Calophyllum

Chemistry of anti FtlV-l active Calophyllum coumarins 98YGK116. 

Yet other compounds have been found to inhibit HIV-1 replication through a specific interaction with HIV-1 RT (i.e., quinoxaline S-2720 [68], 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide [69], dihydrothiazolo-isoindolones [70] and a number of natural substances (e.g., calanolide A and inophyllums, from the tropical rain forest trees Calophyllum lanigerum and Calophyllum inophyllum, respectively) [71,72]. All these and yet other compounds could be considered to be NNRTIs. The most potent among the NNRTIs, some of the HEPT derivatives (E-EBU-dM) [63] and a-... 

Caranfa MJ, Breen AL, Bartus HR, Johnson RK, Hertzberg RP, Westley JW. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn. J Med Chem 1993 36 4131-4138. 

Fig. 10. Calophyllum teysmanii var. inophylloides. From Flora of Malaya. No FRI 12776. Geographical localization Terengganu, Gunong Padang, narrow ridge crest alt. 3300 feet. Date 9/21/1969. T. C. Whitmore. 

Reviews of saturated oxygen heterocycles <00JCS(P1)1291>, routes to 2,2-dimethyl-2H-[l]benzopyrans <00H(53)1193> and pyranonaphthoquinone antibiotics <00T1937>, HIV-1 active Calophyllum coumarins <00H(53)453> and of the application of (3-halovinylaldehydes in heterocyclic synthesis <00H(53)941> have appeared. 

Several types of tree producing non-edible oils, with an estimated annual production potential of more than 20 Mt, are being considering in India for biodiesel production [13-18] karanja (Pongamia pinnata), nahar (Mesua firrua), jatropha (Jatropha curcas), pinnai (Calophyllum L.), neem (Azadirachta indica), mahua (Madhuca Mica) and rubber (Hevea hrasiliensis). All of them have an FFA content of 3-20%. 

Tropical rainforest tree and Malaysian tree A number of natural products have been reported to interact with reverse transcriptase, i.e., baicalin, avarol, avarone, psycho-trine, phloroglucinol derivatives and, in particular, calanolides (from the tropical rainforest tree, Calophyllum lanigerum) and inophyllums (from the Malaysian tree, Calophyllum inophyllum). 

The cyclisation of o-alkenylphenols features in two approaches to the chroman ring system. The Hg-mediated cyclisation of (7) affords the chroman-4-ols (8) and (9) which can be separated after debenzylation, providing the chroman unit of the calophyllum coumarins (95S630). 2-Cyclohexenylphenols undergo a 6-endo cyclisation to fused chromans on treatment with pyridine hydrobromide perbromide (95CJC1727). 

Hay, A.E., Helesbeux, J.J., Duval, O., LabaTed, M., Grellier, P. and Richomme, P. (2004b) Antimalarial xanthones from Calophyllum caledonicum and Garcinia viellardii. Life Sciences 75(25), 3077-3085. 

Pyranocoumarins (C50 Phe pyran-2-one) include a variety of angular and linear compounds. A number of angular pyranocoumarins are spasmolytic and vasodilatory, notably the Ca2+ channel blocker visnadin. The inophyllums B and P from Calophyllum ionophyllum (Guttiferae) are inhibitors of HIV-1 reverse transcriptase. 

RECENT PROGRESS IN CALOPHYLLUM COUMARINS AS POTENT ANTI-HIV AGENTS... 

Numerous dipyranocoumarins have been isolated from different species of Calophyllum. According to their chemical skeleton, they have three heterocycle rings, ring B, C, and D, constructed from a phloroglucinol core A. These compounds fall into three basic structural types (1) tetracycle dipyranocoumarins in which the D rings have a gem-dimethyl group, such as (-l-)-calanolide A (1), (-l-)-calanolide B... 

Scheme 8-1. Chemical structures of naturally occurring Calophyllum coumarins.

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