Fig. 1 · Structure

Cat. No.: A12031
CAS No.: 482-70-2
Formula: C₁₂H₁₀O₂
Mol. Weight: 186.21

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Chimaphilin

Name: Chimaphilin
Brand: Adooq Bioscience
SKU: A12031
Availability: InStock
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Cat. No. A12031 CAS 482-70-2

Chimaphilin is extracted from pyrola [Passiflora incarnata Fisch.] Chimaphilin could inhibit the viability of MCF-7 cells in a concentration-dependent manner, and the IC50 value was 43.30μM for 24h.

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Biological Activity

Bioactivity / Mechanism

In Ndufa9-deficient mouse myoblasts, 50 μM chimaphilin increased oxygen consumption with oligomycin- and antimycin-sensitive responses, supporting functional mitochondrial complex I bypass. The electron-donor pathway was not established. [1]

Literature-reported observations and conditions; not Adooq-tested protocols or general treatment recommendations.

In Vitro Studies

The respiration result comes from an acute assay in complex I-deficient C2C12 cells, with a DMSO control. A related 3-hydroxy analog gave only a slight, inhibitor-insensitive response at 200 μM, limiting generalization across this naphthoquinone family. The experiment did not establish long-term cellular benefit. [1]

Acute respiration response in complex I-deficient myoblasts

Cell-based study · Ndufa9-knockout C2C12 mouse myoblasts; genetically impaired mitochondrial complex I. [1]

At 50 μM, chimaphilin increased oxygen consumption relative to the DMSO trace. Subsequent oligomycin and antimycin decreased this response, supporting functional complex I bypass. The related 3-hydroxy compound at 200 μM produced only a slight inhibitor-insensitive increase. This acute functional experiment does not identify the enzymes donating electrons or establish long-term rescue.

Measured endpoints — not treatment concentrations
Endpoint	Reported result	Reference
Cell-normalized oxygen consumption following chimaphilin addition and subsequent respiratory inhibitors	Qualitative respiration response Increased OCR; response sensitive to oligomycin and antimycin	[1]

Literature-Reported Treatment Conditions

Treatment concentration: 50 μM chimaphilin (Fig 2B); comparator 3-hydroxy-chimaphilin: 200 μM.
Exposure duration: Acute injection during the Seahorse time course; Fig 2B displays approximately 150 minutes of measurement, not a 150-minute pretreatment.
Method: Test compound followed by sequential oligomycin, CCCP and antimycin; parallel DMSO control. Shared methods give inhibitor ranges, not a uniquely specified dose for each Fig 2B injection.
Vehicle: DMSO; final DMSO percentage not specified.
Co-treatment: Respiratory inhibitors are mechanistic probes; this is not a combination anticancer treatment.
Reported limits: Final DMSO fraction and panel-specific inhibitor concentrations are not specified. The chimaphilin experiment is not a concentration-response potency determination.

Methods and source locations

Compound reported in the paper: Chimaphilin; Compound label in the paper: Compound 1

Findings apply to the isolated compound in this cell model; they do not validate an Adooq lot or establish IGF-IR inhibition, clinical benefit, or the electron-donor pathway.

Fig 2B (chimaphilin, DMSO, 3-hydroxy-chimaphilin); Fig 2 caption; Materials and Methods: Seahorse Bioenergetic Analysis and Bioassay-Guided Isolation; Results: Natural Product Screening Reveals Novel Complex I Bypass Factors

Cell-normalized oxygen consumption following chimaphilin addition and subsequent respiratory inhibitors: Seahorse XF96/XFe96 analysis; OCR normalized to cell counts. Figure shows one representative experiment from three; at least six technical wells per condition are averaged. No exact OCR values or uncertainty are reconstructed from curves. — Fig 2B (chimaphilin, DMSO, 3-hydroxy-chimaphilin); Fig 2 caption; Materials and Methods: Seahorse Bioenergetic Analysis and Bioassay-Guided Isolation; Results: Natural Product Screening Reveals Novel Complex I Bypass Factors

In Vivo Studies

An early rat study reported inhibition of carrageenan-induced paw edema by isolated chimaphilin: 51% at 50 mg/kg intraperitoneally (p<0.01) and 33% at 500 mg/kg orally (p<0.05), assessed at the 3-hour edema endpoint. These route-specific acute findings do not establish chronic anti-inflammatory efficacy. [2]

Route-specific inhibition of acute rat paw edema

Animal study · Carrageenan-induced hind-paw edema in rats. [2]

The isolated compound inhibited swelling at the 3-hour edema endpoint. Table I reports 51% inhibition at 50 mg/kg intraperitoneally (p<0.01), while the results text reports 33% inhibition at 500 mg/kg orally (p<0.05). These are route-specific observations, not evidence of equivalent exposure, chronic disease modification, or clinical efficacy.

