Friedelin

CAS# 559-74-0

Friedelin

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Quality Control of Friedelin

Number of papers citing our products

Chemical structure

Friedelin

3D structure

Chemical Properties of Friedelin

Cas No. 559-74-0 SDF Download SDF
PubChem ID 91472 Appearance White powder
Formula C30H50O M.Wt 426.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Friedelanone
Solubility Freely soluble in chloroform; sparingly soluble in ethan
Chemical Name (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
SMILES CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
Standard InChIKey OFMXGFHWLZPCFL-SVRPQWSVSA-N
Standard InChI InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Friedelin

1 Bridelia sp. 2 Calophyllum sp. 3 Cimicifuga sp. 4 Citrus sp. 5 Clerodendrum sp. 6 Inula sp. 7 Mallotus sp. 8 Phyllanthus sp. 9 Putranjiva sp. 10 Quercus sp. 11 Terminalia sp. 12 Vanillosmopsis sp.

Biological Activity of Friedelin

DescriptionFriedelin possesses antioxidant, gastroprotective, anti-diarrhoeal, liver protective, anti-inflammatory, analgesic and antipyretic activities.Friedelin rich fraction (IND-HE) shows estrogenic activity as indicated by vaginal cornification, increase in uterine weight and rise in serum estrogen. Friedelin may be beneficial to mimic insulin action that would be useful in the treatment of diabetes type 2 patients.
TargetsPGE | NOS | Caspase | Estrogen receptor | Progestogen receptor
In vitro

Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. leaves.[Pubmed: 23561182]

Food Chem. 2013 Aug 15;139(1-4):860-5.

The aim of the present study was to evaluate the antioxidant, free radical scavenging and liver protective effects of Friedelin isolated from Azima tetracantha Lam. leaves.
METHODS AND RESULTS:
In in vitro antioxidant study, the free radical scavenging effect of Friedelin on 2,2-diphenyl-picrylhydrazyl (DPPH), hydroxyl, nitric oxide and superoxide radicals were evaluated. Friedelin showed very good scavenging effect on DPPH (IC50 21.1 mM), hydroxyl (IC50 19.8 mM), nitric oxide (IC50 22.1 mM) and superoxide (IC50 21.9 mM) radicals. Friedelin also showed strong suppressive effect on lipid peroxidation. In in vivo antioxidant study, CCl4 induced oxidative stress on rats produced significant increase in serum glutamate oxaloacetate transaminase (SGOT), serum glutamate pyruvate transaminase (SGPT) and lactate dehydrogenase (LDH) levels along with reduction in liver superoxide dismutase (SOD), catalase (CAT), reduced glutathione (GSH) and glutathione peroxidase (GPx) levels. Pre-treatment of rats with Friedelin at 40 mg/kg for 7 days restored these levels to normality and showed liver protection, comparable to the standard, silymarin (25 mg/kg).
CONCLUSIONS:
These results clearly demonstrated that Friedelin possessed marked antioxidant and liver protective effects.

Friedelin and lanosterol from Garcinia prainiana stimulated glucose uptake and adipocytes differentiation in 3T3-L1 adipocytes.[Pubmed: 22988818]

Nat Prod Res. 2013 Mar;27(4-5):417-24.

Friedelin and lanosterol have been isolated from twigs of Garcinia prainiana. Their structures were elucidated by spectroscopic methods. The compounds were examined for their effects on 3T3-L1 adipocytes.
METHODS AND RESULTS:
In the MTT assay, it was found that the compounds had no cytotoxic effects up to 25 µM. Adipocyte differentiation analysis was carried out by Oil Red O staining method. In the presence of adipogenic cocktail (MDI), it was found that Friedelin and lanosterol enhanced intracellular fat accumulation by 2.02 and 2.18-fold, respectively, compared with the vehicle-treated cells. Deoxyglucose uptake assay was used to examine the insulin sensitivity of adipocytes in the presence of the compounds. It was found that Friedelin was able to stimulate glucose uptake up to 1.8-fold compared with insulin-treated cells.
CONCLUSIONS:
It was suggested that Friedelin and lanosterol may be beneficial to mimic insulin action that would be useful in the treatment of diabetes type 2 patients.

