New Serratene Triterpenoids from Palhinhaea cernua and Their Cytotoxic Activity

Abstract

Four new serratene triterpenoids, 3β,21β,24-trihydroxyserrat-14-en-24-(4'-hydroxybenzoate) (1), 3β,21α,24-trihydroxyserrat-14-en-3-(4'-hydroxybenzoate) (2), 3β,14α,15α,21α-tetrahydroxyserrat-14-en-3-(3'-methoxyl-4'-hydroxybenzoate) (3), and 3β,14α,15α,21α-tetrahydroxyserrat-14-en-21-acetyl-3-(4'-hydroxybenzoate) (4), together with two known ones, 5 and 6, were isolated from whole plants of Palhinhaea cernua. The structures of these new compounds were elucidated by spectroscopic methods. All the six compounds were tested for their in vitro cytotoxicity against three human cancer cell lines (K562, SMMC-7721, and SGC7901). Compound 5 showed cytotoxicity against the three test cell lines with IC₅₀ values of 20.3, 34.0, and 22.5 ug/mL, respectively. Compound 1 showed slight cytotoxicity against K562 cell lines with IC₅₀ value of 56.1 ug/mL, while no obvious inhibitory effects were detected for other compounds.

Triterpenoids

“…Lycopodium cernuum). 346 The D:B-friedobaccharane derivatives leonatriol 751 and the corresponding ketone leonatriolone 752 have been isolated from Cassine xylocarpa and Celastrus vulcanicola, respectively. 294 Globostelletins J 753-S 761, from the marine sponge Rhabdastrella globostellata, are isomalabaricanes with cyclopentane side chains.…”

A New Serratane Triterpenoid from Lycopodiella cernua

“…is a synonym of Lycopodiella cernua. Previous phytochemical study of this plant species has led to the isolation of serratane triterpenoids, [2][3][4][5][6] alkaloids, [7][8][9][10][11][12][13] flavonoids, [14] and neolignans. [4] Serratane triterpenoids and lycopodium alkaloids are characteristic components of L. cernua plant.…”

“…Recently, the structural classification, biological activities and hypotheses about biosynthetic pathways of serratane-type triterpenes from Lycopodiaceae family was comprehensively reviewed. [15] As part of our research on novel serratane triterpenoids from L. cernua, [2,6] two serratane triterpenoids, 3β,14α,15α, 21β-tetrahydroxyserrat-15-(3'-methoxyl-4'-hydroxybenzoate) (1), and 16-oxoserrat-14-en-3β,21α-diol (2), were isolated from the whole plant of Lycopodiella cernua (Figure 1). Compound 1 was a new one.…”

“…The 13 C NMR spectra (DEPT) showed signal at δ C 55.8 for a methylene, which was characteristic signal of C-27 in serratane-type triterpenoid. [6] By detailed analysis of the HMBC spectrum of compound 1 and comparison of its NMR data with those of 3β,14α,15α,21α-tetrahydroxyserrat-3-(3′-methoxyl-4′-hydroxybenzoate), [2] the serratane triterpenoid skeleton was assigned as 3,14,15,21-tetrahydroxyserratane. Except 30 carbons signals for a serratane triterpenoid, the remaining signals in the 1 H NMR and 13 C NMR spectra of compound 1 indicated the presence of a 3'-methoxy-4'hydroxybenzoate group through comparing corresponding NMR data with 3β,14α,15α,21α-tetrahydroxyserrat-3-(3'methoxyl-4'-hydroxybenzoate).…”

Palhinosides A–H: Flavone Glucosidic Truxinate Esters with Neuroprotective Activities from Palhinhaea cernua

“…Palhinhaea cernua (family Lycopodiaceae) is widely distributed in southern and eastern China . The whole plants of P. cernua , called “Pu-Di-Wu-Gong” in Chinese, are traditionally used as an herbal medicine for relaxing tendons, healing contusions, and treating rheumatism. , Previous phytochemical investigations of P. cernua indicated the presence of flavones, neolignans, lycopodium alkaloids, and serratene-type triterpenoids. − As part of a search for structurally unique and biologically interesting natural products from plants of the family Lycopodiaceae, ,, the chemical components in the n -BuOH portion of the extract of P. cernua were investigated. As a result, eight new truxinate derivatives, palhinosides A–H ( 1 – 8 ), together with two known compounds, apigenin-7- O -(6″- O - p -coumaroyl)-β- d -glucopyranoside ( 9 ) and methyl 4-hydroxycinnamate ( 10 ), have been isolated.…”