4-Hydroxybenzoic acid: a hypoglycemic constituent of aqueous extract of Pandanus odorus root

Peungvicha, Penchom; Temsiririrkkul, Rungravi; Prasain, Jeevan K.; Tezuka, Yasuhiro; Kadota, Shigetoshi; Thirawarapan, Suwan; Watanabe, Hiroshi

doi:10.1016/s0378-8741(98)00061-0

Cited by 102 publications

(63 citation statements)

References 12 publications

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“…The two new compounds, pandamarilactonine-C (1) 8) and pandamarilactonine-D (2), 9) gave respectively m/z 318.1691 [MϩH] ϩ and m/z 318.1704 [MϩH] ϩ by high-resolution FAB-MS, which established the molecular formulas of the two compounds as C 18 H 23 NO 4 , and indicated that these are isomers of coexisting alkaloids, pandamarilactonine-A and B.…”

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confidence: 94%

“…1) In a recent pharmacological screening, the hypoglycemic effect of an extract of P. odorus was noted. [2][3][4] In our continuing search for structurally unique and biologically active Pandanus alkaloids, new pyrrolidine alkaloids were found in P. amaryllifolius ROXB. [5][6][7] Further investigation of the minor constituents in the fresh leaves of this plant resulted in the isolation of two new alkaloids, pandamarilactonine-C and -D (1, 2).…”

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Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.

et al. 2002

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Two new pyrrolidine alkaloids, pandamarilactonine-C and -D, were isolated from Pandanus amaryllifolius. Based on the total synthesis of pandamarilactonine-C and its related alkaloid, pandamarilactonine-A, the relative stereochemistry of pandamarilactonine-A and -B, which was previously proposed by spectroscopic analysis, was revised.Key words pyrrolidine alkaloid; Pandanus; pandamarilactonine; total synthesis; structure elucidation; structure revisionThe genus Pandanus (Pandanaceae) comprises approximately 600 species that are widely distributed in tropical and subtropical regions. Several Pandanus species are used as a remedy for toothache and rheumatism, and as diuretic, cardiotonic, etc.1) In a recent pharmacological screening, the hypoglycemic effect of an extract of P. odorus was noted.2-4) In our continuing search for structurally unique and biologically active Pandanus alkaloids, new pyrrolidine alkaloids were found in P. amaryllifolius ROXB.5-7) Further investigation of the minor constituents in the fresh leaves of this plant resulted in the isolation of two new alkaloids, pandamarilactonine-C and -D (1, 2). In this communication, we describe the structure elucidation of these alkaloids as well as the total synthesis of pandamarilactonine-C (1) and its related alkaloid, pandamarilactonine-A (3), which resulted in the revision of the relative stereochemistry of pandamarilactonine-A and -B (3, 4), which was previously proposed based on the results of spectroscopic analysis.The crude alkaloid fraction (1.10 g), which was obtained from young leaves of P. amaryllifolius, 5) was initially separated by SiO 2 column chromatography using MeOH/CHCl 3 gradient, and then the 2-5% MeOH/CHCl 3 eluate was subjected to SiO 2 medium pressure liquid chromatography using 2% EtOH/CHCl 3 to give 20 mg of pandamarilactonine-C and 4 mg of pandamarilactonine-D.The two new compounds, pandamarilactonine-C (1) 8) and pandamarilactonine-D (2), 9) gave respectively m/z 318.1691 [MϩH] ϩ and m/z 318.1704 [MϩH] ϩ by high-resolution FAB-MS, which established the molecular formulas of the two compounds as C 18 H 23 NO 4 , and indicated that these are isomers of coexisting alkaloids, pandamarilactonine-A and B.5) The UV, 1 H-and 13 C-NMR spectra of pandamarilactonine-C and -D were very similar to those of pandamarilactonine-A and B, which comprised g-butylidene-a-methyl a,bunsaturated g-lactone and pyrrolidinyl a,b-unsaturated glactone residues, indicating that these four alkaloids are stereoisomers. Unambiguous assignment of all the carbons and protons in 1 8) and 2 9) was realized using 1 H-1 H correlated spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) spectra. Comparing the 13 C-NMR data of 1 and 2 with those of 3 and 4, 5) a significant difference was observed in the chemical shifts at the C-4 position. The signals of 1 (d 130.3) and 2 (d 133.9) appeared in the higher field than those of 3 (d 137.7) and 4 (d 137.7), which can be reasonably interpreted in term...

