A Novel Depsidone and Some New Xanthones from Garcinia Species.

Ito, Chihiro; Miyamoto, Yoshiaki; Nakayama, M.; Kawai, Y.; Rao, K.R.S. Sambasiva; Furukawa, Hiroshi

doi:10.1248/cpb.45.1403

Cited by 74 publications

(77 citation statements)

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“…12) Two anti-staphylococcal acylphloroglucinols have been isolated from this plant previously. 13) Our phytochemical investigation on the methanol extract of this plant led to the isolation of four new acylphloroglucinols, hyperbeanols A-D (1-4), together with the known hypercalin B (5), 14) (1S,4S,5S,10R)-4,10-guaianediol (6), 15) (ϩ)-alismoxide (7), 16) guaia-6,10(14)-dien-4-ol (8), 17 calycinoxanthone D (9), 18) ugaxanthone (10), 19) 2,5-dihydroxyxanthone (11), 20) 1,3-dihydroxy-6-methoxyxanthone (12), 21) 3,6,7-trihydroxy-1-methoxyxanthone (13), 22) 1,2,5-trihydroxyxanthone (14), 23) 1,5-dimhydroxy-2-methoxyxanthone (15), 24) 1,3,5-trihydroxy-6-methoxyxanthone (16), 25) 1-hydroxyxanthone (17), 26) garcimangosone D (18), 27) quercetin-3-O-b-D-glalactopyranoside (19), 28) and quercetin-3-O-a-L-rhamnopyranoside (20). 28) The cytotoxicity of 1-5 against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 were examined.…”

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confidence: 99%

Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Chen

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Polyprenylated acylphloroglucinols, featured a highly oxygenated bicyclo[3.3.1]-nonane-2,4,9-trione or bicyclo[3.2.1]-octane-2,4,8-trione core decorated with C 5 H 9 or C 10 H 17 (prenyl, geranyl, etc.) side chains, were only isolated from the Guttiferae plants so far.1) This type of metabolites were reported to possess a wide variety of biological activities such as antimicrobial, antidepressant, antioxidant, cytotoxic, and anti-human immunodeficiency virus (HIV) effects. 2-7)As an important member of the family Guttiferae, the genus Hypericum have been proved to be a prolific source of this special type metabolites. [8][9][10][11] H. beanii N. Robson is a shrub of this genus and widely distributed in Guizhou and Yunnan Provinces, P. R. China. 12) Two anti-staphylococcal acylphloroglucinols have been isolated from this plant previously.13) Our phytochemical investigation on the methanol extract of this plant led to the isolation of four new acylphloroglucinols, hyperbeanols A-D (1-4), together with the known hypercalin B (5), 14) (1S,4S,5S,10R)-4,10-guaianediol (6), 15) (ϩ)-alismoxide (7), 16) guaia-6,10(14)-dien-4-ol (8), 17 calycinoxanthone D (9), 18) ugaxanthone (10), 19) 2,5-dihydroxyxanthone (11), 20) 1,3-dihydroxy-6-methoxyxanthone (12), 21) 3,6,7-trihydroxy-1-methoxyxanthone (13), 22) 1,2,5-trihydroxyxanthone (14),28) The cytotoxicity of 1-5 against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 were examined. Reported herein are the isolation, structure elucidation, and cytotoxic evaluation of compounds 1-5. The MeOH extract (611 g) of the aerial parts of H. beanii (5.3 kg) was successively partitioned with petroleum ether and ethyl acetate. The petroleum ether soluble fraction (252 g) was subjected to silica gel column chromatography, Sephadex LH-20, and preparative HPLC to afford compounds 1-8. The ethyl acetate portion (167 g) was also purified by column chromatography, semipreparative, and preparative HPLC to obtain compounds 9-20.Compound 1 (d 197.3, 113.6, 193.7), one monobenzoyl group (d 197.0, 136.9, 127.8ϫ2, 128.0ϫ2, 132.2) Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.

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confidence: 99%

Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Chen

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Specifically, the stem bark from G. latissima Miq. which grows in the Central Province of Papua New Guinea, has been found to contain latisxanton-A, latisxanton-B, latisxanton-C, and latisxanton-D compounds belonging to the pyrano xanthone group [4].…”

Section: Introductionmentioning

confidence: 99%

The Antibacterial Activity of Fractions of Ethyl Acetate Garcinia Latissima Miq. Stem Bark Extracts Against Bacillus Subtilis and Pseudomonas Aeruginosa

Ambarwati

Malik²,

Deborah³

et al. 2017

Asian J Pharm Clin Res

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Objective: This research focuses on the antibacterial activities of fractions of ethyl acetate Garcinia latissima Miq. extracts against Bacillus subtilis and Pseudomonas aeruginosa. Methods:For each bacteria, the values of the inhibitory zone diameter were determined using paper discs method, while the minimum inhibitory concentration (MIC) was determined by microdilution and antibacterial assay was determined by bioautography. Fractionation was carried out using gradient elution with silica gel column as stationary phase successively increasing the separation according to the polarity (using combination of eluents; n-hexane, ethyl acetate, and methanol). Results:To determine the diameter of the inhibitory zone for each fraction, the fractions were diluted with dimethyl sulfoxide until the concentration of each fraction was 20,000 ppm. The results showed that fraction B had no inhibitory zone against B. subtilis. The inhibitory zone diameters of fractions A, C, D, E, F, and G against B. subtilis were 7.600±0.000, 6.767±0.202, 7.950±0.477, 7.883±0.901, and 9.233±0.231 mm, respectively. Only Fraction G had an inhibition zone diameter of 7.200±0.173 mm against P. aeruginosa. The active fractions were tested by contact bioautography using silica gel (60 GF254) plate and hexane:chloroform (2:3) as mobile phase for Fractions A, C, D, E, and F and chloroform:ethyl acetate (4:1) as mobile phase for Fraction G. The thin layer chromatography plates were observed under the ultraviolet light at wavelengths of 254 and 366 nm, while the others plate (using in contact bioautography) placing on agar medium that had been inoculated with the bacteria, so the compounds could be diffuse to the medium. The active compound will appeared inhibitory zones in agar medium. The determination of the MIC values using microdilution with methylthiazol tetrazolium salt showed that fractions of the ethyl acetate extracts of G. latissima Miq. stem bark inhibited the growth of B. subtilis more actively than P. aeruginosa. The highest activity of the fractions against B. subtilis was shown by fraction G, which had a MIC value of 78.125 ppm, followed by fractions F (156.25 ppm), E (312.5 ppm), D (625 ppm), C (1250 ppm), B (2500 ppm), and A (5000 ppm). The highest activity of the fractions against P. aeruginosa was Fraction G (5000 ppm), while the MIC values of other fractions were >5000 ppm. Conclusion:Further investigations should be conducted to obtain the new antibacterial compounds in fractions of ethyl acetate extract of G. latissima Miq. stem bark that effective to inhibit the growth of B. subtilis and P. aeruginosa.

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“…This plant is locally named "Ma da" and is found in the North of Thailand. This study resulted in the isolation of six new natural products (1-6), together with thirteen known compounds (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). The biological activities of these compounds against the Plasmodium falciparum strains, TM4 and K1 (a multidrug resistant strain) and their cytotoxicities against a Vero cell line are reported.…”

Section: Introductionmentioning

confidence: 99%