Polycerasoidin and Polycerasoidol, Two New Prenylated Benzopyran Derivatives from Polyalthia cerasoides

González, M. C.; Serrano, Ángel; Zafra‐Polo, M. Carmen; Cortés, Diego; Rao, K.R.S. Sambasiva

doi:10.1021/np50122a022

Cited by 27 publications

(41 citation statements)

References 20 publications

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“…They were identified as oligandrol (2) (Banfield et al 1994), (6E,10E)-isopolycerasoidol (3) (Gonzalez et al 1996) and polycerasoidol (4) (Gonzalez et al 1995). …”

Section: Resultsmentioning

confidence: 99%

“…is a species of trees, mainly distributed in Southeast Asia. In this work, a new benzopyran derivative, pseudindochin (1), and three known compounds, oligandrol (2) (Banfield et al 1994), (6E,10E)-isopolycerasoidol (3) (Gonzalez et al 1996) and polycerasoidol (4) (Gonzalez et al 1995), were isolated from the 95% EtOH extracts of the twigs and leaves of P. indochinensis, which were collected from the Yunnan Province of China. In this paper, we describe the isolation, structural elucidation and cytotoxic activities of the compounds isolated from P. indochinensis.…”

Section: Introductionmentioning

confidence: 99%

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A new benzopyran derivative from Pseuduvaria indochinensis Merr.

Zhao

Yao

Yang

et al. 2013

Natural Product Research

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From the twigs and leaves of Pseuduvaria indochinensis Merr., a new benzopyran derivative, pseudindochin (1), was isolated together with three known compounds, oligandrol (2), (6E,10E)-isopolycerasoidol (3) and polycerasoidol (4). The structure of compound 1 was elucidated on the basis of extensive spectroscopic data interpretation, including 1D, 2D NMR, HR-ESI-MS, UV and IR. Moreover, compounds 1-4 were evaluated in vitro for their cytotoxic activities against HL-60 and SMMC-7721 cell lines, but these compounds were essentially non-cytotoxic (IC50>30 μg/mL).

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“…They were identified as oligandrol (2) (Banfield et al 1994), (6E,10E)-isopolycerasoidol (3) (Gonzalez et al 1996) and polycerasoidol (4) (Gonzalez et al 1995). …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A new benzopyran derivative from Pseuduvaria indochinensis Merr.

Zhao

Yao

Yang

et al. 2013

Natural Product Research

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“…The on-flow LC-1 H-NMR of the second antioxidant compound 7 exhibited three singlet signals owing to methyl groups, two aromatic protons, two olefinic protons and eight aliphatic protons. With these on-line data, it was difficult to suggest a possible structure for 7; however, a cross check of its molecular weight (358) with all known constituents of the Annonaceae family in a database of natural products suggested that 7 might be polycerasoidol, a tocopherol derivative isolated from Polyalthia cerasoides (Annonaceae) (Gonzalez et al, 1995). The 1 H-NMR of polycerasoidol was comparable to the on-flow 1 H-NMR of 7, however, the chemical shifts of the on-flow 1 H-NMR of 7 between 1.90 and 2.10 ppm were not visible due to their location under the suppressed peaks of the LC-solvent system (acetonitrile; 1.90-2.10 ppm).…”

Section: On Flow Analysis Of Crude Extractsmentioning

confidence: 99%

The potential of LC-NMR in phytochemical analysis

2001

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The coupling of high performance liquid chromatography with nuclear magnetic resonance spectroscopy (LC‐NMR) is one of the most powerful methods for the separation and structural elucidation of unknown compounds in mixtures. The recent progress in pulse field gradients and solvent suppression, the improvement in probe technology, and the construction of high field magnets have given a new stimulus to this technique, which has emerged since the mid 1990s as a very efficient method for the on‐line identification of organic molecules. LC‐NMR thus represents a potentially interesting complementary technique to LC‐UV‐MS in phytochemical analysis for the detailed on‐line structural analysis of natural products. Recent applications have fully demonstrated the usefulness of this technique. A brief review of the applications of LC‐NMR in natural product chemistry is presented in this paper, and a summary of the basic principles and modes of operation of LC‐NMR is provided. Selected examples of LC‐NMR analyses of plant metabolites in crude extracts or in enriched fractions are outlined and used to illustrate the different strategies for employing the technique. The practical possibilities and limitations of LC‐NMR in its application to the analysis of crude plant extracts are discussed by means of several examples. Analytical strategies involving LC multi‐coupled (hyphenated) techniques for the chemical screening and dereplication of crude plant extracts are presented. An analysis of the future development of the technique with respect to its application in phytochemical analysis is also given. Copyright © 2001 John Wiley & Sons, Ltd.

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“…With these on-line data, it was difficult to make any suggestion for the possible structure of 8. However, a cross-check of its molecular weight (MW: 358 Da) with all known constituents of the Annonaceae family in a database of natural products suggested 8 to be polycerasoidol, a tocopherol derivative isolated from Polyalthia cerasoides (Annonaceae) (Gonzalez et al, 1995). The 1 H-NMR of polycerasoidol was comparable to the on-flow 1 H-NMR of 8, however, the chemical shifts between 1.90 and 2.10 ppm were not visible due to their location under the suppressed peaks of the LC-solvent system (MeCN, d 1.90-2.10).…”

Section: Combination Of Lc/ms and Lc/nmr With On-line Assays For The mentioning

confidence: 99%

Modern Screening Techniques for Plant Extracts

Hostettmann

Wolfender

Terreaux

2001

Pharmaceutical Biology

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In order to discover new bioactive compounds from plant sources which could become new leads or new drugs, extracts should be simultaneously evaluated by chemical screening and by various biological or pharmacological targets. Chemical screening using hyphenated techniques such as LC/UV and LC/MS, and more recently LC/NMR, quickly provides ample structural information, leading in many cases to the identification of compounds. This allows researchers to distinguish between known compounds (dereplication) and new molecules directly from crude plant extracts. Thus, the tedious isolation of known compounds can be avoided, and a targeted isolation of constituents presenting novel or unusual spectroscopic features can be undertaken. In parallel, extracts are also subjected to various bioassays that should be simple, reproducible, and rapid. This approach will be illustrated by the search for new molluscicidal, antioxidant, and antifungal compounds from tropical plants.

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Polycerasoidin and Polycerasoidol, Two New Prenylated Benzopyran Derivatives from Polyalthia cerasoides

Cited by 27 publications

References 20 publications

A new benzopyran derivative from Pseuduvaria indochinensis Merr.

A new benzopyran derivative from Pseuduvaria indochinensis Merr.

The potential of LC-NMR in phytochemical analysis

Modern Screening Techniques for Plant Extracts

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