Podocarpus Nagilactones

Wih respect to the insecticide activity, Podocarpus macrophyllus is widely known in Japan for its resistance to termite attack. Saeki disclosed in 1970 that the termiticidal activity is entirely due to inumakilactone A (28) and another unidentified compound of similar structure, the former being more active [70]. This second compound was later reported to be nagilactone D (4). 

Nagilactones as an antifeedant from Podocarpus tiagi for herbivorous mammals. Hayashi, Y. Kim, Y. Hayashi, Y. Chairul. BioscL Biotech. Biochem. 1992, 56, 1302-1303. 

Nagilactones from Podocarpus nagi and their effects on the feeding and growth of tobacco budworm. Zhang, M. Ying, B. P. Kubo, I. J. Nat. Prod. 1992, 55, 1057-1062. 

Nagilactone C from Podocarpus purdieanus Wenkert, E. Chang, C.J. Phytochemistry 1974,13,1991. 

Insect-control chemicals from plants. Nagilactone C, a toxic substance from the leaves of Podocarpus nivalis and Podocarpus hallii. Russell, G.B Fenemore, P.G. Singh, P. Aust. J. Biol. Scl 1972,25,1025-1029. 

The plant growth inhibitor nagilactone does not work directly in a stabilized Podocarpus nagi forest. Ohmae, Y. Shibata, K. Yamakura, T. J. Chem. Ecol., 1999,25, 969-984. 

Total synthesis of nagilactone F, a biologically active norditerpenoid dilactone isolated from Podocarpus nagi. Hayashi, Y. Matsumoto, T. Nishizawa, M. Togami, M. Hyono, T. Nishikawa, N. Uemura, M. J. Org. Chem. 1982, 47, 3428-3433. 

Two further cytotoxic nor-diterpenoid dilactones, (73) and (74), have been isolated " from Podocarpus nagi. Nagilactone F (75) has been synthesized from podocarpic acid. Two unusual diterpenoids, hispanonic acid (76) and his-paninic acid (77), both of which possess a seven-membered ring c, have been isolated from Ballota hispanica (Labiatae). Some naphthalenic nor-diterpenoids [e.g. (78)] with the cleistanthane skeleton have been isolated from Vellozia stipitata and V. declinans. 

Ponolactone A and its glucoside are inhibitors of expansion and mitosis in plant cells. Ponolactone A was isolated from Podocarpus nakai and shown to have the structure (25) by a detailed study of its n.m.r. spectrum, utilizing the nuclear Overhauser effect. The C-14 epimer was prepared from the C-7 acetate of nagilactone. Inumakilactone B was isolated" from Podocarpus macrophyllus and shown by a combination of chemical and spectroscopic evidence to have the structure (26). Inumakilactone C was tentatively assigned structure (27) on the basis of spectroscopic evidence. 

Activity-directed fractionation of Podocarpus milanjianus Rendle yielded a series of norditerpenoid dilactones. Four of the seven actives, nagilactones F and G, and milanjilactones A and B, were cytotoxic but not active in vivo. The P388 in vivo actives were isolated and identified as... 

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