Anti-Pseudomonas aeruginosa xanthones from the resin and green fruits of Cratoxylum cochinchinense

Boonnak, Nawong; Karalai, Chatchanok; Chantrapromma, Suchada; Ponglimanont, Chanita; Fun, Hoong‐Kun; Kanjana‐Opas, Akkharawit; Chantrapromma, Kan; Kato, Shigeru

doi:10.1016/j.tet.2009.01.083

Cited by 40 publications

(68 citation statements)

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“…Table 3, compound 11 (dulcisxanthone B) showed moderate activity against both MRSA and VRE with the same minimum inhibitory concentration (MIC) values of 9.37 mg/ml. By comparing these results with those of bmangostin (MRSA: 75, VRE: 150 mg/ml) and a-mangostin (MRSA, VRE: 9.37 mg/ml) which were previously reported, 10) it could be suggested that one O-methylation either at C-3 (11) or C-7 (a-mangostin) of 1,3,6,7-tetraoxygenated xanthone with isoprenyl side chain at C-2 and C-8 was essential for antibacterial activity especially against Gram-positive bacteria. The antibacterial activity against Gram-positive bacteria of b-mangostin whose structure contained two Omethylated groups at C-3 and C-7 was decreased drastically (MIC Ն75 mg/ml).…”

Section: Resultsmentioning

confidence: 55%

“…pruniflorum was subjected to chemical investigation leading to the isolation of two new xanthones, pruniflorone K (1) and L (2), together with thirteen known xanthones identified as cochinchinone A (3), 11) formoxanthone B (4), 8) 1,7-dihydroxy-8-methoxyxanthone (5), 12) cochinchinone I (6), 10) 1,3,7-trihydroxy-2,4-diisoprenylxanthone (7), 13) celebixanthone methyl ether (8), 14) vieillardiixanthone B (9), 15) macluraxanthone (10), 16) dulcisxanthone B (11), 17) norcowanin (12), 18) 5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-2H,6H-pyrano [3,2b]xanthone (13), 19) Garcinone B (14), 20) and brasilixanthone (15). 21) Their structures were elucidated by NMR analysis and comparison of their spectroscopic data with those reported in the literatures.…”

Section: Resultsmentioning

confidence: 99%

“…From our previously proposed biosynthesis, 10) it could be suggested that compound 1 could be derived from formoxanthone A by epoxidation of a geranyl side chain followed by cyclization via a free hydroxyl at C-3. Further dehydration led to a linear chromene ring.…”

Section: Resultsmentioning

confidence: 99%

“…[4][5][6] In the previous work, we reported the isolation of xanthones from the plants of Cratoxylum genus, which were collected in Thailand. We found that several isolated xanthones showed the antibacterial, [7][8][9] antifungal 10) and cytotoxic activities. [7][8][9] Previous investigation of the roots of Cratoxylum formosum ssp.…”

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confidence: 96%

“…pruniflorum had resulted in nine new and nine known xanthones. 7) Herein, this paper describes further investigation of CH 2 Cl 2 extract from the roots of the same plant which led to the isolation of two new xanthones (1, 2) along with thirteen known xanthones (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). In addition, the antibacterial and antifungal activities were also evaluated.…”

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confidence: 99%

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Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum

Boonnak

Karalai

Chantrapromma

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Resultsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 96%

mentioning

confidence: 99%

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Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum

Boonnak

Karalai

Chantrapromma

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Xanthones from the stems of Cratoxylum cochinchinense

Duan

Dai

Chen

et al. 2012

Magnetic Reson in Chemistry

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Four new xanthones, 1-methoxy-3,7,8-trihydroxyxanthone (1), 1-methoxy-4,7,8-trihydroxyxanthone (2), 1-methoxy-4,7-dihydroxyxanthone (3), and 1,4-dimethoxy-2,7-dihydroxyxanthone (4) were isolated from the stems of Cratoxylum cochinchinense along with four known xanthones (5-8). The structures of new compounds were determined by extensive spectroscopic analyses, mainly 1D and 2D NMR and HRESIMS data.

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Two new alkaloids and a new polyphenolic compound from Cotula coronopifolia

et al. 2012

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Two new alkaloid derivatives of the 3-benzazocine skeleton (cotuzine A and B) and a new polyphenolic substance (3-(1,3-dihydroxyprop-2-yl)-4-hydroxyanisol) (corimen) have been isolated from the aerial part (stems, leaves) of the plant Cotula coronopifolia (L.). These three new structures were established by spectroscopic procedures ( 1 H, 13 C,. The stereochemistry of the new alkaloids was established based on different NOE effects revealed on the NOESY spectrum. Mass spectrometry and IR spectroscopy were used to confirm these structures.The interest in nature as a source of potential chemotherapeutic agents continues. Natural products and their derivatives represent more than 50% of all drugs in clinical use in the world. Higher plants contribute no less than 25% of the total [1]. As part of our chemical investigation into some medicinal plants growing in Tunisia [2][3][4] and in order to continue our search for potential biological natural compounds [5], we report here the isolation and structure elucidation of two new alkaloids 1 and 2 and a new polyphenolic compound 3 isolated from the aerial part of Cotula coronopifolia (L.) (Asteraceae). So far not much is known on the ethnopharmacology of this plant [6].Structures of cotuzine A and B (1, 2) and corimen (3) were established by spectroscopic means (1D and 2D NMR) and confirmed by comparison with those of closely related compounds [7,8]. The relative stereochemistry of the alkaloid structure was obtained from the NOESY experiment.Cotuzine A (1) was obtained as an amorphous solid (29 mg) from the butanolic extract of the aerial part (stems, leaves) of the plant Cotula coronopifolia (L.). The IR spectrum indicated the presence of hydroxyl groups (3400-3200 cm -1 ), methyl groups (2963, 2882 cm -1 ), secondary amines (3029, 827 cm -1 ), and double bonds (3021, 1651 cm -1 ). The 13 C NMR spectrum (Table 1) indicates the presence of 21 carbons, including an ethylenic group relative to C-6 and C-6a at 119.9 ppm and 144.6 ppm, respectively, an anomeric carbon at 103.7 ppm, and two (-CH 2 -) groups at 40.5 and 42.2 ppm forming the (-CH 2 -NH-CH 2 -) skeleton. The 1 H NMR spectrum shows a signal at G 5.22 ppm attributable to H-6 coupled with H-5D 1.91 ppm, m) and H-5E (1.83 ppm, m), a doublet relative to CH 3 -8 0.89 ppm, d, J = 6.8 Hz), and three signals relative to three methyl groups: CH 3 -7D 0.91 ppm, s), CH 3 -7E 1.04 ppm, s), and CH 3 -10 0.91 ppm, s).

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Anti-Pseudomonas aeruginosa xanthones from the resin and green fruits of Cratoxylum cochinchinense

Cited by 40 publications

References 21 publications

Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum

Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum

Xanthones from the stems of Cratoxylum cochinchinense

Two new alkaloids and a new polyphenolic compound from Cotula coronopifolia

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