New Compounds from Siberian Gentiana Species. I. Iridoid Glycosides

Оленников, Д. Н.; Чирикова, Н. К.

doi:10.1007/s10600-021-03448-1

Cited by 4 publications

(3 citation statements)

References 23 publications

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“…By comparing their NMR data with those reported in the literatures, the eight known compounds were identified as gentiopicroside (5) [33], 6 -O-β-D-glucopyranosyl-gentiopicroside (6) [34], picrogentioside A (7) [29], loganic acid (8) [35], 1α,2α,3β,24-tetrahydroxyolean-12en-28-oic acid (9) [30], 2α,3α,24-trihydroxyolean-12-en-28-oic acid (10) [36], 1α,2α,3β,24tetrahydroxyursa-12,20(30)-dien-28-oic acid (11) [30], and 1β,2α,3α,24-tetrahydroxyurs-12en-28-oic acid (12) [31], respectively. By comparing their NMR data with those reported in the literatures, the eight known compounds were identified as gentiopicroside (5) [33], 6′-O-β-D-glucopyranosylgentiopicroside (6) [34], picrogentioside A (7) [29], loganic acid (8) [35], 1α,2α,3β,24tetrahydroxyolean-12-en-28-oic acid (9) [30], 2α,3α,24-trihydroxyolean-12-en-28-oic acid (10) [36], 1α,2α,3β,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid (11) [30], and 1β,2α,3α,24-tetrahydroxyurs-12-en-28-oic acid (12) [31], respectively.…”

Section: Identification Of New Compoundssupporting

confidence: 67%

“…Cytotoxicity of compounds was tested by the MTT method according to the manufacturer's instructions. A549 cells were seeded (5 × 10 3 /well) into 96-well plates for 24 h. In addition to an untreated control group, compounds (10,20,40,80, or 160 µM) were added to cells and TNF-α (final concentration,10 ng/mL) was added in after 2 h of incubation. Each group had 3 duplicate wells.…”

Section: Cell Culture and Cytotoxicity Testmentioning

confidence: 99%

“…Phytochemical studies of G. macrophylla [ 7 ] demonstrated the existence of iridoids [ 8 , 9 , 10 , 11 ], flavonoids [ 12 , 13 ], lignans [ 14 ], triterpenoids [ 15 , 16 ], and other constituents [ 8 , 17 , 18 ]. Among these constituents, the main component iridoid gentiopicroside exhibited anti-rheumatic arthritis effect [ 19 , 20 ] and anti-inflammation in rat articular chondrocyte [ 21 ], as well as protective effects on liver injury [ 22 ], gastric mucosal injury [ 23 ], and neuron injury [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

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Terpenoid Glucosides from Gentiana macrophylla That Attenuate TNF-α Induced Pulmonary Inflammation in A549 Cells

Huang,

Luo,

Zhang

et al. 2023

Molecules

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Four previously undescribed terpenoid glucosides, including one sesquiterpenoid di-glucoside (1), two new iridoid glucosides (2, 3), and a new triterpenoid tri-glucoside (4), were isolated from a 70% ethanol extract of the root of Gentiana macrophylla (Gentianaceae), along with eight known terpenoids. Their structures were determined by spectroscopic techniques, including 1D, 2D NMR, and HRMS (ESI), as well as chemical methods. The absolute configuration of compound 1 was determined by quantum chemical calculation of its theoretical electronic circular dichroism (ECD) spectrum. The sugar moieties of all the new compounds were confirmed to be D-glucose by GC analysis after acid hydrolysis and acetylation. Anti-pulmonary inflammation activity of the iridoids were evaluated on a TNF-α induced inflammation model in A549 cells. Compound 2 could significantly alleviate the release of proinflammatory cytokines IL-1β and IL-8 and increase the expression of anti-inflammatory cytokine IL-10.

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