(−)-Regiolone, an α-tetralone from Juglans regia: structure, stereochemistry and conformation
TL;DR: In this paper, a new α-tetralone derivative named (−)-regiolone has been isolated with juglone, betulinic acid and sitosterol from the stem-bark of Juglans regia.
About: This article is published in Phytochemistry.The article was published on 1988-01-01. It has received 71 citations till now. The article focuses on the topics: Tetralone & Juglone.
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TL;DR: Endophytic Phoma are promising sources of natural bioactive and novel metabolites, as well as in vitro antitumor activities against HT-29, SMMC-772, MCF-7, HL-60, MGC80-3, and P388 cell lines are concluded.
Abstract: Through bioassay-guided fractionation, the EtOAc extract of a culture broth of the endophytic fungus Phoma species ZJWCF006 in Arisaema erubescens afforded a new α-tetralone derivative, (3S)-3,6,7-trihydroxy-α-tetralone (1), together with cercosporamide (2), β-sitosterol (3), and trichodermin (4). The structures of compounds were established on the basis of spectroscopic analyses. Compounds 1, 2, and 3 were obtained from Phoma species for the first time. Additionally, the compounds were subjected to bioactivity assays, including antimicrobial activity, against four plant pathogenic fungi (Fusarium oxysporium, Rhizoctonia solani, Colletotrichum gloeosporioides, and Magnaporthe oryzae) and two plant pathogenic bacteria (Xanthomonas campestris and Xanthomonas oryzae), as well as in vitro antitumor activities against HT-29, SMMC-772, MCF-7, HL-60, MGC80-3, and P388 cell lines. Compound 1 showed growth inhibition against F. oxysporium and R. solani with EC50 values of 413.22 and 48.5 μg/mL, respectively. Additionally, compound 1 showed no cytotoxicity, whereas compound 2 exhibited cytotoxic activity against the six tumor cell lines tested, with IC50 values of 9.3 ± 2.8, 27.87 ± 1.78, 48.79 ± 2.56, 37.57 ± 1.65, 27.83 ± 0.48, and 30.37 ± 0.28 μM, respectively. We conclude that endophytic Phoma are promising sources of natural bioactive and novel metabolites.
134 citations
Cites background from "(−)-Regiolone, an α-tetralone from ..."
...All of the above data indicated that compound 1 was an α-tetralone derivative (Talapatra et al. 1988; Liu et al. 2004; Machida et al. 2005)....
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TL;DR: This review summarizes the research on the isolation, structure elucidation, biological activities, biosynthesis, and chemical synthesis of the spirodioxynaphthalenes published over the last 20 years.
116 citations
TL;DR: In this article, eight volatile 1,4-naphthoquinones from acetone extracts of unripe black walnut and English walnut (Juglans regia) fruit were identified by gas chromatography-mass spectrometry assisted by 1H NMR.
89 citations
TL;DR: Four enantiomerically pure new alpha-tetralones were isolated, together with five known ones, from the fruit of Juglans mandshurica MAXIM var.
Abstract: Four enantiomerically pure new α-tetralones, (4S)- and (4R)-5-hydroxy-4-methoxy-α-tetralones and (4S)- and (4R)-5,8-dihydroxy-4-methoxy-α-tetralones were isolated, together with five known ones, (4S)- and (4R)-4,8-dihydroxy-α-tetralones, (4S)-4,8-dihydroxy-5-methoxy-α-tetralone and (4S)- and (4R)-4-hydroxy-α-tetralones, from the fruit of Juglans mandshurica MAXIM. var. sieboldiana MAKINO. Their structures were established on the basis of spectral analysis. To the best of our knowledge, this is the first isolation of the (4R)-4-hydroxy-α-tetralone derivative from Juglans species.
76 citations
TL;DR: The Tamang people in Makawanpur are rich in ethnopharmacological understanding and important medicinal plant species are highlighted by validating their traditional uses by comparing ethnobotanical studies with phytochemical and pharmacological studies.
Abstract: We can conserve cultural heritage and gain extensive knowledge of plant species with pharmacological potential to cure simple to life-threatening diseases by studying the use of plants in indigenous communities. Therefore, it is important to conduct ethnobotanical studies in indigenous communities and to validate the reported uses of plants by comparing ethnobotanical studies with phytochemical and pharmacological studies. This study was conducted in a Tamang community dwelling in the Makawanpur district of central Nepal. We used semi-structured and structured questionnaires during interviews to collect information. We compared use reports with available phytochemical and pharmacological studies for validation. A total of 161 plant species belonging to 86 families and 144 genera to cure 89 human ailments were documented. Although 68 plant species were cited as medicinal in previous studies, 55 different uses described by the Tamang people were not found in any of the compared studies. Traditional uses for 60 plant species were consistent with pharmacological and phytochemical studies. The Tamang people in Makawanpur are rich in ethnopharmacological understanding. The present study highlights important medicinal plant species by validating their traditional uses. Different plant species can improve local economies through proper harvesting, adequate management and development of modern techniques to maximize their use.
72 citations
Cites background from "(−)-Regiolone, an α-tetralone from ..."
...Comparison of local use and phytochemical and pharmacological studies of medicinal plants [94-186]....
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References
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191 citations
TL;DR: 7-Methyljuglone, isodiospyrin, the 2,2′-binaphthyl-1,1′-quinone, and a new quinone (IV) were isolated from the phytochemical deposits of E. coli.
73 citations
TL;DR: 4-Hydroxy-1-naphthalenyl-β- β- D -glucopyranoside, a new natural product, as well as 1,4- naphthoquinone, juglone, and 4,8-dihydroxy- 1-Naphthalene-β are presented.
46 citations
TL;DR: The oligomeric juglones isolated from the barks of Juglandaceae plants, Pterocarya and Juglans, were shown to be 3,3′-bijuglone and unsymmetrical cyclotrijuglone.
45 citations
27 citations