Natural and synthetic chromenes, fused chromenes, and versatility of dihydrobenzo[h]chromenes in organic synthesis.

The Calophyllum genus (Clusiaceae) is composed of ca. 200 species, with a pantropical distribution. Some species are used as medicinal agents to treat a large number of diseases, including gastric ulcers, infections, pain, tumors, and inflammatory processes, among others. A review of the literature regarding the chemical and biological aspects of these plants indicates cytotoxic activity against several cell lines, inhibition of HIV-1 reverse transcriptase, antisecretory and cytoprotective properties, antinociceptive, molluscicidal and antimicrobial effects, etc., related particularly to the presence of coumarins, xanthones, flavonoids, and triterpenes. This review, therefore, deals with the chemistry, and pharmacology or biology of the main plants belonging to the genus Calophyllum, with particular emphasis on C. brasiliense, studied by our research group.

Chemical and pharmacological aspects of the genus Calophyllum.

The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR).

https://www.mdpi.com/1420-3049/16/11/9721/pdf

Soulamarin, a new coumarin from stem bark of Calophyllum soulattri.

A new furanoxanthone from the stem bark of Calophyllum inophyllum.

Our continuing studies on secondary metabolites from the stem bark of Calophyllum soulattri has led to the isolation of another new diprenylated xanthone, phylattrin (1), in addition to five other xanthones and two common sterols. The xanthones are soulattrin (2), caloxanthone C (3), macluraxanthone (4), brasixanthone B (5) and trapezifolixanthone (6) while the sterols are stigmasterol (7) and β-sitosterol (8). The structures of these compounds were determined on the basis of spectroscopic analyses such as 1D and 2D-NMR, HRESIMS, IR and UV. Compounds 1-7 exhibited moderate cytotoxic activities against SNU-1, HeLa, Hep G2, NCI-H23, K562, Raji, LS174T, IMR-32 and SK-MEL-28 cells.

/pdf/phylattrin-a-new-cytotoxic-xanthone-from-calophyllum-5bgxljkd3n.pdf

K.N. Ng

Papers

Mucigerin, a new coumarin from Calophyllum mucigerum (Guttiferae)