Published on Web 02/23/2012
r2012 American Chemical Society
Vol. 14, No. 5
Tripartilactam, a Cyclobutane-Bearing
Tricyclic Lactam from a Streptomyces sp.
in a Dung Beetle’s Brood Ball
Seon-Hui Park,†Kyuho Moon,†Hea-Son Bang,§Seong-Hwan Kim,†Dong-Gyu Kim,†
Jongheon Shin,†and Dong-Chan Oh*,†
Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea, Department of Agricultural
Environment, National Academy of Agricultural Science, Suwon 441-707, Republic of
Korea, and Department of Agricultural Biotechnology, College of Agriculture and Life
Science, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-921, Republic
Received January 16, 2012
Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated
spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Naþ/KþATPase inhibitor (IC50= 16.6 μg/mL).
Diverse insect ecosystems have recently drawn signifi-
cant attention as a new source of natural products with
pharmaceutical potential.1This attention is partly due to
secondary metabolites with selective activity, as shown in
the ecologically well-defined symbiotic systems of the
southern pine beetle (Dendroctonus frontalis)2and the
the potential of microorganisms discovered in insect eco-
communities are unexplored niches. The recent study of
the mud dauber, Sceliphron caementarium, led to the
discovery of a novel antifungal polyene macrocyclic lac-
tam, sceiliphrolactam, although its ecological role has not
been completely determined.4Biomedical investigation of
the gut microbiota of a mantis isolated a fungal species,
Daldinia eschscholzii, that produces new immunosuppres-
sive polyketides known as dalesconols.5Even a fungal
strain isolated from the nest of the fungus-growing
ant (A. dentigerum) yielded a new polyketide
The dung beetle, Copris tripartitus, is a soil-dwelling
insect, the life cycle of which is tightly dependent on the
feces of herbivores.7The brood balls mainly composed of
feces are expected to harbor extensive microbial commu-
nities. Our recentselectiveisolation ofactinomycetes from
†Natural Products Research Institute, College of Pharmacy, Seoul Na-
§National Academy of Agricultural Science.
Department of Agricultural Biotechnology, College of Agriculture and
Life Science, Seoul National University.
Bode, H. B. Angew. Chem., Int. Ed. 2009, 48, 6394. (c) Kaltenpoth, M.
Trends Microbiol. 2009, 17, 529.
(2) (a) Scott, J. J.; Oh, D.-C.; Yuceer, M. C.; Klepzig, K. D.; Clardy,
J.; Currie, C. R. Science2008, 322, 63. (b) Oh, D.-C.; Scott, J. J.; Currie,
C. R.; Clardy, J. Org. Lett. 2009, 11, 633.
2009, 5, 391.
(4) (a) Oh, D.-C.; Poulsen, M.; Currie, C. R.; Clardy, J. Org. Lett.
One 2011, 6, e16763.
(5) Zhang, Y. L.; Ge, H. M.; Zhao, W.; Dong, H.; Xu, Q.; Li, S. H.;
(6) Freinkman, E.; Oh, D.-C.; Scott, J. J.; Currie, C. R.; Clardy, J.
Tetrahedron Lett. 2009, 50, 6834.