Lateriflorin

Lateriflorin at a Glance

Lateriflorin is a flavone glucuronide — chemically 5,6-dihydroxy-7-glucuronyloxy-2’-methoxyflavone — found in the aerial parts of American skullcap (Scutellaria lateriflora). It takes its name directly from the species, and that naming captures its significance: lateriflorin is best understood not as a bioactive molecule but as a species-authentication fingerprint ^{1,2Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}.

Unlike its better-studied co-occurring flavones — baicalin, baicalein, wogonin and scutellarin — lateriflorin has no established standalone pharmacology. It was first isolated as a new compound while researchers were characterising which S. lateriflora flavones bind the serotonin 5-HT7 receptor, and even there the activity was attributed to other flavones, not to lateriflorin itself ^{2Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}.

Its practical value is analytical. Because lateriflorin (with dihydrobaicalin and baicalin) is characteristic of genuine S. lateriflora, its presence or absence helps separate authentic American skullcap from the differently-used Chinese skullcap (S. baicalensis) and, more importantly, from germander (Teucrium) adulterants implicated in “skullcap” hepatotoxicity ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}.

The S. lateriflora Authentication Marker

This is the point of the page. Lateriflorin’s documented role is as a chemotaxonomic marker used in the quality control and authentication of American skullcap.

Validated analytical work (LC-UV/MS, TLC and digital photomicroscopy) characterises the 70% ethanol extract of genuine S. lateriflora by a flavonoid signature predominantly of baicalin, lateriflorin, dihydrobaicalin and baicalein ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}. That fingerprint does two jobs:

• Distinguishing American from Chinese skullcap. In S. lateriflora the medicinally relevant flavones concentrate in the aerial parts (leaves), whereas in S. baicalensis (Chinese skullcap / Huang Qin) the characteristic flavones are root-localised; the two species are chemically and medicinally distinct and should not be conflated ^{3,4Reference 3Costine B et al. · 2022Exploring native Scutellaria species provides insight into differential accumulation of flavones with medicinal propertiesView study →Reference 4Makino T et al. · 2008Comparison of the major flavonoid content of S. baicalensis, S. lateriflora, and their commercial productsView study →}.
• Flagging germander adulteration. The historically dangerous substitution is with germander (Teucrium canadense, T. chamaedrys), a look-alike whose extracts are dominated by phenylpropanoid glycosides — verbascoside and teucrioside — that are absent from true skullcap ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}. Germander carries a documented hepatotoxicity risk, so this substitution is the real safety hazard behind reports of “skullcap” liver injury. An authentic S. lateriflora flavone profile (lateriflorin present; teucrioside absent) is evidence against that adulteration.

In other words, lateriflorin earns its place here as a safety-relevant authenticity check, not as a therapeutic constituent.

What It's Used For

Lateriflorin’s pharmacology is, honestly, close to a blank page. The single primary study in which it was isolated tested the S. lateriflora flavones for serotonin 5-HT7 receptor binding — and found the activity to sit with scutellarin and ikonnikoside I, not with lateriflorin ^{2Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}. There are no dedicated pharmacology, mechanism or pharmacokinetic studies of the isolated molecule.

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. For a marker compound like this there is essentially no therapeutic application to score; the one pharmacological thread below is minimal and was attributed to other flavones, so read the row basis carefully.

01Serotonergic / 5-HT7 Binding (co-isolated flavone)Shaky14%Isolated among S. lateriflora flavones in one 5-HT7 study; activity attributed to scutellarin & ikonnikoside I, not lateriflorin ^{2Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}

Mechanisms

There is no established mechanism of action for lateriflorin. The table below records only what can honestly be said about the molecular class, and flags the absence of direct data.

The load-bearing point is the negative one: lateriflorin has no demonstrated mechanism, and the extract activity it was found alongside belongs to other flavones.

Pharmacokinetics

No pharmacokinetic data exist for isolated lateriflorin — no absorption, oral bioavailability, metabolism or half-life figures have been reported. As a flavone 7-O-glucuronide it is a relatively polar molecule, a chemotype that generally shows poor passive intestinal absorption; within American skullcap it is one of the flavones for which no membrane-crossing was demonstrated (that finding belonged to oroxylin A). Any bioavailability claim would be speculative.

Clinical Trials

There is no clinical data on lateriflorin. It has never been the subject of a human trial as an isolated compound, and it is not administered as an isolate. Human exposure occurs only incidentally, within whole American skullcap preparations, where the relevant clinical evidence concerns the herb (and its major flavone baicalin) rather than this marker molecule.

Last checked: July 2026.

Isolate vs. Plant Studies

Every mention of lateriflorin in the literature is as a constituent of whole S. lateriflora extract, never as an independently studied isolate. It was purified only to elucidate its structure and to serve as an analytical reference for the extract’s fingerprint ^{1,2Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}. There is therefore no isolate pharmacology to transfer to the plant, and no plant effect that can be attributed to lateriflorin. This is the honest ceiling on the molecule: its evidence base is analytical (what it is and where it occurs), not pharmacological (what it does).

Prevalence in Nature

Lateriflorin appears to be essentially species-specific to Scutellaria lateriflora, occurring in the aerial parts as one of the predominant flavonoids of the ethanol extract, alongside baicalin, dihydrobaicalin and baicalein ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}. It is not reported as a notable constituent of Chinese skullcap (S. baicalensis) or of other plants — which is exactly what makes it useful as a marker.

