Drupacine

CAS# 49686-57-9

Drupacine

Catalog No. BCN7065----Order now to get a substantial discount!

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Quality Control of Drupacine

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Chemical structure

Drupacine

3D structure

Chemical Properties of Drupacine

Cas No. 49686-57-9 SDF Download SDF
PubChem ID 21586622 Appearance Powder
Formula C18H21NO5 M.Wt 331.36
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,11S,12S,13R,15S)-13-methoxy-5,7,21-trioxa-19-azahexacyclo[11.7.1.02,10.04,8.011,15.015,19]henicosa-2,4(8),9-trien-12-ol
SMILES COC12CC34CCCN3CC(O1)C5=CC6=C(C=C5C4C2O)OCO6
Standard InChIKey KYTDBKDWDOVRLJ-FLXSYLCISA-N
Standard InChI InChI=1S/C18H21NO5/c1-21-18-8-17-3-2-4-19(17)7-14(24-18)10-5-12-13(23-9-22-12)6-11(10)15(17)16(18)20/h5-6,14-16,20H,2-4,7-9H2,1H3/t14-,15+,16-,17-,18+/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 Drupacine

The twigs and leaves of Cephalotaxus fortunei.

Biological Activity of Drupacine

DescriptionDrupacine and a crude alkaloid extract suppress nematode hatch, activity of mixed life stages, and population numbers on plant roots.
In vitro

Nematotoxicity of drupacine and a Cephalotaxus alkaloid preparation against the plant-parasitic nematodes Meloidogyne incognita and Bursaphelenchus xylophilus.[Pubmed: 23785026 ]

Pest Manag Sci. 2013 Sep;69(9):1026-33.


METHODS AND RESULTS:
Species of Cephalotaxus (the plum yews) produce nematotoxic compounds of unknown identity. Consequently, bioassay-guided fractionation was employed to identify the compound(s) in Cephalotaxus fortunei twigs and leaves with activity against plant-parasitic nematodes. A crude alkaloid extract, particularly Drupacine, was responsible for much of the nematotoxicity. The ED50 of Drupacine for Bursaphelenchus xylophilus was 27.1 μg mL⁻1, and for Meloidogyne incognita it was 76.3 μg mL⁻1. Immersion of M. incognita eggs in 1.0 mg mL⁻1 crude alkaloid extract (the highest tested concentration) reduced hatch by 36%; immersion of second-stage juveniles (J2) resulted in 72-98% immobility. Crude alkaloid extract and Drupacine suppressed protease activity in extracts of the microbivorous nematode Panagrellus redivivus by 50% and 80%, respectively. Application of 0.02-0.5 mg mL⁻1 crude alkaloid extract to soil with M. incognita inoculum did not significantly reduce pepper plant shoot length or weight, compared with nematode-inoculated, water-treated controls, but the number of eggs and J2 per root system respectively decreased by 69% and 73% at 0.5 mg mL⁻1.
CONCLUSIONS:
Drupacine and a crude alkaloid extract suppress nematode hatch, activity of mixed life stages, and population numbers on plant roots. This is the first demonstration of nematotoxicity of crude Cephalotaxus alkaloids and Drupacine.

Protocol of Drupacine

Structure Identification
Yao Xue Xue Bao. 2003 Dec;38(12):919-23.

Synthesis and antitumor activity of the derivatives of cephalotaxine and drupacine.[Pubmed: 15040085]

To make full use of cephalotaxus plant resources and search for antitumor agents with higher activities and lower side effects.
METHODS AND RESULTS:
The C3 hydroxy groups of the cephlotaxine and Drupacine were acylated by taxol side chain and its isomers to give a series of derivatives of cephlotaxine and Drupacine. Six novel alkaloid esters were designed and synthesized. The pharmacological screening results showed that VIIIa, VIIIb, IXa and IXc exhibited significant activities on KB, HCT and Bel in vitro.
CONCLUSIONS:
Novel alkaloid esters are worthy to be intensively studied.

J Chromatogr A. 2009 May 29;1216(22):4663-7.

Completed preparative separation of alkaloids from Cephaltaxus fortunine by step-pH-gradient high-speed counter-current chromatography.[Pubmed: 19393155 ]

Cephalotaxine-type alkaloids are the anti-cancer components in twigs, leaves, roots and seeds of Cephalotaxus fortunine. It is very important to use the limited resource by finding an efficient purification technology of the alkaloids.
METHODS AND RESULTS:
Separation of cephalotaxine-type alkaloids in Cephalotaxus fortunine by step-pH-gradient high-speed counter-current chromatography (step-pH-gradient HSCCC) was studied in this paper. The step-pH-gradient HSCCC was performed on a HSCCC instrument equipped with a 400-mL column, using the upper phase of ethyl acetate-n-hexane-water, with added 0.01% trifluoroacetic acid (TFA) as stationary phase, and the lower phase of ethyl acetate-n-hexane-water, with added 2% NH(4)OH, 0.2% NH(4)OH and 0.05% TFA as mobile phase. For each separation, 800mg of extract of cephalotaxine-type alkaloids was separated to yield 9.3mg of Drupacine, 15.9mg of wilsonine, 130.4mg of cephalotaxine, 64.8mg of epi-wilsonine, 12.8mg of fortunine and 35.6mg of acetylcephalotaxine with purities 81.2%, 85.7%, 95.3%, 97.5%, 89.1% and 96.2%, respectively.
CONCLUSIONS:
The recovery of each alkaloid was more than 90%. The structures of the six alkaloids were identified by electrospray ionization mass spectrum (ESI-MS) and (1)H and (13)C NMR.

