New Crinine-Type Alkaloids with Inhibitory Effect on Induction of Inducible Nitric Oxide Synthase from Crinum yemense

Abstract

The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

“…In the family of NOS, inducible NOS (iNOS) is specifically involved in pathologic aspects with the overproduction of NO and can be expressed in response to proinflammatory agents such as interleukin-1b, tumor necrosis factor-a, and LPS in various cell types including macrophages. As a part of our studies to characterize the bioactive components of natural medicines, we have investigated various NO production inhibitors, i.e., higher unsaturated fatty acids, 27) polyacetylenes, [28][29][30] coumarins, 28,30,31) flavonoids, 29,32) stilbenes, 33,34) lignans, [35][36][37] sesquiterpenes, [38][39][40][41][42][43][44][45] diterpenes, 46,47) triterpenes, [48][49][50][51] diarylheptanoids, [52][53][54] cyclic peptides, 50) alkaloids, 55,56) and phenylpropanoids. 5,6,37) Continuing of these studies, the effects of the principal constituents from E. expansa on NO production from LPS-activated macrophages were examined, and the results were summarized in Table 2.…”

Crinamine from Crinum asiaticum var. japonicum Inhibits Hypoxia Inducible Factor-1 Activity But Not Activity of Hypoxia Inducible Factor-2

“…1). Crinamine has also been isolated from other Crinum, 17,18,20) Brunsvigia, 27,28) and Ammocharis 29) species in the family Amaryllidaceae. Crinamine was reported to have strong cytotoxic, and moderate antimalarial activity.…”

“…Crinamine was reported to have strong cytotoxic, and moderate antimalarial activity. 18,28) In screening of HIF-1 inhibitors, crinamine (1) exhibited significant inhibitory activity against the HIF-1 induced transcriptional activation (IC 50 : 2.7 mM) in a concentration dependent manner (Fig. 2) without inhibition in the U251-pGL3 control cell line.…”

“…Phytochemical studies on this plant reported several phenanthridine alkaloids, triterpene alcohols and flavonoids. [13][14][15] Alkaloids isolated from the bulbs of the tribe Amaryllidaceae have shown various pharmacological effects, such as antiviral, 16) antimalarial, 17) cytotoxic, 15,17,18) and antineoplastic activities, 19) as well as effects on disease of the nervous system. 20) As part of our ongoing molecularly targeted screening projects to develop anticancer and antiviral drugs from natural products, we isolated crinamine (1) 16) from the aerial part of C. asiaticum var.…”

Absolute Stereostructures of Olibanumols A, B, C, H, I, and J from Olibanum, Gum-Resin of Boswellia carterii, and Inhibitors of Nitric Oxide Production in Lipopolysaccharide-Activated Mouse Peritoneal Macrophages

“…In the family of NOS, inducible NOS (iNOS) is specifically involved in pathologic aspects with the overproduction of NO and can be expressed in response to proinflammatory agents such as interleukin-1b, tumor necrosis factor-a, and LPS in various cell types including macrophages, endothelial cells, and smooth muscle cells. As a part of our studies to characterize the bioactive components of natural medicines, we have investigated various NO production inhibitors, i.e., higher unsaturated fatty acids, 39) polyacetylenes, [40][41][42] coumarins, 40,42,43) flavonoids, 41,44,45) stilbenes, 46,47) lignans, [48][49][50] sesquiterpenes, [51][52][53][54][55][56][57][58] diterpenes, 59,60) triterpenes, 19,[61][62][63] diarylheptanoids, [64][65][66] cyclic peptides, 63) alkaloids, 67,68) and phenylpropanoids. 50,69,70) As a continuation of these studies on bioactive constituents of natural medicines, the effects of the mono-and triterpene constituents (1-5, 7-13) from the gum-resin of B. carterii on NO production from LPS-activated macrophages were examined, and the results were summarized in Table 3 …”