Artocarpus flavonoids

Some of the Artocarpus flavonoids, such as artonin I (10), have been regarded as intermolecular [4+2] cyclo-addition product from the isoprenyl portion of a dehydroprenylphenol, as a diene, and the a,p-unsubstituted bond of a chalcone skeleton, as a dienophile. As artonin I... 

Seven Artocarpus flavonoids and morusin (3) were tested for their inhibitory actions on arachidonate-5-lipoxygenase purified from porcine leukocyte [84]. As shown in Fig. (13), the IC50 values varied depending on the structural modification of the compound. The compounds having three hydroxyl groups at positions 2, 4, and 5 on the B ring (compounds 7, 8, 52 and 55) were more potent inhibitors. Thus, the vicinal diol partial structure was important for 5-lipoxygenase inhibition. 

Based on the above descriptions, we examined the inhibitory effect of the Artocarpus flavonoids on TNF-a release stimulated by okadaic acid using BALB/3T3 cells. This experiment was carried out in co-operation with Dr. Fujiki s group (Saitama Cancer Center Research Institute, Japan). All the compounds tested inhibit the TNF-a release stimulated by... 

Isoprenoid-substituted flavonoids from Artocarpus (Moraceae) plants 98H(47)1179. 

Kijjoa, A. et al.. Further prenylated flavonoids from Artocarpus elasticus. Phytochemistry, 47, 875, 1998. 

Seo, E.-K. et ak. Bioactive prenylated flavonoids from the stem bark of Artocarpus kemando. Arch. Pharm. Res., 26, 124, 2003. 

Cidade, H.M. et al., Artelastocarpin and carpelastofuran, two new flavones, and cytotoxicities of prenyl flavonoids from Artocarpus elasticus against three cancer cell lines, Planta Med., 67, 867, 2001. 

Table 16.2 lists more than 80 examples of new isoprenylated chalcones reported in the period 1992 to 2003 (see also Figure 16.7). Almost half of the compounds described here are from the Leguminosae, a trend that is also evident in earlier surveys. Other plant families that are well represented in Table 16.2 are the Moraceae and the Cannabinaceae. The literature on isoprenylated flavonoids in general has been reviewed by Barron and Ibrahim to the end of 1994 57 jjjg phenolic constituents of Glycyrrhiza species (licorice), among which are many isoprenylated chalcones, were the subject of an extensive review that includes literature published up to the end of 1996. Nomura and Hano have reviewed the literature on isoprenylated phenolic compounds of the Moraceae to the end of 1993. More recent descriptions of isoprenylated flavonoids are available for the hop plant, Humulus lupulus (Cannabinaceae),and the Moraceae genera Artocarpus and Dorstenia. ... 

The biological activity of isoprenylated chalcones from the Moraceae has been described both in original papers and reviews. Of particular interest is the potent 5-a-reductase inhibition shown by a geranylated chalcone (84) isolated from leaves of Artocarpus incisus The inhibitory effect is decreased by a factor of 2 when the geranyl substituent is lacking, as in butein (2, 4, 3,4-tetrahydroxychalcone). Compound 41, which was obtained from the leaves of Madura tinctoria together with four known isoprenylated flavonoids, showed inhibitory... 

Nomura, T., Hano, Y., and Aida, M., Isoprenoid-substituted flavonoids from Artocarpus plants (Moraceae), Pleterocycles, 47, 1179, 1998. 

These flavonoids are characteristic constituents of Artocarpus species. 

Table 5. Cytotoxic activities (IC5I), pg/mL) of Artocarpus and Antiaris flavonoids against L-1210 and Colon 38 cells...

The phytochemical composition of avocado (Table 4), combined with its main fatty acid, oleic acid (18 1), represents a potential for lowering plasma cholesterol [34] and increasing antioxidant status. An added benefit may result from its content of phytosterols. Moreover, the presence of chlorogenic and caffeic acids in avocado increases the antioxidant capacity of plasma. In the same way, jackfruit (Artocarpus heterophyllus) contains antioxidants and phytosterols (Table 4) and its flavonoids, particularly the flavonones, have antioxidant activity [4],... 

Heartwood flavonoids are usually present in the free state, though it is possible that they may be loosely associated with other wood components. In the case of Artocarpus heartwood, it appears that at least some of the flavonol morin is present as a calcium chalate (29). Since most heartwood flavonoids have the ability to chelate metals, this may happen in other cases too. 

The cytoprotective effects of various solvent extracts of Artocarpus altilis (Parkinson) Fosberg were evaluated. These effects were determined in human U937 cells incubated with oxidized LDL (OxLDL) using the 4-[3-(4-iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-l, 3-benzene disulfonate (WST-1) assay. Results demonstrated that the EtOAc extract showed cytoprotective activities. To identify the main cytoprotective components, a bioassay guided isolation of the ethyl acetate extract afforded P-sitosterol and six flavonoids. Their chemical structures were established on the basis of spectroscopic evidence and comparison with literature data. One of these compounds was obtained from A. altilis for the first time. The cytoprotective effect offers good prospects for the medicinal applications of. Altilis [34]. 

Flavonoids, 10-oxoartogomezianone, 8-geranyl-3-(hydroxyprenyl)isoetin, hydroxylarto-flavone, isocycloartobiloxanthone, and furanocyclocommunin, together with 12 known compounds, were isolated from heartwood and cortex of Artocarpus altilis, and were... 

Lan, WC Tzeng, CW Lin CC Yen, FL Ko, HH. Prenylated flavonoids from Artocarpus altilis Antioxidant activities and inhibitory effects on melanin production . Phytochemistry, 2013, 89, 78-88. 

Pretorius JC (2003) Flavonoids a review of its commercial application potential as anti-infective agents. Curr Med Chem - Anti-Infective Agents 2 335-353 Radwan MM, Rodriguez-Guzman R, Manly SP et al (2009) Sepicanin A-A new geranyl flavanone from Artocarpus sepicanus with activity against methicUlin-resistant Staphylococcus aureus (MRSA). Phytochem Lett 2 141-143... 

By alkaline hydrolysis of artocarpetin, a flavonoid pigment isolated from the heartwood of Artocarpus inlegrifolia [2860],... 

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