In vivo

Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms.[Pubmed: 25617794 ]

Eur J Pharmacol. 2015 Mar 5;750:167-75.

The current study was aimed to investigate the gastroprotective effects of Friedelin isolated from the hexane extract of leaves of Azima tetracantha.
METHODS AND RESULTS:
Ethanol-induced gastric ulcer model was used to investigate the gastroprotective effects of Friedelin. Antioxidant enzymes, lipid peroxidation, nitric oxide, gastric vascular permeability, pro and anti-inflammatory cytokines and apoptosis level have been investigated. Ethanol caused severe gastric damage and Friedelin pretreatment protected against its deleterious role. Antioxidant enzyme activities, anti-inflammatory cytokines, prostaglandin E2 (PGE2), constitutive nitric oxide synthase (cNOS) and mucus weight have been increased significantly. However, the vascular permeability, pro-inflammatory cytokines, inducible nitric oxide synthase (iNOS), caspase-3 and apoptosis level have significantly been decreased after Friedelin ingestion.
CONCLUSIONS:
The present study has clearly demonstrated the anti-ulcer potential of Friedelin, these findings suggested that Friedelin could be a new useful natural gastroprotective tool against gastric ulcer.

Anti-Diarrhoeal Activity of Friedelin Isolated from Azima tetracantha Lam. in Wistar Rats.[Reference: WebLink]

South Indian Journal of Biological Sciences, 2015,1(1):34-3.

The present study was aimed to evaluate the anti-diarrhoeal activity of Friedelin isolated from leaves of Azima tetracantha Lam.
METHODS AND RESULTS:
The anti-diarrhoeal effect of Friedelin was studied by using castor oil-induced diarrhoea, gastrointestinal motility test, magnesium sulphate-induced diarrhea and castor oil-induced enteropooling in rats. Friedelin (20 mg/kg) showed significant (P < 0.0001) reduction of intestinal transit and gastric emptying which were similar to the anti- motility activity as known compound atropine (0.1 mg/kg). Friedelin (20 mg/kg) also exerted significant anti-enteropooling effects, against castor oil-induced enteropooling in rats. The defaecation frequencies and the faecal droppings wetness were significantly (P < 0.0001) reduced. Additionally, Friedelin (20 mg/kg) revealed significant (P < 0.0001) inhibition (89.64%) of castor oil-induced diarrhea.
CONCLUSIONS:
The overall results elucidated that the anti-diarrhoeal activity of Friedelin may be due to its anti-secretory and anti-motility properties, which consequently provide evidence for the traditional claim.

Protocol of Friedelin

Kinase Assay

Development of an assay for screening β amyloid aggregation inhibitors in vitro and study on inhibitive activity of friedelin.[Reference: WebLink]

Chinese Pharmaceutical Journal, 2005, 40(19):1474-7.

To screen the inhibitors of β amyloid aggregation from natural products.
METHODS AND RESULTS:
A screening assay was established based on ELISA theory to screen the inhibitors of β amyloid aggregation. The inhibition was determined by congo red binding assay and thioflavin T binding assay. Some herbs were screened. The active compounds were isolated and tracing detected. The ethanol extract of Erigeron breviscapine(vant) was found to be active, the active component was isolated and elucidated as Friedelin.
CONCLUSIONS:
A screen assay is successfully established based on ELISA theory for screening the inhibitors of the β amyloid aggregation in vitro. Friedelin prevents the aggregation of synthetic β amyloid in vitro. β.

Animal Research

Estrogenic activity of friedelin rich fraction (IND-HE) separated from Cissus quadrangularis and its effect on female sexual function.[Pubmed: 21808556 ]

Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models.[Pubmed: 21718291]

J Pharm Pharmacol. 2011 Aug;63(8):1070-7.

