14-O-Acetylneoline

Defined Small Molecules Produced by Himalayan Medicinal Plants Display Immunomodulatory Properties.[Pubmed:30404196]

Int J Mol Sci. 2018 Nov 6;19(11). pii: ijms19113490.

Plant-derived compounds that modulate the immune responses are emerging as frontline treatment agents for cancer, infectious diseases and autoimmunity. Herein we have isolated 40 phytochemicals from five Bhutanese Sowa Rigpa medicinal plants-Aconitum laciniatum, Ajania nubegina, Corydalis crispa, Corydalis dubia and Pleurospermum amabile-and tested 14 purified compounds for their immunomodulatory properties using a murine dendritic cell (DC) line, and cytotoxicity against a human cholangiocyte cell line using xCELLigence real time cell monitoring. These compounds were: pseudaconitine, 14-veratryolpseudaconitine, 14-O-Acetylneoline, linalool oxide acetate, (E)-spiroether, luteolin, luteolin-7-O-beta-d-glucopyranoside, protopine, ochrobirine, scoulerine, capnoidine, isomyristicin, bergapten, and isoimperatorin. Of the 14 compounds tested here, scoulerine had adjuvant-like properties and strongly upregulated MHC-I gene and protein expression whereas bergapten displayed immunosuppressive properties and strongly down-regulated gene and protein expression of MHC-I and other co-stimulatory molecules. Both scoulerine and bergapten showed low cytotoxicity against normal healthy cells that were consistent with their immunoregulatory properties. These findings highlight the breadth of immunomodulatory properties of defined compounds from Bhutanese medicinal plants and show that some of these compounds exert their mechanisms of action by modulating DC activity.

Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis.[Pubmed:26240038]

Sci Rep. 2015 Aug 4;5:12845.

Aconitum laciniatum is used in Bhutanese traditional medicine for treating various chronic infections and inflammatory conditions. We carried out in-depth isolation and characterization of the phytochemicals from the root component and determined the anti-inflammatory effects of the isolated compounds against chemically-induced colitis in mice. Five diterpenoid alkaloids - pseudaconitine, 14-veratroylpseudaconine, 14-O-Acetylneoline, neoline, and senbusine A - were isolated from A. laciniatum for the first time. Two of the alkaloids were tested for anti-inflammatory properties in the TNBS-induced colitis model in mice. Various parameters were measured to assess pathology including weight loss, clinical and macroscopic scores, histological structure and IFN-gamma production in the gut. Of the two alkaloids tested, 14-O-Acetylneoline showed significant protection against different parameters of colitic inflammation. Compared to control mice that received TNBS alone, mice treated with 14-O-Acetylneoline experienced significantly less weight loss and had significantly lower clinical scores, macroscopic pathology and grades of histological inflammation. Moreover, colonic IFN-gamma mRNA levels were significantly reduced in mice that received 14-O-Acetylneoline compared to control mice that received TNBS alone. This alkaloid is now considered a novel anti-colitis drug lead compound.

Norditerpenoid alkaloids from the processed tubers of Aconitum carmichaeli.[Pubmed:12913245]

Chem Pharm Bull (Tokyo). 2003 Aug;51(8):999-1002.

Four new and five known norditerpenoid alkaloids were isolated from the processed tubers of Aconitum carmichaeli. The new alkaloids are 14-O-cinnamoylneoline (3), 14-O-anisoylneoline (4) 14-O-veratroylneoline (5), and lipo-14-O-anisoylbikhaconine (8). The known alkaloids are neoline (1), 14-O-Acetylneoline (2), foresaconitine (6), crassicauline A (7), and lipohypaconitine (9). Alkaloids 2, 6, and 7 were isolated from this plant for the first time. The structures of the new alkaloids were established by spectroscopic and chemical methods.