Oxypaeoniflorin

Oxypaeoniflorin at a Glance

Oxypaeoniflorin is a monoterpene glycoside of peony — one of the pinane-type glycosides that, together with the far more abundant paeoniflorin and its isomer albiflorin, make up the characteristic glycoside fraction of peony root ^{1Reference 1Kaneda M et al. · 1972Chemical studies on the oriental plant drugs—XXXIIIView study →}. Structurally it is paeoniflorin carrying an extra hydroxyl group on its benzoyl ester (a para-hydroxybenzoyl instead of a plain benzoyl), which is exactly why it behaves as a stronger antioxidant than its parent ^{2,3Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}.

As an individual molecule it is thinly studied and honest about it: there are no clinical trials, no animal studies, and essentially no pharmacokinetic data on the isolated compound. Its clearest molecule-specific signal is in-vitro antioxidant and anti-inflammatory activity, where the isolated glycoside was several-fold more potent than paeoniflorin at scavenging free radicals ^{2Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →}. It also appears among the constituents flagged in antidepressant network-pharmacology models of peony root, but that is an extract-level, in-silico signal rather than a test of the molecule itself ^{4Reference 4Jin Z et al. · 2026Integrating UHPLC-PDA coupled to Q-TOF-MS, network pharmacology, and antidepressant effects to determine the optimal cultivation years for Paeonia lactiflora rootsView study →}.

The Hydroxylated Paeoniflorin Analog

The whole point of this molecule is a single structural difference from paeoniflorin: oxypaeoniflorin carries an additional phenolic hydroxyl on the benzoyl ester group (a para-hydroxybenzoate). In peony phytochemistry that extra –OH is the classic antioxidant lever — adding phenolic hydroxyls to the paeoniflorin scaffold makes it a better radical scavenger, and oxypaeoniflorin sits on that gradient below its own galloylated derivative but above unmodified paeoniflorin ^{2,3Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}.

The most concrete demonstration: in a rat mesangial-cell model, oxypaeoniflorin’s radical-scavenging IC₅₀ (1.0 × 10⁻⁴ M) was about four times lower than paeoniflorin’s (4.2 × 10⁻⁴ M) — i.e. roughly four-fold more potent — with both compounds tested as isolates ^{2Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →}. This is the reference point for the whole page: a real, molecule-level potency advantage, but measured in cell culture, not in an animal or a person.

One thing this molecule is not: the peony androgen-receptor story belongs to its relatives, not to oxypaeoniflorin itself. When peony-root glycosides were screened for androgen-receptor binding, the active ones were the galloyl- and benzoyl-substituted derivatives (and pentagalloylglucose); plain paeoniflorin was inactive, and oxypaeoniflorin was not among the reported binders ^{5Reference 5Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara Prefecture, JapanView study →}. It is worth stating plainly so its data are not padded with its cousins’.

What It's Used For

Beyond the antioxidant chemistry above, the research on oxypaeoniflorin is sparse and almost entirely in vitro or in silico. What exists splits into two applications.

Evidence by IndicationStrength of support · Beta

Support is an experimental score — weighted by study type (human > animal > in vitro) and volume. A beta, not a validated metric. Both rows are thin and in-vitro/in-silico; read the per-row basis.

01Antioxidant / Anti-Inflammatory (In Vitro)Shaky30%Isolated compound, ~4× paeoniflorin potency + AGE-mesangial mechanism ^{2Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →}; new antioxidative glycoside chemistry ^{3Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}

02Antidepressant Network SignatureShaky12%Extract-level network pharmacology / QTOF-MS profiling only ^{4Reference 4Jin Z et al. · 2026Integrating UHPLC-PDA coupled to Q-TOF-MS, network pharmacology, and antidepressant effects to determine the optimal cultivation years for Paeonia lactiflora rootsView study →}

Mechanisms

The load-bearing mechanism is the simplest one: an added phenolic hydroxyl makes oxypaeoniflorin a better antioxidant than paeoniflorin ^{2,3Reference 2Zhang MH et al. · 2013Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damageView study →Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}. Everything downstream is either the same cell-model readout or a computational association.

Pharmacokinetics

Essentially uncharacterised for the isolate. No dedicated absorption, oral-bioavailability, metabolism or half-life study of oxypaeoniflorin was found; where it has been measured at all, it is as one non-volatile marker among many in a multi-herb peony-containing formula, not as a clean single-compound PK study. By class it is a polar monoterpene glycoside — like paeoniflorin, whose oral bioavailability is notoriously low — so poor gut absorption is the reasonable prior, and any in-vitro potency advantage should be read against that unmeasured caveat. Treat oral bioavailability as not established.

Clinical Trials

There are no clinical trials of oxypaeoniflorin as an isolated compound. Human evidence for peony belongs to whole root and to standardised total glucosides of paeony (TGP) preparations, within which oxypaeoniflorin is only a minor constituent.

Last checked: July 2026.

