Friedelin (Triterpene · Anti-inflammatory · Hepatoprotective)

Compound	Friedelin (Friedelan-3-one; D:A-Friedoolean-3-one)
Chemical class	Terpenoid — Triterpene (Friedeolane skeleton; pentacyclic rearranged ketone)
CAS	559-74-0
Primary source	Celastrus paniculatus (Malkangni), Quercus infectoria (Majuphal/Aleppo oak gall), Celtis sinensis
Key applications	Anti-inflammatory; hepatoprotective; analgesic; antioxidant
Claim strength	Moderate
Typical form	Malkangni Seed Oil; Malkangni Oil Soluble Extract; Majuphal Oil Soluble Extract
Buy from Herbuno	Malkangni Seed Oil - Jyotishmati - Celastrus paniculatus → Majuphal Oil Soluble Extract - Quercus Infectoria Oliv →

Name origin: Friedelin is named after the chemist Eduard Fremy, with the suffix denoting its oleanane-rearranged triterpene skeleton (friedeolane). It is a pentacyclic triterpenoid ketone — the C-3 hydroxyl of the lupane precursor is oxidised to a ketone — distinguishing it from lupane alcohols such as lupeol and betulin. Traditional use: Celastrus paniculatus (Malkangni or Jyotishmati) is one of the most revered nervine tonics in Ayurvedic medicine, described in Charaka Samhita for enhancing intellect, memory, and treating vata disorders. Quercus infectoria galls (Majuphal) are used in Unani medicine for astringency, wound healing, anti-inflammatory, and antifungal applications. Friedelin is a constituent of both. Research trajectory: Friedelin's pharmacological profile — anti-inflammatory, hepatoprotective, analgesic, and antioxidant — has been systematically characterised in rodent models over two decades, with mechanistic work identifying 5-LOX and COX-2 pathway inhibition and NF-κB suppression. Commercial source: Friedelin is available from Herbuno via Malkangni Seed Oil, Malkangni Oil Soluble Extract (Celastrus paniculatus), and Majuphal Oil Soluble Extract (Quercus infectoria).

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Evidence for Friedelin Applications

Anti-inflammatory and analgesic: Friedelin has shown potent dose-dependent anti-inflammatory activity in carrageenan paw oedema, cotton pellet granuloma, and formalin-induced pain models in rodents, comparable to reference standards (indomethacin, aspirin) at 25–100 mg/kg doses. Both 5-LOX and COX-2 are inhibited — a dual-pathway profile analogous to boswellic acids but from a different structural class. Claim strength: Moderate.

Hepatoprotective activity: In CCl₄- and paracetamol-induced hepatotoxicity models, friedelin at 50–200 mg/kg significantly reduces ALT, AST, and total bilirubin elevation, with histological preservation of hepatocyte architecture. The mechanism involves Nrf2-mediated antioxidant enzyme upregulation and mitochondrial membrane potential preservation. Claim strength: Moderate.

Antioxidant: Despite lacking polyphenolic hydroxyl groups typical of flavonoid antioxidants, friedelin demonstrates moderate DPPH scavenging activity — attributed to its α,β-unsaturated ketone functionality reacting with radical species via Michael addition. Cellular antioxidant enzyme (SOD, catalase, GPx) induction provides indirect antioxidant effects in vivo. Claim strength: Moderate.

Antimicrobial and antiproliferative: Friedelin has demonstrated activity against Mycobacterium tuberculosis (MIC 50–100 μg/mL) and antiproliferative effects in several cancer cell lines in preclinical work. Claim strength: Emerging.

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Dosage & Formulator Specification

No human clinical dosing data exist for isolated friedelin. Celastrus paniculatus preparations in Ayurvedic practice are used at 5–15 mL seed oil/day for cognitive and neurological applications, or 3–5 g seed powder. Friedelin content in Malkangni seed oil is in the range of 0.05–0.3%.

For anti-inflammatory and hepatoprotective applications specifically targeting friedelin, bark or leaf extracts from Celastrus paniculatus or Quercus infectoria gall extract (Majuphal) at 250–500 mg standardised preparation are more relevant delivery vehicles than the seed oil, as friedelin concentrates in polar bark/gall fractions.

Friedelin's high lipophilicity (logP ~8) means it requires lipid-based formulation (softgel, nanoemulsion) or surfactant-assisted solubilisation for meaningful oral bioavailability. Solid dispersion in PVP or HPMC matrices has been investigated in pharmaceutical pre-formulation research to improve dissolution.

Celastrus paniculatus preparations should be sourced and dosed conservatively — the plant contains celastrine, malkangunin, and other alkaloids that require quality-controlled, standardised extracts for predictable safety profiles.

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Frequently Asked Questions — Friedelin

What distinguishes the friedeolane triterpene skeleton from lupane and oleanane?
Friedeolane is a rearranged pentacyclic triterpene where multiple ring-methyl migrations have occurred relative to the oleanane parent skeleton. The C-3 ketone of friedelin is characteristic of this rearranged skeleton and is absent in lupane alcohols (lupeol, betulin) and oleanane acids (oleanolic acid, ursolic acid).

Is Malkangni (Celastrus paniculatus) used primarily for friedelin?
No — Malkangni's primary traditional and research applications relate to its fatty acid and sesquiterpene alkaloid content (celastrine, malkangunin) for cognitive and neurological support. Friedelin is a documented constituent contributing to anti-inflammatory and hepatoprotective activity but is not the lead standardisation marker.

Which Herbuno products are the best sources of friedelin for anti-inflammatory formulations?
Malkangni Oil Soluble Extract and Majuphal Oil Soluble Extract are the most relevant Herbuno preparations. The oil-soluble extract format is appropriate given friedelin's high lipophilicity.

Can friedelin contribute to liver health supplement formulations?
Yes, as a supporting anti-inflammatory and hepatoprotective constituent in complex botanical liver formulas. Malkangni and Majuphal are both traditional Ayurvedic and Unani liver-supportive botanicals; friedelin's Nrf2 activation and dual COX/5-LOX inhibition complement silybin, andrographolide, and picroside.

Related compounds: Lupeol, Betulin, Ursolic Acid, Spinasterol

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Claim-strength scale – High = multiple human RCTs; Moderate = limited trials or strong preclinical convergence; Emerging = early-stage lab or animal data.

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