Deacetylasperulosidic Acid

Deacetylasperulosidic Acid at a Glance

Deacetylasperulosidic acid (DAA) is an iridoid glycoside — a bitter monoterpene glucoside carrying a free carboxylic acid — from the coffee family, Rubiaceae. It is best known as the principal iridoid of noni (Morinda citrifolia) fruit, where it is both the most abundant single iridoid and the most abundant phytochemical, and it recurs across other Rubiaceae including cleavers (Galium aparine) and Morinda officinalis ^{1,12Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →Reference 12Ilina T et al. · 2019In vitroPhytochemical profiles and in vitro immunomodulatory activity of ethanolic extracts from Galium aparine LView study →}.

Its main practical role is as a marker molecule: because DAA is abundant, stable to pasteurisation and consistently present, it is used to authenticate and standardise commercial noni products ^{1,2Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →Reference 2Potterat O et al. · 2007Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived productsView study →}. It is also the constituent most often credited with the antioxidant activity of the noni iridoid fraction — but that credit needs care, because the strong human data are for whole noni juice, not isolated DAA ^{5,6,7Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →}.

DAA has low reported toxicity. As a polar glucoside acid, its oral bioavailability is poor, which is the load-bearing caveat when reading its in-vitro and isolate findings against what a serving of juice actually delivers ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}.

The Noni Iridoid Marker

The single most important fact about this molecule is that it is the principal quantified iridoid of noni. In a comparative survey of Morinda citrifolia, DAA was the major iridoid across the plant, with content ranked dried fruit > fruit juice > seed > flower > leaf > root, and DAA in methanolic fruit extracts from different tropical regions ran 13.8–42.9 mg/g (French Polynesian fruit highest, Dominican lowest) ^{1Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →}. Because it is abundant, geographically ubiquitous in genuine noni, and stable through pasteurisation, DAA — alongside asperulosidic acid — serves as an identity and quality-control marker for authentic noni fruit and leaf products, quantified by validated TLC and HPLC-MS methods ^{1,2Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →Reference 2Potterat O et al. · 2007Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived productsView study →}.

DAA is also the constituent most frequently named as the driver of noni’s antioxidant activity, since it dominates the non-sugar iridoid fraction of the juice. This is where the compound-page discipline matters. The human antioxidant evidence is whole juice: in heavy smokers, daily noni juice lowered plasma superoxide anion and lipid-hydroperoxide levels ^{6Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →} and reduced lipid-peroxidation-derived DNA adducts by ~45–57% — an effect the authors tied to the juice’s iridoids, because the iridoid-free placebo did nothing ^{7Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →}. Isolated DAA has been tested only in animals: fed to rats at 15–60 mg/kg/day it produced a dose-dependent fall in malondialdehyde and rise in superoxide-dismutase activity, supporting a contributory role ^{5Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →}. But honesty cuts the other way too — when noni fruit constituents were fractionated and assayed directly, the potent isolated antioxidant was the neolignan americanin A, not an iridoid ^{4Reference 4Su BN et al. · 2005Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activityView study →}. The fair reading: DAA is a plausible and partly-demonstrated contributor to noni’s antioxidant effect, established in humans only as part of the whole juice.

Deacetylasperulosidic Acid in the Asperuloside Family

DAA sits inside a small, tidy family of Rubiaceae iridoids related by loss of acetyl groups. The parent asperuloside is a diacetate-type iridoid glucoside; hydrolysis of its ester gives asperulosidic acid (the free-acid form); removing the remaining acetyl group yields deacetylasperulosidic acid — the fully deacetylated congener. A close positional relative, 10-desacetylasperulosidic acid, differs in where the acetyl is lost and co-occurs with DAA in several Rubiaceae ^{12Reference 12Ilina T et al. · 2019In vitroPhytochemical profiles and in vitro immunomodulatory activity of ethanolic extracts from Galium aparine LView study →}. DAA also travels with monotropein, another iridoid glucoside acid, in Morinda species ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}.

This family relationship is why DAA rarely appears alone. In noni it is quantified next to asperulosidic acid as a paired marker set ^{1,2Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →Reference 2Potterat O et al. · 2007Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived productsView study →}; in cleavers (Galium aparine) the same asperuloside-series iridoids — asperulosidic acid, monotropein and the desacetyl congeners — make up the herb’s bitter cooling principles and are linked to its immunomodulatory (lymphocyte blast-transformation) activity ^{12Reference 12Ilina T et al. · 2019In vitroPhytochemical profiles and in vitro immunomodulatory activity of ethanolic extracts from Galium aparine LView study →}. It is a sibling of the more widely studied iridoids aucubin and harpagide, sharing the C9 iridoid-glucoside skeleton and the same poor-oral-bioavailability problem. (Its nearest relatives — asperuloside, asperulosidic acid and 10-desacetylasperulosidic acid — do not yet have their own pages here.)

