Scavenger and Antioxidant Properties of Prenylflavones Isolated From Artocarpus Heterophyllus

Ko, Feng‐Nien; Cheng, Zhi Jie; Lin, Chun Nan; Teng, Che-Ming

doi:10.1016/s0891-5849(98)00031-8

Cited by 128 publications

(94 citation statements)

References 34 publications

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“…The potency of artocarpanone as an antioxidant might be related to the presence of hydroxyl groups in the form of a resorcinol moiety. It was reported by Ko et al,20) and Cao et al,27) that the number of hydroxyl groups in flavonoids increases the antioxidant ability, however, the most important is the presence of a catechol moiety. The presence of a resorcinol moiety also seems to play a role in the antioxidant activity.…”

Section: Discussionmentioning

confidence: 97%

“…A. heterophyllus has been reported as having some parts that are functional for medicines: the pulp and seed for cooling, tonics, and pectorial; roots for treating diarrhea and fever; wood for a sedative during convulsions; leaves for activating milk production in women and animals, antisyphilic treatment and vermifuge; and leaf ash for treating ulcers and wound. 17) Some scientists have reported the isolation of compounds with biological activities such as antibacterial, 18) antiplatelet, 19) antioxidant, 20) antidiabetic 21) and recently, antiinflammatory 22) properties. To date, research on regulation of melanogenesis has focused on factors that affect tyrosinase, the rate-limiting enzyme in the melanogenic pathway, including research on chemicals that inhibit tyrosinase function.…”

Section: Discussionmentioning

confidence: 99%

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Inhibitory Effect of Artocarpanone from <i>Artocarpus heterophyllus</i> on Melanin Biosynthesis

Arung

Shimizu

Kondo

2006

Biological & Pharmaceutical Bulletin

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Tyrosinase (EC 1.14.18.1; PPO) is known to be a key enzyme involved in melanin biosynthesis in plants, microorganisms and mammalian cells. This enzyme catalyses two different reactions: the hydroxylation of monophenols to odiphenols (monophenolase activity), and the oxidation of odiphenols to o-quinones (diphenolase activity), which, in turn, are polymerized to brown, red or black pigments. 1)Many tyrosinase inhibitors have been tested in cosmetics and pharmaceuticals as a way of preventing overproduction of melanin in epidermal layers.2) Alterations in melanogenesis may be responsible for some of the clinical and histopathological features unique to malignant melanoma, 3) a cancer with a rapidly increasing incidence. 4)These observations led us to focus on the exploration of tyrosinase inhibitors from natural products. Several chemicals of plant origin have been reported as tyrosinase inhibitors. Arbutin, 5) ellagic acid, 6) oxyresveratrol, 7) chlorophorin and norartocarpanone 8) have all been studied for their tyrosinase inhibition properties.Tropical forests constitute 40-50% of the entire forested area of the world. Indonesia has an extraordinarily rich flora and great diversity of vegetation types that parallel the diverse physiography of the land, which is largely covered by evergreen rain forest. The great diversity of tropical plants is reflected in the qualitative and quantitative diversity of plant extracts, or, from a chemical point of view, of their components, which have been used increasingly as medicines in recent years. In Indonesia, several plants are used in a traditional medicine called "Jamu". The uses of Jamu can be distinguished into four categories of medicine: health care, beauty aids (cosmetics), tonics, and protection (a prophylactic against various kinds of disease).9) Such traditional medicinal knowledge as that in Indonesia offers researchers an excellent opportunity to find new bioactive components for medicines.In this paper, we evaluate the effects of artocarpanone isolated from extracts of A. heterophyllus on melanin biosynthesis (mushroom tyrosinase activity and melanin production in B16 melanoma cells) and its antioxidant activity. MATERIALS AND METHODS Plant MaterialThe wood (sapwood and heartwood) of Artocarpus heterophyllus was collected at Samarinda city, Indonesia in August 2003. The plant was indentified by the Laboratory of Dendrology and a voucher specimen (FHT.LA.13.1H) was deposited at the Laboratory of Wood Anatomy, Forestry Faculty, Mulawarman University, Indonesia.Extraction and Bioactivity-Guided Fractionation Based on our screening, the sapwood extract was more potent than the heartwood extract at inhibiting tyrosinase activity (IC 50 ϭ7 and 125 mg/ml respectively). Thus, we focused on sapwood for further investigation. The wood meal of sapwood of A. heterophyllus (2.3 kg) was extracted repeatedly with methanol at room temperature. The methanol extract was concentrated in vacuo to yield a residue of 60.6 g (2.6% of w/w). A portion of the extract (43.1 g) was susp...

