Lycophlegmariols A–D: Cytotoxic serratene triterpenoids from the club moss Lycopodium phlegmaria L.

Phytochemicals from fern species: potential for medicine applications

“…Serratenes are a group of naturally occurring pentacyclic triterpenoids with seven tertiary methyl groups and a seven-membered C ring (instead of eight methyl groups and a sixmembered C ring as found in common pentacyclic triterpenoids), usually with a double bond between C-14 and C-15, and oxygen functionalities at both C-3 and C-21. They have been detected in fern allies and conifers (Pinaceae) (Wittayalai et al 2012;Tanaka et al 2004;Zhou et al 2003a, b).…”

“…longipetiolata (Spring) Ching (Pei et al 2011) 21-episerratenediol-3-acetate H. serrata ), H. kunmingensis , H. miyoshiana (Tong et al 2003b) 21α-hydroxy-serrat-14-en-3β-yl dihydrocoumarate H. serrata 21α-hydroxy-serrat-14-en-3β-yl p-dihydrocaffeate H. serrata 21α-hydroxy-serrat-14-en-3β-yl propanedioic acid monoester H. serrata 21β-hydroxyserrat-14-en-3α-ol H. serrata , H. phlegmaria (=L. phlegmaria) (Wittayalai et al 2012) 2lα-hydroxy-serrat-14-en-3β-yl-acetate H. miyoshiana (Tong et al 2003b) 2lβ-hydroxy-serrat-14-en-3β-yl-acetate H. miyoshiana (Tong et al 2003b), H. phlegmaria (Wittayalai et al 2012) 3-O-acetyltohogenol H. miyoshiana (Tong et al 2003a, b) 3α,21β,24-trihydroxy-serrat-14-en-16-one H. serrata , H. kunmingensis , H. serrata (thunb.) Trev.f.…”

“…Finally, five new serratene-type triterpenes, lycophlegmarin (Shi et al 2005) and lycophlegmariol A-D, along with an abietane-type diterpene have been isolated from the methanol extract of the club moss H. phlegmaria (=L. phlegmaria L.) (Wittayalai et al 2012).…”

Chemical Constituents of Plants from the Genus Phlegmariurus

“…Their structures are shown below, and their names and the corresponding plant sources are listed in the Table. As it can be seen, alkaloids and serratane‐type triterpenoids are the dominant chemical constituents in the plants of the genus Phlegmariurus .…”

“…Lycophlegmarin ( 86 ) exhibited modest growth inhibitory activity in vitro against human hepatoma (BEL‐7402) cells, but showed no cytotoxicity against human leukemia (HL‐60) and human lung adenocarcinoma (A‐549) cell lines . Lycophlegmariols B ( 78 ), D ( 87 ), and 21‐episerratenediol ( 62 ) showed inhibitory effects against MOLT‐3 acute lymphoblastic leukemia (T‐lymphoblast) with IC 50 of 14.7, 3.0, and 2.9 μ m , respectively . Hupermine A ( 58 ) showed weak cell growth inhibitory activity against HL‐60 cells ( IC 50 39 μ m ) .…”