Pigments of Fungi. LII Anisochiral Flavomannin 6,6′,8-Tri-O-methyl Ether from an Australian Dermocybe Toadstool

1999 ◽  
Vol 52 (8) ◽  
pp. 749 ◽  
Author(s):  
Malcolm S. Buchanan ◽  
Melvyn Gill ◽  
Alberto Gimenez ◽  
Somphone Phonh-Axa ◽  
Evelin Raudies ◽  
...  
Keyword(s):  
Natural Product ◽  
Methyl Ether ◽  
Absolute Configuration ◽  
Enantiomeric Purity ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Fruiting Bodies ◽  
The Absolute

Flavomannin 6,6′,8-tri-O-methyl ether occurs in the fruiting bodies of the Australian toadstool Dermocybe sp. WAT 24274 as an anisochiral mixture of the (3S,3′S,P)- and (3R,3′R,M)-enantiomers (5) and (7), respectively, in which the former predominates to the extent of 50% e.e. The structure of the natural product is determined by spectroscopic methods and the absolute configuration and enantiomeric purity are deduced from the c.d. spectrum and by chemical degradation of the natural product to a mixture of stereoisomeric dihydroanthracenones that has been analysed by chiral h.p.l.c.

The First Isolation Of A Phlegmacin Type Pigment From The Ascomycete Xylaria Euglossa

2005 ◽  
Vol 60 (3) ◽  
pp. 333-336 ◽  
Author(s):  
Xing-Na Wang ◽  
Ren-Xiang Tan ◽  
Fei Wang ◽  
Wolfgang Steglich ◽  
Ji-Kai Liu
Keyword(s):  
Methyl Ether ◽  
Absolute Configuration ◽  
Spectroscopic Data ◽  
Nmr Spectra ◽  
Fruiting Bodies ◽  
H Nmr ◽  
The Absolute ◽  
Fungal Pigments

A new pigment, phlegmacin A 8,8’-di-O-methyl ether (1), was isolated from fruiting bodies of Xylaria euglossa (Ascomycota) along with the known fungal pigments (S)-torosachrysone-8-O-methyl ether (2) and emodin-6,8-di-O-methyl ether (3). The structure of compound 1 was established on the basis of its spectroscopic data and the absolute configuration determined as P and 3’S by comparing the CD and 1H NMR spectra of 1 with those of the phlegmacins 4 and 5. Compound 1 represents the first phlegmacin type pigment isolated from the ascomycete

scholarly journals Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

Marine Drugs ◽  
2018 ◽  
Vol 16 (12) ◽  
pp. 474 ◽  
Author(s):  
Wirongrong Kaweetripob ◽  
Chulabhorn Mahidol ◽  
Pittaya Tuntiwachwuttikul ◽  
Somsak Ruchirawat ◽  
Hunsa Prawat
Keyword(s):  
Methyl Ether ◽  
Marine Sponge ◽  
Indole Alkaloids ◽  
Cytotoxic Activities ◽  
Spectroscopic Methods ◽  
The Absolute ◽  
Modified Mosher’S Method

Four sesterterpenes, erectusolides B, C, D, and seco-manoalide-25-methyl ether, two 2-furanone derivatives, erectusfuranones A and B, together with thirteen known sesterterpenes, (6Z)-neomanoalide-24-acetate, two diastereomers of 24-O-methylmanoalide, luffariolide B, manoalide, (6E)- and (6Z)-neomanoalide, seco-manoalide, scalarafuran, 12-acetylscalarolide, 12-epi-O-deacetyl-19-deoxyscalarin, 12-epi-scalarin, and 12-O-deacetyl-12-epi-scalarin, three indole alkaloids, 5-hydroxy-1H-indole-3-carbaldehyde, hyrtiosine A, and variabine B, and one norterpene, cavernosine were isolated from the marine sponge Hyrtios erectus. Their structures were determined by means of spectroscopic methods and the absolute configurations of the asymmetric centers were determined using the modified Mosher’s method. The cytotoxic activities for the isolated compounds have been reported.

