C19-Diterpenoid alkaloid arabinosides from an aqueous extract of the lateral root of Aconitum carmichaelii and their analgesic activities

Abstract

Eight new C19-diterpenoid alkaloid arabinosides, named aconicarmichosides E–L (1–8), were isolated from an aqueous extract of the lateral roots of Aconitum carmichaelii (Fu Zi). Their structures were determined by spectroscopic and chemical methods including 2D NMR experiments and acid hydrolysis. Compounds 1–8, together with the previously reported four neoline 14-O-arabinosides from the same plant, represent the only examples of glycosidic diterpenoid alkaloids so far. At a dose of 1.0 mg/kg (i.p.), as compared with the black control, compounds 1, 2, and 4–6 exhibited analgesic effects with >65.6% inhibitions against acetic acid-induced writhing of mice. Structure–activity relationship was also discussed.

Isotalatizidine, a C19-diterpenoid alkaloid, attenuates chronic neuropathic pain through stimulating ERK/CREB signaling pathway-mediated microglial dynorphin A expression

“…Recently, the focus has greatly shifted to natural plant-derived antinociceptive agents with high efficacy and safety. The main and lateral roots of Aconitum carmichaelii Debx (Ranunculaceae), known as "Wutou" and "Fuzi", respectively, in Chinese, are widely used in traditional Chinese medicine as analgesic, anti-inflammatory, anti-rheumatic, and immunosuppressive agents [3][4][5]. More than a hundred chemicals have been isolated from the different parts of this herb [6], of which the diterpenoid alkaloids are the main pharmacologically active constituents.…”

Neuropharmacological effects of Aconiti Lateralis Radix Praeparata

“…Li et al, also found four unreported C 19 ‐diterpenoid alkaloids in Fuzi , named carmichasines A‐D (1‐4) . From an aqueous extract of Fuzi, Guo found eight unreported arabinosides aconicarmichosides E‐L (1‐8) . C 19 ‐diterpenoid alkaloids are the major bioactive compounds.…”

Gastrodin Derivatives from Gastrodia elata

“…Undoubtedly, chemical reactions occur during decocting, and the resulting artificial products are highly suspected of playing important roles in the theory of Chinese medicine, although concrete proof is yet to be reported in many cases. Thus, we systematically studied the chemical constituents of an aqueous extract of "tian ma" to unravel the chemical and biological diversity of certain traditional Chinese medicines [26][27][28][29][30][31][32][33][34][35][36][37]. We previously reported on 51 compounds from the aqueous extract, including seven new p-hydroxybenzyl-substituted amino acids, seven new p-hydroxybenzyl-substituted glutathione derivatives, one new N,N-bis(p-hydroxybenzyl)-substituted ergothioneine, and one new bis(p-hydroxybenzyl)-substituted 9,9′-neolignan with a novel carbon skeleton [38][39][40][41].…”