Delatisine, a novel diterpenoid alkaloid from Delphinium elatum L.

Chemistry and biological activities of hetisine-type diterpenoid alkaloids

“…3 ). Among them, delatisine (95) from D. elatum possesses an N –C(19)–O–C(2) mixed acetal unit, 41 and orgetine (96) from A. recemulosum 42 features an N –C(20)–OH mixed acetal group. Generally, methoxy groups are rarely found in C 20 -DAs.…”

An overview of the chemical constituents from the genus Delphinium reported in the last four decades

“…90 14-Hydroxyhetisinone N-oxide (327) from D. gracile is a rare hetisine-type N-oxide, 95 and delatisine (326) from D. elatum possesses an N-C (19) -O-C (2) mixed acetal unit. 96 In addition, several structurally novel hetisine-type C 20 -DAs were reported. Anthriscifolsine A (325) from D. anthriscifolium var.…”

New C20-Diterpenoid Alkaloids from Delphinium laxicymosum var pilostachyum

“…The only acetyl group was readily located on C-13 based on the HMBC correlation between H-13 (δ H 5.10 dd) and the carbonyl carbon of the acetyl group (δ C 170.0 s). The -orientation of both OH-11 and OAc-13 could also be supported by the following evidence: i) the large coupling constants (J = 9.6 Hz) between H-11 and H-9 demonstrated that H-11 was on -orientation; and ii) the W coupling signal between H-11 and H-13 in the 1 H-1 H COSY spectrum suggested that both H-11 and H-13 are oriented on axial bonds (-orientation) [20][21][22]. Finally, comparisons of 1D-and 2D-NMR data (Table 1) and MS data between compounds 1 and 2 led to the determination of the structure of laxipilosdine as 2.…”

“…The orientation of OAc-13 could be assigned to  according to the W coupling signal between H-11 and H-13 in the 1 H-1 H COSY spectrum. The W coupling suggested that both H-11 and H-13 are axial bonds (orientation) [20][21][22]. The above findings led to the determination of the structure of laxipilostine as 1.…”

“…Chen et al [20][21][22]. Finally, comparisons of 1D-and 2D-NMR data (Table 1) and MS data between compounds 1 and 2 led to the determination of the structure of laxipilosdine as 2.…”