Its absolute content has not been separately quantified; commercial-quality surveys report the herb’s flavonoid biomarkers (baicalin, baicalein, wogonin) rather than lateriflorin, and those surveys document wide variability between products — some commercial tinctures contain almost none — so even the marker’s presence is product-dependent ^{5Reference 5Gao J et al. · 2008Validation of a HPLC method for flavonoid biomarkers in skullcap (Scutellaria) and its use to illustrate wide variability in the quality of commercial tincturesView study →}. In American skullcap the medicinally relevant flavones localise to the aerial parts/leaves, in contrast to the root localisation seen in Chinese skullcap ^{3,4Reference 3Costine B et al. · 2022Exploring native Scutellaria species provides insight into differential accumulation of flavones with medicinal propertiesView study →Reference 4Makino T et al. · 2008Comparison of the major flavonoid content of S. baicalensis, S. lateriflora, and their commercial productsView study →}.

Discovery & Synthesis

Lateriflorin was first isolated and named in 2003 by Stefan Gafner and colleagues at Tom’s of Maine, reported in the Journal of Natural Products as a new compound — one of the flavone glucuronides obtained by fractionating the 70% ethanol extract of dried S. lateriflora (“mad-dog skullcap”) during a study of the herb’s flavones and the 5-HT7 receptor ^{2Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}. Its structure — 5,6-dihydroxy-7-glucuronyloxy-2’-methoxyflavone — was established by NMR (¹H, ¹³C, NOESY) and MS ^{2Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}. The name is a straightforward eponym of the source species, lateriflora.

No total synthesis of lateriflorin has been reported, and none would be expected: the molecule is not a commercial target but a reference standard, obtained by isolation from the plant for use in authentication assays ^{1,2Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →Reference 2Gafner S et al. · 2003Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria laterifloraView study →}. There is accordingly no manufacturing story to tell beyond extraction/isolation for analytical use.

Patents: not yet researched.

Toxicity & Safety

There is no isolate toxicology for lateriflorin — no acute, repeat-dose, genotoxicity or reproductive data — because it has never been administered as a purified compound. It is a minor flavone glucuronide of a herb with a long traditional-use record, and nothing about the molecule suggests intrinsic hazard.

The important safety point is contextual and, in a sense, inverted: lateriflorin’s relevance to safety is that its presence marks authentic American skullcap and thereby argues against the substitution that actually causes harm. Reports of hepatotoxicity attributed to “skullcap” have been linked not to S. lateriflora itself but to adulteration with germander (Teucrium spp.), whose phenylpropanoid glycosides (verbascoside, teucrioside) replace the true-skullcap flavone fingerprint ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}. Lateriflorin is thus part of the analytical guard-rail against a hepatotoxic look-alike, not a source of risk in its own right.

Safety at a Glance

✅ Low / no toxicity

• No toxicity signal for the molecule itself. A minor characteristic flavone glucuronide of a traditionally used herb, present only incidentally in whole-herb preparations.
• The real hazard is adulteration, not lateriflorin. Genuine S. lateriflora shows a lateriflorin/baicalin/dihydrobaicalin fingerprint; germander (Teucrium) shows verbascoside/teucrioside instead and carries a documented hepatotoxicity risk — the substitution behind “skullcap” liver injury ^{1Reference 1Gafner S et al. · 2003Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopyView study →}.
• No isolate human safety, pharmacokinetic or reproductive data. Do not infer effects — for good or ill — from the parent herb or from co-occurring flavones.

Dosage

Lateriflorin is not dosed. It is an analytical marker, not a supplement, and is not sold or taken as an isolate. Human exposure is only incidental — as a minor flavone glucuronide within American skullcap (Scutellaria lateriflora) aerial-part preparations, whose flavonoid content varies widely between commercial products ^{5Reference 5Gao J et al. · 2008Validation of a HPLC method for flavonoid biomarkers in skullcap (Scutellaria) and its use to illustrate wide variability in the quality of commercial tincturesView study →}. Any figures relevant to intake belong to the American skullcap herb monograph, not to this molecule. There is no research dose for isolated lateriflorin, and nothing here is a personal recommendation.

References

1. Gafner S, Bergeron C, Batcha LL, Angerhofer CK, Sudberg S, Sudberg EM, Guinaudeau H, Gauthier R (2003). Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopy. Journal of AOAC International. https://pubmed.ncbi.nlm.nih.gov/12852558/
2. Gafner S, Bergeron C, Batcha LL, Reich J, Arnason JT, Burdette JE, Pezzuto JM, Angerhofer CK (2003). Inhibition of [3H]-LSD binding to 5-HT7 receptors by flavonoids from Scutellaria lateriflora. Journal of Natural Products. https://pubmed.ncbi.nlm.nih.gov/12713409/
3. Costine B, Zhang M, Chhajed S, Pearson B, Chen S, Nadakuduti SS (2022). Exploring native Scutellaria species provides insight into differential accumulation of flavones with medicinal properties. Scientific Reports. https://pubmed.ncbi.nlm.nih.gov/35915209/
4. Makino T, Hishida A, Goda Y, Mizukami H (2008). Comparison of the major flavonoid content of S. baicalensis, S. lateriflora, and their commercial products. Journal of Natural Medicines. https://pubmed.ncbi.nlm.nih.gov/18404307/
5. Gao J, Sanchez-Medina A, Pendry BA, Hughes MJ, Webb GP, Corcoran O (2008). Validation of a HPLC method for flavonoid biomarkers in skullcap (Scutellaria) and its use to illustrate wide variability in the quality of commercial tinctures. Journal of Pharmacy & Pharmaceutical Sciences. https://pubmed.ncbi.nlm.nih.gov/18445366/