6′-O-Galloylalbiflorin

6′-O-Galloylalbiflorin at a Glance

6′-O-Galloylalbiflorin is a galloylated monoterpene glycoside found in the root of peony (Paeonia lactiflora) — structurally, it is albiflorin carrying a galloyl (3,4,5-trihydroxybenzoyl) ester at the 6′ position. It sits within a small family of galloyl/benzoyl monoterpene glycosides that peony root produces alongside the far more abundant paeoniflorin and albiflorin.

Its single point of research interest is androgen-receptor (AR) activity. In one Japanese study screening peony-root constituents as “androgen modulators,” 6′-O-galloylalbiflorin was the strongest AR binder among the peony monoterpene glycosides tested and behaved as an AR antagonist (anti-androgen) in a prostate-cancer cell line ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. That result is why it matters.

It is otherwise a thin molecule: essentially one research group has characterised its specific activity, there is no pharmacokinetic or clinical data, and the safety flag below reflects an absence of adverse signals rather than a completed toxicology package. Read the per-application gaps closely — this is a molecule to watch, not one to draw conclusions from.

The Galloyl Ester of Albiflorin

The defining fact about this molecule is what the galloyl group does to albiflorin. Albiflorin itself, and its isomer paeoniflorin, showed no androgen-receptor binding at all in the same assay; only after galloylation did an albiflorin-based glycoside become a strong AR binder ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. The authors concluded that both the albiflorin scaffold and the galloyl moiety are required for the strong binding — neither piece works alone ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}.

Within that study’s ranked set of peony monoterpene glycosides, 6′-O-galloylalbiflorin was the standout:

• 6′-O-galloylalbiflorin — strong AR binding, IC₅₀ 33.7 µg/mL ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}
• 3′-O-galloylpaeoniflorin, 6′-O-benzoylpaeoniflorin, 6′-O-galloylpaeoniflorin — only weak binding (12–31% inhibition at 120 µg/mL) ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}
• Albiflorin and paeoniflorin (ungalloylated) — no activity ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}

One important honesty caveat on the “strongest” framing: in the same paper, pentagalloylglucose — a gallotannin, not a monoterpene glycoside — bound the AR far more strongly still (IC₅₀ 4.1 µg/mL) ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. So 6′-O-galloylalbiflorin is the strongest AR binder among the peony monoterpene glycosides, not the strongest peony AR ligand overall. See the galloyl/benzoyl siblings and 3′-O-galloylpaeoniflorin / 6′-O-benzoylpaeoniflorin for the rest of the series.

What It's Used For

The molecule-specific evidence is narrow and entirely preclinical: a single in-vitro androgen-receptor study ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}, plus a supporting mention in an anti-inflammatory structure–activity screen of peony monoterpenoids where albiflorin derivatives came off worse than the paeoniflorins ^{2Reference 2Bi X et al. · 2017Anti-inflammatory effects, SAR, and action mechanism of monoterpenoids from Radix Paeoniae Alba on LPS-stimulated RAW 264.7 cellsView study →}.

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. Every row here rests on isolated-molecule in-vitro work from essentially one group, so the scores are deliberately low.

01Anti-Androgen / AR BindingShaky24%Single in-vitro isolate study: AR binding IC₅₀ 33.7 µg/mL + LNCaP-FGC growth inhibition + AR-antagonist read-out ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}

02Anti-Inflammatory (Monoterpenoid)Shaky14%A galloylalbiflorin among peony monoterpenoids in an LPS-macrophage SAR screen — and one of the weaker actives ^{2Reference 2Bi X et al. · 2017Anti-inflammatory effects, SAR, and action mechanism of monoterpenoids from Radix Paeoniae Alba on LPS-stimulated RAW 264.7 cellsView study →}

Mechanisms

The load-bearing point is the SAR: the pharmacology lives in the galloyl group grafted onto albiflorin, not in the monoterpene glycoside core. Everything else here is thin around that one finding.