Drupacine Dilution Calculator

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Preparing Stock Solutions of Drupacine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0179 mL 15.0893 mL 30.1787 mL 60.3573 mL 75.4466 mL
5 mM 0.6036 mL 3.0179 mL 6.0357 mL 12.0715 mL 15.0893 mL
10 mM 0.3018 mL 1.5089 mL 3.0179 mL 6.0357 mL 7.5447 mL
50 mM 0.0604 mL 0.3018 mL 0.6036 mL 1.2071 mL 1.5089 mL
100 mM 0.0302 mL 0.1509 mL 0.3018 mL 0.6036 mL 0.7545 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 Drupacine

Completed preparative separation of alkaloids from Cephaltaxus fortunine by step-pH-gradient high-speed counter-current chromatography.[Pubmed:19393155]

J Chromatogr A. 2009 May 29;1216(22):4663-7.

Cephalotaxine-type alkaloids are the anti-cancer components in twigs, leaves, roots and seeds of Cephalotaxus fortunine. It is very important to use the limited resource by finding an efficient purification technology of the alkaloids. Separation of cephalotaxine-type alkaloids in Cephalotaxus fortunine by step-pH-gradient high-speed counter-current chromatography (step-pH-gradient HSCCC) was studied in this paper. The step-pH-gradient HSCCC was performed on a HSCCC instrument equipped with a 400-mL column, using the upper phase of ethyl acetate-n-hexane-water, with added 0.01% trifluoroacetic acid (TFA) as stationary phase, and the lower phase of ethyl acetate-n-hexane-water, with added 2% NH(4)OH, 0.2% NH(4)OH and 0.05% TFA as mobile phase. For each separation, 800mg of extract of cephalotaxine-type alkaloids was separated to yield 9.3mg of Drupacine, 15.9mg of wilsonine, 130.4mg of cephalotaxine, 64.8mg of epi-wilsonine, 12.8mg of fortunine and 35.6mg of acetylcephalotaxine with purities 81.2%, 85.7%, 95.3%, 97.5%, 89.1% and 96.2%, respectively. The recovery of each alkaloid was more than 90%. The structures of the six alkaloids were identified by electrospray ionization mass spectrum (ESI-MS) and (1)H and (13)C NMR.

Nematotoxicity of drupacine and a Cephalotaxus alkaloid preparation against the plant-parasitic nematodes Meloidogyne incognita and Bursaphelenchus xylophilus.[Pubmed:23785026]

Pest Manag Sci. 2013 Sep;69(9):1026-33.

BACKGROUND: Species of Cephalotaxus (the plum yews) produce nematotoxic compounds of unknown identity. Consequently, bioassay-guided fractionation was employed to identify the compound(s) in Cephalotaxus fortunei twigs and leaves with activity against plant-parasitic nematodes. RESULTS: A crude alkaloid extract, particularly Drupacine, was responsible for much of the nematotoxicity. The ED50 of Drupacine for Bursaphelenchus xylophilus was 27.1 microg mL(-)(1), and for Meloidogyne incognita it was 76.3 microg mL(-)(1). Immersion of M. incognita eggs in 1.0 mg mL(-)(1) crude alkaloid extract (the highest tested concentration) reduced hatch by 36%; immersion of second-stage juveniles (J2) resulted in 72-98% immobility. Crude alkaloid extract and Drupacine suppressed protease activity in extracts of the microbivorous nematode Panagrellus redivivus by 50% and 80%, respectively. Application of 0.02-0.5 mg mL(-)(1) crude alkaloid extract to soil with M. incognita inoculum did not significantly reduce pepper plant shoot length or weight, compared with nematode-inoculated, water-treated controls, but the number of eggs and J2 per root system respectively decreased by 69% and 73% at 0.5 mg mL(-)(1). CONCLUSION: Drupacine and a crude alkaloid extract suppress nematode hatch, activity of mixed life stages, and population numbers on plant roots. This is the first demonstration of nematotoxicity of crude Cephalotaxus alkaloids and Drupacine.

[Synthesis and antitumor activity of the derivatives of cephalotaxine and drupacine].[Pubmed:15040085]

Yao Xue Xue Bao. 2003 Dec;38(12):919-23.

AIM: To make full use of cephalotaxus plant resources and search for antitumor agents with higher activities and lower side effects. METHODS: The C3 hydroxy groups of the cephlotaxine and Drupacine were acylated by taxol side chain and its isomers to give a series of derivatives of cephlotaxine and Drupacine. RESULTS: Six novel alkaloid esters were designed and synthesized. The pharmacological screening results showed that VIIIa, VIIIb, IXa and IXc exhibited significant activities on KB, HCT and Bel in vitro. CONCLUSION: Novel alkaloid esters are worthy to be intensively studied.

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