Coumarins, acridone alkaloids and a flavone from Citrus grandis

Wu, Tian Shung; Huang, Soon-Cen; Jong, Ting‐Ting; Lai, Jeng Shiow; Kuoh, Chang Sheng

doi:10.1016/0031-9422(88)83146-7

Cited by 34 publications

(16 citation statements)

References 10 publications

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“…sarcodactylis SWINGLE. Furthermore, 23 compounds: xanthyletin (2), 12) nordentatin (3), 12) atalantoflavon (4), 30) lonchocarpol A (5), 42) 6,7-dimethoxycoumarin (9), 35) erythrisenegalone (10), 36) lupinifolin (11), 36) b-sitosterol (12), 30) stigmasterol (13), 30) cis-p-coumaric acid (18), 41) nomilin (19), 30) limonin (20), 35) lupeol (21), 30) 5,7-dimethoxycoumarin (22), 30) hiravanone (23), 30) citrumedin-A (24), 30) 7-methoxycoumarin (25), 30) leptodactylone (26), 30) citflavanone (27), 30) 7,8-dimethoxycoumarin (28), 30) citrusin (29), 30) limonexic acid (30) 30) and C-glycosylflavone-vitexin (31) 30) were also isolated from the stem bark of this plant. Their structures were identified by comparison of their spectroscopic data (UV, IR, NMR and mass spectrometry) with values in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…Various species of Citrus have been used as food, and their peel, leaves and root have been also used as folk medicine or spice in Taiwan. 1) Species of Citrus have been reported to contain various bioactive coumarins, 2) flavonoids, 3) tetranortriterpenoids 4) and monoterpenoids. 5) Wu et al [6][7][8][9][10][11][12][13][14][15][16] and Furukawa and colleagues [17][18][19][20][21] have reported the isolation of several acridone alkoids from the Citrus genus.…”

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confidence: 99%

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Anti-inflammatory Principles from the Stem and Root Barks of Citrus medica

Chan

Shen

et al. 2010

Chem. Pharm. Bull.

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Bioassay-guided investigation of the anti-inflammatory principles from the stem and root barks of Citrus medica L. var. sarcodactylis SWINGLE has led to the isolation of a new coumarin, namely citrumedin-B (1) and thirty known compounds. The anti-inflammatory components were xanthyletin (2), nordentatin (3), atalantoflavon (4) and lonchocarpol A (5) which displayed potent nitric oxide (NO)-reducing activity in microglial cells. The structure of this new compound was completely elucidated using a combination of 2D NMR techniques (correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC)) and HR-electrospray ionization (ESI)-MS analyses. The known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. These results can be inferred from the treatment of allergic response and inflammatory properties of Citrus medica L. var. sarcodactylis SWINGLE in traditional Chinese medicine.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Anti-inflammatory Principles from the Stem and Root Barks of Citrus medica

Chan

Shen

et al. 2010

Chem. Pharm. Bull.

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“…The other known isolates, i.e., (AE )-syringaresinol (14) [35], (þ)-catechin (15) [36], (À)-epicatechin (16) [37], scopoletin (17) [38], a mixture of b-sitosterol (18) and stigmasterol (19) 2. Biological Studies.…”

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Antimycobacterial Butanolides from the Root of Lindera akoensis

Chang

Cheng

Peng

et al. 2008

Chemistry & Biodiversity

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Three racemic butanolides, majorenolide (1), majorynolide (2), and majoranolide (3), with 18 known compounds, including ten butanolides, i.e., litsenolide A(2) (4), litsenolide B(2) (5), litsenolide C(1) (6), litsenolide C(2) (7), hamabiwalactone A (8), hamabiwalactone B (9), litseakolide A (10), litseakolide B (11), isoobtusilactone (12), and obtusilactone (13); one lignan, i.e., (+/-)-syringaresinol (14), two flavans, i.e., (+)-catechin (15), and (-)-epicatechin (16), one coumarin, i.e., scopoletin (17), and four steroids, i.e., a mixture of beta-sitosterol (18) and stigmasterol (19), and a mixture of beta-sitosteryl-3-O-beta-D-glucoside (20) and stigmasteryl-3-O-beta-D-glucoside (21) were isolated from the root of Lindera akoensis. The structures of the isolates were elucidated by in-depth spectroscopic analysis. Compounds 1-3 were previously assigned a delta-lactone structure, which was then revised to a gamma-lactone structure, based on 1D-NMR data. The cigar-HMBC technique was used to confirm the accuracy of the gamma-lactone structure, and the zero [alpha] (20)_D value of compounds 1-3 suggested that they were considerably racemized. Nine butanolides 1-3, 4-8, and 10 showed antimycobacterial activities against M. tuberculosis H(37)Rv, with MIC values of 15-50 microg/ml.

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“…No use for this citrus molasses has yet been determined. Many natural products, such as flavone aglycones [1][2][3], flavone glycoside [4], limonoids [5], coumarin [6], and acridone alkaloid derivatives, have been reported in citrus plants. Highly methoxylated flavonoids found in the peel of citrus species have been reported as cell differentiators [7].…”

Section: Introductionmentioning

confidence: 99%

Flavonoid glycosides and limonoids from Citrus molasses

et al. 2007

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Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its organic constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-beta-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-beta-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were determined as (2R,3R)-7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using (1)H-NMR, (13)C-NMR, and 2D-NMR. Of these compounds, flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides.

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Coumarins, acridone alkaloids and a flavone from Citrus grandis

Cited by 34 publications

References 10 publications

Anti-inflammatory Principles from the Stem and Root Barks of Citrus medica

Anti-inflammatory Principles from the Stem and Root Barks of Citrus medica

Antimycobacterial Butanolides from the Root of Lindera akoensis

Flavonoid glycosides and limonoids from Citrus molasses

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