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Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

Inhibitory Effect of Artocarpanone from <i>Artocarpus heterophyllus</i> on Melanin Biosynthesis

Arung

Shimizu

Kondo

2006

Biological & Pharmaceutical Bulletin

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“…For this reason, brain homogenate was used for the investigation of lipid peroxidation as an assessment of oxidative stress (Ko et al, 1998). F-11 was more effective than an MeOH extract, used as pattern solution, and quercetin or tocopherol in inhibiting lipid peroxidation (TBARS) showing an IC 50 value of 1.77 ppm.…”

Section: Resultsmentioning

confidence: 99%

Antioxidant Activity of an Unusual 3-Hydroxyindole Derivative Isolated from Fruits of Aristotelia chilensis (Molina) Stuntz

Céspedes

Alarcón

Valdez‐Morales

et al. 2009

Zeitschrift Für Naturforschung C

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3-Hydroxyindole was isolated from the EtOH extract of fruits of Aristotelia chilensis during analyses by HPLC/MS and GC/MS and identifi ed by its mass fragmentation pattern and spectrophotometric data. Additionally, this extract showed an interesting antioxidant activity in DPPH, crocin and TBARS assays. The presence of this type of compound in this fruit species permits us to explain its strong antioxidant activity and its important part in the biosynthetic pathway of phenolic and alkaloid compounds in this plant. Therefore this compound could be useful for the development of future nutraceutical and antioxidant protective agents.Key words: Hydroxyindole, Antioxidant Activity, Aristotelia chilensis IntroductionAnthocyanins, fl avonoids and phenolic acids are compounds which occur very often in many plant families. Their different biological activities, including antioxidant, antimicrobial, carcinogenic, cytotoxic, anti-infl ammatory and mutagenic properties, make them interesting objects of research (Middleton and Kandaswami, 1993). Recently, attenuation has been payed to the dietary indole amines melatonin and serotonin in different plant foods, including grapes and berries, thus further supporting the hypothesis that health benefi ts associated with Mediterranean dietary style are due to plant food chemical diversity (Iriti and Faoro, 2008). The presence of hydroxyindole in fruits tissues is relevant for their important biological activities. Additionally, the importance of indole moieties in the biosynthesis of phenolics is documented (Applewhite et al., 1994).We have under continuous study different extracts of edible fruits of southern Chile. Recently, we have published the antioxidant and cardioprotective activities of phenolic extracts from fruits of Chilean black berry (Céspedes et al., 2008), which have traditionally been consumed for the treatment of diarrhea and dysentery. Previously, we have reported the alkaloid composition of the leaves of Aristotelia chilensis (Céspedes et al., 1993;Silva et al., 1997). There are some reports about the antioxidant activity and a partial composition of anthocyanidins (Miranda-Rottman et al., 2002;Escribano-Bailon et al., 2006).In continuation of our search for more specifi c antioxidant activities, in the present paper we report the antioxidant activity of an unusual 3-hydroxyindole derivative and of a very interesting fraction obtained during a metabolomic analysis of fruits of A. chilensis. The occurrence of 3-hydroxyindole helps us to explain the antioxidant, chemopreventive, cardiopreventive, and anti-infl ammatory activities of this fruit. Material and Methods Plant materialPlants and fruits of Aristotelia chilensis (Molina) Stuntz (Elaeocarpaceae) were collected from fi elds at the foothills of Los Andes Mountains (900 m, 38°38'57'' S, 71°52'32'' W) on a track at the shore of "Quepe" lake, very near to "Conguillio" National Park, Cherquenco district, near Temuco City, Chile, in January 2006. The samples were identifi ed botanically by Professor Fernando Per...

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“…Rat brain homogenates, widely adopted biomaterial for the investigation of lipid peroxidation [15], were carried out to examine the antioxidant properties of the compounds 1 -14. The extent of in vitro lipid peroxidation was measured by lipid-derived malondialdehyde (MDA) production.…”

Section: Inhibitory Effects Of the Test Compounds In Rat Brain Homogementioning

confidence: 99%

Antioxidant and neuroprotective effects of synthesized sintenin derivatives

Yang

Zhang

Cong

et al. 2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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Three series of sintenin derivatives (compounds 1 -14) were designed and prepared and their antioxidative and neuroprotective effects were evaluated. The in vitro models of scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, chelating ferrous ions, inhibiting the rat brain homogenates lipid peroxidation, and protecting neurons damaged by hydrogen peroxide were employed for bioassays. It was found that sintenin derivatives 4 and 13 showed remarkable antioxidative and neuroprotective activities.

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Scavenger and Antioxidant Properties of Prenylflavones Isolated From Artocarpus Heterophyllus

Cited by 128 publications

References 34 publications

Inhibitory Effect of Artocarpanone from <i>Artocarpus heterophyllus</i> on Melanin Biosynthesis

Inhibitory Effect of Artocarpanone from <i>Artocarpus heterophyllus</i> on Melanin Biosynthesis

Antioxidant Activity of an Unusual 3-Hydroxyindole Derivative Isolated from Fruits of Aristotelia chilensis (Molina) Stuntz

Antioxidant and neuroprotective effects of synthesized sintenin derivatives

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