What It's Used For

DAA’s evidence is modest, coherent and split by vehicle: the human data are whole noni juice, while the isolated-molecule data are all preclinical (rat and cell), spanning antioxidant, immune/anti-inflammatory and lipid-lowering signals ^{5,8,10Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →Reference 8Oh JS et al. · 2021AnimalDeacetylasperulosidic acid ameliorates pruritus, immune imbalance, and skin barrier dysfunction in 2,4-dinitrochlorobenzene-induced atopic dermatitis NC/Nga miceView study →Reference 10Esakkimuthu S et al. · 2019Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida LView 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. The human antioxidant data are whole juice; isolate scores stay modest because DAA itself has been tested only preclinically.

01Antioxidant / DNA-protective (iridoid fraction)Shaky40%Human whole-juice RCTs (smokers) + rat isolate; iridoid-free placebo inactive ^{5,6,7Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →}

02Anti-inflammatory / immune-modulatingShaky34%Isolate mouse + keratinocyte/mast-cell/eosinophil models (MAPK, NF-κB) ^{8,9Reference 8Oh JS et al. · 2021AnimalDeacetylasperulosidic acid ameliorates pruritus, immune imbalance, and skin barrier dysfunction in 2,4-dinitrochlorobenzene-induced atopic dermatitis NC/Nga miceView study →Reference 9Oh JS et al. · 2021Effects of deacetylasperulosidic acid on atopic dermatitis through modulating immune balance and skin barrier function in HaCaT, HMC-1, and EOL-1 cellsView study →}

03AntihyperlipidemicShaky24%Single isolate rat study (DAA from Spermacoce hispida) ^{10Reference 10Esakkimuthu S et al. · 2019Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida LView study →}

Mechanisms

The unifying theme is a redox-plus-NF-κB story: an antioxidant iridoid that also damps NF-κB/MAPK-driven inflammatory transcription. The antioxidant arm is the only one with human (whole-juice) support.

Pharmacokinetics

DAA is a highly polar iridoid glucoside acid, so — like its siblings aucubin and the wider iridoid class — its oral bioavailability is expected to be poor: the intact glycoside is hydrophilic and acid-/glycosidase-labile, and much of an oral dose is subject to gut-microbial hydrolysis of the sugar. It is nonetheless absorbable enough to be measured: a validated LC-MS/MS method detected DAA isomers (with monotropein) in rat plasma after oral Morinda officinalis extract, confirming systemic exposure as part of a whole-plant matrix ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}. No human ADME — Cmax, half-life or oral bioavailability of isolated DAA — has been characterised, and the plasma-level data that exist are for the extract, not the purified molecule ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}.

Clinical Trials

There are no controlled trials of isolated DAA. The human evidence is entirely whole noni juice — two randomised, double-blind, placebo-controlled antioxidant trials in heavy smokers ^{6,7Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →} — within which DAA is a marker constituent, not the tested agent.

Last checked: July 2026.

Isolate vs. Plant (Juice) Studies

This molecule is a clean case of the isolate-vs-plant split. The human efficacy evidence is a plant product — standardised noni juice, whose antioxidant and DNA-protective effects in smokers are juice results, with DAA present as its principal iridoid marker rather than the isolated test article ^{6,7Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →}. The isolated-molecule evidence is preclinical: rat antioxidant ^{5Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →}, mouse/cell atopic-dermatitis ^{8,9Reference 8Oh JS et al. · 2021AnimalDeacetylasperulosidic acid ameliorates pruritus, immune imbalance, and skin barrier dysfunction in 2,4-dinitrochlorobenzene-induced atopic dermatitis NC/Nga miceView study →Reference 9Oh JS et al. · 2021Effects of deacetylasperulosidic acid on atopic dermatitis through modulating immune balance and skin barrier function in HaCaT, HMC-1, and EOL-1 cellsView study →} and rat antihyperlipidemic ^{10Reference 10Esakkimuthu S et al. · 2019Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida LView study →} studies test purified DAA directly, which is a genuine mechanistic strength but stops short of human confirmation. The correct framing: meaningful clinical juice evidence + a modest but real preclinical isolate base — the two are not interchangeable, and the direct chemical assays are a reminder that other noni constituents (americanin A, scopoletin, other iridoids) share the credit ^{4Reference 4Su BN et al. · 2005Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activityView study →}.

