Epoxysesquithujene, a novel sesquiterpenoid from Valeriana hardwickii var. hardwickii

Mathela, C. S.; Chanotiya, Chandan Singh; Sati, S. C.; Sammal, S. S.; Wray, Victor

doi:10.1016/j.fitote.2007.01.005

Cited by 11 publications

(12 citation statements)

References 6 publications

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“…hardwickii, a rare aromatic Himalayan herb used in traditional medicine. [44] Interestingly, this compound represents about 50 % of the essential oil extracted from this plant but had previously never been found in any other Valeriana sp. While its constitution could be firmly established, the stereochemical relationship between the cyclopropane, the methyl branch and the remote epoxide remained undetermined.…”

Section: Resultsmentioning

confidence: 88%

“…While its constitution could be firmly established, the stereochemical relationship between the cyclopropane, the methyl branch and the remote epoxide remained undetermined. [44] To answer this question, we first prepared a mixture of all four possible isomers 42-45 by epoxidation of a 1:1 mixture of 5 and 6 with mCPBA followed by conversion of the ketone groups in 41 a-d into the corresponding endocyclic olefins (Scheme 14). Gratifyingly, the 13 C NMR spectra of 42-45 are sufficiently resolved such that all four compounds are discernable in the mixture.…”

Section: Resultsmentioning

confidence: 99%

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A Gold‐Catalyzed Entry into the Sesquisabinene and Sesquithujene Families of Terpenoids and Formal Total Syntheses of Cedrene and Cedrol

Fürstner

Schlecker

2008

Chemistry A European J

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A concise entry into the bicyclic cyclopropyl ketone derivatives 5 and 6 by way of a gold-catalyzed Ohloff-Rautenstrauch-type enyne cycloisomerization is described. The required substrates were prepared by an asymmetric addition of the branched allylzinc reagent 21 to the alkynyl aldehyde 17 mediated by the deprotonated bisoxazoline (BOX) ligand 22. Compounds 5 and 6 were then converted into a host of different members of the sesquisabina- and sesquithuja families of terpenoids, inter alia with the aid of iron-catalyzed cross-coupling reactions. As the relative and absolute configuration of 5 and 6 could be unambiguously established, the synthetic samples allowed the previously unknown stereostructures of various such terpenoids to be unraveled, including cis-sesquisabinene hydrate (33), 7-epi-sesquithujene (36), sesquisabinene B (37) and epoxy-sesquithujene (45). Moreover, the preparation of 6 also constitutes a formal total synthesis of cedrene (11) and cedrol (12).

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

A Gold‐Catalyzed Entry into the Sesquisabinene and Sesquithujene Families of Terpenoids and Formal Total Syntheses of Cedrene and Cedrol

Fürstner

Schlecker

2008

Chemistry A European J

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“…Phytochemical investigations have shown the Valeriana hardwickii rhizome to possess essential oil [6] constituting α -kessyl acetate, valeracetate, 8-epikessyl glycol diacetate, maaliol, kessanyl acetate [8], bornyl acetate, methyl linoleate, cuparene, α -cedrene [9] and epoxysesquithujene [10] among terpenoids.…”

Section: Introductionmentioning

confidence: 99%

Antispasmodic and Antidiarrheal Activities of Valeriana hardwickii Wall. Rhizome Are Putatively Mediated through Calcium Channel Blockade

Bashir

Memon

Gilani

2011

Evidence-Based Complementary and Alternative Medicine

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Valeriana hardwickii is indigenous to Pakistan, Burma and Ceylon, where it is traditionally being used as an antispasmodic and antidiarrheal, besides its culinary use as spice. The aim of this paper was to provide pharmacological validation to these medicinal uses. The crude aqueous-methanolic extract of Valeriana hardwickii rhizome (Vh.Cr) was studied on isolated rabbit jejunum and castor oil-induced diarrhea in mice for spasmolytic and antidiarrheal properties, respectively. Vh.Cr caused concentration-dependent (0.01–1 mg/mL) relaxation of spontaneous contractions in isolated rabbit jejunum and inhibited K+-induced contractions (0.01–0.3 mg/mL), similar to verapamil, suggestive of calcium channel blockade (CCB). The CCB effect was confirmed when pretreatment of the jejunum preparations with Vh.Cr produced a concentration-dependent (0.03–0.1 mg/mL) rightward shift in the Ca++ concentration-response curves, as caused by verapamil. Vh.Cr exhibited dose-dependent (100–300 mg/kg) protection against castor oil-induced diarrhea in mice. Loperamide, a standard antidiarrheal drug, similarly prevented the diarrhea. These data indicate the presence of CCB effect in the extract of Valeriana hardwickii rhizome, possibly mediating its antispasmodic and antidiarrheal activities and provide a scientific base for its traditional use in hyperactive gut disorders.

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“…Epoxysesquithujene, a novel sesquiterpenoid, was isolated from V. hardwickii var. hardwickii [280]. The main constituents of root oil of V. pyrolaefolia were valeranone and patchouli alcohol [473].…”

Section: The Genus Valerianamentioning

confidence: 99%

Himalayan Aromatic Medicinal Plants: A Review of their Ethnopharmacology, Volatile Phytochemistry, and Biological Activities

Joshi¹,

2016

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Aromatic plants have played key roles in the lives of tribal peoples living in the Himalaya by providing products for both food and medicine. This review presents a summary of aromatic medicinal plants from the Indian Himalaya, Nepal, and Bhutan, focusing on plant species for which volatile compositions have been described. The review summarizes 116 aromatic plant species distributed over 26 families.

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Epoxysesquithujene, a novel sesquiterpenoid from Valeriana hardwickii var. hardwickii

Cited by 11 publications

References 6 publications

A Gold‐Catalyzed Entry into the Sesquisabinene and Sesquithujene Families of Terpenoids and Formal Total Syntheses of Cedrene and Cedrol

A Gold‐Catalyzed Entry into the Sesquisabinene and Sesquithujene Families of Terpenoids and Formal Total Syntheses of Cedrene and Cedrol

Antispasmodic and Antidiarrheal Activities of Valeriana hardwickii Wall. Rhizome Are Putatively Mediated through Calcium Channel Blockade

Himalayan Aromatic Medicinal Plants: A Review of their Ethnopharmacology, Volatile Phytochemistry, and Biological Activities

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