Alkaloids of Delphinium staphisagria. The structure and stereochemistry of delphisine, neoline, chasmanine, and homochasmanine

Pelletier, S. William; Ďjarmati, Z.; Lajšić, Stevan; Camp, Wilson H. De

doi:10.1021/ja00425a035

Cited by 46 publications

(46 citation statements)

References 3 publications

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“…1 represent the absolute configurations of 1 – 8 . Additionally, based on the splitting pattern of H-1 in the 1 H NMR spectra ( Table 1 ), the ring A in 1 – 8 has a boat conformation in CD 3 OD 52 , 53 , which is consistent with that of the aglycones in crystals 50 , 54 , 55 .…”

Section: Resultssupporting

confidence: 59%

“…This was supported by acid hydrolysis of the neoline l-arabinoside isomers 48 as well as of 2 , 3 , and 5 . Because the absolute configuration of the co-occurring aglycones, including neoline 52 , 53 , 54 , isotalatizidine 55 , fuziline 50 , talatizamine, 5 , 51 and chasmanine 51 , 52 , 53 , 54 , were previously determined by chemical transformation and/or X-ray crystallography, the structures as shown in Fig. 1 represent the absolute configurations of 1 – 8 .…”

Section: Resultsmentioning

confidence: 99%

“…Because the ring A conformation in solution may be affected by the presence of acid in the samples 43 , 52 , 53 , 56 and because trifluoroacetic acid (TFA) was used in the isolation procedure, compounds 1 – 8 were suspected to be obtained as trifluoroacetates 57 , 58 , 59 . Although the 13 C NMR spectra of 1 − 8 did not displayed the corresponding resonances of TFA, the presence of TFA in the samples were confirmed by the 19 F NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

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C19-Diterpenoid alkaloid arabinosides from an aqueous extract of the lateral root of Aconitum carmichaelii and their analgesic activities

Guo

Xia

Meng

et al. 2018

Acta Pharmaceutica Sinica B

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Eight new C19-diterpenoid alkaloid arabinosides, named aconicarmichosides E–L (1–8), were isolated from an aqueous extract of the lateral roots of Aconitum carmichaelii (Fu Zi). Their structures were determined by spectroscopic and chemical methods including 2D NMR experiments and acid hydrolysis. Compounds 1–8, together with the previously reported four neoline 14-O-arabinosides from the same plant, represent the only examples of glycosidic diterpenoid alkaloids so far. At a dose of 1.0 mg/kg (i.p.), as compared with the black control, compounds 1, 2, and 4–6 exhibited analgesic effects with >65.6% inhibitions against acetic acid-induced writhing of mice. Structure–activity relationship was also discussed.

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Section: Resultssupporting

confidence: 59%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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C19-Diterpenoid alkaloid arabinosides from an aqueous extract of the lateral root of Aconitum carmichaelii and their analgesic activities

Guo

Xia

Meng

et al. 2018

Acta Pharmaceutica Sinica B

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“…lc. They are similar to those found in other aconitine and lycoctonine type alkaloids in which the boat form of the ring A is stabilized by the intramolecular hydrogen bonding (20)(21)(22)(23)(24)(25). The projection of the structure is shown in Fig.…”

Section: Resultssupporting

confidence: 83%

The lycoctonine family of alkaloids: a stereochemical revision

Edwards¹,

Przybylska²

1982

Can. J. Chem.

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A redetermination of the structure of des(oxymethylene)lycoctonine hydriodide has shown that a wrong choice had been made between the real and false mirror image peaks for the atoms of the 1-methoxyl group in the original pseudosymmetric Fourier synthesis. It has been demonstrated that lycoctonine samples from many sources are identical, and that no rearrangement took place in forming des(oxymethylene)lycoctonine. Hence all alkaloids that have been related to lycoctonine have a 1α-methoxyl group.

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“…Some literature assignments of 13 C NMR signals of mesaconitine (5) and condelphine (7) have been revised supported by 2D NMR data (Tables S1-S4 †). Due to repulsion between 1a-OMe (in the equatorial position)/12-H e 0 proposed by Pelletier and coworkers, 13,21,22 the A-ring of norditerpenoid alkaloid free bases with 1a-OMe adopting chair conformations are twisted. This signicant proximity decreases when the A-rings adopt boat conformations as the O-atom ips to the axial position and therefore away from 12-H e 0 , e.g.…”

Section: Resultsmentioning

confidence: 99%