| Uses |
Friedelin is a flavonoid extract which displays radical scavenging and anti-typhoid activity. |
| Uses |
Friedelin can be used as a starting material in the synthesis of:
- Friedel-3-enol acetate, friedel-2-oxo-3-enol acetate, friedel-2-ene derivatives and friedelin ketoxime.
- Oxygenated friedelin derivatives as potent DNA topoisomerase IIα inhibitors.
- Its 1,4-pyrazine derivatives as potent antimicrobial agents.
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| Definition |
ChEBI: Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone. |
| General Description |
Friedelin, a pentacyclic triterpene, is found in several plants like Cissus quadrangularis, Celastrus vulcanicola, Terminalia?avicennioides, and Alangium salvifolium. It is known to act as a histamine H1 receptor?(H1R) antagonist, anti-microbial, anti-HIV, and anti-cancer agent. |
| Synthesis |
Crude bamboo powder as raw materials, take 1kg, add 5 times the amount of n-hexane, heating and reflux extraction 4 times, each time 2h, combined extract, concentrated to extract, washed with 70% ethanol, and then extracted with ethyl acetate, ethyl acetate extract was concentrated to a small volume, add an appropriate amount of silica gel, stirring, dry on a silica gel column, in turn, 8:1, 19:1, 24:1, 47:1 chloroform-methanol Eluted with 8:1, 19:1, 24:1, 47:1 chloroform-methanol mixed solution, collect the eluent rich in uninhibited terpene components, eluent desolvation with ethanol reflux solubilization, cooling crystallization, repeated 2 times, filtered out the crystals dry that is, cork ketone product 3.1g, content of 92.7%.
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| in vivo |
Friedelin (40 mg/kg, p.o., single dose) exhibits potent anti-inflammatory activity in the carrageenan (HY-125474)-induced acute inflammation Wistar rat model[2]. Friedelin (30 mg/kg, i.p., once daily, for 14 days) alleviats neuronal dysfunction and memory impairment in the scopolamine (HY-N0296)-induced neurodegeneration mouse model[3]. Friedelin (40 μM, local injection near the right Achilles tendon, once weekly, for 4 weeks) prevents the progression of tendinopathy in the type I collagenase (HY-E70005A)-induced tendinopathy C57BL/6 mouse model[4].
| Animal Model: |
Scopolamine (HY-N0296)-induced neurodegeneration mice model[3] |
| Dosage: |
30 mg/kg |
| Administration: |
Intraperitoneal injection (i.p.), once daily, for 14 days |
| Result: |
Improved scopolamine-induced oxidative stress, neurodegeneration, and memory impairment.
| Animal Model: |
Carrageenan (HY-125474)-induced acute inflammation Wistar rats model[2] |
| Dosage: |
40 mg/kg |
| Administration: |
Oral gavage (p.o.), single dose |
| Result: |
Maximally inhibited acute inflammatory response, significantly reduced paw edema thickness.
| Animal Model: |
Collagenase Type I (HY-E70005A)-induced tendinopathy C57BL/6 mice model[4] |
| Dosage: |
40 μM |
| Administration: |
Local injection near the right Achilles tendon, once weekly, for 4 weeks |
| Result: |
Significantly improved tendon mechanical strength, reduced inflammatory cell infiltration, restored ordered collagen fiber arrangement. |
|
| IC 50 |
CYP2; CYP3 |
FRIEDELIN Preparation Products And Raw materials
| Raw materials |
6β,27-Dihydroxy-D:A-friedooleanan-3-one-->6β-Hydroxy-D:A-friedooleanan-3-one-->Kokoonol-->21-hydroxyfriedelan-3-one-->24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-, (4α,5β,8α,9β,10α,13α,14β)--->3,4-Seco-3,4-epoxyfriedelane-3-one |
| Preparation Products |
D:A-Friedoolean-3-ene |
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