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DOI: 10.1055/s-0031-1280264
© Georg Thieme Verlag KG Stuttgart · New York
Antifungal Sesquiterpenes from Cedrus deodara
Publication History
received May 30, 2011
revised September 5, 2011
accepted September 7, 2011
Publication Date:
06 October 2011 (online)
Abstract
Two new sesquiterpenes, (E)-(2S,3S,6R)-atlantone-2,3-diol (1) and (E)-(2S,3S,6S)-atlantone-2,3,6-triol (2), along with two known sesquiterpenes, atlantolone (3) and (E)-α-atlantone (4), were isolated from Cedrus deodara Loud. The structures of the new compounds were elucidated on the basis of UV, IR, NMR, HR-ESI-QTOF-MS, and EI mass spectral studies. The n-hexane and chloroform extracts of sawdust and compounds 3 and 4 from the plant exhibited antifungal activity against Aspergillus flavus, A. niger, A. ochracoeus, A. parasiticus, and A. sydowii. A weak activity was also recorded against A. parasiticus and A. sydowii for compound 1, while Trichophyton rubrum was inhibited by compound 2 and the extracts.
Key words
Cedrus deodara - Pinaceae - sesquiterpenes - atlantone - antifungal activity
References
- 1 Daoubi M, Hernaandez-Galaan R, Benharref A, Collado I G. Screening study of lead compounds for natural product-based fungicides: antifungal activity and biotransformation of 6α,7α-dihydroxy-β-himachalene by Botrytis cinerea. J Agric Food Chem. 2005; 53 6673-6677
- 2 Shah B N, Nayak B S, Seth A K, Jalalpure S S, Patel K N, Patel M A, Mishra A D. Search for medicinal plants as a source of anti-inflammatory and anti-arthritic agents – a review. Pharmacogn Mag. 2006; 2 77-86
- 3 Sharma P R, Shannmugavel M, Saxena A K, Qazi G N. Induction of apoptosis by a synergistic lignan composition from Cedrus deodara in human cancer cells. Phytother Res. 2008; 22 1587-1594
- 4 Narula A P S, Dev S. Studies in sesquiterpenes – LI. β-Himachalene epoxides – stereochemistry and solvolysis. Tetrahedron. 1977; 33 813-816
- 5 Tiwari A K, Srinivas P V, Kumar S P, Rao J M. Free radical scavenging active components from Cedrus deodara. J Agric Food Chem. 2001; 49 4642-4645
- 6 Bhandari P, Kumar N, Singh B, Kaul V K. Cucurbitacins from Bacopa monnieri. Phytochemistry. 2007; 68 1248-1254
- 7 Chaudhary A, Kaur P, Singh B, Pathania V. Chemical composition of hydrodistilled and solvent volatiles extracted from woodchips of Himalayan Cedrus: Cedrus deodara (Roxb.) Loud. Nat Prod Commun. 2009; 4 1257-1260
- 8 Chaudhary A, Sharma P, Nadda G, Tewary D K, Singh B. Chemical composition and larvicidal activities of Cedrus deodara essential oil and its fractions against Plutella xylostella. J Insect Sci. ; accepted
- 9 Werf M J V, Swarts H J, De Bont J A M. Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. Appl Environ Microbiol. 1999; 65 2092-2102
- 10 Demyttenaere J C R, Belleghem K V, Kimpe N D. Biotransfromation of (R)-(+)- and (S)-(−)-limonene by fungi and use of solid phase microextraction for screening. Phytochemistry. 2001; 57 199-208
- 11 Thappa R K, Dhar K L, Atal C K. A new monoterpene triol from Zantwoxylum budrunga. Phytochemistry. 1976; 15 1568
- 12 Kozma E, Cristea I, Muller N. A novel route to trans-epoxidation of terpinen-4-ol. Monatshefte für Chemie. 2004; 135 35-40
- 13 Shankaranarayan R, Krishnappa S, Bisarya S C, Dev S. Studies in sesquiterpenes-LIII deodarone and atlantolone. New sesquiterpenoids from the wood of Cedrus deodara Loud. Tetrahedron. 1977; 33 1201-1205
- 14 Pande B S, Krishnappa S, Bisarya S C, Dev S. Studies in sesquiterpenes-XLVII. Cis and trans-atlantones from Cedrus deodara Loud. Tetrahedron. 1977; 27 841-844
- 15 Crawford R J, Erman W F, Broaddus C D. Metalation of limonene. A novel method for the synthesis of bisabolane sesquiterpenes. J Am Chem Soc. 1972; 94 4298-4306
- 16 De Boer H J, Kool A, Broberg A, Mziray W R, Hedberg I, Levenfors J J. Antifungal and antibacterial activity of some herbal remedies from Tanzania. J Ethnopharmacol. 2005; 96 461-469
- 17 Parveen R, Azmi M A, Tariq R M, Mahmood S M, Hijazi M, Mahmud S, Naqvi S N H. Determination of antifungal activity of Cedrus deodara root oil and its compounds against Candida albicans and Aspergillus fumigatus. Pakistan J Bot. 2010; 42 3645-3649
- 18 Zeng W C, Jia L R, Zhang Y, Cen J Q, Chen X, Gao H, Feng S, Huang Y N. Antibrowning and antimicrobial activities of the water-soluble extract from pine needles of Cedrus deodara. J Food Sci. 2011; 76 318-323
- 19 Cos P, Vlietinck A J, Berghe B V, Maes L. Anti-infective potential of natural products: how to develop a stronger in vitro proof-of-concept. J Ethnopharmacol. 2006; 106 290-302
- 20 Sharma N, Ghosh P, Sharma U K, Sood S, Sinha A K, Gulati A. Microwave-assisted efficient extraction and stability of juglone in different solvents from Juglans regia: Quantification of six phenolic constituents by validated RP-HPLC and evaluation of antimicrobial activity. Anal Lett. 2009; 42 2592-2609
Dr. Bikram Singh
Natural Plant Products Division
CSIR-Institute of Himalayan Bioresource Technology
IHBT Communication No. 2104
Palampur, H. P., 176 061
India
Phone: +91 18 94 23 04 26
Fax: +91 1894 23 04 33
Email: bikramsingh@ihbt.res.in