Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Abstract

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

Plant-Derived Nutraceuticals and Immune System Modulation: An Evidence-Based Overview

“…Some labdane diterpenoids, isolated from plant matrix, include the following: andrographolide ( Figure 9 ) (from Andrographis paniculata (Burm.f.) Nees) [ 211 ], labda-8(17), 12-diene-15, 16-dial (from Curcuma amada Roxb) [ 212 ], podoimbricatin C (a 12,17-cyclo-labdane diterpenoid from Dacrycarpus imbricatus (Blume) de Laub) [ 213 ] chapecoderins A-C (from Echinodorus macrophyllus (Kunth) Micheli), [ 214 ], (4R,5S,9S,10R)-13-des-ethyl-13-oxolabda-8(17),11E-dien-19-oic acid (from Juniperus oblonga M. Bieb) [ 215 ], leoheteronin D and leojaponin A (from Leonurus japonicus Houtt) [ 216 ], marrubasch A-F and marrubenol (from Marrubium aschersonii P.Magnus), marrulibanoside (from Marrubium globosum Boiss. and Balansa) [ 217 ], vitexlimolides A–C (from Vitex limonifolia Wall.…”

“…Compounds from J. oblonga have shown anti-tumor effects, through moderate cytotoxicity against human tumor cell lines obtained from various human tissues, including: hepatocellular carcinoma (HepG2), breast cancer (MCF-7), and cervical carcinoma cancer (HeLa) [ 215 ]. The berries from J. oblonga also have antimicrobial activity and anti-inflammatory effects.…”

Advances on Natural Abietane, Labdane and Clerodane Diterpenes as Anti-Cancer Agents: Sources and Mechanisms of Action

“…A recent work led to the isolation of a new labdane diterpene, (1R,4aS,5R,8aS)-1,4a-dimethyl-5-[(1E)-3-oxobut-1-en-1-yl]decahydronaphthalene-1-carboxylic acid ( 23 ) ( Figure 4 ), from Juniperus oblonga (Cupressaceae) together with other known compounds [ 121 ]. Isolated compounds were assessed for their cytotoxic effects against, MCF-7, HeLa, and HepG2 human cancer cell lines.…”