Three Novel Monoterpenoid Glycosides From Fruits Of Eleutherococcus Henryi

Abstract:

The phytochemical investigation on the fruits of Eleutherococcus henryi (Araliaceae) resulted in the discovery of three novel monoterpene glycosides, eleuhenryiside A (1), eleuhenryiside B (2), and eleuhenryiside C (3), as well as a known lignan, (-)-kobusin (4). Their chemical structures were elucidated by mass, 1 D- and 2 D-NMR spectroscopy. The chemical structures of new compounds 1-3 were determined to be (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-glucopyranoside, (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-glucopyranoside, and (-)-(4 R)-4,7-dihydroxy-1-menthene 7-O-β-glucopyranoside, respectively. The anti-neuroinflammatory and anti-inflammatory activities of these compounds were evaluated with LPS-stimulated BV2 microglia and RAW264.7 macrophage, respectively. The results showed that new compounds 1 and 3 have inhibitory effects of NO production with IC₅₀ values of 32.50 ± 1.60 and 3.54 ± 0.20 μM in LPS-stimulated BV2 microglia. Also, (-)-kobusin (4) has abilities to inhibit NO production with the IC₅₀ values of 14.25 ± 2.69 and 36.35 ± 6.27 μM in BV2 and RAW264.7 cells, respectively, which indicated that it may possess the potential anti-neuroinflammatory and anti-inflammatory activities.

Graphical Abstract

KEYWORD:

• Eleutherococcus henryi
• Araliaceae
• monoterpenoid glycosides
• eleuhenryiside A
• eleuhenryiside B
• eleuhenryiside C

Disclosure statement

No potential conflict interest was reported by the authors.

Additional information

Funding

This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korea government [grant number NRF-2017R1A5A2015805]; the Doctoral Scientific Research Starting Foundation of Gannan Medical University [grant number QD201905]; and the Natural Science Foundation of Hunan Province, China [grant number 2019JJ40223].