Cytotoxic Serratane Triterpenes fromDiphasiastrum complanatumwith a Hydroxy Group at C-27

Abstract

Four serratane-type triterpenes ( 1- 4) were isolated from D. COMPLANATUM. Their chemical structures were elucidated as 14alpha,15alpha,20beta,21beta,24,27alpha,29-heptahydroxyserrat-3-one ( 1), 3beta,14alpha,15alpha,20beta,21beta,24,27alpha,29-octahydroxyserratane ( 2), 3alpha,14alpha,20beta,21beta,24,27alpha,29-heptahydroxyserratane ( 3) and 3beta,14alpha,21beta,24,27alpha-pentahydroxyl-serratane-29-yl ( E)- P-coumarate ( 4) by spectroscopic methods (MS, 1D and 2D NMR) and X-ray crystallography. Interestingly, the most characteristic methylene (C-27) of the serratane ring C was oxidized to a methine. Compound 4 showed significant cytotoxic activity against the human leukemia K562/S and the doxorubicin-resistant K562/R cell lines, but the other compounds were inactive.

Triterpenoids

“…298 The structure of duboscic acid 535 was confirmed by X-ray analysis. 301 The structure of complanatumol A 542 was confirmed by X-ray analysis. 299 21b-Hydroxychiratan-22one 541 is a constituent of the rhizomes of Drynaria fortunei.…”

“…300 Complanatumols A 542-D 545, from Diphasiastrum complanatum, are the first examples of 27-hydroxy serratane triterpeneoids. 301 The structure of complanatumol A 542 was confirmed by X-ray analysis. The serratane acetate 546 has been reported from Lycopodium obscurum 302 and the noronocerane 547 is from the same species.…”

Phlegmacaritones A and B, a Pair of Serratane-Related Triterpenoid Epimers with an Unprecedented Carbon Skeleton from Phlegmariurus carinatus

“…Serratane triterpenoids are a group of fused-pentacyclic triterpenes containing an unusual seven-membered central ring C and oxygenated methines at C-3 and C-21. Previous pharmacological studies suggested that they are potential cytotoxic − and cancer chemopreventive − agents.…”

New Serratene Triterpenoids from Palhinhaea cernua and Their Cytotoxic Activity

“…This group of triterpenoids was mainly discovered from plants belonging to the Pinaceae, Huperziaceae, and Lycopodiaceae families, together with a few other plant species, e.g., Primula rosea [4], Imperata cylindrical [5], Polypodium vulgare [6], and Lemmaphyllum microphyllum [7]. Recently, we have studied several plants of the Lycopodiaceae family and revealed some new serratene-type triterpenoids from those species [8][9][10][11]. Palhinhaea cernua, a typical pteridophyte of the Lycopodiaceae family, has been used as a traditional Chinese folk medicine for centuries to treat rheumatism, whooping coughs, hepatitis, nephrolith, and others [12].…”