40 min. Two diterpenoid alkaloids, a pair of epimers, namely, pyroaconitine and 16-epi-pyroaconitine, were further isolated from processed aconitine. 0.03 mg/kg aconitine induced arrhythmias in normal rats, while the converted products did not exhibit arrhythmias under an equal dose. In the antiarrhythmic assay, 16-epi-pyroaconitine could dose-dependently delay the onset time of VPB, reduce the incidence of VT, and increase the arrhythmia inhibition rate, demonstrating comparatively strong antiarrhythmic activity. Conclusively, compared with the prototype compound aconitine, the converted products exhibited lower cardiotoxicity. Further investigations on the cardiotoxicity indicated that pyroaconitine with β configuration had a stronger cardiotoxicity than 16-epi-pyroaconitine with α configuration. Furthermore, 16-epi-pyroaconitine could antagonize the arrhythmogenic effect caused by the prototype compound aconitine; the antiarrhythmic effect of 16-epi-pyroaconitine was stronger than lidocaine and propafenone, which had the potential to be developed as antiarrhythmic drugs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Attenuated Structural Transformation of Aconitine during Sand Frying Process and Antiarrhythmic Effect of Its Converted Products

Wang

Pei

Yan

2021

Evidence-Based Complementary and Alternative Medicine

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“…Aconitum spp. (monkshood) is one of the most extracted and isolated sources of DAs, where more than half of natural DAs were isolated from [ 10 , 11 , 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Classification, Toxicity and Bioactivity of Natural Diterpenoid Alkaloids

Thawabteh

Lelario

et al. 2021

Molecules

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Diterpenoid alkaloids are natural compounds having complex structural features with many stereo-centres originating from the amination of natural tetracyclic diterpenes and produced primarily from plants in the Aconitum, Delphinium, Consolida genera. Corals, Xenia, Okinawan/Clavularia, Alcyonacea (soft corals) and marine sponges are rich sources of diterpenoids, despite the difficulty to access them and the lack of availability. Researchers have long been concerned with the potential beneficial or harmful effects of diterpenoid alkaloids due to their structural complexity, which accounts for their use as pharmaceuticals as well as their lousy reputation as toxic substances. Compounds belonging to this unique and fascinating family of natural products exhibit a broad spectrum of biological activities. Some of these compounds are on the list of clinical drugs, while others act as incredibly potent neurotoxins. Despite numerous attempts to prepare synthetic products, this review only introduces the natural diterpenoid alkaloids, describing ‘compounds’ structures and classifications and their toxicity and bioactivity. The purpose of the review is to highlight some existing relationships between the presence of substituents in the structure of such molecules and their recognised bioactivity.

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“…4 In alkaloids possessing hydroxyl groups at C-14 and C-10, the C-14 carbon shows an upfield shift of ca. 3.0 ppm, e.g.…”

Section: Introductionmentioning

confidence: 99%

“…When C-14 bears a hydroxyl group, this carbon appears at 75-76 ppm, as in delphirine (75.7), delphinifoline (76.4), delphidine (75.0) and 18-methoxygadesine (75.3). 4 In alkaloids possessing hydroxyl groups at C-14 and C-10, the C-14 carbon shows an upfield shift of ca. 3.0 ppm, e.g.…”

Section: Introductionmentioning

confidence: 99%

Complete spectral assignments of tatsidine by two‐dimensional NMR techniques

Snyder

Zhang

Joshi

et al. 1989

Magnetic Reson in Chemistry

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Homonuclear 'H COSY, long-range COSY and relay coherence transfer (RCT) correlation spectroscopy NMR experiments were used together with fixed-evolution HETCOR and selective INEPT spectra for complete "C and 'H spectral peak assignments for tatsidine. Stereochemical and conformational assignments were made from the two-dimensional NOE spectrum. The results of these studies confirmed the location of the methylenedioxy group at C-7/C-8.KEY WORDS Long-range COSY Double quantum coherence correlation spectroscopy (DQCOSY) Fixed-evolution HETCOR HOMO 2DJ 2D NOE Difference saturation transfer Norditerpenoid alkaloid selective INEPT Tatsidine

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Carbon-13 and Proton NMR Shift Assignments and Physical Constants of Norditerpenoid Alkaloids

Cited by 38 publications

References 114 publications

Attenuated Structural Transformation of Aconitine during Sand Frying Process and Antiarrhythmic Effect of Its Converted Products

Attenuated Structural Transformation of Aconitine during Sand Frying Process and Antiarrhythmic Effect of Its Converted Products

Classification, Toxicity and Bioactivity of Natural Diterpenoid Alkaloids

Complete spectral assignments of tatsidine by two‐dimensional NMR techniques

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