Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic dothideomycete sp. LRUB20.
Two new natural products, 2-hydroxymethyl-3-methylcyclopent-2-enone (1) (synthetically known) and cis-2-hydroxymethyl-3-methylcyclopentanone (2), and a known compound, asterric acid (3), were isolated from the endophytic fungus mitosporic Dothideomycete sp. LRUB20, which was isolated from the stem of the Thai medicinal plant Leea rubra. Compound 2 was separated and identified in the form of its 2,4-dinitrophenylhydrazone derivative (5). Compounds 1, 3, and hydrazone 5 exhibited mild antimycobacterial activity, both with MIC values of 200 microg/mL. Compounds 1, 3, and 4 were inactive (at 50 microg/mL) toward Vero, KB, NCI-H187, and BC cell lines. Hydrazone 5 showed only mild cytotoxicity against the Vero cell line with an IC(50) value of 21.7 microg/mL; however, it was inactive toward KB, NCI-H187, and BC cell lines. Endophytic fungi may be a source for the production of building blocks for organic syntheses.
Chomcheon
Porntep
P
Program of Biotechnology and Department of Chemistry, Faculty of Science, and Department of Microbiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Thailand.
Sriubolmas
Nongluksna
N
Wiyakrutta
Suthep
S
Ngamrojanavanich
Nattaya
N
Chaichit
Narongsak
N
Mahidol
Chulabhorn
C
Ruchirawat
Somsak
S
Kittakoop
Prasat
P
D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D002522:Chlorocebus aethiops; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D018547:Plant Stems / Q000382:microbiology; D010946:Plants, Medicinal / Q000382:microbiology*; D013785:Thailand; D014709:Vero Cells
C514408:2-hydroxymethyl-3-methylcyclopent-2-enone; D003517:Cyclopentanes; C013905:cyclopentenone