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confidence: 99%

Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.

et al. 2002

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“…Leaves have been used as a food flavouring and traditional medicine in Philippines, Indonesia and Thailand. Hot water extract of roots and leaves of this plant show hypoglycaemia indications (Peungvicha et al, 1998). R. nasutus (RN) has also been used in Thai traditional medicine for the treatment of various diseases including eczema (Visweswara et al, 2010), pulmonary tuberculosis (Visweswara et al, 2013), hepatitis (Bukke et al, 2011), diabetes hypertension and various skin diseases (Visweswara et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Anti-oxidant properties and anti-hemolytic activity of Psidium guajava, Pandanous odorus and Rhinacanthus nasutus

Thephinlap¹,

Pangjit²,

Suttajit³

et al. 2013

J. Med. Plants Res.

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The ethanolic extracts of leaves of Psidium guajava (PG), Pandanous odorus (PO), Rhinacanthus nasutus (RN) contained polyphenolic compounds in the order of PG > RN > PO. All the extracts exhibited 2,2-diphenyl-1-picryhydrazyl (DPPH) and 2,2'-azino-bis 3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radicals scavenging activities. PG showed a marked antioxidant effect whereas PO and RN were comparable. Interestingly, they were able to bind with ferric (Fe 3+ ) and ferrous (Fe 2+) ion and completed within 5 min of incubation times. In accordance with previous results, PG extract could effectively protect erythrocytes from iron induced hemolysis with the activity higher than PO and RN. Based on all results, tested leaf extracts of three Thai medicinal plants might be used for alleviating or preventing harmfulness in many oxidative stress disorders.

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“…In these cultures, the aerial root is used to relieve several internal diseases including stomachache, food poisoning, and urinary tract problems [22,23]. Whistler [22], and Peungvicha et al [24] reported that Pandanus tectorius leave was used for internal ailments, inflammation, sores, relieving stomachaches, and food poisoning. …”

Section: Introductionmentioning

confidence: 99%

Thermodynamic, chemical and electrochemical investigation of pandanus tectorius extract as corrosion inhibitor for steel in sulfuric acid solutions

Al-Turkustani

2013

Eur. J. Chem.

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KEYWORDSThe corrosion inhibition characteristics of pandanus tectorius extract on corrosion of steel in 1 M H2SO4 were investigated using chemical and electrochemical measurements at various temperatures (30, 40, 50 and 60 °C). The effect of acid concentration on the corrosion rate of steel increases with acid concentration (0.25-2.00 M) showing first order corrosion reaction without changing the reaction mechanism. The results showed that when the concentration of pandanus tectorius extract increased from 5% to 15% (v:v), the rate of steel corrosion is decreased, which indicated that pandanus tectorius extract are good inhibitor for steel corrosion in 1 M H2SO4 at 30 °C and attains 88.02% at 15% (v:v) from weight loss method. Electrochemical results showed that the investigated extract was acted as mixed type inhibitor. The free energy of adsorption ΔGads for pandanus tectorius, indicates that the process was spontaneous and physically adsorbed (physisorption) onto the steel surface. Also, scanning electron microscopy (SEM) is used to support the obtained result. The trend of inhibition efficiency with temperature suggests physical adsorption of this extract on the corroding steel surface. Thermodynamic functions ∆Eapp, ∆H* and ∆S* has been calculated and are discussed.

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4-Hydroxybenzoic acid: a hypoglycemic constituent of aqueous extract of Pandanus odorus root

Cited by 102 publications

References 12 publications

Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.

Isolation and Structure Elucidation of Two New Alkaloids, Pandamarilactonine-C and -D, from Pandanus amaryllifolius and Revision of Relative Stereochemistry of Pandamarilactonine-A and -B by Total Synthesis.

Anti-oxidant properties and anti-hemolytic activity of Psidium guajava, Pandanous odorus and Rhinacanthus nasutus

Thermodynamic, chemical and electrochemical investigation of pandanus tectorius extract as corrosion inhibitor for steel in sulfuric acid solutions

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