Conditions shared by the study groups

Treatment course: Edema inhibition evaluated 3 h after carrageenan injection.
Vehicle: Assay control: 1% Tween 80–0.9% NaCl solution.

Study groups and reported outcomes
Group / dose	Comparator	Observed result	Reference
Intraperitoneal chimaphilin 50 mg/kg	Vehicle-treated edema control. Table I also includes indomethacin and aspirin reference treatments; their doses differ from chimaphilin.	51% edema inhibition at 3 h; p<0.01. Table I footnote d denotes significance; no n or variance is supplied.	[2]
Oral chimaphilin 500 mg/kg	Vehicle-treated edema control. Table I also includes indomethacin and aspirin reference treatments; their doses differ from chimaphilin.	33% edema inhibition; p<0.05, reported in the results text. The assay section defines the edema endpoint as 3 h.	[2]

Intraperitoneal chimaphilin: Model: Rats with carrageenan-induced hind-paw edema; strain, sex and group size not specified in this article.; Route: Intraperitoneal; Reported limits: Administration frequency, dosing time relative to carrageenan, sample size, variance and strain/sex are not specified in this article. Further procedural details are referred to an earlier paper and have not been imported.

Oral chimaphilin: Model: Rats with carrageenan-induced hind-paw edema; strain, sex and group size not specified in this article.; Route: Oral; Reported limits: Administration frequency, dosing time relative to carrageenan, sample size, variance and strain/sex are not specified in this article. Further procedural details are referred to an earlier paper and have not been imported.

Methods and source locations

Compound reported in the paper: Chimaphilin; Compound label in the paper: Compound I

Route-specific acute rat edema observations for isolated chimaphilin; no Adooq lot validation or human efficacy inference.

p. 5355, final results paragraph (oral edema result); p. 5356, Table I compound I and footnotes, Assay for Anti-inflammatory Activity; p. 5357, Compound I (Chimaphilin)

Intraperitoneal chimaphilin · p. 5356, Table I, compound I anti-inflammatory column (i.p.) and footnotes a/d; Assay for Anti-inflammatory Activity

Oral chimaphilin · p. 5355, final results paragraph; p. 5356, Assay for Anti-inflammatory Activity

Specifications

Manufacturer	Adooq Bioscience
CAS Number	482-70-2
Formula	C₁₂H₁₀O₂
Molecular Weight	186.21
SMILES	CC1=CC2=C(C=C1)C(=O)C=C(C2=O)C

Storage & Solubility

In Vitro Solubility

Reported Solubility

No reported solubility data are available for this product.

Preparing Stock Solutions

Stock preparation is unavailable for this product molecular weight.

Calculated stock concentrations do not establish solvent solubility. Refer to the reported solubility data for experimental guidance.

Storage

Store powder at -20°C, keep desiccated.
In powder form, the chemical is stable for 36 months.
In solution, store at -20°C and use within 1 month to prevent loss of potency. Aliquot to avoid multiple freeze/thaw cycles.

Research References

[1] Vafai SB, Mevers E, Higgins KW, et al. Natural Product Screening Reveals Naphthoquinone Complex I Bypass Factors. PloS one (2016). PMID: 27622560 DOI: 10.1371/journal.pone.0162686 Source material
[2] Kosuge T, Yokota M, Sugiyama K, et al. Studies on bioactive substances in crude drugs used for arthritic diseases in traditional Chinese medicine. III. Isolation and identification of anti-inflammatory and analgesic principles from the whole herb of Pyrola rotundifolia L. Chemical & pharmaceutical bulletin (1985). PMID: 3879592 DOI: 10.1248/cpb.33.5355 Source material

Publications

2 publications citing this product

Dong F, .et al. , Can J Physiol Pharmacol, 2018, Jan;96(1):1-7 PMID: 28177668
Wan Daqian, .et al. , Chem Biol Interact., 2015, Jul 25;237:25-30 PMID: 25980584