Nardoaristolone B

Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi.[Pubmed: 30227591]

Molecules. 2018 Sep 17;23(9). pii: E2367.

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

Org Lett. 2014 Aug 15;16(16):4252-5.

Total synthesis of (±)-nardoaristolone B and its analogues.[Pubmed: 25080212]

The first total synthesis of Nardoaristolone B, a nor-sesquiterpenoid with an unusual fused ring system and having protective effects on the injury of neonatal rat cardiomyocytes, has been accomplished.
METHODS AND RESULTS:
Stereoselective synthesis of its novel analogues inlcuding exo-cyclopropyl ring fusion is also part of this disclosure. In addition, an alternate and more efficient one-step method to make a 3/5/6 tricyclic ring system using the Robinson annulation method has been developed toward the generation of a library of compounds around this skeleton.

Org Lett. 2013 Mar 1;15(5):1000-3.

Nardoaristolones A and B, two terpenoids with unusual skeletons from Nardostachys chinensis Batal.[Pubmed: 23394111]

METHODS AND RESULTS:
Nardoaristolone A and Nardoaristolone B, two novel terpenoids derived from the aristolane-type sesquiterpenoid, were isolated from the underground parts of Nardostachys chinensis Batal.
CONCLUSIONS:
Nardoaristolone A is the first reported aristolane-chalcone derivative, while Nardoaristolone B possesses a nor-aristolane sesquiterpenoid skeleton with an unusual 3/5/6 tricyclic ring system. Their structures were elucidated by spectroscopic measurements, and the absolute configurations were established by single-crystal X-ray diffraction experiments.

ACS Omega, 2019, 4(1):2188-2195.

Insect-Repellent and Mosquitocidal Effects of Noreremophilane- and Nardoaristolone-Based Compounds[Reference: WebLink]

METHODS AND RESULTS:
Here, we disclose novel mosquito-repellentsynthetic hydrindanesbased on noreremophilanes and Nardoaristolone B which show increasedactivity against adult females of Aedes aegypti.The noreremophilanes and Nardoaristolone B with hydrindane skeletonare structurally related to nootkatone with decalin skeleton, a well-studiednatural product extracted from a grape fruit.
CONCLUSIONS:
Out of our library ofcompounds synthesized based on the noreremophilanes and nardoaristoloneB scaffolds, NDS-100598 (compound 20) exhibits higherrepellent and knock-down effects at a very low concentration (0.25mg/cm²), while a few analogues showed considerably enhancedactivity compared to racemic nootkatone. This is the first reportdocumenting insect-repellent and knock-down activity of the noreremophilanesclass of compounds.