Friedelin was isolated from Azima tetracantha Lam. leaves collected from Kallakurichi, Villuppuram district, Tamil Nadu, India. The anti-inflammatory, analgesic and antipyretic activities of Friedelin have been investigated in Wistar rats and mice.
METHODS AND RESULTS:
Friedelin was isolated from the hexane extract of leaves of A. tetracantha using column chromatography. The effects of Friedelin on inflammation were studied by using carrageenan-induced hind paw oedema, croton oil-induced ear oedema, acetic acid-induced vascular permeability, cotton pellet-induced granuloma and adjuvant-induced arthritis. The analgesic effect of Friedelin was evaluated using the acetic acid-induced abdominal constriction response, formalin-induced paw licking response and the hot-plate test. The antipyretic effect of Friedelin was evaluated using the yeast-induced hyperthermia test in rats. In the acute phase of inflammation, maximum inhibitions of 52.5 and 68.7% (P<0.05) were noted with 40 mg/kg Friedelin in carrageenan-induced paw oedema and croton oil-induced ear oedema, respectively. Administration of Friedelin (40 mg/kg) significantly (P<0.05) decreased the formation of granuloma tissue induced by cotton pellet at a rate of 36.3%. In the adjuvant-induced arthritis test Friedelin inhibited 54.5% of paw thickness. Friedelin inhibited acetic acid-induced vascular permeability in mice. Friedelin also produced significant (P<0.05) analgesic activity in the acetic acid-induced abdominal constriction response and formalin-induced paw licking response. In the hot-plate test, Friedelin did not show any significant results when compared with control. Treatment with Friedelin showed a significant (P<0.05) dose-dependent reduction in pyrexia in rats.
CONCLUSIONS:
The results suggested that Friedelin possessed potent anti-inflammatory, analgesic and antipyretic activities.

Pharmacognosy Res. 2010 May;2(3):138-45.

Women experience menopause differently across the world, in terms of their symptomology. Many experience symptoms of menopause like hot flashes, joint pain and loss of libido. Estrogen replacement is the prescribed therapy for most of the sexual dysfunction observed in menopausal women. Many women are reluctant to use exogenous hormone therapy for treatment of menopausal symptoms and are turning to botanical and dietary supplements for relief.
METHODS AND RESULTS:
In the present study IND-HE (Friedelin rich fraction) was studied for estrogenic activity as well as its effect on sexual behavior in overiectomized female Wistar rats. The rats were divided into 4 groups of six rats each. The Group 1 received distilled water, Group II - IND-HE (75 mg/kg p. o.), Group III - IND-HE (100 mg/kg p. o.) and Group IV received estrogen (estradiol) (1 mg/kg in olive oil suspension, s.c. bi-weekly). The treatment period was 8 weeks. On 1 day, one month and two month of treatment the sexual behavior was studied. At the end of the treatment the blood was withdrawn from retro-orbital plexus. The animals were sacrificed and uterus was removed, weighed and histology was studied. In different group of rats estrous cycle was studied which indicate estrogenic activity and for progestogenic activity of deciduoma formation was studied.The result indicated that IND-HE (75 and 100 mg/kg p.o.) improved sexual behavior parameters. IND-HE (75 and 100) significantly (P< 0.01) decreased darting and hopping latency. The darting frequency and hopping frequency was significantly (P< 0.01) improved in IND-HE (75 and100 mg/kg p.o.) as well as estrogen group. Lordosis interval (LI) was increased significantly in estrogen group after 1(st) month (P< 0.05), and after 2(nd) month (P< 0.01). IND-HE (100) treatment showed increase in LI after 1(st) month (P< 0.05) remained during 2(nd) month (P< 0.01). While IND-HE (75) treatment increased LI only after 2(nd) month (P< 0.05).IND-HE (75 and 100 mg/kg p.o.) showed estrogenic activity as indicated by vaginal cornification, increase in uterine weight and rise in serum estrogen.

Friedelin Dilution Calculator

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Friedelin Molarity Calculator

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Preparing Stock Solutions of Friedelin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3436 mL 11.7178 mL 23.4357 mL 46.8713 mL 58.5892 mL
5 mM 0.4687 mL 2.3436 mL 4.6871 mL 9.3743 mL 11.7178 mL
10 mM 0.2344 mL 1.1718 mL 2.3436 mL 4.6871 mL 5.8589 mL
50 mM 0.0469 mL 0.2344 mL 0.4687 mL 0.9374 mL 1.1718 mL
100 mM 0.0234 mL 0.1172 mL 0.2344 mL 0.4687 mL 0.5859 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Friedelin

Friedelin and lanosterol from Garcinia prainiana stimulated glucose uptake and adipocytes differentiation in 3T3-L1 adipocytes.[Pubmed:22988818]

Nat Prod Res. 2013 Mar;27(4-5):417-24.

