7-Isopentenyloxy-gamma-fagarine | CAS:23417-92-7

7-Isopentenyloxy-gamma-fagarine

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Product Name	7-Isopentenyloxy-gamma-fagarine
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CAS No.:	23417-92-7
Catalog No.:	CFN98242
Molecular Formula:	C₁₈H₁₉NO₄
Molecular Weight:	313.4 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Yellow powder
Source:	The fruits of Evodia lepta
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
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Size /Price /Stock	10 mM * 1 mL in DMSO / Inquiry
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Description:

7-Isopentenyloxy-gamma-fagarine has highly cytotoxicity against the MCF-7and Jurkat cell line. It has been used as a precursor for the chemical asymmetric synthesis of the enantiopure alkaloids: evoxine, anhydroevoxine and evodine.

In vitro:

Planta Med. 2009 Nov;75(14):1509-16.

Cytotoxic activity and cell cycle analysis of quinoline alkaloids isolated from Haplophyllum canaliculatum Boiss.[Pubmed: 19551611 ]

METHODS AND RESULTS:
Bioassay-guided fractionation of Haplophyllum canaliculatum Boiss. (Rutaceae) extract resulted in isolation of five quinoline alkaloids: 7-Isopentenyloxy-gamma-fagarine, atanine, skimmianine, flindersine and perfamine. This is the first isolation of these compounds from this endemic species. The antitumor activity of these five isolates was evaluated against RAJI, Jurkat, KG-1a, HEP-2, MCF-7, HL-60 and HL-60/MX1 tumor cell lines. The highest cytotoxic effect was observed on acute lymphoblastic leukemia cell lines.
CONCLUSIONS:
7-Isopentenyloxy-gamma-fagarine, atanine, skimmianine and flindersine exhibited very high cytotoxicity against the RAJI cell line with IC(50) values of 1.5, 14.5, 15.6 and 14.9 microg/mL, respectively and 7-Isopentenyloxy-gamma-fagarine, atanine and skimmianine exhibited very high cytotoxicity against the Jurkat cell line with IC(50) values of 3.6, 9.3 and 11.5 microg/mL, respectively. 7-Isopentenyloxy-gamma-fagarine was also highly cytotoxic against the MCF-7 cell line (IC(50) = 15.5 microg/mL.

7-Isopentenyloxy-gamma-fagarine Description

Source:	The fruits of Evodia lepta
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:

Org Biomol Chem. 2007 Sep 21;5(18):2983-91.

Synthesis, structure and stereochemistry of quinoline alkaloids from Choisya ternata.[Pubmed: 17728865]

METHODS AND RESULTS:
A range of seventeen quinoline alkaloids, involving several types of oxidations during their biosynthetic pathways, have been isolated from leaves of Choisya ternata. In addition to the nine known quinoline alkaloids, eight new members of the furoquinoline family, derived mainly from prenylation at C-5 (including two novel hydroperoxides), have been identified. The absolute configurations and enantiopurity values of all chiral quinoline alkaloids have been determined.
CONCLUSIONS:
One of the isolated alkaloids, 7-Isopentenyloxy-gamma-fagarine, has been used as a precursor for the chemical asymmetric synthesis of the enantiopure alkaloids: evoxine, anhydroevoxine and evodine. The possible roles of oxygenase and other oxygen-atom-transfer enzymes, in the biosynthetic pathways of the C. ternata alkaloids, have been discussed.

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

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.1908 mL	15.9541 mL	31.9081 mL	63.8162 mL	79.7703 mL
5 mM	0.6382 mL	3.1908 mL	6.3816 mL	12.7632 mL	15.9541 mL
10 mM	0.3191 mL	1.5954 mL	3.1908 mL	6.3816 mL	7.977 mL
50 mM	0.0638 mL	0.3191 mL	0.6382 mL	1.2763 mL	1.5954 mL
100 mM	0.0319 mL	0.1595 mL	0.3191 mL	0.6382 mL	0.7977 mL

CFN96762	Isodictamnine	484-74-2	199.20	C₁₂H₉NO₂
CFN96763	Isopteleine	2181-84-2	229.23	C₁₃H₁₁NO₃
CFN96765	Isomaculosidine	518-96-7	259.26	C₁₄H₁₃NO₄
CFN96362	Robustine	2255-50-7	215.2	C₁₂H₉NO₃
CFN98858	gamma-Fagarine	524-15-2	229.2	C₁₃H₁₁NO₃
CFN95126	Maculosidin	522-19-0	259.3	C₁₄H₁₃NO₄
CFN96010	Haplopine	5876-17-5	245.2	C₁₃H₁₁NO₄
CFN92555	Skimmianin	83-95-4	259.3	C₁₄H₁₃NO₄
CFN98242	7-Isopentenyloxy-gamma-fagarine	23417-92-7	313.4	C₁₈H₁₉NO₄
CFN90488	Evodine	6989-38-4	329.35	C₁₈H₁₉NO₅