Pharmacokinetics

No pharmacokinetic data exist for 6′-O-galloylalbiflorin — no absorption, bioavailability, metabolism or half-life figures have been reported. On structure alone it is a large, polar galloylated monoterpene glucoside, a chemotype that is generally poorly absorbed orally and liable to hydrolysis by gut flora and esterases; by read-across, its parent albiflorin and the sister glycoside paeoniflorin are both known for low oral bioavailability. This matters directly: the AR-binding IC₅₀ was measured in a cell-free/cell assay ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}, and there is no evidence those concentrations are reachable in the body after eating peony root. Bioavailability is the biggest single hole in the anti-androgen story.

Clinical Trials

There is no clinical data. 6′-O-galloylalbiflorin has never, to the accessible record, been given to humans as an isolated compound, and it is not a marketed supplement. Its entire evidence base is preclinical and in-vitro.

Last checked: July 2026.

Isolate vs. Plant Studies

Unusually for this database, every finding on this molecule is on the isolate — the AR-binding and prostate-cell data are for 6′-O-galloylalbiflorin purified from peony root, not for a peony extract standardised to it ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. That is a double-edged fact. On one hand, the effect is cleanly attributable to the molecule rather than to a co-occurring constituent. On the other, there is no whole-plant or extract study showing that a peony preparation delivers enough of this minor glycoside — past first-pass hydrolysis and poor absorption — to reproduce the in-vitro AR antagonism in a living system. No human trial of peony (whether crude root, decoction, or the standardised total glucosides of paeony extract) has been tied to this constituent’s anti-androgen activity. The isolate result should not be read forward onto peony the herb.

Prevalence in Nature

6′-O-Galloylalbiflorin is documented essentially only from peony root (Paeonia lactiflora, Paeoniae radix), where it occurs as a minor galloylated member of the monoterpene-glycoside pool dominated by paeoniflorin and albiflorin ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. It belongs to a broader galloyl/benzoyl series — the sibling glycosides 6′-O-galloylpaeoniflorin, 3′-O-galloylpaeoniflorin and 6′-O-benzoylpaeoniflorin — that the same peony-root chemistry produces ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}.

It is at least water-extractable: galloylated albiflorins have been isolated from an aqueous extract of P. lactiflora roots (in work whose new compound was the di-galloyl analogue 2′,6′-di-O-galloylalbiflorin), which is relevant because it means a peony decoction could in principle carry the compound rather than it being an artefact of organic-solvent extraction ^{3Reference 3Song J et al. · 2026Monoterpenes from an aqueous extract of Paeonia lactiflora roots and their lipid-lowering effectView study →}. No quantified concentration (% dry weight, mg/g) has been reported, so its true abundance in the root is unknown — the number belongs in this compound’s gaps tracker, not on the page.

Discovery & Synthesis

6′-O-Galloylalbiflorin appears in the literature as a known compound by 2009, when the Nara-Prefecture group of Washida and colleagues isolated it (as compound 2) from locally grown and processed Paeonia lactiflora roots while searching for androgen modulators, and characterised its structure by spectroscopic analysis ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. Its earlier first isolation is not well pinned in the accessible record — it was already treated as “known” in that paper. The same group described neighbouring galloylated monoterpene glycosides — 4-O-galloylalbiflorin and 4′-O-galloylpaeoniflorin — in a companion 2009 report, filling in the family’s chemistry ^{4Reference 4Washida K et al. · 2009Two new galloylated monoterpene glycosides, 4-O-galloylalbiflorin and 4′-O-galloylpaeoniflorin, from the roots of Paeonia lactiflora (Paeoniae radix)View study →}. (Those are distinct positional isomers; findings on them, such as a later report that 4-O-galloylalbiflorin inhibits CYP3A/2C9/2D in human liver microsomes ^{5Reference 5Sun Y et al. · 2021Sun Y, He M, Sun Y, Wei J (2021). 4-O-galloylalbiflorin inhibits the activity of CYP3A, 2C9, and 2D in human liver microsomes. Xenobiotica. https://pubmed.ncbi.nlm.nih.gov/34082641/View study →}, are not transferable to the 6′-O compound.)

