Abstract
The Annonaceous acetogenins are a growing class of compounds endogenous to the plant family Annonaceae that have been shown to have significant cytotoxic, in vivo antitumor, and pesticidal properties. Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST). The LC50 values determined by the BST correlated with the concentration of acetogenins in the twigs and hence showed the relative bioactivity of the monthly extracts. The results revealed that the months of May, June, and July were the top three months for acetogenin production. There was a one to two order of magnitude decrease in activity in late fall to winter. A single extract sample from each month was then evaluated using liquid chromatography/(+)electrospray ionization/tandem mass spectrometry (LC/(+)ESI-MS/MS). Concentrations of the three major and most active Annonaceous acetogenins, bullatacin, asimicin, and trilobacin, were directly evaluated without any further sample preparation in the crude CH2Cl2 extracts of the twigs. All three compounds (MW 622), possess a 4-OH and showed a characteristic neutral loss of 112 amu from the sodiated parent molecule (m/z 645). The m/z 533 daughter ions were monitored and quantified using 'spiked' amounts of pure analytes to construct calibration curves. These results showed that the contents of bullatacin and the mixture of asimicin and trilobacin increased significantly in May and June, with bullatacin at 13 and 15 ppm, respectively, and the mixture of asimicin and trilobacin at 47 and 51 ppm, respectively in the dry weight of the twigs. Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents. Purification of the F005 (partitioned fraction) sample yielded thymoquinone (C10H 12O2, MW164) and thymol (C10H14O, MW 150) as the most bioactive compounds in the BST. Thymoquinone showed selective cytotoxicity towards the PC-3 (prostate) human tumor cancer cell line with an ED50 comparable to Adriamycine® a standard chemotherapeutic agent. In the National Cancer Institute (NCI) 60 human tumor cell panel, thymoquinone displayed interesting selectivities towards SF-539 (CNS), M-14 (melanoma), PC-3, and OVCAR-5 (ovarian). Thymol was not found to be cytotoxic, but did show pesticidal activity comparable to rotenone.
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Claims 11
Claim · model-written summary
LC50 values from the brine shrimp test correlated with acetogenin concentration in Asimina triloba twigs.
- Taxon
- Asimina triloba
Asimina trilobae0 - Compound
- acetogeninse1
- Outcome
- LC50 values determined by the BSTe1
Not reportedDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST)”
e1“The LC50 values determined by the BST correlated with the concentration of acetogenins in the twigs and hence showed the relative bioactivity of the monthly extracts”
Claim · model-written summary
May, June and July were the top three months for acetogenin production in Asimina triloba.
- Taxon
- Asimina trilobaAsimina trilobae0
- Outcome
- acetogenin productione1
- Qualifier
- the months of May, June, and Julye1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST)”
e1“The results revealed that the months of May, June, and July were the top three months for acetogenin production”
Claim · model-written summary
Bioactivity of Asimina triloba twigs decreased by one to two orders of magnitude in late fall to winter.
- Taxon
- Asimina trilobaAsimina trilobae0
- Outcome
- activitye1
- Direction
- decreasee1
- Value
- one to two order of magnitudee1
- Setting
- late fall to wintere1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST)”
e1“There was a one to two order of magnitude decrease in activity in late fall to winter”
Claim · model-written summary
Bullatacin content in Asimina triloba twigs increased significantly in May and June, at 13 and 15 ppm.
- Taxon
- Asimina trilobaAsimina trilobae0
- Organ / stage
- twigse1
- Outcome
- contents of bullatacine1
- Direction
- increasede1
- Value
- 13 and 15 ppme1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST)”
e1“These results showed that the contents of bullatacin and the mixture of asimicin and trilobacin increased significantly in May and June, with bullatacin at 13 and 15 ppm, respectively, and the mixture of asimicin and trilobacin at 47 and 51 ppm, respectively in the dry weight of the twigs”
Claim · model-written summary
The mixture of asimicin and trilobacin in Asimina triloba twigs increased significantly in May and June, at 47 and 51 ppm.
- Taxon
- Asimina trilobaAsimina trilobae0
- Organ / stage
- twigse1
- Outcome
- the mixture of asimicin and trilobacine1
- Direction
- increasede1
- Value
- 47 and 51 ppme1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monthly twig samples of Asimina triloba extracted with CH2Cl2 were monitored for biological activity using the brine shrimp lethality test (BST)”
e1“These results showed that the contents of bullatacin and the mixture of asimicin and trilobacin increased significantly in May and June, with bullatacin at 13 and 15 ppm, respectively, and the mixture of asimicin and trilobacin at 47 and 51 ppm, respectively in the dry weight of the twigs”
Claim · model-written summary
Thymoquinone was identified as one of the most bioactive compounds in the brine shrimp test of Monarda fistulosa fractions.
- Taxon
- Monarda fistulosa
Monarda fistulosae0 - Compound
- thymoquinonee1
- Outcome
- most bioactive compounds in the BSTe1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“Purification of the F005 (partitioned fraction) sample yielded thymoquinone (C10H 12O2, MW164) and thymol (C10H14O, MW 150) as the most bioactive compounds in the BST”
Claim · model-written summary
Thymol was identified as one of the most bioactive compounds in the brine shrimp test of Monarda fistulosa fractions.
- Taxon
- Monarda fistulosaMonarda fistulosae0
- Compound
- thymole1
- Outcome
- most bioactive compounds in the BSTe1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“Purification of the F005 (partitioned fraction) sample yielded thymoquinone (C10H 12O2, MW164) and thymol (C10H14O, MW 150) as the most bioactive compounds in the BST”
Claim · model-written summary
Thymoquinone showed selective cytotoxicity towards the PC-3 prostate tumor cell line, with an ED50 comparable to Adriamycine.
- Taxon
- Monarda fistulosaMonarda fistulosae0
- Treatment
- thymoquinonee1
- Outcome
- cytotoxicity towards the PC-3 (prostate) human tumor cancer cell linee1
- Direction
- comparablee1
- Comparator
- Adriamycinee1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“Thymoquinone showed selective cytotoxicity towards the PC-3 (prostate) human tumor cancer cell line with an ED50 comparable to Adriamycine® a standard chemotherapeutic agent”
Claim · model-written summary
Thymoquinone displayed interesting selectivities in the NCI 60 human tumor cell panel.
- Taxon
- Monarda fistulosaMonarda fistulosae0
- Compound
- thymoquinonee1
- Outcome
- selectivitiese1
- Qualifier
- SF-539 (CNS), M-14 (melanoma), PC-3, and OVCAR-5 (ovarian)e1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“In the National Cancer Institute (NCI) 60 human tumor cell panel, thymoquinone displayed interesting selectivities towards SF-539 (CNS), M-14 (melanoma), PC-3, and OVCAR-5 (ovarian)”
Claim · model-written summary
Thymol was not cytotoxic.
- Taxon
- Monarda fistulosaMonarda fistulosae0
- Compound
- Thymole1
- Outcome
- cytotoxice1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“Thymol was not found to be cytotoxic”
Claim · model-written summary
Thymol showed pesticidal activity comparable to rotenone.
- Taxon
- Monarda fistulosaMonarda fistulosae0
- Treatment
- Thymole1
- Outcome
- pesticidal activitye1
- Direction
- comparablee1
- Comparator
- rotenonee1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Monarda fistulosa L. (Lamiaceae), also known as wild bergamot, was subjected to bioactivity-directed fractionation using the BST to identify the in vitro bioactive constituents”
e1“Thymol was not found to be cytotoxic, but did show pesticidal activity comparable to rotenone”