New lycosinine derivative from <i>Hippeastrum breviflorum</i>

Sebben, Camila; Giordani, Raquel Brandt; Andrade, Jean Paulo de; Berkov, Strahil; Osorio, Edison Javier; Sobral, Marcos; de Almeida, Mauro Vieira; Henriques, Amélia Teresinha; Bastida, Jaume; Zuanazzi, José Ângelo Silveira

doi:10.1016/j.bjp.2015.06.005

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Original Articles • Rev. bras. farmacogn. 25 (4) • Jul-Aug 2015 • https://doi.org/10.1016/j.bjp.2015.06.005 copy

New lycosinine derivative from Hippeastrum breviflorum

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

A new lycosinine derivative, 9-O-demethyllycosinine B, was isolated from the native Brazilian Hippeastrum breviflorumHerb., Amaryllidaceae, along with the well-known alkaloids lycosinine B and lycorine. The structure of the new compound was established by physical and spectroscopic methods. 9-O-demethyllycosinine B is the third lycosinine variant identified in the Amaryllidaceae family.

Keywords
Hippeastrum breviflorum ; Amaryllidaceae; Alkaloids; Lycorine; 9-O-demethyllycosinine B; Lycosinine B

H	∆ (J in Hz)	HMQC^a a Multiplicities determined by DEPT experiment.		HMBC
1	6.84 dt (7.0; 1.0)	130.3 d		C-3, C-4a, C-10a
2	6.74 t (7.0)	118.7 d		C-4, C-10b
3	7.10 dd (7.0; 1.0)	124.0 d		C-1, C-4a, C-11
		120.2 s	(C-4)
		151.1 s	(C-4a)
6	9.45 s	191.0s		C-6a, C-7, C-8
		125.6 s	(C-6a)
7	7.43 s	107.9 d		C-6, C-6a, C-8, C-9, C-10a
		148.5 s	(C-8)
		155.1s	(C-9)
10	6.74 s	117.8 d		C-6, C-6a, C-8, C-9, C-10b
		141.1 s	(C-10a)
		131.7 s	(C-10b)
11(2H)	2.95 m	28.3 t		C-3, C-4a, C-10b, C-12
12β	3.15 dt (9.0, 8.5)	56.9 t		C-4a, C-10b, C-11, NMe
12α	3.32 dd (8.5; 3.0)	56.9 t		C-4a, C-10b, C-11
OMe	3.92 s	55.1 q		C-8, C-9
NMe	2.24 s	38.5 q		C-4a, C-12

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[1] * Corresponding author. E-mail: zuanazzi@ufrgs.br (J.Â.S. Zuanazzi).