状芸香素

化合物

状芸香素(英語:Chalepensin)是一种呋喃香豆素类化合物。该化合物最初于1967年从叙利亚芸香英语Ruta chalepensisRuta chalepensis[1]中分离出来,并由此得名。在芸香属的其他植物中也发现了这种物质,包括芸香[2]山芸香西班牙语Ruta montana[3]

状芸香素
IUPAC名
6-(2-Methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
识别
CAS号 13164-03-9  checkY
PubChem 128834
ChemSpider 114167
SMILES
 
  • CC(C)(C=C)C1=CC2=C(C=C3C(=C2)C=CO3)OC1=O
ChEBI 3572
KEGG C09165
性质
化学式 C16H14O3
摩尔质量 254.28 g·mol−1
熔点 82—83 °C(180—181 °F;355—356 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

化学性质

状芸香素形成无色针状结晶,熔点为82-83 °C。[4]

研究

状芸香素已被证明对雌性大鼠具有抗生育作用。[2][5][6]这可能是状芸香素对卵巢产生毒性作用的结果。[5]这种抗生育效应可能为南美传统上使用叙利亚芸香英语Ruta chalepensis[6]和现代使用芸香油(芸香属植物提取的油)[7]作为堕胎药的做法提供了一些科学依据。

状芸香素还被证明对变异链球菌英语Streptococcus mutans耐甲氧西林金黄色葡萄球菌具有抗菌活性。[8]

相关化合物

已知几种与状芸香素具有相同核心化学结构的化合物,包括叙利亚芸香素芸香内酯5-甲氧基状芸香素5,8-二甲氧基状芸香素

参考资料

  1. ^ Brooker, Robert M.; Eble, John N.; Starkovsky, Nicolas A. Chalepensin, chalepin, and chalepin acetate, three novel furocoumarins from ruta chalepensis. Lloydia. 1967, 30 (1): 73–77. 
  2. ^ 2.0 2.1 Kong, Y.; Lau, C.; Wat, K.; Ng, K.; But, P.; Cheng, K.; Waterman, P. Antifertility Principle of Ruta graveolens. Planta Medica. 1989, 55 (2): 176–178. PMID 2748734. doi:10.1055/s-2006-961917. 
  3. ^ Touati, Driss; Atta-Ur-Rahman; Ulubelen, Ayhan. Alkaloids from Ruta montana. Phytochemistry. 2000, 53 (2): 277–279. PMID 10680183. doi:10.1016/S0031-9422(99)00486-0. 
  4. ^ 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. Cytotoxic and Antiplatelet Aggregation Principles of Ruta Graveolens. Journal of the Chinese Chemical Society. 2003, 50: 171–178. doi:10.1002/jccs.200300024. 
  5. ^ 5.0 5.1 Ulubelen, A.; Ertugrul, L.; Birman, H.; Yigit, R.; Erseven, G.; Olgac, V. Antifertility effects of some coumarins isolated from Ruta chalepensis andR. Chalepensis var.latifolia in rodents. Phytotherapy Research. 1994, 8 (4): 233–236. S2CID 85292230. doi:10.1002/ptr.2650080409. 
  6. ^ 6.0 6.1 Nahar, Lutfun; Al-Majmaie, Shaymaa; Al-Groshi, Afaf; Rasul, Azhar; Sarker, Satyajit D. Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential. Molecules. 2021, 26 (6): 1609. PMC 7999183 . PMID 33799365. doi:10.3390/molecules26061609 . 
  7. ^ Ciganda, Carmen; Laborde, Amalia. Herbal Infusions Used for Induced Abortion. Journal of Toxicology: Clinical Toxicology. 2003, 41 (3): 235–239. PMID 12807304. S2CID 44851492. doi:10.1081/CLT-120021104. 
  8. ^ Al-Majmaie, Shaymaa; Nahar, Lutfun; Rahman, M. Mukhlesur; Nath, Sushmita; Saha, Priyanka; Talukdar, Anupam Das; Sharples, George P.; Sarker, Satyajit D. 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. 2021, 26 (4): 1114. PMC 7923287 . PMID 33669881. doi:10.3390/molecules26041114 .