Elsevier

Tetrahedron

Volume 23, Issue 5, May 1967, Pages 2491-2493
Tetrahedron

Terpenoids—CVII: The structure of nardostachone

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Abstract

A new diethenoid, bicyclic ketone, C15H22O, named nardostachone, has been isolated from the roots ofNardostachys jatamansi D.C. On the basis of spectral evidences and its conversion to tetrahydronootkatone on hydrogenation, it has been represented by the stereoformulae I.

References (4)

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Cited by (13)

  • Sesquiterpenoids with various carbocyclic skeletons from Nardostachys chinensis with nitric oxide inhibitory activity

    2021, Phytochemistry Letters
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    The 95% aqueous ethanol extract of the roots and rhizomes of N. chinensis was subjected to column chromatography over macroporous resin, Sephadex LH-20, and C18-ODS and then purified by preparative HPLC to yield 21 sesquiterpenoids (1-21). The known compounds were identified as eudesmane K (4) (Demole and Enggist, 1983), 1-hydroxylaristolone (5) (Chen et al., 2017), debilon (6) (Itokawa et al., 1993), nardostachone (7) (Sastry et al., 1967), 3-Oxokanshone H (8) (Chen et al., 2017), 1(10)-aristolen-2-one (9) (Dellar et al., 1994), (-)-(14β,15β)-aristolone (10) (Furusawa et al., 2006), nardoaristolone B (11) (Liu et al., 2013), kanshone F (12) (Tanitsu et al., 2002), narchinol A (13) (Hikino et al., 1972), desoxo-nachinol (14) (Itokawa et al., 1993), kanshone A (15) (Itokawa et al., 1993), nardosinonediol (16) (Itokawa et al., 1993), ardosinone (17) (Itokawa et al., 1993), nardonoxide (18) (Luo et al., 1987), kanshone E (19) (Anjana et al., 1988), isonardosmone (20) (Anjana et al., 1988), and kanshone N (21) (Yoon et al., 2018) (Fig. S1), based on comparison of their spectroscopic data with the literature values. The structures of the new compounds 1-3 were elucidated by analysis of HRESIMS, UV, IR, 1D/2D NMR, and circular dichroism data.

  • Nardostachys jatamansi (D.Don) DC.: An invaluable and constantly dwindling resource of the Himalayas

    2020, South African Journal of Botany
    Citation Excerpt :

    N. jatamansi rhizomes are extensively exploited for the preparation of drugs due to the presence of biologically active and industrially important phytochemicals such as coumarins, alkaloids, lignans, neoloignans, sesquiterpenes, sesquiterpenoids and their derivatives, with a wide range of biological properties (Table 6) (Bagchi et al., 1990; 1991a, b; Chatterjee et al., 2005; Saroya, 2011; Purnima et al., 2015). Other major compounds also present in underground tissues include actinidine (alkaloid), jatamansin and jatamansinol (coumarins), nardostachone, valeranone, jatamansinone, nardosinone, jatamol A and jatamol B (sesquiterpenoids) (Zinzius, 1961; Biswas, 1963; Sastry et al., 1967; Bagchi et al., 1991b; Singh et al., 2013; Monga and Kumar, 2013; Bose et al., 2019; Dhiman and Bhattacharyya, 2020). Some important phytochemicals derived from N. jatamansi are listed in Fig 4.

  • Nardostachys jatamansi (D.Don) DC.-Challenges and opportunities of harnessing the untapped medicinal plant from the Himalayas

    2020, Journal of Ethnopharmacology
    Citation Excerpt :

    Jatamanshic acid, a new bi-cyclic sesquiterpene was also isolated and its chemical structure was established on the basis of chemical degradation, NMR, IR and UV absorption patterns (Chaudhry et al., 1957). Calarenol, a monoethynoid tricyclic tertiary alcohol (C15H24O), nardostachone - a ketonic compound having the molecular formula, C15H22O (Sastry et al., 1967), spirojatamol - a sesquiterpenoid (Bagchi et al., 1990) and nardostachysin - a terpenoid ester (Chatterjee et al., 2000) are the other compounds reported from the plant. A sesquiterpene acid, nardin, and a pyranocoumarin were also isolated from the rhizomes, and their chemical structures established using spectral studies (Chatterjee et al., 2005).

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