Prevalence in Nature

Oxypaeoniflorin is a minor, widely co-occurring glycoside of the genus Paeonia. It was first characterised from Chinese peony root (Paeonia lactiflora) alongside paeoniflorin, albiflorin and benzoylpaeoniflorin ^{1Reference 1Kaneda M et al. · 1972Chemical studies on the oriental plant drugs—XXXIIIView study →}, and has since been reported from the root and root-bark epidermis of white and red peony ^{7Reference 7Xiao H et al. · 2026Quality evaluation of the root bark epidermis of peony by HPLC-DAD-ESI-MS/MSView study →}, the cortex (Moutan) and seeds of tree peony (P. suffruticosa) ^{3Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}, and P. lactiflora flower extracts ^{6Reference 6Zhou H et al. · 2023Skin health properties of Paeonia lactiflora flower extracts and tyrosinase inhibitors and free radical scavengers identified by HPLC post-column bioactivity assaysView study →}. In tree-peony cortex it also appears in galloylated form (galloyl-oxypaeoniflorin), one of the antioxidative glycosides that fraction is known for ^{3Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}.

Across these sources it travels with the dominant paeoniflorin rather than substituting for it, and no clean quantified content figure (percent dry weight, or a reliable range) is documented for oxypaeoniflorin specifically — the occurrence story is qualitative. Because paeonol and the glycoside ratios differ between white peony root, red peony root and tree-peony bark, oxypaeoniflorin’s exact level is expected to be chemotype- and processing-dependent, but that has not been mapped for this molecule.

Discovery & Synthesis

Oxypaeoniflorin was structurally characterised in 1972 by M. Kaneda, Y. Iitaka and S. Shibata, in the Tetrahedron paper that established the absolute structures of paeoniflorin, albiflorin, oxypaeoniflorin and benzoylpaeoniflorin from Chinese peony root — the study that placed the whole paeoniflorin glycoside family on a firm structural footing ^{1Reference 1Kaneda M et al. · 1972Chemical studies on the oriental plant drugs—XXXIIIView study →}. Its name reflects the chemistry: it is the oxy- (hydroxylated) member of the paeoniflorin series. Subsequent isolation work extended it to tree-peony (Moutan) cortex and seeds, where it and its galloyl derivative were reported as new antioxidative glycosides ^{3Reference 3Yoshikawa M et al. · 1992Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortexView study →}.

Oxypaeoniflorin today is obtained by extraction and chromatographic isolation from peony, not by manufacture; no total synthesis of note and no commercial production route was identified, consistent with its status as a minor research-grade constituent.

Patents: not yet researched.

Toxicity & Safety

Oxypaeoniflorin carries a low flag, but that reflects the absence of red flags rather than a characterised safety profile. It is a minor glycoside of peony root, a plant with a long record of dietary and medicinal use, and no specific toxicity has been attributed to the isolated compound. It has, however, never been through a dedicated toxicology or drug-interaction assessment as an isolate — so “low” here means no signal in a thin literature, not demonstrated safe.

Safety at a Glance

✅ Low / no toxicity

• No specific toxicity reported. A minor constituent of peony root, a widely used medicinal plant, with no adverse effect attributed to the isolated molecule.
• Safety is inferred, not demonstrated. There are no toxicology, genotoxicity, or reproductive studies on isolated oxypaeoniflorin; the “low” rating rests on absence of data, not reassuring data.
• Drug interactions unassessed. No CYP/transporter interaction work exists for this molecule; any real-world exposure is as part of whole peony or total glucosides of paeony, where the herb/preparation page governs safety.

Reproductive, developmental and pregnancy safety are not characterised for isolated oxypaeoniflorin; because intake is decided at the level of the whole herb or preparation, those judgements belong on the peony monograph rather than on this molecule page.

References

1. Kaneda M, Iitaka Y, Shibata S (1972). Chemical studies on the oriental plant drugs—XXXIII. The absolute structures of paeoniflorin, albiflorin, oxypaeoniflorin and benzoylpaeoniflorin isolated from Chinese paeony root. Tetrahedron, 28(16), 4309–4317. https://www.sciencedirect.com/science/article/abs/pii/S0040402001889535
2. Zhang MH, Feng L, Zhu MM, Gu JF, Wu C, Jia XB (2013). Antioxidative and anti-inflammatory activities of paeoniflorin and oxypaeoniflora on AGEs-induced mesangial cell damage. Planta Medica. https://pubmed.ncbi.nlm.nih.gov/23881455/
3. Yoshikawa M, Uchida E, Kawaguchi A, Kitagawa I, Yamahara J (1992). Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, a paeonol glycoside, from Chinese moutan cortex. Chemical & Pharmaceutical Bulletin. https://pubmed.ncbi.nlm.nih.gov/1423794/
4. Jin Z, He HQ, Zhang LP, Yu M, Zou ZM (2026). Integrating UHPLC-PDA coupled to Q-TOF-MS, network pharmacology, and antidepressant effects to determine the optimal cultivation years for Paeonia lactiflora roots. Journal of Separation Science. https://pubmed.ncbi.nlm.nih.gov/41940663/
5. Washida K, Itoh Y, Iwashita T, Nomoto K (2009). Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara Prefecture, Japan. Chemical & Pharmaceutical Bulletin. https://pubmed.ncbi.nlm.nih.gov/19721258/
6. Zhou H, Li T, Li B, Sun S (2023). Skin health properties of Paeonia lactiflora flower extracts and tyrosinase inhibitors and free radical scavengers identified by HPLC post-column bioactivity assays. Heliyon. https://pubmed.ncbi.nlm.nih.gov/37560664/
7. Xiao H, Huang X, Xie F, Fan M, Xie Y, Wang S, Gao J (2026). Quality evaluation of the root bark epidermis of peony by HPLC-DAD-ESI-MS/MS. Molecules. https://pubmed.ncbi.nlm.nih.gov/41752367/

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