Agrostophyllin, a naturally occurring phenanthropyran derivative from Agrostophyllum khasiyanum
TL;DR: Agrostophyllin, the first naturally occurring phenanthropyran derivative, was isolated from the orchid AgrostophyLLum khasiyanum and it was shown to be able to biosynthesise nonvolatile substance such as polymethine.
About: This article is published in Phytochemistry.The article was published on 1988-01-01. It has received 26 citations till now. The article focuses on the topics: Agrostophyllum & Derivative (chemistry).
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01 Jan 2016
TL;DR: Orchid phytochemicals that have been studied include alkaloids, bibenzyls, phenanthrenes, stilbenoids, phenols, flavonoids, anthocyanins and polysaccharides, which exhibit antioxidant, anti-inflammatory, antimicrobial, antihelminthic, anticoagulant, antidiabetic and lipid-lowering properties.
Abstract: Orchid phytochemicals that have been studied include alkaloids, bibenzyls, phenanthrenes, stilbenoids, phenols, flavonoids, anthocyanins and polysaccharides. Many of these compounds exhibit antioxidant, anti-inflammatory, antimicrobial, antihelminthic, anticoagulant, antidiabetic and lipid-lowering properties. Some compounds are cytotoxic, prevent angiogenesis and tumour spread and promote programmed cell death of cancer cells. Some compounds protect nerve cells against chemicals and oxygen deprivation (stroke), promote nerve cell regeneration, protect the skin from ultraviolet damage, protect the liver against poisons such as carbon tetrachloride, prevent calcium loss from bone and enhance foetal lung maturation. This chapter provides a short account of the characteristics of the various groups of compounds, including their properties.
54 citations
Cites background from "Agrostophyllin, a naturally occurri..."
...They have been isolated from Agrostophyllum callosum and A. khasiyanum (Majumder and Sabzabadi 1988), Bletilla striata (Honda and Yamaki 1989, 2000; Bai et al. 1991), B. formosana (Lin et al. 2005), Bulbophyllum reptens (Majumder et al. 1999), B. maculosum (Cirrhopetalum maculosum) (Majumder et al.…...
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TL;DR: Flavanthrin, the first dimeric 9,10-dihydrophenanthrene derivative, was isolated from the orchid Eria flava which also yielded the previously reported 9, 10-dibhrenanthrene coelonin this paper.
54 citations
TL;DR: The mechanistic studies show an allylic inversion, as supported by NMR data and an X-ray crystal structure analysis, as well as an intermolecular reaction, as determined by crossover experiments and clearly indicate product formation by a [3,3]sigmatropic rearrangement in the step forming the new C-C bond.
Abstract: The gold-catalyzed conversion of allyl-(ortho-alkynylphenyl)methyl ethers was investigated, and allylated isochromenes were obtained. An optimization of the catalysis conditions with respect to different phosphane and carbene ligands on gold, different counterions, and different solvents was conducted. Subsequently, the scope and limitations of this reaction were investigated with 21 substrates. The mechanistic studies show an allylic inversion, as supported by NMR data and an X-ray crystal structure analysis, as well as an intermolecular reaction, as determined by crossover experiments. There is no competition of protodeauration even in the presence of water. All these observations differ from other related conversions and clearly indicate product formation by a [3,3]sigmatropic rearrangement in the step forming the new C-C bond.
47 citations
TL;DR: The structures of coelogsinanthridin and coeloginanthrin were established as 3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene and 3,4,5-triHydroxy-2,4-dimETHoxyphenanthene, respectively, which may have biological activities of phytoalexins and endogenous plant growth regulators.
45 citations
TL;DR: A review of the literature on orchids that are used in traditional medicine has been reviewed in this work indicating a great potential of such organisms as source of chemical entities for the development of new drugs as mentioned in this paper.
Abstract: The Orchidaceae family is the largest group of flowering plants in the Angiosperm monocotyledons spread on our planet. Its members, called orchids, are herbs or epiphytes with showy flowers distributed mainly in tropical regions. Several classes of phytoconstituents have been so far isolated from therapeutically-used orchids showing a great chemical diversity. Among them, phenolic derivatives have been studied for their biological activities, especially in the field of cancer, inflammation, and neurodegeneration. On the other hand, limited information has been so far obtained on the numerous alkaloids and terpenoids isolated from several orchid species. Recent articles revealed pronounced effects of some alkaloids on the CNS. Published literature on orchids that are used in traditional medicine has been reviewed in this work indicating a great potential of such organisms as source of chemical entities for the development of new drugs.
44 citations
References
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562 citations
TL;DR: In this article, the 13 C NMR spectra of 15 neolignans of several structural types and two lignans were analyzed and their carbon shifts assigned, and the shifts of pyrogallol ether and ethyl phenyl carbinyl ether models were used in this connection.
96 citations
TL;DR: Moscatilin, a new bibenzyl derivative isolated from the orchid Dendrobium moscatum, was shown to have the structure 4,4′-dihydroxy-3,3′,5-trimethoxybibensyl.
81 citations
TL;DR: An amorphous phenanthrene, named nudol has been isolated from Eulophia nuda, Eria carinata and E. stricta and was identified as 2,7-dihydroxy-3,4-dimethoxyphenanthrene.
74 citations
TL;DR: Two new polyoxygenated phenanthrene derivatives, confusarin and confusaridin, are isolated from the orchid Eria confusa and are shown to be 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene and 2,6- dihydrox-2,6,7, 8-tetramethoxyrene, respectively.
46 citations