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Planta Medica International Open 2016; 3(03): e55-e59
DOI: 10.1055/s-0042-112226
Letter
Georg Thieme Verlag KG Stuttgart · New York

Naturally Occurring Anti-TB Agents: Isolation, Chemical Transformations and In Vitro Antitubercular Activities of Secondary Metabolites of Rhizomes of Alpinia galanga

Tushar R. Valkute
1   Division of Organic Chemistry, CSIR-National Chemical Laboratory (CSIR-NCL), Pune, India
,
Manisha Arkile
2   Combi-Chem Bioresource Centre, CSIR-National Chemical Laboratory (CSIR-NCL), Pune, India
,
Dhiman Sarkar
2   Combi-Chem Bioresource Centre, CSIR-National Chemical Laboratory (CSIR-NCL), Pune, India
,
Asish K. Bhattacharya
1   Division of Organic Chemistry, CSIR-National Chemical Laboratory (CSIR-NCL), Pune, India
› Author Affiliations
Further Information

Publication History

received 27 April 2016
revised 17 June 2016

accepted 04 July 2016

Publication Date:
15 September 2016 (online)

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Abstract

A bioactivity-guided chemical examination of the acetone extract of the rhizomes of Alpinia galanga led to the isolation of six secondary metabolites, eucalyptol derivative (1) and phenylpropanoids (2–6). The structures of all of the isolated compounds (1–6) were elucidated on the basis of their spectral data. The isolated compounds (1–6) were in vitro assayed against active and dormant phenotypes of Mycobacterium tuberculosis H37Ra, respectively. Interestingly, 1′S-1′-acetoxychavicol acetate (2) showed good antitubercular activities against both active and dormant phenotypes of M. tuberculosis with IC50 values of 1.04 µM and 2.69 µM, respectively. Tsuji-Trost and homodimerization reactions of the active compound (2) respectively resulted in the formation of two analogues, 7 and 8. Both of these synthesized analogues were also found to be active in vitro against active [IC50 s of 3.24 and 3.87 µM, respectively, for compounds 7 and 8] and dormant [IC50 s of 8.33 and 2.41 µM, respectively, for compounds 7 and 8] phenotypes of M. tuberculosis H37Ra, respectively.

Key words

Alpinia galanga - Zingiberaceae - phenyl propanoids - natural products - antitubercular activity

Supporting Information

 

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