Calozeylanic acid, a new bark acid from three species (guttiferae)

Samaraweera, Upasiri; Sotheeswaran, Subramaniam; Uvais, M.; Sultanbawa, S.

doi:10.1016/s0040-4039(01)92426-8

Cited by 6 publications

(7 citation statements)

References 3 publications

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“…In the initial phase of this study, we utilized TLC to identify those extracts that contained coumarins. A small aliquot of the crude extract was dissolved in CH 2 Cl 2 and chromatographed against (-)-calanolide B (2) and soulattrolide (8), representing the 4-n-propyl and 4-phenyl subclasses, on Si gel plates. The plates were developed with hexane-EtOAc (7:3), allowed to air-dry, and then sprayed with vanillin-H 2 SO 4 ; over the course of several hours, pyranocoumarin spots turned a characteristic deep blue.…”

Section: Resultsmentioning

confidence: 99%

“…inophylloide has shown much less diversity in pyranocoumarin content, and only four such compounds have been found in the NCI collection. The two most abundant pyranocoumarins produced by this species were (-)-calanolide B (2) and soulattrolide (8), which differ only in the coumarin C-4 substituent (n-propyl vs phenyl, respectively). We have also isolated soulattrolone ( 13), the 12-keto derivative of soulattrolide (8), and a novel phenylketopyranocoumarin, calanone (14).…”

Section: Pyranocoumarins Frommentioning

confidence: 99%

“…The two most abundant pyranocoumarins produced by this species were (-)-calanolide B (2) and soulattrolide (8), which differ only in the coumarin C-4 substituent (n-propyl vs phenyl, respectively). We have also isolated soulattrolone ( 13), the 12-keto derivative of soulattrolide (8), and a novel phenylketopyranocoumarin, calanone (14). 29 It is noteworthy that two chemotypes of C. teysmannii var.…”

Section: Pyranocoumarins Frommentioning

confidence: 99%

“…31,32 We did not explore further the coumarin-containing extracts from C. inophyllum and C. soulattri, because the chemistry of these species had already been extensively explored by several groups. For example, soulattrolide (8) was first isolated and reported in 1977 from C. soulattri by Gunasekera and co-workers. 23 More recently, the pyranocoumarins from C. inophyllum were described by a group at SmithKline Beecham.…”

Section: Pyranocoumarins Frommentioning

confidence: 99%

“…Plants from the genus Calophyllum (Guttiferae, Clusiaceae) have proven to be a rich source of natural products, including xanthones, − steroids, triterpenes, , coumarins, − and benzopyrans . In 1992, we reported a series of dipyranocoumarins, the calanolides, from C. lanigerum var.…”

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confidence: 99%

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Pyranocoumarins from Tropical Species of the Genus Calophyllum: A Chemotaxonomic Study of Extracts in the National Cancer Institute Collection

et al. 1998

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(+)-Calanolide A, a novel dipyranocoumarin from the Malesian tree Calophyllum lanigerum var. austrocoriaceum, and a closely related compound, (-)-calanolide B, isolated from Calophyllum teysmannii var. inophylloide, are representatives of a distinct class of nonnucleoside HIV-1 specific reverse-transcriptase inhibitor under development as an AIDS chemotherapeutic. NCI repository specimens totalling 315 organic extracts from 31 taxa of Calophyllum were analyzed for related pyranocoumarins using a simple TLC system. A total of 127 extracts was initially classified as "positive"; eight out of the 31 taxa examined, representing perhaps 28 species already described (1/7-1/8 of all the species in this genus), contained prenylated coumarins, suggesting that these compounds, while sometimes abundantly present, are not widespread in the genus. Representative members of the TLC-positive extracts were partitioned between CH2C12 and 25% aqueous MeOH; the CH2C12-soluble materials were then analyzed by TLC and 1H NMR to confirm the presence of pyranocoumarins. The anti-HIV activity of the partitioned extracts are also presented. This study suggested that there are several distinctive coumarin chemotaxonomic markers distinguishing species of this genus.

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Section: Resultsmentioning

confidence: 99%