Chalepensin Names IUPAC name 6-(2-Methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
Other namesXyloltenin; 3-(α,α-dimethylallyl)psoralen
Identifiers ChEBI ChEMBL ChemSpider KEGG InChI=1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3
Key: FYCCCUNGXGKNJV-UHFFFAOYSA-N
Properties C 16 H 14 O 3 Molar mass −1 Melting point 82–83 °C (180–181 °F; 355–356 K) Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Chalepensin is a chemical compound of thefuranocoumarin class. Originally isolated in 1967 fromfringed rue (Ruta chalepensis ),[ 1] Ruta common rue (Ruta graveolens )[ 2] mountain rue (Ruta montana ).[ 3]
Chemical properties [ edit ] Chalepensin forms colorless crystalline needles with a melting point of 82-83 °C.[ 4]
Chalepensin has been shown to have antifertility effects in female rats.[ 2] [ 5] [ 6] [ 5] [ 6] Ruta ) in South America[ 7] abortifacient .
Chalepensis has also been shown to have antibacterial activity againstStreptococcus mutans methicillin-resistantStaphylococcus aureus (MRSA).[ 8]
Several chemical compounds that have the same core chemical structure as chalepensin are known, includingchalepin ,rutamarin ,5-methoxychalepensin , and5,8-dimethoxychalepensin .
Chalepin
Rutamarin
5-Methoxychalepensin
5,8-Dimethoxychalepensin
^ Brooker, Robert M.; Eble, John N.; Starkovsky, Nicolas A. (1967). "Chalepensin, chalepin, and chalepin acetate, three novel furocoumarins from ruta chalepensis".Lloydia .30 (1):73– 77. {{cite journal }}: CS1 maint: multiple names: authors list (link )^a b Kong, Y.; Lau, C.; Wat, K.; Ng, K.; But, P.; Cheng, K.; Waterman, P. (1989). "Antifertility Principle ofRuta graveolens".Planta Medica .55 (2):176– 178.doi :10.1055/s-2006-961917 .PMID 2748734 . ^ Touati, Driss; Atta-Ur-Rahman; Ulubelen, Ayhan (2000). "Alkaloids from Ruta montana".Phytochemistry .53 (2):277– 279.doi :10.1016/S0031-9422(99)00486-0 .PMID 10680183 . ^ Wu, Tian-Shung; Shi, Li-Shian; Wang, Jhi-Joung; Iou, Song-Chou; Chang, Hsien-Chang; Chen, Yuh-Pan; Kuo, Yao-Haur; Chang, Ya-Ling; Tenge, Che-Ming (2003). "Cytotoxic and Antiplatelet Aggregation Principles ofRuta Graveolens".Journal of the Chinese Chemical Society .50 :171– 178.doi :10.1002/jccs.200300024 . ^a b Ulubelen, A.; Ertugrul, L.; Birman, H.; Yigit, R.; Erseven, G.; Olgac, V. (1994). "Antifertility effects of some coumarins isolated fromRuta chalepensis andR. Chalepensis var.latifolia in rodents".Phytotherapy Research .8 (4):233– 236.doi :10.1002/ptr.2650080409 .S2CID 85292230 . ^a b Nahar, Lutfun; Al-Majmaie, Shaymaa; Al-Groshi, Afaf; Rasul, Azhar; Sarker, Satyajit D. (2021)."Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential" .Molecules .26 (6): 1609.doi :10.3390/molecules26061609 PMC 7999183 PMID 33799365 . ^ Ciganda, Carmen; Laborde, Amalia (2003). "Herbal Infusions Used for Induced Abortion".Journal of Toxicology: Clinical Toxicology .41 (3):235– 239.doi :10.1081/CLT-120021104 .PMID 12807304 .S2CID 44851492 . ^ Al-Majmaie, Shaymaa; Nahar, Lutfun; Rahman, M. Mukhlesur; Nath, Sushmita; Saha, Priyanka; Talukdar, Anupam Das; Sharples, George P.; Sarker, Satyajit D. (2021)."Anti-MRSA Constituents from Ruta chalepensis (Rutaceae) Grown in Iraq, and in Silico Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether" .Molecules .26 (4): 1114.doi :10.3390/molecules26041114 PMC 7923287 PMID 33669881 . 
