Functionalized para-substituted benzenes as 1,8-cineole production modulators in an endophytic Nodulisporium species.
A Nodulisporium species (designated Ti-13) was isolated as an endophyte from Cassia fistula. The fungus produces a spectrum of volatile organic compounds (VOCs) that includes ethanol, acetaldehyde and 1,8-cineole as major components. Initial observations of the fungal isolate suggested that reversible attenuation of the organism via removal from the host and successive transfers in pure culture resulted in a 50 % decrease in cineole production unrelated to an overall alteration in fungal growth. A compound (CPM1) was obtained from Betula pendula (silver birch) that increases the production of 1,8-cineole by an attenuated Ti-13 strain to its original level, as measured by a novel bioassay method employing a 1,8-cineole-sensitive fungus (Sclerotinia sclerotiorum). The host plant produces similar compounds possessing this activity. Bioactivity assays with structurally similar compounds such as ferulic acid and gallic acid suggested that the CPM1 does not act as a simple precursor to the biosynthesis of 1,8-cineole. NMR spectroscopy and HPLC-ES-MS indicated that the CPM1 is a para-substituted benzene with alkyl and carboxyl substituents. The VOCs of Ti-13, especially 1,8-cineole, have potential applications in the industrial, fuel and medical fields.
Department of Plant Sciences, Montana State University, and Endophytics LLC, Suite 201, 920 Technology Blvd, Bozeman, MT 59717, USA.
Jared
J
Nigg
Department of Plant Sciences, Montana State University, and Endophytics LLC, Suite 201, 920 Technology Blvd, Bozeman, MT 59717, USA.
Gary
G
Strobel
Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
W Berk
WB
Knighton
Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
Jonathan
J
Hilmer
Department of Plant and Wildlife Sciences, Brigham Young University, Provo, UT 84602, USA.
Brad
B
Geary
Biotechnology Division, Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.
Syed
S
Riyaz-Ul-Hassan
Department of Chemistry, University of Central Florida, 4104 Libra Drive, Orlando, FL 32816, USA.
James K
JK
Harper
Department of Chemistry, University of Central Florida, 4104 Libra Drive, Orlando, FL 32816, USA.
Domenic
D
Valenti
Department of Chemistry, University of Central Florida, 4104 Libra Drive, Orlando, FL 32816, USA.
Yuemin
Y
Wang
D001554:Benzene / Q000737:chemistry* / Q000378:metabolism*; D002366:Cassia / Q000382:microbiology*; D003511:Cyclohexanols / Q000378:metabolism*; D060026:Endophytes / Q000145:classification / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism*; D000077591:Eucalyptol; D008969:Molecular Sequence Data; D015394:Molecular Structure; D039821:Monoterpenes / Q000378:metabolism*; D010802:Phylogeny; D013098:Xylariales / Q000145:classification / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism*
D003511:Cyclohexanols; D039821:Monoterpenes; D001554:Benzene; D000077591:Eucalyptol