16-O-caffeoyl-16-hydroxylhexadecanoic acid, a medicinal plant-derived phenylpropanoid, induces apoptosis in human hepatocarcinoma cells through ROS-dependent endoplasmic reticulum stress.

Background: Hepatocellular carcinoma (HCC) is the leading cause of cancer death, and novel chemotherapeutic drugs for treating HCC are urgently needed. 16-O-caffeoyl-16-hydroxylhexadecanoic acid (CHHA) is a new phenylpropanoid isolated by our group from Euphorbia nematocypha which is commonly used to treat solid tumors. However, the underlying mechanisms responsible for the CHHA-induced apoptosis in cancer cells, particularly in HCC, remain unknown.

Chemical Constituents of the Aerial Parts of Euphorbia nematocypha.

Chemical constituents of the dried aerial parts of Euphorbia nematocypha were investigated. A new oleanane triterpenoid, trans, trans-2',4'- hexadienedioicacid-1'-β-amyrin ester (1), together with, β-amyrin (2), β-amyrin acetate (3), betulinic acid (4), ellagic acid (5), oleanolic acid (6), β-sitosterol (7), kaempferol (8), quercetin (9), lupeol (10) and pseudo-taraxasterol (11) were isolated from the methylene chloride extract. Their structures were elucidated on the basis of extensive spectroscopic (1D- & 2D-NMR) and ESI-MS analysis and comparison with data reported in the literature.

A new phenylpropanoid from the roots of Euphorbia nematocypha.

A phytochemical investigation of the ethanolic extracts of the dried roots of Euphorbia nematocypha resulted in the isolation of a new phenylpropanoid, 16-O-caffeoyl-16-hydroxylhexadecanoic acid (1), together with 23 known compounds (2-24). Their structures were elucidated on the basis of spectroscopic data. Compound 1 was first to be isolated as a caffeic acyl long chain alkyl acid from the family Euphorbiaceae.