In addition to 16 known triterpenoids, eight new compounds were isolated from various Lycopodium plants, and their structures were established by spectroscopic evidence and by chemical correlation with the known specimens. For the latter purpose, two new methods-acetonide formation under forced condition and degradation of monosulphonate-played important role (see text). Thus, lycoplanatol (isolated from L. complanatum, L. annatinum, and L. alpinum(?)), epilycoplanatol (isolated from L. clavatum), and lycocryptol (isolated from L. cryptomerium) were shown to be serrat-14-en-3β,21β,24,30-tetraol(1), serrat-14-en-3α,21β,24,30-tetraol(2), and serrat-14-en-3β,21α,24,30-tetraol(3), respectively. New triterpenoid-acids, lycernuic acid-A and -B (both isolated from L. cernuum) were settled to be 3β,21β-dihydroxyserrat-14-en-24-oic acid(4) and 3β,21β,30-trihydroxyserrat-14-en-24-oic acid(5) respectively. Minor triterpenoids of L. clavatum, lyclaninol and lyclanitin (isolated also from L. complanatum) were proved to be serrat-14-en-3α,20β,21β,24-tetraol(6) and serrat-14-en-3α,20β,21β,24,30-pentaol(7) respectively. The most highly oxygenated specimen, 16-oxolyclanitin (isolated from L. clavatum) was shown to be 16-oxoserrat-14-en-3α,20β,21β,24, 30-pentaol(8) (hydroxy lycoclavanin).
