Novel Anti‐Inflammatory Constituents of <i>Artocarpus rigida</i>

Lu, Yi‐Huang; Lin, Chun‐Nan; Ko, Horng‐Huey; Yang, Sheng‐Zehn; Tsao, Lo‐Ti; Wang, Jih-Pyang

doi:10.1002/hlca.200390207

Cited by 38 publications

(30 citation statements)

References 14 publications

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“…It should be noted that this plant species is different from A. rigida, the latter of which has been extensively investigated. [2][3][4][5][6][7][8] As part of an ongoing project on bioactive compounds from Thai plants for the treatment of tropical diseases, the plant species was investigated and it was found that the CHCl 3 and MeOH extracts exhibited antiplasmodial and antimycobacterial activities. Both crude extracts also showed cytotoxic activity against human epidermoid carcinoma of the nasopharynx (KB), human breast cancer (BC), and human small cell lung cancer (NCI-H187) cells.…”

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confidence: 99%

Bioactive Constituents of the Root Bark of Artocarpus rigidus subsp. rigidus

et al. 2006

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Investigation of the chemical constituents of the root bark of Artocarpus rigidus BLUME subsp. rigidus has led to the isolation of six, structurally diverse phenolic compounds. These included two new compounds with modified skeletons, the flavonoid 7-demethylartonol E (1) and the chromone artorigidusin (2), together with four known phenolic compounds, the xanthone artonol B (3), the flavonoid artonin F (4), the flavonoid cycloartobiloxanthone (5), and the xanthone artoindonesianin C (6). Compounds 1, 4, and 5 exhibited antiplasmodial activity against Plasmodium falciparum. All compounds showed antimycobacterial activity against Mycobacterium tuberculosis, with 4 being the most active compound (MIC 6.25 m mg/ml). Compounds 5 and 6 were active against KB cells, whereas 2, 5, and 6 showed varying toxicity to BC cells. Compounds 1-3, 5, and 6 were active in the NCI-H187 cytotoxicity assay, with 3 being the most active compound (IC 50 1.26 m mg/ml).

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confidence: 99%

Bioactive Constituents of the Root Bark of Artocarpus rigidus subsp. rigidus

et al. 2006

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“…The UV (λ max 234, 340, and 360 nm) and IR (ν max 3364, 1615, 1456 cm −1 ) spectra showed absorption characteristics of a stilbenoid derivative 15–19. The molecular formula of C 19 H 16 O 4 was determined by HRESIMS, and was consistent with a 14-carbon stilbene nucleus bearing a prenyl group substituent.…”

Section: Resultsmentioning

confidence: 93%

“…Previously, prenylflavonoids and stilbenoids have been isolated from A. rigida 13–19. Lin and associates investigated the root bark of this species collected in Taiwan, and reported several stilbenoids and prenylated flavonoids 15–19.…”

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confidence: 99%

Cytotoxic and NF-κB Inhibitory Constituents of Artocarpus rigida

et al. 2010

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Four new prenylated flavonoids (1–4), a new stilbenoid (5), and nine known compounds were isolated from the twigs of Artocarpus rigida, collected in Indonesia. The structures of the new compounds were determined by analysis of their spectroscopic data, and the absolute configuration at C-12 of 1 and 2 and the known compounds artonin O (6), artobiloxanthone (7), and cycloartobiloxanthone (8), was determined by analysis of their CD and NMR spectroscopic data. Several of the compounds were cytotoxic towards HT-29 human colon cancer cells, with the most potent being compound 2 and the known compounds 6 and 8. Of the substances obtained, compounds 1 and 7 were the most active in the NF-κB p50 and p65 assay, respectively.

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“…Methyl-substituted oxepines 48 have also been postulated as intermediates in the metabolism of arenes by liver enzymatic systems [39]. Some annelated oxepines are found in nature and these include bauhiniastatin (49) [40], janoxepin (50) [41], and perillosin (51) [42], and some relevant pharmacological activities have been described for some dibenzoxepine derivatives inter alia anxiolytic activity for 52 [43] and anti-inflammatory action for artocarpol (53), a natural product isolated from the root bark of Artocarpus rigida [44].…”

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confidence: 99%

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Vaquero

Cuadro

Herradón

2011

Modern Heterocyclic Chemistry

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The replacement of a carbon atom by a heteroatom in a seven-membered carbocycle leads to the corresponding seven-membered heterocyclic ring system. Different types of heterocycles can be formed depending on the nature of the carbocycle. In a cycloheptatriene the replacement can involve any of the six sp 2 hybridized carbons or the sp 3 carbon atom, whereas in cycloheptane all carbon atoms are equivalent and replacement affords exclusively the fully saturated heterocyclic systems. Partially saturated seven-membered heterocycles can be viewed as derivatives or related systems of these two main seven-membered heterocyclic units arising from carbon replacement in cycloheptatriene and in cycloheptane. Replacement of the sp 3 hybridized carbon atom in cycloheptatriene by a nitrogen leads to an azacycloheptatriene known as 1H-azepine (1) and the corresponding 2H-, 3H-, and 4H-azepines (2-4) are the tautomeric forms generated by the replacement of the sp 2 carbons. 1H-Azepine is an unstable red oil that is prone to rearrange to the also unstable 3H-azepine in the presence of acids and bases. However, this tautomer seems to be more stable than both 4H-and 2H-azepine. The structures related to 1H-azepine that bear an oxygen or sulfur atom are known as oxepine (5) and thiepine (6) (thiepin is favored by Chemical Abstracts Service). Oxepine is much more stable than thiepine and has been synthesized, isolated, and characterized at room temperature while thiepine has not been detected to date. Stable monocyclic thiepines were prepared and characterized in the 1980s. Azepines, oxepines, and thiepines that are constrained to planar or almost planar conformations should be antiaromatic molecules with negative resonance energy and, as a consequence, these compounds are unknown.The fully saturated seven-membered heterocycle containing one nitrogen is azepane (7) (hexahydroazepine or perhydroazepine); the oxygen and sulfur analogues are known as oxepane (8) and thiepane (9). All of these compounds are stable and show typical behavior of secondary amine, ether and thioether, respectively. TwoModern Heterocyclic Chemistry, First Edition. Edited

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Novel Anti‐Inflammatory Constituents of Artocarpus rigida

Cited by 38 publications

References 14 publications

Bioactive Constituents of the Root Bark of Artocarpus rigidus subsp. rigidus

Bioactive Constituents of the Root Bark of Artocarpus rigidus subsp. rigidus

Cytotoxic and NF-κB Inhibitory Constituents of Artocarpus rigida

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

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