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Fig. 1 · Structure
Cat. No.
A13830
CAS No.
1699-46-3
Formula
C19H23NO4
Mol. Weight
329.39

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(S)-Reticuline

Cat. No. A13830 CAS 1699-46-3
(S)-Reticuline is the (S)-enantiomer of Reticuline. An enantiomer of a tetrahydrobenzylisoquinoline alkaloid. Reticuline is a chemical compound found in a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata.

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Publications for (S)-Reticuline

1 publication citing this product

  1. Ana Rubio, .et al. , Drug Test Anal, 2023, Jul 31 PMID: 37525530
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Biological Activity

Bioactivity / Mechanism

(S)-Reticuline inhibited predominantly L-type calcium-channel currents in rat A7r5 smooth-muscle cells, measured with Ba2+ as the charge carrier. This functional evidence supports calcium-entry inhibition as a contributor to vascular relaxation; target selectivity and direct binding were not established. [1]

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

In Vitro Studies

In endothelium-denuded rat aortic rings precontracted with KCl, (S)-reticuline induced concentration-dependent relaxation. The reported concentration producing 50% relaxation was (2.8 ± 0.3) × 10−4 M (mean ± SEM; n = 4 rings). [1]

Human primary-cell profiling showed context-dependent effects: parent (S)-reticuline increased IL1A and soluble TNF-α readouts in the LPS system, while bronchial epithelial ICAM1 did not meet the authors’ affected-biomarker criterion. Effects of sulphated derivatives should be distinguished from those of the parent compound. [2]

L-type channel current inhibition in A7r5 cells

Cell-based study · A7r5 rat embryonic thoracic aortic smooth-muscle cells [1]

(S)-Reticuline reduced inward Ba2+ current through predominantly L-type calcium channels; nicardipine provided a comparator.

Measured endpoints — not treatment concentrations
EndpointReported resultReference
Peak inward Ba2+ current densitypA/pF Control: −4.6 ± 0.4; 100 μM (S)-reticuline: −1.98 ± 0.14; mean ± SEM; n = 5; P < 0.01[1]

Literature-Reported Treatment Conditions

Treatment concentration
100 μM
Exposure duration
Acute perfusion; inhibition developed around 30 s
Method
Bath application during whole-cell recording
Reported limits
Reticuline solvent and numerical enantiomeric purity are not specified in the retrieved relevant methods.
Methods and source locations

Compound reported in the paper: (S)-Reticuline; Compound label in the paper: (S)-reticuline

Cellular channel-function evidence; does not establish selective binding or clinical efficacy.

Chemical isolation; whole-cell recording; Results, L-type Ba2+ current; Fig. 2a–f

Peak inward Ba2+ current density: Whole-cell patch clamp; 10 mM external Ba2+; 100-ms depolarization from −80 to +10 mV — Results, Effects of (S)-reticuline on L-type Ba2+ current; Fig. 2a–f, pp. 119–120

Relaxation of KCl-precontracted isolated rat aorta

Cell-based study · Endothelium-denuded aortic rings from male Wistar rats (200–300 g) [1]

Cumulative (S)-reticuline relaxed KCl-precontracted rings.

Measured endpoints — not treatment concentrations
EndpointReported resultReference
Concentration producing 50% relaxation of 80 mM KCl-elicited contractionHalf-relaxation concentration (2.8 ± 0.3) × 10−4 M; mean ± SEM; n = 4 aortic rings[1]

Literature-Reported Treatment Conditions

Method
Cumulative addition to isolated-organ bath
Reported limits
Individual reticuline titration steps, fixed exposure time per step and solvent are not specified in the retrieved relevant text.
Methods and source locations

Compound reported in the paper: (S)-Reticuline; Compound label in the paper: (S)-reticuline

Isolated-tissue assay; not an in-vivo blood-pressure experiment.

Aorta preparation; vasorelaxant activity in precontracted rings; Fig. 1c and Results p. 118

Concentration producing 50% relaxation of 80 mM KCl-elicited contraction: Isometric tension; cumulative addition after contraction plateau; nicardipine and papaverine comparators — Results, Effects of extracellular Ca2+ on (S)-reticuline modulation of KCl-induced contractions; Fig. 1c, p. 118

Context-dependent biomarker changes in human primary cells

Cell-based study · BioMAP human primary-cell systems: LPS-stimulated peripheral blood mononuclear/endothelial co-culture and BE3C bronchial epithelial cells [2]

The parent compound increased selected inflammatory readouts; its profile differed from those of sulphated derivatives.

Measured endpoints — not treatment concentrations
EndpointReported resultReference
IL1A and soluble TNF-α in the LPS systemDirection relative to DMSO control Positive for both markers[2]
ICAM1 in BE3C bronchial epithelial cellsThreshold classification Parent (S)-reticuline: - (not classified as affected); both O-sulphates: Negative[2]

Literature-Reported Treatment Conditions

Treatment concentration
3.7, 11, 33 and 100 μM (Figure 3 labels)
Method
Human primary-cell disease-model profiling
Vehicle
DMSO
Reported limits
Exposure duration and replicate count for these readouts are not specified in the retrieved assay section/Table S4; no assay-level dose-to-efficacy inference is made.
Methods and source locations

Compound reported in the paper: (S)-Reticuline; Compound label in the paper: (S)-reticuline

Biomarker profile only; no universal anti-inflammatory action or disease efficacy established.

