A naturally occurring naringenin derivative exerts potent bone anabolic effects by mimicking oestrogen action on osteoblasts

Br J Pharmacol. 2012 Mar;165(5):1526-42. doi: 10.1111/j.1476-5381.2011.01637.x.

Abstract

Background and purpose: Naringenin and its derivatives have been assessed in bone health for their oestrogen-'like' effects but low bioavailability impedes clinical potential. This study was aimed at finding a potent form of naringenin with osteogenic action.

Experimental approach: Osteoblast cultures were harvested from mouse calvaria to study differentiation by naringenin, isosakuranetin, poncirin, phloretin and naringenin-6-C-glucoside (NCG). Balb/cByJ ovariectomized (OVx) mice without or with osteopenia were given naringenin, NCG, 17β-oestradiol (E2) or parathyroid hormone (PTH). Efficacy was evaluated by bone microarchitecture using microcomputed tomography and determination of new bone formation by fluorescent labelling of bone. Plasma levels of NCG and naringenin were determined by HPLC.

Key results: NCG stimulated osteoblast differentiation more potently than naringenin, while isosakuranetin, poncirin or phloretin had no effect. NCG had better oral bioavailability than naringenin. NCG increased the mRNA levels of oestrogen receptors (ERs) and bone morphogenetic protein (an ER responsive gene) in vivo, more than naringenin. In OVx mice, NCG treatment in a preventive protocol increased bone formation rate (BFR) and improved trabecular microarchitecture more than naringenin or E2. In osteopenic mice, NCG but not naringenin, in a therapeutic protocol, increased BFR and improved trabecular microarchitecture, comparable with effects of PTH treatment. Stimulatory effects of NCG on osteoblasts were abolished by an ER antagonist. NCG transactivated ERβ but not ERα. NCG exhibited no uterine oestrogenicity unlike naringenin.

Conclusions and implications: NCG is a potent derivative of naringenin that has bone anabolic action through the activation of osteoblast ERs and exhibited substantial oral bioavailability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anabolic Agents / pharmacology*
  • Animals
  • Biological Availability
  • Body Weight / drug effects
  • Bone Diseases, Metabolic / genetics
  • Bone Diseases, Metabolic / metabolism
  • Bone Morphogenetic Proteins / metabolism
  • Cell Differentiation / drug effects
  • Cell Differentiation / genetics
  • Estrogens / metabolism
  • Estrogens / pharmacology*
  • Female
  • Flavanones / pharmacology*
  • Flavonoids / pharmacology
  • Glucosides / pharmacology
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Osteoblasts / drug effects*
  • Osteoblasts / metabolism
  • Osteoblasts / physiology
  • Osteogenesis / drug effects*
  • Osteogenesis / physiology
  • Ovariectomy
  • Parathyroid Hormone / pharmacology
  • Phloretin / pharmacology
  • Rats
  • Rats, Wistar
  • Receptors, Estrogen / genetics
  • Receptors, Estrogen / metabolism
  • Skull / cytology
  • Skull / drug effects
  • Skull / metabolism

Substances

  • Anabolic Agents
  • Bone Morphogenetic Proteins
  • Estrogens
  • Flavanones
  • Flavonoids
  • Glucosides
  • Parathyroid Hormone
  • Receptors, Estrogen
  • naringenin-6-C-glucoside
  • poncirin
  • naringenin
  • Phloretin
  • isosakuranetin