Ambrosin is a sesquiterpene lactone found in the plant Ambrosia artemisiifolia, commonly known as ragweed. It exhibits a variety of biological activities, including anti-inflammatory, cytotoxic, and antimicrobial properties. Ambrosin has shown promise in the treatment of cancer cells, particularly leukemia and melanoma. The compound is also being investigated for its potential to treat inflammatory diseases such as rheumatoid arthritis and asthma. Research on ambrosin focuses on understanding its mechanism of action and optimizing its therapeutic potential. The synthesis of ambrosin is complex and involves multiple steps. Due to its potential therapeutic benefits, ambrosin is a subject of ongoing research and development. '
ambrosin: from Ambrosia maritime; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Ambrosia | genus | A plant genus of the family ASTERACEAE. The POLLEN is one cause of HAYFEVER.[MeSH] | Asteraceae | A large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 92119 |
| CHEMBL ID | 115843 |
| CHEBI ID | 2629 |
| SCHEMBL ID | 3463663 |
| MeSH ID | M0056367 |
| Synonym |
|---|
| ACON0_000311 |
| ACON1_002230 |
| NCGC00179698-01 |
| nsc-85235 |
| 509-93-3 |
| ambrosin |
| C09292 |
| 6beta-hydroxy-4-oxo-10alphah-ambrosa-2,11(13)-dien-12-oic acid gamma-lactone |
| MEGXP0_001652 |
| azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methylene-, (3as-(3aalpha,6beta,6aalpha,9abeta,9balpha))- |
| 10alphah-ambrosa-2,11(13)-dien-12-oic acid, 6beta-hydroxy-4-oxo-, gamma-lactone |
| 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methyleneazuleno(4,5b)furan-2,9-dione |
| CHEMBL115843 |
| chebi:2629 , |
| (3as,6s,6ar,9ar,9br)-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,9b-hexahydroazuleno[8,7-b]furan-2,9-dione |
| unii-6xi048644b |
| 6xi048644b , |
| azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methylene-, (3as,6s,6ar,9ar,9br)- |
| ambrosin [mi] |
| qe9ho4ln0u , |
| unii-qe9ho4ln0u |
| ambrosin (+/-)-form [mi] |
| ambrosin, (+/-)- |
| 64813-79-2 |
| (+/-)-ambrosin |
| azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methylene-, (3as,6s,6ar,9ar,9br)-rel- |
| SCHEMBL3463663 |
| Q27105752 |
| DTXSID60877831 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " No toxic signs could be detected neither after oral administration of 5 g/kg of dried leaves of the plant as a powder or as a methanolic extract, nor after the incorporation of 50,000 ppm powdered leaves in the feed during 4 weeks." | ( Toxicity and mutagenicity of the molluscicidal plant Ambrosia maritima L. Alard, F; Geerts, S; Stievenart, C; Thilemans, L; Vanparys, P, 1991) | 0.28 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " In silico studies showed that bioavailability and BBB permeability could be favorable for ambrosin over curcumin." | ( Ambrosin, a potent NF-κβ inhibitor, ameliorates lipopolysaccharide induced memory impairment, comparison to curcumin. Choucry, MA; El Awdan, SA; El Senousy, AS; El-Marasy, SA; Hassan, A; Khalil, MNA; Omar, FA, 2019) | 2.18 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Inhibitory concentration 50 (IC50) values were obtained from dose-response curves." | ( Anti-cancer stem cell activity of a sesquiterpene lactone isolated from Ambrosia arborescens and of a synthetic derivative. Almanza, G; Huang, X; Kempengren, S; Malakpour, A; Oredsson, S; Rodrigo, G; Smiljanic, S; Sotillo, WS; Sterner, O; Villagomez, R, 2017) | 0.46 |
| Class | Description |
|---|---|
| sesquiterpene lactone | Any member of a diverse class of complex, multicyclic phytochemicals showing a variety of skeleton arrangements and bioactivities, and having in common a sesquiterpenoid structure including a lactone ring. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID156154 | The compound was evaluated for cytotoxicity against prostate cancer cell line PC-3 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID143338 | The compound was evaluated for cytotoxicity against lung cancer cell line NCI-H522 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID80540 | The compound was evaluated for cytotoxicity against colon cancer cell line HCT116 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID100999 | The compound was evaluated for cytotoxicity against melanoma cell line LOX-IMVI | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID310936 | Cytotoxicity against human KB cells | 2007 | Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8 | Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity. |
| AID200440 | The compound was evaluated for cytotoxicity against renal cancer cell line SN12C | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID201281 | The compound was evaluated for cytotoxicity against CNS cancer cell line CNS SF-539 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID387024 | Cytotoxicity against human KB cells | 2008 | European journal of medicinal chemistry, Oct, Volume: 43, Issue:10 | Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones. |
| AID145736 | The compound was evaluated for cytotoxicity against ovarian cancer cell line OVCAR-5 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| AID103437 | The compound was evaluated for cytotoxicity against breast cancer cell line MCF-7 | 1995 | Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17 | Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 6 (42.86) | 18.7374 |
| 1990's | 3 (21.43) | 18.2507 |
| 2000's | 2 (14.29) | 29.6817 |
| 2010's | 3 (21.43) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (46.32) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 15 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||