No total synthesis of 6′-O-galloylalbiflorin has been reported; it is obtained only by extraction and chromatographic isolation from peony root. There is no commercial production — it exists as a research isolate.

Patents: not yet researched.

Toxicity & Safety

6′-O-Galloylalbiflorin carries a low flag, but read that flag carefully: it reflects the absence of any reported adverse signal plus read-across from its low-toxicity parent glycosides (albiflorin, paeoniflorin) and from peony root’s long dietary/medicinal use — not a completed toxicology package. No dedicated genotoxicity, repeat-dose, reproductive or interaction study exists for this isolated molecule. Safety here is inferred, not demonstrated.

Two honest caveats worth flagging. First, its documented pharmacology is anti-androgenic ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}; were meaningful systemic exposure ever achieved, AR antagonism is a mechanism with obvious endocrine implications (male reproductive/hormonal), so “low toxicity” is a statement about acute/general safety, not an endocrine all-clear. Second, a related positional isomer (4-O-galloylalbiflorin) inhibits the drug-metabolising enzymes CYP3A, 2C9 and 2D in human liver microsomes ^{5Reference 5Sun Y et al. · 2021Sun Y, He M, Sun Y, Wei J (2021). 4-O-galloylalbiflorin inhibits the activity of CYP3A, 2C9, and 2D in human liver microsomes. Xenobiotica. https://pubmed.ncbi.nlm.nih.gov/34082641/View study →} — that is a different molecule, and no such data exist for 6′-O-galloylalbiflorin, but it flags a metabolic-interaction question this branch of the family raises.

Safety at a Glance

✅ Low / no toxicity

• No adverse signal reported. Occurs as a minor constituent of long-used peony root; parent glycosides are low-toxicity.
• Anti-androgenic mechanism. The one documented activity is AR antagonism; relevant to hormone-sensitive contexts if systemic exposure were ever shown.
• Essentially no safety data. No genotoxicity, reproductive, repeat-dose or interaction study on this isolate — the low flag is read-across, not evidence.
• Possible enzyme-interaction question. A related isomer (4-O-galloylalbiflorin) inhibits CYP3A/2C9/2D; untested for the 6′-O compound.

Pregnancy and lactation decisions belong to the peony herb page, where intake is actually decided, not to this molecule-level page.

Dosage

There is no dose for 6′-O-galloylalbiflorin. It has never been dosed in humans, it is not sold as a supplement, and the only quantitative figure in its literature is a laboratory binding IC₅₀ (33.7 µg/mL) — an assay concentration, not an intake ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. Any real-world exposure is incidental, as a minor constituent of peony-root preparations standardised (when standardised at all) to paeoniflorin rather than to this compound. There is no research dose to report, and nothing here is a personal recommendation.

References

1. 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 (Tokyo). https://pubmed.ncbi.nlm.nih.gov/19721258/
2. Bi X, Han L, Qu T, et al. (2017). Anti-inflammatory effects, SAR, and action mechanism of monoterpenoids from Radix Paeoniae Alba on LPS-stimulated RAW 264.7 cells. Molecules. https://pubmed.ncbi.nlm.nih.gov/28468284/
3. Song J, Du X, Gong S, et al. (2026). Monoterpenes from an aqueous extract of Paeonia lactiflora roots and their lipid-lowering effect. Natural Product Research. https://pubmed.ncbi.nlm.nih.gov/41493857/
4. Washida K, Yamagaki T, Iwashita T, Nomoto K (2009). Two new galloylated monoterpene glycosides, 4-O-galloylalbiflorin and 4′-O-galloylpaeoniflorin, from the roots of Paeonia lactiflora (Paeoniae radix). Chemical & Pharmaceutical Bulletin (Tokyo). https://pubmed.ncbi.nlm.nih.gov/19801879/
5. Sun Y, He M, Sun Y, Wei J (2021). 4-O-galloylalbiflorin inhibits the activity of CYP3A, 2C9, and 2D in human liver microsomes. Xenobiotica. https://pubmed.ncbi.nlm.nih.gov/34082641/