Anti-neuroinflammatory effects of sesquiterpenoids isolated from Nardostachys jatamansi

Yoon, Chi–Su; Kim, Kwan-Woo; Lee, Sang-Chan; Kim, Youn‐Chul; Oh, Hyuncheol

doi:10.1016/j.bmcl.2017.11.041

Cited by 31 publications

(24 citation statements)

References 28 publications

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“…The 13 C-NMR and DEPT data indicated the presence of a carbonyl carbon (δ 199.6 (C-9)), an olefinic methine carbon (δ 138.2 (C-1)), a sp 2 quaternary carbon (δ 140.7 (C-10)), a methoxy carbon (δ 56.4 (7-OCH 3 )), a sp 3 quaternary carbon (δ 40.7 (C-5)), three sp 3 methine carbons (δ 75.6 (C-7), 70.0 (C-6), and 31.1 (C-4)), three methylene carbons (δ 40.5 (C-8), 25.8 (C-2), and 25.7 (C-3)), and two methyl carbons (δ 19.3 (C-11) and 15.2 (C-12)). These results suggested that 7-methoxydesoxonarchinol ( 3 ) is structurally similar to the nardosinone-type sesquiterpenoid of desoxonarchinol A found in our previous study [ 5 ]. However, in the 1 H-NMR spectrum of 7-methoxydesoxonarchinol ( 3 ) the signals corresponding to the two olefinic protons (H-7 and H-8) observed in desoxonarchinol A were not observed.…”

Section: Resultssupporting

confidence: 82%

“…Furthermore, several sesquiterpenoids isolated from this species were identified as regulators of the serotonin transport system [ 4 ]. Plants belonging to the genus Nardostachys contain various potentially bioactive chemical components, such as monoterpenoids, sesquiterpenoids, triterpenoids, and lignans [ 4 , 5 , 6 ]. For example, we recently showed that these species contain various terpenoids with anti-neuroinflammatory effects [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

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Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi

et al. 2018

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Nardostachys jatamansi contains various types of sesquiterpenoids that may play an important role in the potency of plant’s anti-inflammatory effects, depending on their structure. In this study, five new sesquiterpenoids, namely kanshone L (1), kanshone M (2), 7-methoxydesoxo-narchinol (3), kanshone N (4), and nardosdaucanol (5), were isolated along with four known terpenoids (kanshone D (6), nardosinanone G (7), narchinol A (8), and nardoaristolone B (9)) from the rhizomes and roots of Nardostachys jatamansi. Their structures were determined by analyzing 1D and 2D NMR and MS data. Among the nine sesquiterpenoids, compounds 3, 4, and 8 were shown to possess dose-dependent inhibitory effects against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in BV2 microglial cells. Furthermore, compounds 3, 4, and 8 exhibited anti-neuroinflammatory effects by inhibiting the production of pro-inflammatory mediators, including prostaglandin E2 (PGE2), inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX-2) proteins, as well as pro-inflammatory cytokines, such as interleukin (IL)-1β, IL-12 and tumor necrosis factor-α (TNF-α), in LPS-stimulated BV2 microglial cells. Moreover, these compounds were shown to inhibit the activation of the NF-κB signaling pathway in LPS-stimulated BV2 microglial cells by suppressing the phosphorylation of IκB-α and blocking NF-κB translocation. In conclusion, five new and four known sesquiterpenoids were isolated from Nardostachys jatamansi, and compounds 3, 4, and 8 exhibited anti-neuroinflammatory effects in LPS-stimulated BV2 microglial cells through inhibiting of NF-κB signaling pathway.

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Section: Resultssupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi

et al. 2018

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“…The agents that suppress the inflammatory cytokines and mediators, such as TNF‐α, IL‐6, and PGE 2 , could serve as promising candidates for developing new anti‐inflammatory drugs (Yoon et al, ). In our study, we revealed that the active CHCl 3 ‐ and EtOAc‐soluble fractions could inhibit the production of IL‐6 and PGE 2 .…”

Section: Resultsmentioning

confidence: 99%

“…The expression of iNOS and COX‐2, the pivotal inducible enzymes for NO and PGE 2 production, increased in the stimulated macrophages (Kim et al, ). Therefore, down‐regulating the expression of iNOS and COX‐2 mRNA can reduce the production of NO and PGE 2 , which exhibit anti‐inflammatory effects (Yoon et al, ). Our results indicated that compounds 6 and 7 suppressed NO and PGE 2 production by inhibiting iNOS and COX‐2 mRNA levels, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Anti‐inflammatory effects of chemical components from Ginkgo biloba L. male flowers on lipopolysaccharide‐stimulated RAW264.7 macrophages

Li¹,

Li²,

Hou

et al. 2019

Phytotherapy Research

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Ginkgo biloba L., well known as living fossil, have various pharmacological activities. Eighteen compounds were isolated from Ginkgo male flowers including a novel matsutake alcohol glycoside, Ginkgoside A (1), and 17 known compounds—calaliukiuenoside (2), benzylalcohol O‐α‐l‐arabinopyranosyl‐(1 → 6)‐β‐d‐glucopyranoside (3), amentoflavone (4), sciadopitysin (5), bilobetin (6), isoginkgetin (7), olivil 4‐O‐β‐d‐glucopyranoside (8), dihydrodehydrodiconiferyl alcohol‐4‐O‐β‐d‐glucoside (9), (+)‐cyclo‐olivil‐6‐O‐β‐d‐glucopyranoside (10), (−)‐isolariciresinol 4‐O‐β‐d‐glucopyranoside (11), coniferin (12), trans‐cinnamic acid‐4‐O‐β‐d‐glucopyranoside (13), p‐coumaryl alchol glucoside (14), stroside B (15), methylconiferin (16), cis‐p‐coumaric acid 4‐O‐β‐d‐glucopyranoside (17), and cis‐coniferin (18). Thirteen of these compounds had not previously found in Ginkgo. All extractive fractions and isolated compounds were evaluated for their anti‐inflammatory ability in the lipopolysaccharide‐induced RAW264.7 macrophages. The ethanol extract of Ginkgo flowers and the chloroform and ethyl acetate fractions can significantly decrease nitric oxide (NO), interleukin‐6 (IL‐6), and prostaglandin E2 (PGE2) production at 100 μg/ml. The most effective compounds, bilobetin (6) and isoginkgetin (7), elevated the NO inhibition ratios to 80.19% and 82.37% at 50 μM, respectively. They also exhibited significant dose‐dependent inhibitory effects on tumor necrosis factor‐α, IL‐6, PGE2, inducible NO synthase mRNA, and cyclooxygenase‐2 mRNA levels. So they can be promising candidates for the development of new anti‐inflammatory agents.

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Nardostachys jatamansi (D. Don) DC (Caprifoliaceae)

Akbar

2020

Handbook of 200 Medicinal Plants

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Anti-neuroinflammatory effects of sesquiterpenoids isolated from Nardostachys jatamansi

Cited by 31 publications

References 28 publications

Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi

Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi

Anti‐inflammatory effects of chemical components from Ginkgo biloba L. male flowers on lipopolysaccharide‐stimulated RAW264.7 macrophages

Nardostachys jatamansi (D. Don) DC (Caprifoliaceae)

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