10-Desacetylasperulosidic Acid

10-Desacetylasperulosidic Acid at a Glance

10-Desacetylasperulosidic acid (also written 10-deacetylasperulosidic acid) is a bitter iridoid glycoside acid — a monoterpene glucoside of the asperuloside family. It occurs across the coffee family (Rubiaceae) and is one of the dominant iridoids of cleavers (Galium aparine) aerial parts, the herb’s cooling, bitter principle ^{1,2Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →}.

As an isolated molecule it is very data-thin. There is essentially no pharmacology performed on 10-desacetylasperulosidic acid on its own; what is written about it is occurrence and chemistry, and what is written about its activity is really about the whole iridoid fraction of the plant, or about closely related family members. This page is deliberately short and says so plainly.

The single most important caveat is one of identity: 10-desacetylasperulosidic acid is not the same compound as deacetylasperulosidic acid (DAA), the well-studied noni iridoid, nor as asperulosidic acid. They differ only in where a group sits on the iridoid skeleton, their names look almost identical, and the literature frequently conflates them — so much of the “activity” attributed to this molecule actually belongs to one of its positional relatives.

A Minor Asperuloside-Family Iridoid

Iridoids are C9/C10 monoterpene glucosides — the broad class that also includes widespread markers such as aucubin and harpagide. Within it, the asperuloside series is a tightly related cluster found throughout the Rubiaceae: asperuloside itself, asperulosidic acid, deacetylasperulosidic acid (DAA), and this compound, 10-desacetyl­asperulosidic acid. They interconvert biosynthetically and differ only by small changes — an acetyl group present or absent, a carboxylic acid free or esterified, and which position on the ring bears the change.

That last point is the trap. “10-desacetyl-” and “deacetyl-” are different molecules, distinguished by the position of the missing acetyl group:

• Deacetylasperulosidic acid (DAA) — the heavily studied noni (Morinda citrifolia) iridoid, the one with in-vivo antioxidant data and the one most people mean when they cite “DAA.” In the LDL-oxidation work on Oldenlandia diffusa, it is DAA (not this molecule) that showed activity ^{4Reference 4Kim DH et al. · 2005Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidationView study →}; and noni’s signature iridoid is DAA and asperulosidic acid, not 10-desacetylasperulosidic acid ^{5Reference 5Su BN et al. · 2005Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activityView study →}.
• Asperulosidic acid — another close relative, and the family member with the clearer anti-inflammatory data (see below) ^{3Reference 3He J et al. · 2018Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 MacrophagesView study →}.
• 10-Desacetylasperulosidic acid — this molecule, distinguished by loss of the acetyl at the 10-position. Its own dedicated pharmacology is minimal.

Where 10-desacetylasperulosidic acid is documented is as an occurrence marker. It is a genuine, named constituent of cleavers (Galium aparine) and sweet woodruff (Galium odoratum), reported as one of the dominant iridoids of both ^{1,2Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →}, and it sits within the iridoid pool of Hedyotis / Oldenlandia diffusa (bai hua she she cao), a Rubiaceae used in traditional Chinese medicine whose activity is credited to a whole family of iridoids, anthraquinones and flavonoids rather than any single one ^{4Reference 4Kim DH et al. · 2005Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidationView study →}. Read this molecule as a chemotaxonomic marker of Rubiaceae bitters, not as a drug in its own right.

What It's Used For

There is no dedicated pharmacology on isolated 10-desacetylasperulosidic acid. The evidence that touches it is (a) whole-herb work in which it is one of several co-occurring iridoids, and (b) studies of its family relatives, which cannot be assumed to transfer to this specific isomer.

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. Scores here are low by design: no application rests on the isolated molecule, only on the whole herb or on family relatives.

01Immunomodulatory (whole-herb marker)Shaky18%In-vitro immunomodulatory activity of the iridoid-rich cleavers extract, in which it is one major iridoid ^{1Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →}

02Anti-inflammatory (iridoid family)Shaky16%NF-κB/MAPK suppression by relatives asperuloside & asperulosidic acid, not this isomer ^{3Reference 3He J et al. · 2018Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 MacrophagesView study →}

Mechanisms

No mechanism has been characterised for isolated 10-desacetylasperulosidic acid. The table below records family-level mechanisms of the asperuloside series, shown for its relatives and cited as context only.

None of these has been demonstrated for the 10-desacetyl isomer itself — they are shown here to mark where the family’s biology sits, not to claim it for this molecule.

Pharmacokinetics

No pharmacokinetic data exist for 10-desacetylasperulosidic acid specifically. As a polar iridoid glycoside acid it shares the pharmacokinetic liability of the class: iridoid glucosides are generally poorly absorbed orally and are cleaved by gut β-glucosidase, so in-vitro potency of any relative overstates what an oral dose of the intact glycoside would deliver. Any absorption, metabolism and half-life figures would have to be measured; none are on record here.

Clinical Trials

None. There are no clinical trials of isolated 10-desacetylasperulosidic acid, and none are known to be planned. Human exposure is only as one iridoid among many in cleavers and related Rubiaceae.

