29-Hydroxyfriedelan-3-one | CAS:39903-21-4

29-Hydroxyfriedelan-3-one

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Description:

Reference standards.

In vitro:

Planta Med. 2001 Feb;67(1):65-9.

Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.[Pubmed: 11270725]

METHODS AND RESULTS:
The crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) from Monteverde, Costa Rica, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-Hydroxyfriedelan-3-one. The structures of these compounds were elucidated on the basis of NMR spectral analysis. Molecular orbital calculations have been carried out using the semi-empirical PM3 and Hartee-Fock 3-21G ab initio techniques on the quinone-methide nortriterpenoids tingenone and netzahualcoyonol, as well as on the nucleotide bases adenine, guanine, cytosine, and thymine.
CONCLUSIONS:
The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.

29-Hydroxyfriedelan-3-one Description

Source:	The herbs of Euonymus alatus (Thunb.) Sieb
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Phytochemistry,1984,23(3):631-3.

The chemistry of toxic principles from Maytenus nemerosa[Reference: WebLink]

METHODS AND RESULTS:
Maytenus nemerosa has been fractionated systematically by following the toxicity of extracts, partitioned solutions and column chromatographic fractions against cultured KB cells. Several compounds were isolated in this fashion, including 3-oxo-20(29)-lupen-30-al, β-amyrin, 29-Hydroxyfriedelan-3-one, 30-hydroxy-20(29)-lupen-3-one, 30-hydroxyfriedelan-3-one and lup-20(29)-ene-3β,30-diol, as well as tingenone, 20-hydroxytingenone and galactitol.
CONCLUSIONS:
3-Oxo-20(29)-lupen-30-al was shown to be cytotoxic for the first time; the structural basis of this cytotoxicity was investigated, in part, by bioassay of four products obtained by chemical transformation of single, isolated principles.

Product Name	29-Hydroxyfriedelan-3-one
Price:
CAS No.:	39903-21-4
Catalog No.:	CFN98632
Molecular Formula:	C₃₀H₅₀O₂
Molecular Weight:	442.7 g/mol
Purity:	>=98%
Type of Compound:	Triterpenoids
Physical Desc.:	Powder
Source:	The herbs of Euonymus alatus (Thunb.) Sieb
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Triterpenoids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.2589 mL	11.2943 mL	22.5887 mL	45.1773 mL	56.4717 mL
5 mM	0.4518 mL	2.2589 mL	4.5177 mL	9.0355 mL	11.2943 mL
10 mM	0.2259 mL	1.1294 mL	2.2589 mL	4.5177 mL	5.6472 mL
50 mM	0.0452 mL	0.2259 mL	0.4518 mL	0.9035 mL	1.1294 mL
100 mM	0.0226 mL	0.1129 mL	0.2259 mL	0.4518 mL	0.5647 mL

CFN98804	Friedelanol	5085-72-3	428.7	C₃₀H₅₂O
CFN99806	Epifriedelanol	16844-71-6	428.7	C₃₀H₅₂O
CFN98223	Epifriedelanol acetate	2259-07-6	470.8	C₃₂H₅₄O₂
CFN98936	Friedelin	559-74-0	426.7	C₃₀H₅₀O
CFN98632	29-Hydroxyfriedelan-3-one	39903-21-4	442.7	C₃₀H₅₀O₂
CFN99784	Shionone	10376-48-4	426.72	C₃₀H₅₀O