Friedelin and lanosterol have been isolated from twigs of Garcinia prainiana. Their structures were elucidated by spectroscopic methods. The compounds were examined for their effects on 3T3-L1 adipocytes. In the MTT assay, it was found that the compounds had no cytotoxic effects up to 25 microM. Adipocyte differentiation analysis was carried out by Oil Red O staining method. In the presence of adipogenic cocktail (MDI), it was found that Friedelin and lanosterol enhanced intracellular fat accumulation by 2.02 and 2.18-fold, respectively, compared with the vehicle-treated cells. Deoxyglucose uptake assay was used to examine the insulin sensitivity of adipocytes in the presence of the compounds. It was found that Friedelin was able to stimulate glucose uptake up to 1.8-fold compared with insulin-treated cells. It was suggested that Friedelin and lanosterol may be beneficial to mimic insulin action that would be useful in the treatment of diabetes type 2 patients.

Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models.[Pubmed:21718291]

J Pharm Pharmacol. 2011 Aug;63(8):1070-7.

OBJECTIVES: Friedelin was isolated from Azima tetracantha Lam. leaves collected from Kallakurichi, Villuppuram district, Tamil Nadu, India. The anti-inflammatory, analgesic and antipyretic activities of Friedelin have been investigated in Wistar rats and mice. METHODS: Friedelin was isolated from the hexane extract of leaves of A. tetracantha using column chromatography. The effects of Friedelin on inflammation were studied by using carrageenan-induced hind paw oedema, croton oil-induced ear oedema, acetic acid-induced vascular permeability, cotton pellet-induced granuloma and adjuvant-induced arthritis. The analgesic effect of Friedelin was evaluated using the acetic acid-induced abdominal constriction response, formalin-induced paw licking response and the hot-plate test. The antipyretic effect of Friedelin was evaluated using the yeast-induced hyperthermia test in rats. KEY FINDINGS: In the acute phase of inflammation, maximum inhibitions of 52.5 and 68.7% (P<0.05) were noted with 40 mg/kg Friedelin in carrageenan-induced paw oedema and croton oil-induced ear oedema, respectively. Administration of Friedelin (40 mg/kg) significantly (P<0.05) decreased the formation of granuloma tissue induced by cotton pellet at a rate of 36.3%. In the adjuvant-induced arthritis test Friedelin inhibited 54.5% of paw thickness. Friedelin inhibited acetic acid-induced vascular permeability in mice. Friedelin also produced significant (P<0.05) analgesic activity in the acetic acid-induced abdominal constriction response and formalin-induced paw licking response. In the hot-plate test, Friedelin did not show any significant results when compared with control. Treatment with Friedelin showed a significant (P<0.05) dose-dependent reduction in pyrexia in rats. CONCLUSIONS: The results suggested that Friedelin possessed potent anti-inflammatory, analgesic and antipyretic activities.

Estrogenic activity of friedelin rich fraction (IND-HE) separated from Cissus quadrangularis and its effect on female sexual function.[Pubmed:21808556]

Pharmacognosy Res. 2010 May;2(3):138-45.

