Macluraxanthone
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| Names | |
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| Preferred IUPAC name
5,9,10-Trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6-one | |
| Identifiers | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C23H22O6 | |
| Molar mass | 394.423 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Macluraxanthone is a naturally occurring organic compound with the formula C23H22O6.[1] Belonging to the xanthone family,[2] it is a trihydroxylated xanthone characterized by the presence of a pyran ring and a prenyl chain.[3]
Its structure features a catechol moiety,[2] a xanthene core, and a chromene ring.[4] Acetylation of macluraxanthone yields a triacetate derivative with the formula C29H28O9. X-ray crystallography of a synthesized derivative (Di-p-bromobenzenesulfonyl-macluraxanthone) reveals a planar xanthene ring system and a screw boat conformation in the chromene ring.[4] Macluraxanthone has demonstrated antimalarial and larvicidal activity,[2] including effects against Plasmodium falciparum and vector mosquito larvae.[5] Additional studies have reported antibacterial activity against Enterococcus faecalis.[4]
References
[edit]- ^ Sangsuwon, Chanyapat; Jiratchariyakul, Weena (2015). "Antiproliferative Effect of Lung Cancer Cell Lines and Antioxidant of Macluraxanthone from Garcinia Speciosa Wall". Procedia - Social and Behavioral Sciences. 197: 1422–1427. doi:10.1016/j.sbspro.2015.07.089.
- ^ a b c Teixeira, Jorge Ginja; Veiga, Alfredina; Dias, Cristina Barrocas; Teixeira, Dora Martins (2017). "Electroanalytical Study of Macluraxanthone: A Natural Product with a Strong Antioxidant and Antimalarial Activity". Electroanalysis. 29 (9): 2062–2070. doi:10.1002/elan.201700181. ISSN 1040-0397. Retrieved 28 May 2025.
- ^ Ng, Ida May Jen; Mah, Siau Hui; Chua, Caroline Lin Lin (8 June 2020). "Immuno-modulatory effects of macluraxanthone on macrophage phenotype and function". Natural Product Research. 35 (23). Informa UK Limited: 5409–5414. doi:10.1080/14786419.2020.1775223. ISSN 1478-6419. PMID 32508145. Retrieved 28 May 2025.
- ^ a b c Boonnak, Nawong; Chantrapromma, Suchada; Fun, Hoong-Kun; Karalai, Chatchanok (2008). "Synthesis and Crystal Structure of Di-p-bromobenezenesulfonyl-macluraxanthone". Analytical Sciences: X-ray Structure Analysis Online. 24: X71 – X72. doi:10.2116/analscix.24.x71. ISSN 1348-2238. Retrieved 29 May 2025.
- ^ Teh, Soek; Ee, Gwendoline; Mah, Siau; Lim, Yang; Ahmad, Zuraini (2013-02-04). "Cytotoxicity and Structure-Activity Relationships of Xanthone Derivatives from Mesua beccariana, Mesua ferrea and Mesua congestiflora towards Nine Human Cancer Cell Lines". Molecules. 18 (2): 1985–1994. doi:10.3390/molecules18021985. ISSN 1420-3049. PMC 6270040. PMID 23381024.