ChemInform Abstract: X‐Ray Crystal Structure of (.+‐.)‐Pandamarine (I), the Major Alkaloid of Pandanus amaryllifolius.

Byrne, Lindsay T.; Guevara, B. Q.; Patalinghug, WC; Recio, B. V.; Ualat, C. R.; White, Allan H.

doi:10.1002/chin.199308274

Cited by 2 publications

(8 citation statements)

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“…Pandamarine ( 1 , Scheme ) is an alkaloid that was isolated in 1992 by Byrne’s group from the leaves of the tropical plant Pandanus amaryllifolius . Pandamarilactone-1 ( 2 , Scheme ), was also isolated from the same plant one year later .…”

supporting

confidence: 87%

“…Biogenetically, the isolation team have proposed that pandamarine ( 1 ) might be the spiro- N,N -ketalization product of a symmetric bis -lactam ( 3 , Scheme ). , This proposal is consistent with the fact that pandamarine ( 1 ) occurs as a racemate. It was suggested that this possible biogenetic intermediate 3 might in turn be obtained from (2 S )-4-hydroxy-4-methylglutamic acid ( 4 , Scheme ) since this amino acid was found in a related species, P.…”

mentioning

confidence: 99%

“…Pandamarine’s structure was determined by X-ray diffraction and consists of both a diazaspiro[4.5] and a 5-ylidenepyrrol-2(5 H )-one unit, connected by a carbon chain (C7–C9, 1 , Scheme ). The diazaspiro[4.5] motif is found in a small number of other natural products such as haplophytine, isoschizogamine, and the related alkaloids leuconoxine, the leuconodines, and melodinine E .…”

mentioning

confidence: 99%

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First Total Synthesis of Pandamarine

2015

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First Total Synthesis of Pandamarine

2015

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“…2-1 to fr. [2][3][4][5][6][7][8][9][10][11][12]. Fraction 2-6 (130 mg) was separated on a Sephadex LH-20 column eluted with chloroform-MeOH (1 : 1) chloroform to afford six fractions (fr.…”

Section: Experimental General Experimental Procedures High Resolutionmentioning

confidence: 99%

“…3) In addition, their antioxidant activity 4) and antihyperglycemic effects 5) have been reported. Various alkaloids have also been isolated form P. amaryllifolius, [6][7][8][9] and several studies have reported their isolation and structure. [10][11][12][13][14][15] Here, we report the isolation of a novel p-coumaroyl dimethyl malate (1) in addition to three known p-comaroyl malate derivatives (2)(3)(4) (Fig.…”

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<i>p</i>-Coumaroyl Malate Derivatives of the <i>Pandanus amaryllifolius</i> Leaf and Their Isomerization

et al. 2017

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A novel p-coumaroyl dimethyl malate (1) was isolated from the Pandanus amaryllifolius leaf in addition to three known analogs of p-coumaroyl dimethyl malate (2-4), and their structures were elucidated by analysis of the spectroscopic data. The p-coumaroyl malate derivatives were isolated as a mixture of E and Z isomers. To determine the cause of isomerization, the p-coumaroyl malate isolated in this study was synthesized. We concluded that the Z isomer might be an artifact generated from the E isomer through purification steps. Key words Pandanus amaryllifolius; p-coumaroyl dimethyl malate; isomerizationPandanus amaryllifolius (also known as the Pandan leaf) belongs to the Pandanus genus (Pandanaceae), and grows in Southeast Asia where it is traditionally used while cooking common nonaromatic rice to impart the aroma of cooked rice. 2-Acetyl-1-pyrroline was isolated from P. amaryllifolius and is the key aroma compound in cooked rice.1,2) Pandan leaves are also used medicinally in South East Asia for such purposes as refreshing the fatigued body and, reducing fever.3) In addition, their antioxidant activity 4) and antihyperglycemic effects 5) have been reported. Various alkaloids have also been isolated form P. amaryllifolius, [6][7][8][9] and several studies have reported their isolation and structure. [10][11][12][13][14][15] Here, we report the isolation of a novel p-coumaroyl dimethyl malate (1) in addition to three known p-comaroyl malate derivatives (2-4) (Fig. 1). We also describe the possible isomerization of 1 during the purification. Results and Discussionp-Coumaroyl malate derivatives (1, 2, and 4) and pcoumaric acid (3) were isolated from P. amaryllifolius. Raw P. amaryllifolius leaves purchased in the market were first treated by steam distillation to remove essential oil. After removal of essential oil, the leaves were dried and extracted with methanol (MeOH) under reflux, and organic solvent was removed by vacuum evaporation resulting in MeOH extracts. These extracts were separated by Diaion HP-20 column chromatography and successively eluted with water, 50% aqueous MeOH, MeOH and acetone. The 50% MeOH eluate was separated by gel permeation chromatography using TOSOH Toyopeal HW-40 (F) column, yielding 12 fractions (fr. 2-1 to 2-12). Of them, fr. 2-6 was further subjected to Sephadex LH-20 column chromatography to afford six fractions (fr. 2-6-1 to 2-6-6). Fraction 2-6-2 was purified by reverse phase HPLC to isolate compound 1. Compound 2 was isolated from fr. 2-7 by Sephadex LH-20 chromatography followed by HPLC purification using an octadecyl-silica (ODS) column. Then, fr. 2-9 was fractionated by reverse phase HPLC to give compounds 3 and 4.

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ChemInform Abstract: X‐Ray Crystal Structure of (.+‐.)‐Pandamarine (I), the Major Alkaloid of Pandanus amaryllifolius.

Cited by 2 publications

References 1 publication

First Total Synthesis of Pandamarine

First Total Synthesis of Pandamarine

<i>p</i>-Coumaroyl Malate Derivatives of the <i>Pandanus amaryllifolius</i> Leaf and Their Isomerization

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