Women experience menopause differently across the world, in terms of their symptomology. Many experience symptoms of menopause like hot flashes, joint pain and loss of libido. Estrogen replacement is the prescribed therapy for most of the sexual dysfunction observed in menopausal women. Many women are reluctant to use exogenous hormone therapy for treatment of menopausal symptoms and are turning to botanical and dietary supplements for relief. In the present study IND-HE (Friedelin rich fraction) was studied for estrogenic activity as well as its effect on sexual behavior in overiectomized female Wistar rats.The rats were divided into 4 groups of six rats each. The Group 1 received distilled water, Group II - IND-HE (75 mg/kg p. o.), Group III - IND-HE (100 mg/kg p. o.) and Group IV received estrogen (estradiol) (1 mg/kg in olive oil suspension, s.c. bi-weekly). The treatment period was 8 weeks. On 1 day, one month and two month of treatment the sexual behavior was studied. At the end of the treatment the blood was withdrawn from retro-orbital plexus. The animals were sacrificed and uterus was removed, weighed and histology was studied. In different group of rats estrous cycle was studied which indicate estrogenic activity and for progestogenic activity of deciduoma formation was studied.The result indicated that IND-HE (75 and 100 mg/kg p.o.) improved sexual behavior parameters. IND-HE (75 and 100) significantly (P< 0.01) decreased darting and hopping latency. The darting frequency and hopping frequency was significantly (P< 0.01) improved in IND-HE (75 and100 mg/kg p.o.) as well as estrogen group. Lordosis interval (LI) was increased significantly in estrogen group after 1(st) month (P< 0.05), and after 2(nd) month (P< 0.01). IND-HE (100) treatment showed increase in LI after 1(st) month (P< 0.05) remained during 2(nd) month (P< 0.01). While IND-HE (75) treatment increased LI only after 2(nd) month (P< 0.05).IND-HE (75 and 100 mg/kg p.o.) showed estrogenic activity as indicated by vaginal cornification, increase in uterine weight and rise in serum estrogen.

Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. leaves.[Pubmed:23561182]

Food Chem. 2013 Aug 15;139(1-4):860-5.

The aim of the present study was to evaluate the antioxidant, free radical scavenging and liver protective effects of Friedelin isolated from Azima tetracantha Lam. leaves. In in vitro antioxidant study, the free radical scavenging effect of Friedelin on 2,2-diphenyl-picrylhydrazyl (DPPH), hydroxyl, nitric oxide and superoxide radicals were evaluated. Friedelin showed very good scavenging effect on DPPH (IC50 21.1 mM), hydroxyl (IC50 19.8 mM), nitric oxide (IC50 22.1 mM) and superoxide (IC50 21.9 mM) radicals. Friedelin also showed strong suppressive effect on lipid peroxidation. In in vivo antioxidant study, CCl4 induced oxidative stress on rats produced significant increase in serum glutamate oxaloacetate transaminase (SGOT), serum glutamate pyruvate transaminase (SGPT) and lactate dehydrogenase (LDH) levels along with reduction in liver superoxide dismutase (SOD), catalase (CAT), reduced glutathione (GSH) and glutathione peroxidase (GPx) levels. Pre-treatment of rats with Friedelin at 40 mg/kg for 7 days restored these levels to normality and showed liver protection, comparable to the standard, silymarin (25 mg/kg). These results clearly demonstrated that Friedelin possessed marked antioxidant and liver protective effects.

Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms.[Pubmed:25617794]

Eur J Pharmacol. 2015 Mar 5;750:167-75.

The current study was aimed to investigate the gastroprotective effects of Friedelin isolated from the hexane extract of leaves of Azima tetracantha. Ethanol-induced gastric ulcer model was used to investigate the gastroprotective effects of Friedelin. Antioxidant enzymes, lipid peroxidation, nitric oxide, gastric vascular permeability, pro and anti-inflammatory cytokines and apoptosis level have been investigated. Ethanol caused severe gastric damage and Friedelin pretreatment protected against its deleterious role. Antioxidant enzyme activities, anti-inflammatory cytokines, prostaglandin E2 (PGE2), constitutive nitric oxide synthase (cNOS) and mucus weight have been increased significantly. However, the vascular permeability, pro-inflammatory cytokines, inducible nitric oxide synthase (iNOS), caspase-3 and apoptosis level have significantly been decreased after Friedelin ingestion. The present study has clearly demonstrated the anti-ulcer potential of Friedelin, these findings suggested that Friedelin could be a new useful natural gastroprotective tool against gastric ulcer.

Description

Friedelin is isolated from isolated from the leaves of Maytenus ilicifolia(Mart). Friedelin is a noncompetitive inhibitor of CYP3A4 with IC50 and Kivalues of 10.79 μM and 6.16 μM, respectively. Friedelin is also a competitive inhibitor of CYP2E1 with IC50 and Ki values of 22.54 μM and 18.02 μM, respectively.

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