Isolation and characterization of isomeric tibetin spiroethers from the roots of Tanacetum dolichophyllum (Kitam.) Kitam

Abstract

The roots of Tanacetum dolichophyllum (Kitam.) Kitam. (syn. Hippolytia dolichophylla (Kitam.) K.Bremer & Humphries) were collected from high altitude area of Munsyari, district Pithoragarh (Uttarakhand, India) yielded essential oil by steam distillation method and the oil was analysed by TLC and GC-MS. The GC-MS analysis of the essential oil sample showed the dominance of two constituents visible in sesquiterpene range. These constituents were isolated by column chromatography. The structures of these compounds were determined on the basis of ¹H-NMR,¹³C NMR, COSY, 135-DEPT, and HRMS (ESI-TOF) spectral data. The two major compounds were identified as isomeric C₁₄-Tibetin spiroethers, namely (E)-2-(2’,4’-heptadiyn-1’-ylidene)-1,6-dioxaspiro[4.4]non-3-ene and (Z)-2-(2’,4’-heptadiyn-1’-ylidene)-1,6-dioxaspiro[4.4]non-3-ene.

Graphical Abstract

Keywords:

• Tanacetum dolichophyllum
• essential oil
• tibetin spiroethers
• NMR data

Acknowledgments

The authors are thankful to the Botanical Survey of India, Dehradun for identification of plant specimen and Dr. C.S. Chanotiya, CIMAP, Lucknow and Advanced Instrumental Research Facility (AIRF), Jawaharlal Nehru University (JNU), New Delhi for GC/MS analysis of oil sample.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This study was supported by University Grants Commission.