Its Role in Plants

In the Rubiaceae, DAA and its asperuloside-series relatives are bitter iridoid glucosides — the class functions largely in chemical defence against herbivores and pathogens, the bitterness itself a deterrent, with the reactive iridoid aglycone (liberated when the sugar is cleaved on tissue damage) able to cross-link proteins. In cleavers these iridoids are described as the herb’s “bitter cooling principles” and are linked to measurable immunomodulatory activity in the plant extract ^{12Reference 12Ilina T et al. · 2019In vitroPhytochemical profiles and in vitro immunomodulatory activity of ethanolic extracts from Galium aparine LView study →}. Iridoids like DAA arise from the monoterpene (secoiridoid/iridoid) pathway off geranyl diphosphate, shared across the iridoid-bearing families. These are plant-biology roles and should not be read as human pharmacology.

Prevalence in Nature

DAA is a Rubiaceae iridoid, most concentrated and best documented in noni (Morinda citrifolia), where it is the major iridoid of the fruit at ~13.8–42.9 mg/g of methanolic fruit extract and ranks dried fruit > juice > seed > flower > leaf > root ^{1Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →}. It occurs across the wider family: in cleavers (Galium aparine) aerial parts alongside asperulosidic acid, monotropein and 10-desacetylasperulosidic acid ^{12Reference 12Ilina T et al. · 2019In vitroPhytochemical profiles and in vitro immunomodulatory activity of ethanolic extracts from Galium aparine LView study →}; in Indian mulberry (Morinda officinalis) root, where it co-occurs with monotropein ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}; and in the seeds of Spermacoce hispida ^{10Reference 10Esakkimuthu S et al. · 2019Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida LView study →}. Broad reviews of Morinda citrifolia consistently list DAA among the plant’s defining iridoids ^{13Reference 13Hou S et al. · 2025ReviewMorinda citrifolia L.: a comprehensive review on phytochemistry, pharmacological effects, and antioxidant potentialView study →}. Absolute content outside noni fruit is rarely quantified as a clean percentage, and varies with species, plant part, provenance and processing ^{1Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →}.

Discovery & Synthesis

DAA was characterised as part of the iridoid chemistry of the Rubiaceae — the deacetylated congener of asperulosidic acid — and isolated from noni (Morinda citrifolia) fruit juice among the plant’s principal iridoid glucosides in phytochemical surveys of noni ^{3,4Reference 3Samoylenko V et al. · 2006New constituents from noni (Morinda citrifolia) fruit juiceView study →Reference 4Su BN et al. · 2005Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activityView study →}. Its rise to prominence is analytical rather than synthetic: once shown to be the most abundant, geographically consistent and pasteurisation-stable iridoid in genuine noni, it became the standardisation/authentication marker quantified by validated TLC and HPLC-MS assays ^{1,2Reference 1Deng S et al. · 2011Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifoliaView study →Reference 2Potterat O et al. · 2007Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived productsView study →}. Manufacture today is by extraction/isolation from noni and related Rubiaceae for use as an analytical reference standard; a first total synthesis of DAA is not well documented, and there is no indication it is produced synthetically at scale.

Patents: not yet researched.

Toxicity & Safety

DAA carries a low toxicity flag. It is a constituent of a widely-consumed food (noni juice), it is itself anticlastogenic (DNA-protective) rather than genotoxic in the assays reported ^{5Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →}, and its documented isolate effects are anti-inflammatory and antioxidant ^{8,9Reference 8Oh JS et al. · 2021AnimalDeacetylasperulosidic acid ameliorates pruritus, immune imbalance, and skin barrier dysfunction in 2,4-dinitrochlorobenzene-induced atopic dermatitis NC/Nga miceView study →Reference 9Oh JS et al. · 2021Effects of deacetylasperulosidic acid on atopic dermatitis through modulating immune balance and skin barrier function in HaCaT, HMC-1, and EOL-1 cellsView study →}. The honest caveats are about absence of data, not evidence of harm: no dedicated repeat-dose, reproductive or human safety package exists for the isolated molecule, and its poor oral bioavailability means most of an oral dose is not systemically available in the first place ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}.

Whole noni juice has its own, separate safety literature (rare idiosyncratic hepatotoxicity reports, and a high potassium content relevant in renal impairment) — but those are properties of the whole product and its other constituents, not attributable to DAA, and belong to the noni product page rather than this molecule page.

