Nardosinanes

Nardosinanes such as (-)-kanshone A, including some struetural variants, and nar-dosinone, a 1,2-dioxolane (cyclie peroxide) isolated from Nardostachys chinensis (Valerianaceae) formally emerge from eremophilane by migration of the isopropyl-group from C-7 to C-6. 

Bowden, B.F., J.C. Coll, and S.J. Mitchell Studies of Australian Soft Corals. XIX. Two New Sesquiterpenes with the Nardosinane Skeleton from a Paralemnalia Species. Aust. J. Chem. 33, 885 (1980). 

IzAC, R.R., P. Schneider, M. Swain, and W. Fenical New Vorsesquiterpenoids of Apparent Nardosinane Origin from the Pacific Soft-Coral Paralemnalia thyrsoides. Tetrahedron Lett. 23, 817 (1982). 

Australian soft corals. XIX Two new sesquiterpenes with the nardosinane skeleton from a Paralemmdia species. Aust. ]. Chem., 33,885-890. 

Cheng, S.-Y, Lin, E.-H., Huang, J.-S., Wen, Z.-H., and Duh, C.-Y. (2010b) Ylangene-type and nardosinane-type sesquiterpenoids ftom the soft corals Lemnalia Jlava and Paralemnalia thyrsoides. Chem. Pharm. Bull, 58, 381-385. 

Kapojos, M.M., Mangindaan, R.E.P., Nakazawa, T., Oda, T, Ukai, K., and Namikoshi, M. (2008) Three new nardosinane type sesquiterpenes from an Indonesian soft coral Nephthea sp. Chem. Pharm. Bull, 56, 332-334. 

Kel om, A., Brick-Peres, M., and Fernandes, L. (1990) A new nardosinane sesquiterpene from the Brazilian endemic gorgonian PhyUt orgia dilatata. J. Nat. Prod.. 53, 750-752. 

In the order Octocorallia, oxygenated sesquiterpenes are currently known only in the four families of Alcyonacea, Gorgonacea, Stolonifera and Telestacea, the number of publications about them, and thus the number of isolated structures, increasing in this (alphabetical) order. The compotmds show considerable structural variation and many different carbon skeletons, both original and conventional, have been fotmd in several species of these four families. These unusual carbon skeletons may be regarded as speciflc to the family from which they were characterized as, with the exception of nardosinane, none of them seems to have yet been identifled in metabolites of species belonging to another family. Figures 20.20 and 20.23 present these carbon skeletons and illustrate them with some examples. 

Lemnacamol is the first representative of the carbon skeleton of nardosinane. It was discovered in 1975 in the Indo-Pacific species Lemnalia camosa and foimd five years later in the Australian species Pareiylhropodium Julvum, now renamed Rhytisma julvum Julvum (Bowden et al, 1980b). Several other related derivatives of the nor type were discovered later in several species of Lemnalia and Paralem-nalia and in certain species of Gorgonacea (see below). 

The term nardosinane comes from the terrestrial plant Nardostachys chinensis (Valerianaceae). ll,12-Epoxynardosin-l(10)-ene is the first example of nardosinane isolated from a gorgonian (Kelecom et al, 1990). 

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