scholarly journals Determination of the Absolute Configuration of the Pseudo‐Symmetric Natural Product Elatenyne by the Crystalline Sponge Method

2016 ◽  
Vol 55 (8) ◽  
pp. 2678-2682 ◽  
Author(s):  
Sylvia Urban ◽  
Robert Brkljača ◽  
Manabu Hoshino ◽  
Shoukou Lee ◽  
Makoto Fujita
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
The Absolute

scholarly journals De novo synthesis, structural assignment and biological evaluation of pseudopaline, a metallophore produced by Pseudomonas aeruginosa

2019 ◽  
Vol 10 (27) ◽  
pp. 6635-6641 ◽  
Author(s):  
Jian Zhang ◽  
Tianhu Zhao ◽  
Rongwen Yang ◽  
Ittipon Siridechakorn ◽  
Sanshan Wang ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Total Synthesis ◽  
Natural Product ◽  
Absolute Configuration ◽  
De Novo ◽  
Biological Evaluation ◽  
De Novo Synthesis ◽  
Structural Assignment ◽  
The Absolute

The first total synthesis and isolation of pseudopaline was reported, which allows determination and confirmation of the absolute configuration of the natural product.

scholarly journals Chiral Resolution and Absolute Configuration of 3α,6β-Dicinnamoyloxytropane and 3α,6β-Di(1-ethyl-1H-pyrrol-2-ylcarbonyloxy)tropane, Constituents of Erythroxylum Species

2014 ◽  
Vol 9 (1) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Marcelo A. Muñoz ◽  
Solange Arriagada ◽  
Pedro Joseph-Nathan
Keyword(s):  
Stationary Phase ◽  
Natural Product ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Normal Phase ◽  
Vibrational Circular Dichroism ◽  
Chiral Resolution ◽  
Case Characteristic ◽  
The Absolute

Chiral resolution of (±)-3α,6β-dicinnamoyloxytropane (1) and (±)-3α,6β-di(1-methyl-1 H-pyrrol-2-ylcarbonyloxy)tropane (2), prepared by esterification of (±)-3α,6β-tropanediol (3), was achieved using an amylose-derived HPLC stationary phase and normal phase conditions. The corresponding vibrational circular dichroism (VCD) spectra provided the absolute configuration of the enantiomers as (-)-(3 R,6 R)-1, (+)-(3S,6S)- 1, (-)-(3 R,6 R)-2 and (+)-(3S,6S)- 2. In each case, characteristic VCD bands for the absolute configuration determination of the 3α,6β-tropandiol esters were observed. While the absolute configuration of natural 1, previously isolated from Erythroxylum hypericifolium, could not be established due to the lack of literature optical rotation values, that of catuabine E, previously isolated from E. vacciniifolium, is now assigned as (-)-(3 R,6 R)-2 by comparison with the optical rotation values of the prepared samples and the reported rotation of the natural product.

scholarly journals Shushe Acids A-D from Ganoderma Applanatum

2017 ◽  
Vol 12 (3) ◽  
pp. 1934578X1701200
Author(s):  
Qi Luo ◽  
Yan-Jiao Zhang ◽  
Zhi-Qiang Shen ◽  
Peng Chen ◽  
Yong-Xian Cheng
Keyword(s):  
Succinic Acid ◽  
Natural Product ◽  
Gallic Acid ◽  
Spectroscopic Methods ◽  
Fruiting Bodies ◽  
Ganoderma Applanatum ◽  
Prevention And Treatment ◽  
New Compounds ◽  
Derivatives Of ◽  
Mcf 7

Ganoderma applanatum is a fungus used for the prevention and treatment of a variety of disorders in China. In the present study, four new compounds, named shushe acids A-D (1-4), were isolated from the fruiting bodies of this species. Their structures were identified on the basis of spectroscopic methods. Compounds 1-4 are all natural product hybrids composed of derivatives of gallic acid, glycerol and succinic acid. None of the four compounds showed activity against the MCF-7 cell line.

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