Diterpenoid alkaloids

Pelletier, S. W.; Page, S. W.

doi:10.1039/np9840100375

Cited by 22 publications

(6 citation statements)

References 27 publications

(42 reference statements)

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“…9a). 32,33,36 However, 7-H displayed in the SXRD data of mesaconitine (5) and condelphine (7) shown in an angle imitating depiction A1 do not show a typical b-orientation (Fig. 3).…”

Section: Resultsmentioning

confidence: 92%

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The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers

et al. 2020

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“…9a). 32,33,36 However, 7-H displayed in the SXRD data of mesaconitine (5) and condelphine (7) shown in an angle imitating depiction A1 do not show a typical b-orientation (Fig. 3).…”

Section: Resultsmentioning

confidence: 92%

“…The depiction A1 is currently the most popular reported in the eld of phytochemistry. [32][33][34][35][36] The depiction clearly displays three rings, A-, B-and C-ring, in suitable shapes. However, the conformations of some rings, e.g.…”

Section: Resultsmentioning

confidence: 95%

The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers

et al. 2020

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“…Diterpenoid alkaloids are a kind of nitrogen-containing diterpenes that derive from a terpene-amino acid conjugated biosynthesis. According their structural characteristics, the majority of them are classified as typical diterpenoid alkaloids, including C 18 -, C 19 -, and C 20 -diterpenoid alkaloids 1 2 3 4 . Till now, only a few atypical diterpenoid alkaloids have been reported, such as concavine, chamobtusin A, and haterumaimides 4 .…”

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confidence: 99%

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

Chen

et al. 2015

Sci Rep

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Fusicoccane diterpenoids usually possess a fused 5-8-5 tricyclic ring system, which are biogenetically generated from geranylgeranyl diphosphate (GGDP). In our report, three novel diterpenoid alkaloids with fusicoccane skeleton, pericolactines A–C (1–3), were isolated from Periconia sp.. Their structures with absolute configurations were determined by spectroscopic analyses and quantum chemical ECD calculation. Pericolactines A–C (1–3) are a new class of diterpenoid alkaloids with an unusual fused 5-5-8-5 tetracyclic ring system, which derive from a geranylgeranyl diphosphate (GGDP) and serine conjugated biosynthesis. They belong to the atypical diterpenoid alkaloids.

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“…ロイドであり，kobusine (4), [21][22][23]25) pseudokobusine (5), [21][22][23]25) karakoline (8), 26) subcusine (9), 27) delcosine (10), [28][29][30][31][32][33] 14-acetyldelcosine (11), 33) lucidusculine (12) [20][21][22][23]25) 及び luciculine (13) [20][21][22][23]25) は標品との混融試験及びスペクトルデータを比較することにより同定した．1-Acetylluciculine (14), 34) Chart 2 931 No. 11 ‰avadine (15), 35) ‰avamine (16) 35) 及び dehydroluciculine ( 17 ) 36) は合成標品との比較により同定した．Isotalatizidine (18), 26) 14-dehydrodelcosine (19), 26) 18-methoxygadesine (20), 37) browniine (21), 26) 14-acetylbrowniine (22), 26,33) virescenine (23), 26) nevadensine (24) 38) 及び macrocentridine 53) anisoezochasmaconitine (48), 34) ezocha- …”

unclassified

“…11 ‰avadine (15), 35) ‰avamine (16) 35) 及び dehydroluciculine ( 17 ) 36) は合成標品との比較により同定した．Isotalatizidine (18), 26) 14-dehydrodelcosine (19), 26) 18-methoxygadesine (20), 37) browniine (21), 26) 14-acetylbrowniine (22), 26,33) virescenine (23), 26) nevadensine (24) 38) 及び macrocentridine 53) anisoezochasmaconitine (48), 34) ezocha- …”

unclassified

Studies on Structural Elucidation of <i>Aconitum</i> Diterpenoid Alkaloid by LC-APCI-MS and Effects of <i>Aconitum</i> Diterpenoid Alkaloid on Cutaneous Blood Flow

浩二

2002

YAKUGAKU ZASSHI

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The chemical constituents of Aconitum yesoense var. macroyesoense and Aconitum japonicum were examined using high-resolution spectral analysis. Twelve novel alkaloids were isolated from A. yesoense var. macroyesoense together with 20 known alkaloids. Eight novel alkaloids were isolated from A. japonicum together with 15 known alkaloids. An HPLC atmospheric pressure chemical ionization-mass spectrometry (HPLC APCI MS) method was useful for the simultaneous determination of 21 Aconitum alkaloids found in A. yesoense var. macroyesoense and A. japonicum. These compounds were fairly stable under the conditions used, and the protonated molecules or fragment ions characteristic of the molecule appeared as base peaks in the mass spectra and were used for selected ion monitoring. HPLC APCI MS is a very promising approach for structural investigations of positional isomers and stereoisomers. This method was applied successfully to stereoisomeric Aconitum alkaloids diŠering in conˆguration at C-1, -6, or -12.Comparison of the APCI spectra showed that the abundance of fragment ions was signiˆcantly higher for the C-1, -6, or -12 b-form alkaloid than for C-1, -6, or -12 a-form alkaloid. The main alkaloid constituents in the root of A. yesoense var. macroyesoense, Aconitum alkaloids of the C 20 -diterpenoid type, kobusine and pseudokobusine, and their acyl derivatives were examined for their peripheral vasoactivities by measuring laser-‰owmetrically the cutaneous blood ‰ow in the hind foot of mice after intravenous administration. It is thought that the hydroxyl groups of alkaloids, especially a free OH group of pseudokobusine at C-6, were important for action on the peripheral vasculature leading to dilatation, and the results indicated that esteriˆcation of the hydroxyl group at C-15 with either anisoate, veratroate, or p-nitrobenzoate may contribute to enhancement of the activity of the parent alkaloids.

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Diterpenoid alkaloids

Cited by 22 publications

References 27 publications

The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers

The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

Studies on Structural Elucidation of <i>Aconitum</i> Diterpenoid Alkaloid by LC-APCI-MS and Effects of <i>Aconitum</i> Diterpenoid Alkaloid on Cutaneous Blood Flow

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