Terpenoids

The second major active chemistry class. Includes the highest fat-phase-partitioning antioxidants and the most important 5-LOX inhibitors.

Monoterpenes (C10)

• Thymol (thyme): logP 3.3, radical chain termination, antimicrobial, quorum sensing inhibition
• Carvacrol (oregano, thyme): logP 3.5, similar to thymol
• Cinnamaldehyde (cinnamon): logP 1.9, TRPA1 agonist, the most potent natural quorum sensing inhibitor characterized. In volatile form — the tingle is compound-presence confirmation.
• Menthol, limonene: sensory and antimicrobial

Diterpenes (C20)

• Carnosic acid (rosemary): logP ~4–5 (highest fat-phase partitioning among food antioxidants), thermally stable to 200°C, EU-approved food antioxidant (E392). The primary in-fryer antioxidant.
• Carnosol (rosemary, sage): similar profile to carnosic acid, Nrf2 activation
• Tanshinone IIA (dan shen/red sage): pro-angiogenic through eNOS activation. Fat-soluble, present in botanical matter.

Triterpenes (C30)

• AKBA (acetyl-11-keto-beta-boswellic acid): logP 6–8, highly lipophilic (stays in botanical matter rather than extracting into brine — consume the matter directly), specific 5-LOX inhibitor, MMP-3/9 inhibitor. The mechanism behind frankincense in traditional medicine. Paired with myrrh (opioid receptor) for complete pain pathway coverage.
• Oleanolic acid: in olive leaves alongside oleuropein
• Ursolic acid: in rosemary, thyme — anti-inflammatory, Nrf2

Sesquiterpenes (C15)

• Thymoquinone (Nigella sativa): logP 1.9, potent 5-LOX + Nrf2 + mast cell compound. Partially aqueous-extractable. Stays in seeds in significant fraction — consume the seeds.
• Curcuminoids (turmeric): technically diarylheptanoids but similar solubility profile. logP 3.3, fat required for absorption. Piperine ×20 absorption. Fermentation environment (acidic, with piperine) maximizes extraction.
• Gingerols → shogaols: gingerols convert to shogaols (more potent TRPV1 agonists) in acidic fermentation environment.

Carotenoids (C40 tetraterpenes)

• Astaxanthin: unique among antioxidants — spans the full lipid bilayer (polar ends outside, non-polar middle). Mitochondrial membrane protection, renal tubular cell protection. Must be taken with fat. 12mg daily.
• Beta-carotene: pro-vitamin A, at high isolated doses actually pro-oxidant (ATBC trial). Obtain from food matrix.

Abietic Acid (pine resin, diterpene acid)

• logP ~6 — extremely lipophilic, continuous partitioning into stored oil
• The primary antioxidant in pine pitch lining ancient amphoras
• Now understood as pinosylvin + abietic acid complex providing both antioxidant and SIRT1 effects
• → [[Roman Amphora System]]

The Paired Frankincense-Myrrh Pharmacology

Used paired across Egyptian, Greek, Roman, Islamic, Indian medicine simultaneously:

• Frankincense (Boswellia): AKBA → 5-LOX → leukotriene synthesis inhibition
• Myrrh (Commiphora): furanosesquiterpenes → opioid receptor partial agonism + TRPV1 modulation

Together they cover:

1. 5-LOX pathway (frankincense) — the pathway missed by NSAIDs
2. COX pathway — addressed by other botanical compounds
3. Opioid-mediated analgesia (myrrh) — central sensitization relevant
4. TRPV1 modulation (myrrh) — neurogenic inflammation

The traditional pairing makes mechanistic sense — they are non-redundant, complementary targets.

Connections

• [[In-Fryer Antioxidants]] — carnosic acid, thymol
• [[Botanical Pack]] — sources
• [[Phase 2 - Mast Cell Stabilization]] — AKBA, thymoquinone
• [[Quorum Sensing]] — cinnamaldehyde
• [[Roman Amphora System]] — abietic acid historical use
• [[Ancient Wisdom]] — frankincense/myrrh connection