Isolation and cytotoxicity of triterpenes from the roots of Phyllanthus pulcher Wall. ex Mll. Arg. (Euphorbiaceae)

Abstract

The dried powdered roots of Phyllanthus pulcher Wall. ex Müll. Arg. (Euphorbiaceae), were sequentially extracted with dichloromethane (DCM), ethyl acetate (EtOAc) and methanol (MeOH). The extracts were tested for cytotoxic activity against three human cancer cell lines: MCF-7 (breast), NCI-H460 (lung) and DU-145 (prostate). The DCM extract exhibited the strongest cytotoxic activity compared with EtOAc and MeOH extracts. Hence from the DCM extract, five pentacyclic triterpenes, 3α-acetoxyl-25-hydroxyolean-12-en-28-oic acid (1), glochidone (2), 12(13)-dehydro-3α-acetoxyolean-28-oic acid (3), lupanyl acetate (4) and glochidonol (5) were isolated and identified by spectroscopic analyses ( 1 H NMR, C NMR, FT-IR, UV, DEPT, HMQC, HMBC and HREIMS). This is the first report on the isolation of 4 from a natural source, whereas 1 and 3 have already been isolated from the families Hamamelidaceae and Compositae (Asteraceae), respectively. However this is the first study reporting the presence of 1 and 3 in the Euphorbiaceae family. The isolated tritepenes 1-5 were tested against the three human tumour cell lines as stated above. Only compounds 1 and 5 exhibited cytotoxic activity, 5 being most potent with IC 50 values ranging 7.5-13.4 µg/mL (17.1-30.5 µM).

Triterpenoids and Steroids Isolated from Aerial Parts of Glochidion multiloculare

“…This is the first report of these compounds from G. multiloculare. This work supports the subsumption of Glochidion into Phyllanthus as the compounds reported here, especially glochidonol and glochidone, were also reported in many Phyllanthus species e.g., P. caroliniensis, P. stipulates, P. urinaria, P. fraternus (Catapan et al, 2000) and P. pulcher (Bagalkotkar et al, 2011).…”

The Genus Phyllanthus: An Ethnopharmacological, Phytochemical, and Pharmacological Review

“…In pentacyclic triterpenoids, compounds 15–36, compounds 37–49, and compounds 50–65 are oleanane type, friedelane type, and lupine type, respectively. Glochidone and lupeol are representatives of lupine type triterpenoids, which were suggested to have antitumor activities and mainly isolated from Phyllanthus species [ 68 , 80 , 96 ].…”

“…Different extracts of the plants have been assessed for anticancer effects and the related mechanisms. Cancer cell lines such as NCI-H1703, MDA-MB-231, HeLa, 143B, PC-3, MCF-7, HepG2, A549, SKOV3, and HT-29 were considerably inhibited by P. emblica , P. urinaria , P. polyphyllus , P. watsonii , and P. pulcher [ 57 , 68 , 302 – 309 ]. In addition, P. emblica showed no toxicity to normal cells (MRC5).…”

Isolation and analgesic property of lupeol from Diospyros mespiliformis stem bark

“…Other details were shown in Figures 2 to 4. The assignment of these NMR signals, aided by the UV-visible, IR and DSC data; and comparisons with relevant literatures (Igoli and Alexander, 2008;Bagalkotkar et al, 2011) identified the compound as lup-20(29)-en-3β-ol (lupeol; Figure 5).…”