No reproductive or developmental-toxicity dataset exists for isolated DAA. Pregnancy and lactation are a per-herb / per-product decision made where intake is decided (the noni product page), not adjudicated on this molecule page; no isolate-specific verdict is issued here.

Safety at a Glance

✅ Low / no toxicity

• Low reported toxicity, and DNA-protective. A constituent of widely-consumed noni juice; isolated DAA is anticlastogenic and antioxidant in animal assays, not genotoxic ^{5Reference 5Ma DL et al. · 2013AnimalIn vivo antioxidant activity of deacetylasperulosidic acid in noniView study →}.
• Human data are whole juice, not the isolate. Antioxidant/DNA-protective effects are demonstrated for noni juice (an iridoid mixture), so they cannot be attributed to DAA alone ^{6,7Reference 6Wang MY et al. · 2009Antioxidant activity of noni juice in heavy smokersView study →Reference 7Wang MY et al. · 2013Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokersView study →}.
• Poor oral bioavailability. As a polar glucoside acid it is incompletely absorbed and glycosidase-/acid-labile, so in-vitro potency overreads real oral exposure ^{11Reference 11Li C et al. · 2016AnimalLC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extractView study →}.
• No isolate safety package. No dedicated repeat-dose, reproductive or human toxicology exists for purified DAA; safety is inferred from the food source, not directly characterised.

Dosage

There is no established or recommended human dose for isolated DAA. The cited figures are preclinical research doses and do not convert to human self-dosing:

Human exposure is realistically via whole noni juice, where DAA is one iridoid among many and intake is measured in millilitres of juice, not milligrams of purified compound. These are doses studied in research and are not a personal recommendation.

References

1. Deng S, West BJ, Palu AK, Jensen CJ (2011). Determination and comparative analysis of major iridoids in different parts and cultivation sources of Morinda citrifolia. Phytochemical Analysis. https://pubmed.ncbi.nlm.nih.gov/20799271/
2. Potterat O, von Felten R, Dalsgaard PW, Hamburger M (2007). Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived products. Journal of Agricultural and Food Chemistry. https://pubmed.ncbi.nlm.nih.gov/17696360/
3. Samoylenko V, Zhao J, Dunbar DC, Khan IA, Rushing JW, Muhammad I (2006). New constituents from noni (Morinda citrifolia) fruit juice. Journal of Agricultural and Food Chemistry. https://pubmed.ncbi.nlm.nih.gov/16910736/
4. Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD (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/
5. Ma DL, Chen M, Su CX, West BJ (2013). In vivo antioxidant activity of deacetylasperulosidic acid in noni. Journal of Analytical Methods in Chemistry. https://pubmed.ncbi.nlm.nih.gov/24371540/
6. Wang MY, Lutfiyya MN, Weidenbacher-Hoper V, Anderson G, Su CX, West BJ (2009). Antioxidant activity of noni juice in heavy smokers. Chemistry Central Journal. https://pubmed.ncbi.nlm.nih.gov/19807926/
7. Wang MY, Peng L, Jensen CJ, Deng S, West BJ (2013). Noni juice reduces lipid peroxidation-derived DNA adducts in heavy smokers. Food Science & Nutrition. https://pubmed.ncbi.nlm.nih.gov/24804023/
8. Oh JS, Seong GS, Kim YD, Choung SY (2021). Deacetylasperulosidic acid ameliorates pruritus, immune imbalance, and skin barrier dysfunction in 2,4-dinitrochlorobenzene-induced atopic dermatitis NC/Nga mice. International Journal of Molecular Sciences. https://pubmed.ncbi.nlm.nih.gov/35008651/
9. Oh JS, Seong GS, Kim YD, Choung SY (2021). Effects of deacetylasperulosidic acid on atopic dermatitis through modulating immune balance and skin barrier function in HaCaT, HMC-1, and EOL-1 cells. Molecules. https://pubmed.ncbi.nlm.nih.gov/34070943/
10. Esakkimuthu S, Nagulkumar S, Darvin SS, et al. (2019). Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida L. Journal of Ethnopharmacology. https://pubmed.ncbi.nlm.nih.gov/31434002/
11. Li C, Dong J, Tian J, Deng Z, Song X (2016). LC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extract. Biomedical Chromatography. https://pubmed.ncbi.nlm.nih.gov/26053360/
12. 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/
13. Hou S, Ma D, Wu S, Hui Q, Hao Z (2025). Morinda citrifolia L.: a comprehensive review on phytochemistry, pharmacological effects, and antioxidant potential. Antioxidants (Basel). https://pubmed.ncbi.nlm.nih.gov/40227265/

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