A new diospyrol glycoside from Diospyros mollis Griff.

Paphassarang, S.; Becchi, Michel; Raynaud, Jean

doi:10.1016/s0040-4039(00)99927-1

Cited by 9 publications

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“…4,5,7,16,17 Some of the Ebenaceae and Liliaceae plants are used in folk medicine for the treatment of parasitic diseases (e.g., schistosomiasis), but their application is accompanied by severe toxic side effects. [4][5][6]10,11,13,15,16 Surprisingly, in contrast to the many investigations on binaphthalenes of synthetic origin, in the reports on naturally occurring binaphthalenes, 5−14 the phenomenon of axial chirality was taken into consideration only for some of these biaryls; 18 for others of those compounds, no ECD investigations were performed, and frequently not even optical rotation values were measured. 4 In this paper, we describe the isolation and structural elucidation of seven natural products with naphthalene basic structures from the root cultures of the West African liana Triphyophyllum peltatum, among them new axially chiral binaphthalenes and binaphthoquinones as well as related (bi)naphthalene glucosides.…”

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Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African LianaTriphyophyllum peltatum

et al. 2016

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Root cultures of the West African liana Triphyophyllum peltatum were initiated from stem explants of in vitro cultivated shoots. From these organ cultures, three new binaphthalenes, one binaphthoquinone, and two (bi)naphthalene glucosides were isolated, with substitution patterns related to those of the naphthylisoquinoline alkaloids, which are the "normal" main metabolites of T. peltatum. The structures of the diglucoside dioncoquinoside A (1) and of the axially chiral biaryls triphyoquinols A1 (3), A2 (4), and B (5), triphyoquinoside A (6), and triphyoquinone A (7) were elucidated by spectroscopic analysis (HRESIMS, 1D and 2D NMR) and by application of electronic circular dichroism (ECD) spectroscopy in combination with the exciton chirality method and quantum-chemical ECD calculations. The root cultures likewise produced the known alkaloids dioncophylline A (8), 5'-O-demethyldioncophylline A (9), dioncopeltine A (10), habropetaline A (11), and 5'-O-methyldioncophylline D (12a/b), the naphthalene glucoside plumbaside A (2), and the naphthoquinones plumbagin (13), droserone (14), and 8-hydroxydroserone (15).

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Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African LianaTriphyophyllum peltatum

et al. 2016

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“…The anti hookworm property of the Diospyros mollis berries was scientifically tested (14). The chemistry of the active principle of Diospyros mollis bellies has also been extensively investigated (15)(16)(17)(18).As far as the discovery of drug from the plants of Thailand is concerned the highlight must be the discovery of Plaunotol from Plao-Noi [Croton sublyratirs Kurz (Euphorbiaceae)] by the Japanese scientists at Sankyo company. The structure of the compound was proved to be the diterpene by spectroscopic method and synthesis (19).…”

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Bioactive natural products from Thai plants

Mahidol¹,

Sahakitpichan²,

Ruchirawat³

1994

Pure and Applied Chemistry

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Abstract.The investigation of Thai medicinal plants for the potential therapeutic agents is surveyed with a particular emphasis on the search for antimalarial agents. The study on Diospyros mollis, Croton sublyratus, and Phyllanthus amarus is described.Thailand is uniquely located to represent the fauna and flora which characterizes the biogeographic province of Indo-Burma. A number of the eastern Himalaya temperate taxa penetrate south into the northern mountains of Thailand while the southern part is evergreen forest thus making this area one of the richest floristic regions of the world (1). It has been estimated that the vascular plants in Thailand are not less than 10,000 species of about 1,763 genera from 245 families (2). The numbers of alkaloidcontaining plants are estimated to be only about 266 species of 176 genera in 67 families based on the Thai plants names and parts of the uncompleted flora of Thailand (3).The potential of natural products as therapeutic agents in the treatment of malaria is enormous. Quinine was introduced as an antimalaiial for more than a century ago. Quinine also served as a prototype as an antimalarial leading to the discovery of synthetic antimalarials based on the quinoline compounds. 4-and 8-Aminoquinoline derivatives have proved their efficacy as antimalarials. Mefloquine, a quinoline methanol derivative, has recently been introduced as an antimalarial.The Chinese has a long history of use of a herb called Qing hao (Artemisia annua) for the treatment of malaria. The pure compound was isolated in 1972 and named Qinghaosu (QHS) or Arteannuin meaning the "active principle of Qing hao"(4) In Thailand, interests for the use of herbal medicine for the treatment of malaria has been long standing. Lately many groups of Thai scientists have been working on various plants to scrutinize the validity of these 'claims' as well as searches for new antimalarial agents from plants. During the second world war, Professor Ketusingh attempted to use 30 herbal medicine to treat malaria. The treatments were applied to 543 patients with infections with P. falciparum (255 patients) and P. vivax. (288 patients)(5). From the study the plant of Oroxylum indicum showed the total cure rate as high as 65.7% and it is very interesting to note the definite prefeicnce for the plants of Azadirachta and Nyctanthes arbor-tritis for the treatment of those patients infected with P. vivaxScientists at Division of Medical Research, Department of Medical Sciences, Ministry of Public Health and at AFRIMS (Aimed Force Research Institute for Medical Science) have been interested in the search for antimalarial agents from Thai medicinal plants (6).After screening many plants, the four plants (Brucea javanica, Picrasma javanica, Celastrus paniculatus, and Tiliacora triandra ) which exhibited the minimal inhibitory concentration (MIC) of not more than 25 microgram per millilitre were then further studied by extraction with various solvents, each solvent extract was then again tested. The chloroform extracts gave the b...

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“…Leaves Paphassarang et al (1984) Ephedraceae 31 1-Methyl-2,3-methylenedioxy-6-naphthalenecarboxylic acid methyl ester …”

Section: Diospyros Molllismentioning

confidence: 99%

Naturally occurring naphthalenes: chemistry, biosynthesis, structural elucidation, and biological activities

Ibrahim

Mohamed

2015

Phytochem Rev

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In the recent years, discovery, identification, and development of biologically active compounds have gained a lot of importance. Naphthalenes are a class of arenes, consisting of two ortho-fused benzene rings. Naphthalene derivatives displayed a wide range biological activities, such as antimicrobial, antioxidant, cytotoxic, anti-inflammatory, anti-protozoal, and anti-platelet aggregation. This review summarizes the research on the isolation, structural elucidation, biological activities, and biosynthesis of the naphthalene derivatives published over the last years. In the present review, 122 naphthalene derivatives isolated from plants, liverworts, fungi, and insects are discussed in term of their sources, physical and spectral data, and biological activities.

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A new diospyrol glycoside from Diospyros mollis Griff.

Cited by 9 publications

References 9 publications

Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African LianaTriphyophyllum peltatum

Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African LianaTriphyophyllum peltatum

Bioactive natural products from Thai plants

Naturally occurring naphthalenes: chemistry, biosynthesis, structural elucidation, and biological activities

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