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Journal ArticleDOI

24-Methylene cycloartanyl p-hydroxycinnamate from the orchid Cirrhopetalum elatum

01 Jan 1985-Phytochemistry (Pergamon)-Vol. 24, Iss: 9, pp 2120-2122

TL;DR: From the orchid Cirrhopetalum elatum was isolated a new triterpene of the cycloartane series, which was shown to be 24-methylenecycloartanyl p -hydroxycinnamate from spectral and chemical evidence.

AbstractFrom the orchid Cirrhopetalum elatum was isolated a new triterpene of the cycloartane series, which was shown to be 24-methylenecycloartanyl p -hydroxycinnamate from spectral and chemical evidence.

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Citations
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Journal ArticleDOI
TL;DR: A compilation of the triterpenoids isolated during the period 1982–1989 along with their occurrence, available physical data, spectroscopy and X-ray analysis used for their characterization, is included.
Abstract: Triterpenoids isolated and characterized from various sources are reviewed. The newer techniques used in their isolation and structure elucidation, the newer skeleton triterpenoids characterized, chemical modifications and synthetic studies reported are discussed. A compilation of the triterpenoids isolated during the period 1982–1989 along with their occurrence, available physical data, spectroscopy and X-ray analysis used for their characterization, is included. The biological activities of the triterpenoids are also described.

85 citations

Journal ArticleDOI
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.
Abstract: Moscatilin, a new bibenzyl derivative isolated from the orchid Dendrobium moscatum , was shown to have the structure 4,4′-dihydroxy-3,3′,5-trimethoxybibenzyl.

76 citations

Journal ArticleDOI
TL;DR: The feasibility of the above approach was established using the well characterised steryl ferulate mixture γ-oryzanol obtained from rice bran oil, and the methods were subsequently applied to the analysis of theSteryl ferulates present in seeds of maize.
Abstract: Approaches to the isolation and characterisation of intact steryl ferulates were investigated. Alkaline washing of the total lipid extract obtained from seeds allowed preliminary separation of a phenolic ester containing fraction from the abundant neutral lipids (comprising largely triacylglycerides, sterols and steryl fatty acyl esters). Subsequent thin-layer chromatography (silica gel) afforded purified steryl ferulates. Separation of individual molecular species was achieved by reversed-phase (ODS) high-performace liquid chromatography (HPLC) using the acetate derivatives of the steryl ferulates, or by high-temperature gas chromatography (GC) of the underivatised steryl ferulates or their acetates or trimethylsilyl ethers. Characterisation of intact individual molecular species was based on the electron impact mass spectra obtained by GC—mass spectrometry (MS) of the underivatised ferulates or their trimethylsilyl ethers, or by direct insertion probe MS of the acetates of the steryl ferulates obtained by preparative HPLC. The feasibility of the above approach was established using the well characterised steryl ferulate mixture γ-oryzanol obtained from rice bran oil. The methods were subsequently applied to the analysis of the steryl ferulates present in seeds of maize ( Zea mays ).

53 citations

Journal ArticleDOI
Abstract: Flavanthrin, the first dimeric 9,10-dihydrophenanthrene derivative, was isolated from the orchid Eria flava which also yielded the previously reported 9,10-dihydrophenanthrene coelonin ( 2a ). The structure of flavanthrin was established as the 1.1'-dimer ( 1a ) of its congener coelonin from spectral and chemical evidence.

51 citations

Journal ArticleDOI
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.
Abstract: From the orchid Eria confusa were isolated two new polyoxygenated phenanthrene derivatives, confusarin and confusaridin, which were shown to be 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene and 2,6-dihydroxy-3,4,7,8-tetramethoxyphenanthrene, respectively.

44 citations


References
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Journal ArticleDOI
Abstract: The carbon-13 NMR spectra of lanosta-8-en-3β-ol, lanosta-8, 24-dien-3β-ol, lanosta-7,9(11)-dien-3β-ol, lanostan-3β-ol, eupha-8-en-3β-ol, eupha-8,24-dien-3β-ol, ursa-12-en-3β-ol (α-amyrin) and oleana-12-en-3β-ol (β-amyrin) have been obtained and completely assigned. The results of this study provide chemical shift data for methyl, methylene, methine and quaternary carbon atoms in tetra- and pentacyclic triterpenoid spectra. The carbon-13 NMR spectrum of a triterpenoid provides a unique fingerprint for the molecule.

104 citations

Journal ArticleDOI
TL;DR: Rubicoumaric acid and rubifolic acid isolated from Rubia cordifolia have been shown to be 30-hydroxy-3β-p-Hydroxycoumaryloxy-urs-12-ene-28-oic acid or 3β,30-dihydroxy-urs 12-ene,28- oic acid respectively on the basis of 1H NMR, 13C NMR and mass spectral and chemical evidence.
Abstract: Rubicoumaric acid and rubifolic acid isolated from Rubia cordifolia have been shown to be 30-hydroxy-3β-p-hydroxycoumaryloxy-urs-12-ene-28-oic acid and 3β,30-dihydroxy-urs-12-ene-28-oic acid(30-hydroxyursolic acid) respectively on the basis of 1H NMR, 13C NMR and mass spectral and chemical evidence.

32 citations

Journal ArticleDOI
Abstract: Oxoflavidin, a new phenolic compound isolated from the Himalayan orchid Coelogyne elata was shown to be 2,7-dihydroxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran-5-one (2d) by spectral and chemical evidence.

24 citations

Journal ArticleDOI
TL;DR: The triterpenes of the five Lithocarpus species examined comprised members of the friedo- and unrearranged oleanane groups, viz. friedelin, friedelan-3β-ol, taraxerol and β-amyrin, with three new cycloartane triterPenes found in L. polystachya.
Abstract: The triterpenes of the five Lithocarpus species examined comprised members of the friedo- and unrearranged oleanane groups, viz. friedelin, friedelan-3β-ol, taraxerol and β-amyrin. Glutinol was also present, except in L. harlandi where friedelan-2α,3β-diol was found. In addition, three new cycloartane triterpenes, lithocarpolone (21,24-epoxy-24-hydroxymethyl-cycloartan-3-one), lithocarpdiol (21,24-epoxy-24-hydroxymethyl-cycloartan-3β-ol). and 24-methylenecycloartan-3β,21-diol were found in L. polystachya , and their structures determined.

21 citations