Last checked: July 2026.

Major Natural Sources

Source (botanical)	Part	Notes
Cleavers (Galium aparine)	Aerial parts	One of the dominant iridoids of the herb 1,2Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →
Sweet woodruff (Galium odoratum)	Aerial parts	Reported among its dominant iridoids 2Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →
Hedyotis / Oldenlandia diffusa (bai hua she she cao)	Whole herb	Within the Rubiaceae iridoid pool; relatives (DAA, asperulosidic acid) often reported 4Reference 4Kim DH et al. · 2005Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidationView study →

Concentrations are not well quantified for this specific iridoid — reports name it qualitatively as a dominant or co-occurring constituent rather than giving a percentage of dry weight. The unmeasured figures are logged in this compound’s gaps tracker.

Prevalence in Nature

10-Desacetylasperulosidic acid is a Rubiaceae iridoid. Its firmest documented occurrence is in the genus Galium: it is listed among the dominant iridoids of both cleavers (G. aparine) and sweet woodruff (G. odoratum), together with geniposidic acid, monotropein, scandoside, asperulosidic acid and asperuloside ^{1,2Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →}. It belongs to the same broad iridoid pool as its relatives in Hedyotis / Oldenlandia diffusa ^{4Reference 4Kim DH et al. · 2005Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidationView study →}. As with most iridoid glycosides, its absolute content varies with species, plant part, provenance and drying, and is rarely reported quantitatively ^{2Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →}.

Note the recurring confusion with noni: the iridoid that dominates Morinda citrifolia (noni) and carries its antioxidant data is deacetylasperulosidic acid (DAA), the positional relative — not the 10-desacetyl isomer described here ^{5Reference 5Su BN et al. · 2005Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activityView study →}.

Discovery & Synthesis

10-Desacetylasperulosidic acid appears in the phytochemical literature as a named Rubiaceae iridoid glycoside, but a clear primary source for its first isolation and structure elucidation is not well documented — it is reported chiefly within surveys of the asperuloside-series iridoids of Galium, Hedyotis and related genera rather than as a landmark isolation ^{1,2,4Reference 1Ilina T et al. · 2019In vitroPhytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine LView study →Reference 2Mihaylova R et al. · 2025ReviewTargeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal PlantsView study →Reference 4Kim DH et al. · 2005Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidationView study →}. There is no notable total synthesis on record; like most iridoid glycosides it is obtained, when needed, by extraction from Rubiaceae plant material rather than by manufacture. Its close relative’s methyl ester has been the subject of preparative methods work, but the free acid itself has no established commercial production.

Patents: not yet researched.

Toxicity & Safety

10-Desacetylasperulosidic acid carries a low flag. This reflects its class — bitter iridoid glycosides of edible/traditional Rubiaceae such as cleavers, consumed for centuries as part of the whole herb — not a dedicated safety dataset. There is no isolate toxicology: no repeat-dose, genotoxicity or reproductive study characterises the pure compound, so the flag is a class-level inference, not evidence of safety.

Safety at a Glance

✅ Low / no toxicity

• Class of long dietary/traditional exposure. Consumed only as one of several iridoids in cleavers and related Rubiaceae, herbs with a long record of customary use.
• No isolate safety data. No repeat-dose, genotoxicity or reproductive-toxicity study exists for the pure molecule; absence of findings is not evidence of safety.
• Do not import a relative’s data. Safety (and activity) reports for deacetylasperulosidic acid (DAA) or asperulosidic acid are for different compounds and should not be read across to this isomer.

No reproductive or developmental data exist for isolated 10-desacetylasperulosidic acid, and pregnancy/lactation decisions belong to the herb page where intake is actually decided (cleavers), not to this molecule-level page. No interaction studies (CYP, transporter) have been conducted on the isolate.

Dosage

There is no established dose for 10-desacetylasperulosidic acid. It has never been administered to humans as an isolate; intake is incidental, as one of several iridoids in cleavers and related Rubiaceae. As an iridoid glycoside acid it is expected to be poorly absorbed orally, so even the isolate figures that exist for its relatives would not translate into a meaningful human dose. Any numbers you see attached to “DAA” belong to the different compound deacetylasperulosidic acid. These notes are not a personal recommendation.

References

1. Ilina T, Kashpur N, Granica S, et al. (2019). Phytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine L. Plants (Basel). https://pubmed.ncbi.nlm.nih.gov/31775336/
2. Mihaylova R, et al. (2025). Targeting Inflammation with Natural Products: A Mechanistic Review of Iridoids from Bulgarian Medicinal Plants. Molecules. https://pubmed.ncbi.nlm.nih.gov/40941985/
3. He J, et al. (2018). Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages. International Journal of Molecular Sciences. https://pubmed.ncbi.nlm.nih.gov/30002289/
4. Kim DH, et al. (2005). Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidation. Archives of Pharmacal Research. https://pubmed.ncbi.nlm.nih.gov/16276972/
5. Su BN, et al. (2005). Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity. Journal of Natural Products. https://pubmed.ncbi.nlm.nih.gov/15844957/