Two new triterpenoids from the seeds of blackberry (Rubus fructicosus)

Nat Prod Res. 2016;30(8):904-11. doi: 10.1080/14786419.2015.1076820. Epub 2015 Aug 25.

Abstract

Two new ursane-type triterpenoids (1, 2) attached to isopropylidenedioxy group were isolated from the seeds of blackberry (Rubus fructicosus L., Rosaceae) along with two known ursane-type triterpenoids, 2,3-O-isopropylidenyl-2α,3α,19α-trihydroxyurs-12-en-28-oic acid (3) and 1β-hydroxyeuscaphic acid (4). The chemical structures of 1 and 2 were determined to be 2,3-O-isopropylidene-1β,2β,3β,19α-tetrahydroxyurs-12-en-28-oic acid and 1,2-O-isopropylidene-1β,2α,3α,19α-tetrahydroxyurs-12-en-28-oic acid, respectively, based on spectroscopic data. Additionally, their cytotoxic activity towards HL-60 human leukaemia cells was evaluated. Among them, 3 demonstrated a clear cytotoxic activity with 72.8 μM of IC50 value.

Keywords: Rosaceae; Rubus fructicosus; blackberry; cytotoxic activity; isopropylidenedioxy; ursane-type triterpenoid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Plant Extracts / chemistry
  • Rubus / chemistry*
  • Seeds / chemistry*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification

Substances

  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Triterpenes