Honyumine, a New Linear Pyranoacridone Alkaloids from Citrus grandis Osbeck

Wu, Tong; Shiow-Chyn, Huang; Jong, Ting‐Ting; Jeng-Shiow, Lai; Furukawa, Hiroshi

doi:10.3987/r-1986-01-0041

Cited by 13 publications

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“…A lot of scientific reports have been published regarding the compositions and significant bioactivity of the Citrus peels. C. grandis belongs to the family Rutaceae, which is cultivated throughout Taiwan, Indochina, and Southern China [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. The peels of mature fruits of C. grandis have been used in traditional Chinese medicine for treating the common cold and cancer, and relieving exhaustion [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…The peels of mature fruits of C. grandis have been used in traditional Chinese medicine for treating the common cold and cancer, and relieving exhaustion [ 12 ]. Many natural products such as flavonoids, coumarins, and terpenoids have been isolated from C. grandis [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. Among these, various principles have been reported to exhibit antioxidant [ 13 , 14 , 15 , 16 ], anti-inflammatory [ 16 , 17 , 18 , 19 , 20 ], anti-microbial [ 21 , 22 , 23 , 24 ], and anti-cancer effects [ 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

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Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis

et al. 2017

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A series of chromatographic separations performed on the ethanol extracts of the peels of Citrus grandis has led to the characterization of forty compounds, including seventeen coumarins, eight flavonoids, two triterpenoids, four benzenoids, two steroids, one lignan, one amide, and five other compounds, respectively. The chemical structures of the purified constituents were identified on the basis of spectroscopic elucidation, including 1D- and 2D-NMR, UV, IR, and mass spectrometric analysis. Most of the isolated compounds were examined for their inhibition of superoxide anion generation and elastase release by human neutrophils. Among the isolates, isomeranzin (3), 17,18-dihydroxybergamottin (12), epoxybergamottin (13), rhoifolin (19), vitexicarpin (22) and 4-hydroxybenzaldehyde (29) displayed the most significant inhibition of superoxide anion generation and elastase release with IC50 values ranged from 0.54 to 7.57 μM, and 0.43 to 4.33 μM, respectively. In addition, 7-hydroxy-8-(2′-hydroxy-3′-methylbut-3′-enyl)coumarin (8) and 17,18-dihydroxybergamottin (12) also exhibited the protection of neurons against Aβ-mediated neurotoxicity at 50 μM.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis

et al. 2017

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“…Citrus is one genus of the economically and medicinally important Rutaceae family, which has shown extensive biological and pharmacological activities, including antitumor [ 2 , 3 , 4 , 5 , 6 , 7 ], antiallergic [ 8 ], antioxidant [ 9 , 10 , 11 , 12 ], antiplatelet aggregation [ 13 ], anti-microbial [ 14 , 15 , 16 , 17 ], and anti-inflammatory activity [ 18 , 19 , 20 , 21 , 22 ]. Moreover, Citrus species have been reported to contain various bioactive coumarins, flavonoids, tetranortriterpenoids, monoterpenoids, and acridone alkaloids [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. Previously, several anti-inflammatory compounds have been isolated from the stems and root barks of the titled plant [ 18 ].…”

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confidence: 99%

Constituents of the Fruits of Citrus medica L. var. sarcodactylis and the Effect of 6,7-Dimethoxy-coumarin on Superoxide Anion Formation and Elastase Release

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Investigation of the chemical constituents from the fruits of Citrus medica L. var. sarcodactylis Swingle has led to the characterization of a new sesquiterpene 1 along with thirty-two known compounds. The structure of 1 was established on the basis of 2D NMR spectroscopic and mass spectrometric analyses, and the known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature. In addition, most of the isolated compounds were evaluated for the activity assayed by the in vitro inhibition of superoxide anion generation and elastase release by human neutrophils. The results showed that only 6,7-dimethoxycoumarin (5) exhibited significant inhibition of superoxide anion generation, with IC50 value of 3.8 ± 1.4 μM.

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Electron impact mass spectra of some acridones substituted with hydroxyl, methoxyl, alkyl and alkenyl groups

Lin

Furukawa

1992

Org. Mass Spectrom.

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Forty-four acridones were examined by mass spectrometry. The fragmentations were studied, and included cleavage of the carbon-oxygen bond of methoxyl groups, cleavage of the carbowarbon bonds of y,y-dimethylpyranyl groups, cleavage of isoprenyl groups and the formation of doubly charged molecular ions and daughter ions. The tendency for fission of carbon-oxygen bond in the methoxyl group for acridones is about 300 : 200 : 8 : 1 for the C(2), C(4), C(5) and C(6) positions, respectively. The isoprenyl group is very sensitive to its position in fragmentation, and mass spectrometry can be a powerful aid in distinguishing between C(2)-and C(4)-isoprenyl isomers. $0 ? O R z OMe Me R' R2 R3

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Honyumine, a New Linear Pyranoacridone Alkaloids from Citrus grandis Osbeck

Cited by 13 publications

References 0 publications

Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis

Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis

Constituents of the Fruits of Citrus medica L. var. sarcodactylis and the Effect of 6,7-Dimethoxy-coumarin on Superoxide Anion Formation and Elastase Release

Electron impact mass spectra of some acridones substituted with hydroxyl, methoxyl, alkyl and alkenyl groups

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