Three New Polyacetylene Glycosides from the Roots of Heracleum dissectum and Their Triglyceride Accumulating Activities in 3T3‐L1 Cells

Abstract

Continually phytochemical study of the roots of Heracleum dissectum had led to the isolation of three previously undescribed polyacetylene glycosides (1–3), together with seven known compounds, including one polyacetylene (8) and six coumarins (4–7 and 9–10) using diverse chromatographic methods. The structures of these three new compounds were characterized and identified as deca‐4,6‐diyn‐1‐yl β‐d‐glucopyranosyl‐(1→6)‐β‐d‐glucopyranosyl‐(1→2)‐β‐d‐glucopyranoside (1), (8Z)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d‐glucopyranosyl‐(1→6)‐β‐d‐glucopyranosyl‐(1→2)‐β‐d‐glucopyranoside (2), and (8E)‐dec‐8‐ene‐4,6‐diyn‐1‐yl β‐d‐glucopyranosyl‐(1→6)‐β‐d‐glucopyranosyl‐(1→2)‐β‐d‐glucopyranoside (3) based on their physicochemical properties and extensive analyses of various spectroscopic data. Their triglycerides accumulating activities were assayed and the results showed that the three new polyacetylene glycosides (1–3) exhibited triglyceride accumulating activities in 3T3‐L1 adipocytes.

Hogweed Seed Oil: Physico–Chemical Characterization, LC-MS Profile, and Neuroprotective Activity of Heracleum dissectum Nanosuspension

“…Bergapten has been previously found only in the roots of H. dissectum [13,20], isoimperatorin has been identified in the fruits of H. leskowii [92], while 7, 18, 20, 22, and 34 have been detected for the first time for these species and genus. Among the 8-O-substituted furanocoumarins are: a) esters of xanthotoxol (8-hydroxypsoralen), which has been previously isolated from the roots of H. dissectum; the identified esters include heraclenol (prangenin hydrate, komaline, 6) [15,16,23], xanthotoxin (13) [13], and imperatorin (24) [13]; b) heraclenin (prangenin, 15), which has been detected in H. candicans [93], H. canescens [94], and H. sibiricum [95]; and c) 8-geranyloxypsoralen (32), which has been found in H. candicans [93].…”

“…The known phytocomponents [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ] found in the roots and herb of H. dissectum include aliphatic compounds [ 14 , 15 ], terpenes [ 14 , 16 , 21 ], and phenolics [ 13 , 14 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ] ( Table 1 ).…”

“…The basic phenolic group of H. dissectum is coumarins, including simple coumarins [ 18 , 20 , 21 , 22 , 23 ], linear and angular furanocoumarins, dihydrofuranocoumarins, and dihydropyranocoumarins [ 13 , 15 , 16 , 18 , 19 , 20 , 21 , 22 ]. The analysis of essential oils of herbs [ 24 ], lamina, and petiole [ 25 ] has shown the presence of monoterpenes, sesquiterpenes, aliphatic alcohols, and esters.…”

Polyacetylene Glycosides: Isolation, Biological Activities and Synthesis

“…[133] Some antidiabetic drugs such as acarbose, miglitol, and voglibose are inhibitors of these enzymes, with a mechanism of action based not only slowing down the breakdown of starch in glucose in the small intestine, but also decreasing its bioavailability resulting in a reduction of the glucose levels entering the bloodstream. [134] PAGs 9, 10, and 11 [130] can accelerate the accumulation of triglycerides in 3T3-L1 cells (cells that store body fat and control temperature) (Figure 8). These PAGs provided an in vivo antidiabetic effect since they can efficiently transport glucose from the cellular medium to adipocytes, which are metabolized and converted into triglycerides.…”