Results, Biological activities of (S)-reticuline O-sulphates in human cells; Methods, Prediction of biological activities; Fig. 3; SI Tables S4–S5

IL1A and soluble TNF-α in the LPS system: BioMAP profiling; authors required a significant same-direction change at more than two of four concentrations — Fig. 3b,e; Supplementary Table S5, sheet1 rows 32 and 36, parent-compound column C

ICAM1 in BE3C bronchial epithelial cells: Same profiling assay and classification rule — Fig. 3e; Supplementary Table S5, sheet1 row 70, columns C–E

In Vivo Studies

Reticuline (0.25 mg/kg by intragastric gavage) reduced airway resistance and BALF inflammatory-cell counts in lean and obese mice with HDM-associated asthma. Body weight, serum insulin and lung IL-13 were unchanged under these conditions. [3]

Reticuline in lean and obese mice with HDM-associated asthma

Animal study · Male BALB/c mice, initially 6–8 weeks old; low- or high-fat diet for 11 weeks; HDM-associated allergic airway inflammation [3]

Reticuline reduced airway resistance and inflammatory-cell recruitment in this preclinical model. Metabolic measures and IL-13 were unaffected.

Measured endpoints — not treatment concentrations
EndpointReported resultReference
Baseline and methacholine-evoked total airway resistanceQualitative comparison Reduced with reticuline versus diet-matched HDM-placebo groups; n = 6 per group[3]
BALF total cells, neutrophils, eosinophils and lymphocytesQualitative comparison Reduced with reticuline in both diet groups; n = 6 per group[3]
Body weight, serum insulin and lung IL-13Negative findings No treatment effect reported for body weight, serum insulin or IL-13[3]

Conditions shared by the study groups

Route
Intragastric gavage
Frequency
Once on each of Days 21, 22, 23 and 24
Treatment course
Four administrations; 2 h before HDM on Days 22–24
Vehicle
Placebo comparator: PBS containing 5% DMSO
Study groups and reported outcomes
Group / doseComparatorObserved resultReference
Reticuline, HDM-challenged lean mice
0.25 mg/kg		Diet-matched HDM plus placebo; diet-matched PBS plus placebo baselineLower airway resistance and BALF inflammatory-cell counts than diet-matched HDM plus placebo; n = 6 per group.[3]
Reticuline, HDM-challenged obese mice
0.25 mg/kg		Diet-matched HDM plus placebo; diet-matched PBS plus placebo baselineLower airway resistance and BALF inflammatory-cell counts than diet-matched HDM plus placebo; n = 6 per group.[3]
Reticuline, HDM-challenged lean mice
Model: Male BALB/c mice, low-fat diet, HDM-challenged
Reported limits: No pharmacokinetic exposure or human efficacy measurement in this experiment.
Reticuline, HDM-challenged obese mice
Model: Male BALB/c mice, high-fat diet, HDM-challenged
Reported limits: No pharmacokinetic exposure or human efficacy measurement in this experiment.
Methods and source locations

Compound reported in the paper: (S)-Reticuline; Compound label in the paper: Reticuline

Applies to the depicted reticuline in the stated mouse model; no Adooq product-lot or clinical validation.

Sections 2.1–2.9 and 3.1–3.3; Figs. 1, 2 and 4

Baseline and methacholine-evoked total airway resistance: FlexiVent; measured within 24 h of final challenge; mean ± SD per Section 2.9 — Sections 2.3 and 3.1; Fig. 1E–F

BALF total cells, neutrophils, eosinophils and lymphocytes: Total/differential cell counts; mean ± SD; Fig. 2 marks P < 0.001 versus HDM — Sections 2.5 and 3.2; Fig. 2A–D

Body weight, serum insulin and lung IL-13: Body weight; serum insulin; lung-homogenate IL-13 ELISA; n = 6 per group — Section 3.1, Fig. 1C–D; Section 3.3, Fig. 4D

Reticuline, HDM-challenged lean mice · Sections 2.1–2.3 and 3.1–3.2; Figs. 1B,E,F and 2A–D

Reticuline, HDM-challenged obese mice · Sections 2.1–2.3 and 3.1–3.2; Figs. 1B,E,F and 2A–D

Specifications

Manufacturer Adooq Bioscience
CAS Number 1699-46-3
Formula C19H23NO4
Molecular Weight 329.39
Synonyms 7-Isoquinolinol
SMILES
CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC

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. [1] Medeiros MA, Nunes XP, Barbosa-Filho JM, et al. (S)-reticuline induces vasorelaxation through the blockade of L-type Ca(2+) channels. Naunyn-Schmiedeberg's archives of pharmacology (2009). PMID: 18825370 DOI: 10.1007/s00210-008-0352-1 Source material
  2. [2] Matsumura E, Nakagawa A, Tomabechi Y, et al. Microbial production of novel sulphated alkaloids for drug discovery. Scientific reports (2018). PMID: 29789647 DOI: 10.1038/s41598-018-26306-7 Source material
  3. [3] Lyu X, Liu J, Liu Z, et al. Anti-inflammatory effects of reticuline on the JAK2/STAT3/SOCS3 and p38 MAPK/NF-κB signaling pathway in a mouse model of obesity-associated asthma. The clinical respiratory journal (2024). PMID: 38286741 DOI: 10.1111/crj.13729 Source material

Publications

1 publication citing this product

  1. Ana Rubio, .et al. , Drug Test Anal, 2023, Jul 31 PMID: 37525530

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