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2,3/1,10-seco, 3-nor guaianolide-type sesquiterpenoids and their derivatives with hypoglycemic activity from Achillea alpina
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Eleven new seco-guaianolide sesquiterpenoids (
1
–
11
)
and two new guaianolide dimers (
12
and
13
), along with
five known guaianolide derivatives were isolated from the aerial part of
Achillea alpina
L. Compounds
1
–
3
represented
three unique 2,3-oxygen inserted guaianolides and
4
–
8
were five special 3-nor guaianolide sesquiterpenoids. Compounds 9–11
were three novel 1,10-seco-guaianolides, while 12 and 13 were two novel
1,10-seco-guaianolides involved heterodimeric [4 + 2] adducts. The
new structures of 1–13 including their absolute configurations were
determined by spectroscopic data analysis, combined with quantum
electronic circular dichroism (ECD) calculations. To evaluate the
hypoglycemic activity of
1
–
18
, glucose consumption
was used to investigate in palmitic acid (PA)-mediated HepG2-insulin
resistance (IR) cells, and compound 9 displayed the strongest reversal
IR activity. A mechanistic study has revealed that the potential
compound 9 appeared to be mediated hypoglycemic activity via inhibition
of the ROS/TXNIP/NLRP3/caspase-1 pathway.
Title: 2,3/1,10-seco, 3-nor guaianolide-type sesquiterpenoids and their derivatives with hypoglycemic activity from Achillea alpina
Description:
Eleven new seco-guaianolide sesquiterpenoids (
1
–
11
)
and two new guaianolide dimers (
12
and
13
), along with
five known guaianolide derivatives were isolated from the aerial part of
Achillea alpina
L.
Compounds
1
–
3
represented
three unique 2,3-oxygen inserted guaianolides and
4
–
8
were five special 3-nor guaianolide sesquiterpenoids.
Compounds 9–11
were three novel 1,10-seco-guaianolides, while 12 and 13 were two novel
1,10-seco-guaianolides involved heterodimeric [4 + 2] adducts.
The
new structures of 1–13 including their absolute configurations were
determined by spectroscopic data analysis, combined with quantum
electronic circular dichroism (ECD) calculations.
To evaluate the
hypoglycemic activity of
1
–
18
, glucose consumption
was used to investigate in palmitic acid (PA)-mediated HepG2-insulin
resistance (IR) cells, and compound 9 displayed the strongest reversal
IR activity.
A mechanistic study has revealed that the potential
compound 9 appeared to be mediated hypoglycemic activity via inhibition
of the ROS/TXNIP/NLRP3/caspase-1 pathway.
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