Cyanidin-3-Glucoside

Chrysanthemin; C3G Anthocyanin (glycoside)

Function

Cyanidin-3-glucoside is a glycosylated anthocyanin phytochemical widely found in blackberries, blueberries, black rice, purple corn, cherries, red cabbage, and other dark red or purple plant foods. It is one of the most common anthocyanins in the human diet and contributes strongly to red-purple pigmentation.

Cyanidin-3-glucoside functions as a polyphenolic antioxidant pigment involved in plant defense, ultraviolet protection, and oxidative stress regulation. In nutritional research, it has been studied for effects on endothelial signaling, glucose metabolism, inflammatory mediators, mitochondrial responses, and vascular biology.

Because it contains a glucose moiety attached to cyanidin, cyanidin-3-glucoside is more water-soluble and stable within plant vacuoles than free anthocyanidins. It contributes significantly to the phytochemical composition of berries and pigmented grains.

Production

Plants synthesize cyanidin-3-glucoside through flavonoid and anthocyanin biosynthesis pathways derived from phenylalanine metabolism. Enzymes including chalcone synthase, flavonoid hydroxylases, anthocyanidin synthase, and glycosyltransferases participate in its production.

Environmental conditions such as light exposure, ripeness, temperature, and stress influence anthocyanin accumulation. Pigments are stored in vacuoles where they support coloration and oxidative protection.

After ingestion, cyanidin-3-glucoside undergoes digestion, intestinal metabolism, microbial transformation, and hepatic conjugation. Some metabolites can circulate transiently and interact with vascular and cellular signaling systems.

Regulation

Cyanidin-3-glucoside activity is regulated by food matrix, pH stability, intestinal absorption, microbiome composition, and conjugation pathways. Processing and storage can affect anthocyanin stability and bioavailability.

Research suggests cyanidin-3-glucoside may influence nitric oxide pathways, inflammatory signaling, oxidative stress responses, endothelial function, and glucose transport regulation. Biological effects depend on dose, metabolite generation, and tissue exposure.

Regular consumption from berries, purple grains, and pigmented vegetables provides cyanidin-3-glucoside together with fiber, vitamin C, flavonoids, and minerals that collectively support redox and vascular signaling.

Chemical Identity

Molecular Formula: C21H21O11
Molar Mass: 449.390 g/mol
PubChem CID: 197081

Key Biological Functions

  • Human/animal/clinical studies report vascular benefits via ↑eNOS/NO and anti-inflammatory markers for anthocyanin-rich extracts (includes C3G).

Key Foods / Plant Sources

Top Foods
  • Black rice; black beans; purple corn; blueberries/blackcurrants
Additional Sources
  • Anthocyanin-rich grains and berries (glycosylated forms)

Bioavailability & Inhibitors

Inhibitor / Factor Effect on Activity / Absorption
Heat/light/alkali reduce anthocyanin stability; acidic matrices preserve pigments.
Note: Factors relate to activation and cellular signaling context. Educational only.

Cellular Pathways Involved

  • Endothelial NO synthase activation; redox/anti-inflammatory pathways; gut microbial phenolic metabolism.

Low Intake / Context

  • No classical dietary deficiency.

Linked Cancers

  • Cardiovascular; neurovascular (diet research)

Linked Ailments / Conditions

  • Inflammation; oxidative stress

SUMMARY OF EFFECTS ON THE BODY

  • Immune: anthocyanin antioxidants
  • Cardiovascular: NO/vascular function
  • Digestive: microbiome metabolism
  • Skin/Collagen: capillary reinforcement
  • Cellular: oxidative defense

Research

Anthocyanin intervention data (blackcurrant/blueberry) and stability reviews; PubChem record.