Isolation and structural characterization of new piperidine alkaloids from Prosopis affinis

被引：7

作者：

Reina, Luis ^{[1
]}

Bennadji, Zohra ^{[2
]}

Vinciguerra, Vittorio ^{[3
]}

Ferreira, Fernando ^{[1
,4
]}

Moyna, Guillermo ^{[5
]}

Menendez, Pilar ^{[1
]}

机构：

[1] UdelaR, Fac Quim, Dept Quim Organ, Montevideo 11800, Uruguay

[2] Inst Nacl Invest Agr, Programa Nacl Invest Prod Forestal, Tacuarembo 45000, Uruguay

[3] Univ Tuscia, Dipartimento Innovaz Nei Sistemi Biol Agroaliment, I-01100 Viterbo, Italy

[4] UdelaR, Ctr Univ Tacuarembo, Espacio Ciencia & Tecnol Quim, Tacuarembo 45000, Uruguay

[5] UdelaR, CENUR Litoral Norte, Dept Quim Litoral, Paysandu 60000, Uruguay

来源：

PHYTOCHEMISTRY LETTERS | 2015年 / 14卷

关键词：

Conformational equilibrium; Nandubay; Piperidine alkaloids; Prosopis affinis; CASSIA-SPECTABILIS; GENUS PROSOPIS; GLANDULOSA; MESQUITE; LEAVES; FIELD;

D O I：

10.1016/j.phytol.2015.10.022

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The isolation of three new N-methylated piperidine-3-ol alkaloids from the bark of Prosopis affinis Spreng. (Nandubay) is described. Together with MS and IR data, results from 1D and 2D NMR experiments allowed for the identification of N-methyl-2-isocassine, N-methyl-6-isocassine, and N-methyl-6-isocarnavaline. Inspection of 1D-NOESY spectra and coupling constant data revealed that the heterocyclic moiety of the alkaloids is in fast conformational equilibrium in solution, and this behavior had to be taken into account in order to determine the relative configuration of the chiral centers of the piperidine rings. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

引用

页码：265 / 269

页数：5

共 50 条

[1] Isolation and characterization of galactomannans from Prosopis affinis as potential gum substitutes
Vilaro, Pilar
Bennadji, Zohra
Budelli, Eliana
Moyna, Guillermo
Panizzolo, Luis
Ferreira, Fernando
FOOD HYDROCOLLOIDS, 2018, 77 : 711 - 719
[2] PIPERIDINE ALKALOIDS .3. NEW ALKALOIDS FROM PROSOPIS-AFRICANA (PROSAFRINE AND PROSAFRININE
KHUONGHUU, Q
GOUTAREL, R
MONSEUR, X
RATLE, G
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1972, 81 (7-8): : 443 - +
[3] ISOLATION OF NEW TRICYCLIC PIPERIDINE ALKALOIDS FROM BUDDLEJA-DAVIDII
RODER, E
WIEDENFELD, H
HOENIG, A
PLANTA MEDICA, 1985, 51 (02) : 164 - 165
[4] Neurotoxicity of Prosopis juliflora: from Natural Poisoning to Mechanism of Action of Its Piperidine Alkaloids
Amaral da Silva, Victor Diogenes
Mendes da Silva, Andre Mario
Castro e Silva, Juliana Helena
Costa, Silvia Lima
NEUROTOXICITY RESEARCH, 2018, 34 (04) : 878 - 888
[5] Neurotoxicity of Prosopis juliflora: from Natural Poisoning to Mechanism of Action of Its Piperidine Alkaloids
Victor Diogenes Amaral da Silva
André Mario Mendes da Silva
Juliana Helena Castro e Silva
Silvia Lima Costa
Neurotoxicity Research, 2018, 34 : 878 - 888
[6] PIPERIDINE ALKALOIDS .2. STRUCTURE OF PROSOPINE AND PROSOPININE, ALKALOIDS FROM PROSOPIS-AFRICANA (GUILL AND PERR) TAUB
KHUONGHUU, Q
RATLE, G
MONSEUR, X
GOUTAREL, R
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1972, 81 (7-8): : 425 - +
[7] NEW ALKALOIDS FROM PROSOPIS-JULIFLORA DC
AHMAD, VU
BASHA, A
HAQUE, W
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1978, 33 (03): : 347 - 348
[8] Two new alkylated piperidine alkaloids from Western honey mesquite:: Prosopis glandulosa Torr. var. Torreyana
Samoylenko, Volodymyr
Dunbar, D. Chuck
Jacob, Melissa R.
Joshi, Vaishali C.
Ashfaq, Mohammad K.
Muhammad, Ilias
NATURAL PRODUCT COMMUNICATIONS, 2008, 3 (01) : 35 - 40
[9] Two new alkylated piperidine alkaloids from western honey mesquite:: Prosopis glanduloso tort. var. torreyana
Samoylenko, V
Dunbar, D. C.
Jacob, M. R.
Joshi, V. C.
Ashfaq, M. K.
Ilias, M.
PLANTA MEDICA, 2008, 74 (03) : 360 - 360
[10] ON ALKALOIDS .16. ISOLATION AND CHARACTERIZATION OF SOME NEW ALKALOIDS FROM VINCA MAJOR
KAUL, JL
TROJANEK, J
LLOYDIA, 1966, 29 (01): : 26 - &

← 1 2 3 4 5 →