Stereochemistry and NMR Data Assignment of Cyclopeptide Alkaloids from Zizyphus Oxyphylla

The structures of (3 S,7 R,13 S)-6-[2-(dimethylamino)-3-phenylpropanoyl]-19-methoxy-2-oxa-6,9,15-triazatetracyclo[16.3.1.03,7. 09,13]docosa-1-(22),16,18,20-tetraene-8,14-dione (1), nummularin-C (2) and nummularin-R (3) have been previously determined mainly based on mass spectrometric data. Stereochemistry and complete 1H and 13C NMR spectroscopic data assignments of these compounds are now described. Compounds 1 and 2 are reported for the first time from

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Melitidin: A Flavanone Glycoside from Citrus grandis ‘Tomentosa’

Natural Product Communications ◽

10.1177/1934578x1300800411 ◽

2013 ◽

Vol 8 (4) ◽

pp. 1934578X1300800 ◽

Cited By ~ 2

Author(s):

Wei Zou ◽

Yonggang Wang ◽

Haibin Liu ◽

Yulong Luo ◽

Si Chen ◽

...

Keyword(s):

Citric Acid ◽

Chinese Medicine ◽

Mass Spectrometric ◽

Mass Spectrometric Data ◽

Spectrometric Data ◽

Antitussive Effect ◽

First Time ◽

Flavanone Glycoside ◽

Resolution Mass ◽

C Nmr

Citrus grandis ‘Tomentosa’ is a traditional Chinese medicine, used as an antitussive. In this research, melitidin, a flavanone glycoside, was isolated from this species for the first time by using chromatographic methods. The structure was confirmed through comprehensive analyses of its ultraviolet, infrared, 1H and 13C NMR, HMBC and HMQC spectroscopic and high-resolution mass spectrometric data. Meliditin showed a good antitussive effect on cough induced by citric acid in Guinea pig, suggesting that it was a contributor to the antitussive effect of C. grandis ‘Tomentosa’.

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Oleanane-type Triterpene Glycosides from Glycyrrhiza Uralensis

Natural Product Communications ◽

10.1177/1934578x0700200304 ◽

2007 ◽

Vol 2 (3) ◽

pp. 1934578X0700200 ◽

Cited By ~ 1

Author(s):

Jinwei Li-Yang ◽

Jun-ichiro Nakajima ◽

Nobuhito Kimura ◽

Kazuki Saito ◽

Shujiro Seo

Keyword(s):

Natural Products ◽

Spectroscopic Data ◽

2D Nmr ◽

Mass Spectrometric ◽

Triterpene Glycosides ◽

Glycyrrhiza Uralensis ◽

Nmr Data ◽

Nmr Methods ◽

First Time ◽

C Nmr

Chemical investigation of the roots of Glycyrrhiza uralensis resulted in the isolation of six oleanane-type triterpene glycosides (1 – 6), including one new saponin (1) and two (2 and 3) obtained as natural products for the first time. The new licorice saponin (1) was identified as 22β–acetoxylglycyrrhizin from [α]D, mass spectrometric, and UV, IR, and NMR spectroscopic data.. Full assignments of 1H and 13C-NMR data for compounds 2, 3, 4, 5 and 6 were made for the first time according to 2D NMR methods.

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Chemical Constituents of Gentiana Macrophylla Pall. From Shaanxi

Natural Product Communications ◽

10.1177/1934578x0600100702 ◽

2006 ◽

Vol 1 (7) ◽

pp. 1934578X0600100 ◽

Cited By ~ 3

Author(s):

Qianliang Chen ◽

Wenji Sun ◽

Guangzhong Tu ◽

Zhangyan Shi ◽

Yongmin Zhang

Keyword(s):

Oleanolic Acid ◽

Chemical Constituents ◽

2D Nmr ◽

Mass Spectrometric ◽

Shaanxi Province ◽

The Novel ◽

Mass Spectrometric Data ◽

Spectrometric Data ◽

Gentiana Macrophylla ◽

First Time

A novel amide, qinjiaoamide and a novel iridoid, erythrocentaurin acid, together with seven known compounds [erythrocentaurin (3), roburic acid (4), oleanolic acid (5), gentiopicroside (6), swertiamarine (7), sweroside (8), and 6′-O-β-D-glucosylgentiopicroside (9)], were isolated from the root of Gentiana macrophylla Pall. from Shaanxi Province, China. The novel compounds were identified as N-pentacosyl-2-carboxy-benzoyl amide (1) and 5-carboxyl-3,4-dihydrogen-1H-2-benzopyran-1-one (2), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR) and mass spectrometric data. Among the known compounds, erythrocentaurin (3) was isolated from the genus Gentiana for the first time.

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Cyclization of 17-ethylenedioxy-3α,5-cyclo-6,7-seco-5α-androstane-6,7-diol

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19790128 ◽

1979 ◽

Vol 44 (1) ◽

pp. 128-144 ◽

Cited By ~ 3

Author(s):

Helena Velgová ◽

Dietrich Zeigan ◽

Günther Engelhardt ◽

Antonín Trka

Keyword(s):

Acetic Anhydride ◽

Intramolecular Cyclization ◽

Boron Trifluoride ◽

Boron Trifluoride Etherate ◽

Mass Spectrometric ◽

Cyclic Ethers ◽

Mass Spectrometric Data ◽

Spectrometric Data ◽

H Nmr ◽

C Nmr

Intramolecular cyclization of 17-ethylenedioxy-3α,5-cyclo-6,7-seco-5α-androstane-6,7-diol (I) on treatment with p-toluenesulphonyl chloride in pyridine gives 17-ethylenedioxy-3α,5-cyclo-B-homo-7-oxa-5α-androstane (III) and 17-ethylenedioxy-3,5-methylene-6-oxaandrostane (II). The cyclic ethers II and III after deketalization and treatment with boron trifluoride etherate in acetic anhydride yield 3β,7-dihydroxy-6,7-secoandrost-5-en-17-one (XIV) along with a small quantity of 3β,5-cyclo-A-homo-6-oxa-5β-androstane-17-one (XIII). Proof of the structures in question is based on IR, 1H NMR, 13C NMR and mass spectrometric data.

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