Synthesis of novel antimicrobial aryl himachalene derivatives from naturally occurring himachalenes

Authors

  • Abha Chaudhary Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Swati Sood Plant Pathology and Microbiology Laboratory, Hill Area Tea Science Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Pralay Das Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Pushpinder Kaur Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Isha Mahajan Plant Pathology and Microbiology Laboratory, Hill Area Tea Science Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Arvind Gulati Plant Pathology and Microbiology Laboratory, Hill Area Tea Science Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India
  • Bikram Singh Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, P.O. Box 6, Palampur (H.P.)-176 061, India

Keywords:

himachalenes, Cedrus deodara, essential oil, antimicrobial activity

Abstract

Five new 2,9,9-trimethyl-6,7,8,9-tetrahydro-benzocyclohepten-5-ylidene-amine derivatives (16a-16e) were synthesized from α-dehydro-ar-himachalene (11) that was originally prepared from an isomeric mixture of α, β and γ himachalenes (10), the abundant sesquiterpenes of Cedrus deodara essential oil. In addition, different aryl himachalenes derivatives (9, 12, 14 and 15) were also formed from 11. The structures of the synthesized compounds were confirmed on the basis of their NMR, IR and mass spectral data. The prepared compounds were tested against a group of sixteen organisms including gram positive and gram negative bacterial and fungal strains. The introduction of a series of substituted imine groups into aryl himachalenes at 5th position (16a-16e) enhanced antimicrobial activity as compared to the aromatized derivatives (9, 12, 14 and 15) against gram-positive bacteria Bacillus subtilis, Micrococcus luteus and Staphylococcus aureus, and mycotoxigenic fungi Aspergillus parasiticus, A. ochraceous and A. sydowii. graphical Abstract, Figure 1

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Published

2014-11-18

How to Cite

Chaudhary, A., Sood, S., Das, P., Kaur, P., Mahajan, I., Gulati, A., & Singh, B. (2014). Synthesis of novel antimicrobial aryl himachalene derivatives from naturally occurring himachalenes. EXCLI Journal, 13, 1216–1225. Retrieved from https://www.excli.de/excli/article/view/774

Issue

Vol. 13 (2014)

Section

Original articles

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