Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra

doi:10.1016/0031-9422(80)83083-4

Phytochemistry

Volume 19, Issue 6, 1980, Pages 1199-1202

https://doi.org/10.1016/0031-9422(80)83083-4 Get rights and content

Abstract

Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a rarely occurring modified phenylalanine dipeptide, have been isolated together with 4 furanoflavones, karanjin, lancheolatin B, kanjone and pinnatin, a simple flavone, kanugin, a chromenoflavanone (−)-isolonchocarpin, two furanodiketones pongamol and ovalitenone, and β-sitosterol from the petrol and chloroform extracts of the flowers of Pongamia glabra. The structure of pongaglabol has been established as 5-hydroxyfurano(8,7-4″,5″)flavone on the basis of spectral and chemical evidence.

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Karanjin
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Citation Excerpt :
The first ever isolation and structure determination of karanjin from P. pinnata was reported by Prof. Limaye in 1925, which became a trademark compound of this plant species (Limaye, 1925). Later, karanjin was isolated from other parts of the plant; such as root bark (Tanaka et al., 1992), flower (Talapatra et al., 1980), and stem bark (Saha et al., 1991). Rao et al. (1939) attempted to isolate karanjin by distillation of P. pinnata oil, by precipitation from the alcoholic extract obtained by pressing the kernels in a country-press for continuously 30 h.
Karanjin [IUPAC: 3-methoxy-2-phenylfuro-(2,3-h-chrome-4-ol)], a bioactive furanoflavonoid and a potent biomolecule, was first isolated from Pongamia pinnata (L.). The crude extracts from root, leaf and seed having active constituent karanjin is highly valued in both traditional and modern knowledge systems. This review highlights, critically assesses, and presents the probable biosynthetic pathways of karanjin and its isolation methodologies with a view to actualizing its full potential. Karanjin exhibits multiple health benefits and applications, with evident anti-diabetic, anti-cancer, anti-inflammatory, anti-hyperglycemic, antioxidant, anti-colitis, anti-ulcer, and anti-Alzheimer properties. Consequently, the physiochemical properties and biological effects of karanjin have been detailed and analyzed. The efficacy of karanjin has been attenuated by toxicological studies that have proven karanjin to be non-toxic at physiological conditions as substantiated by in vitro and in vivo studies. In addition, the multiple insect repellent/insecticidal properties of karanjin and its availability as an acaricide/bio-insecticide have been reviewed. This review article underscores and endorses the immense potential for novel drug leads in various medicinal and industrial applications, suggesting a deeper insight into its metabolic fate, bioavailability, and cellular effects that await further investigations.
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Chinese water chestnut, the bulb of Heleocharis dulcis, has been widely consumed as fruit or vegetable in China since ancient times. It exhibits health-promoting properties that leads to an extensive study of their active components. Successive chromatography of active fragments of H. dulcis resulted in isolation of five new chalcone-flavonone heterodimers (1–3, 6, 9), four new diverse flavonoids (4, 5, 7, 8), and sixteen known flavonoids derivatives (10–25) were elucidated on the basis of their IR, UV, NMR, MS spectrometry data analysis and references from H. dulcis for the first time. Among these isolates, compounds 4, 7, 9, 12, 13, and 17 showed moderate neuroprotective activity, which increased the cell survival rate from 49.23 ± 3.68% for the model to 67.75 ± 2.75%, 57.83 ± 2.46%, 67.98 ± 2.74%, 58.65 ± 3.43%, 56.14 ± 1.99%, and 56.70 ± 1.38% at 10 μM, respectively. Moreover, compounds 1–3, 15, 16, 18, and 20 were found to moderately improve the HepG2 cell survival rates from 39.53% (APAP, 10 mM) to 45.53–53.44%. The outcome of the study provided crucial information regarding the structural diversity and health benefits of the edible bulbs of H. dulcis.
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Sphaeranthus africanus has been used in traditional Vietnamese medicine to treat sore throat, and to relieve pain and swelling. However, the anti-inflammatory activity of this plant had not yet been investigated. Previously, we isolated five carvotacetones (1–5) from this plant that displayed cytotoxicity against several cancer cell lines.
The objective of this study was to isolate further constituents from S. africanus and to investigate the anti-inflammatory activity of all constituents. Furthermore, the anti-proliferative activity of the newly isolated compounds was evaluated.
Compounds were isolated from the upper parts of S. africanus by chromatographic methods. Structures were determined using spectroscopic techniques, like NMR and MS. All nine compounds isolated from S. africanus were evaluated for inhibitory activity against COX-1 and COX-2 isoenzymes in-vitro, COX-2 mRNA expression and influence on NO production. The anti-proliferative activities of newly isolated compounds (6–9) were evaluated by XTT viability assay with four cancer cell lines, namely CCRF-CEM, MDA-MB-231, HCT-116, and U-251 cells.
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Citation Excerpt :
Purification of a dichloromethane extract of the roots of M. brandisiana by (repeated) chromatography provided thirty-one flavonoids (Fig. 1), among which brandisianones A-E (1, 2, 12, 14, and 21) have not been previously reported. The known compounds were first isolated in this plant and identified by comparison of their physical and spectroscopic data with literature values as lanceolatin B (3) (Tanaka et al., 1992; Mbafor et al., 1995; Lee and Morehead, 1995), pongaglabol (4) (Ahmad et al., 1999; Talapatra et al., 1980), pinnatin (5) (Das et al., 1994), 6″,6″-dimethylchromeno-[2″,3′′:7,8]-flavone (6) (Lee and Kim, 2006; Xia and Lee, 2013; Magalhães et al., 1996), candidine (7) (Yadav et al., 2014; Jain and Sharma, 1974), 5-methoxy-6″,6″-dimethylchromeno-[2″,3′′:7,8]-flavone (8) (Andrei et al., 2000), 5-hydroxy-6″,6″-dimethylchromeno-[2″,3′′:7,6]-flavone (9) (Jain and Sharma, 1974), 5-methoxy-6″,6″-dimethylchromeno-[2″,3′′:7,6]-flavone (10) (Camele et al., 1980), 7-hydroxy-8,4′-dimethoxyisoflavone (11) (http://www.ncbi.nlm.nih.gov/pubmed?term=Puebla%20P%5BAuthor%5D&cauthor=true&cauthor_uid=21076386 Puebla et al., 2010), 7-O-8-bis-(3,3-dimethylallyl)-5-hydroxyflavanone (13) (Bohlmann and Misra, 1984), (−)-isolonchocarpin (15) (Rao and Raju, 1979), obovatin (16) (Andrei et al., 2000; Peralta et al., 2011; Arriaga et al., 2009), ovalitenin A (17) (Gupta and Krishnamurti, 1977), lonchocarpine (18) (Lee and Kim, 2006; Lima et al., 2013), 2′-methoxyfurano-[2″,3′′:4′,3′]-dihydrochalcone (19), ovalitenin B (20) (Gupta and Krishnamurti, 1977; Tanaka et al., 1992), pongamol (22) (Lee and Kim, 2006), 2′,6′-dimethoxyfurano-[2″,3′′:4′,3′]-β-hydroxydihydrochalcone (23) (Hishmat et al., 1989), 2′-hydroxy-6″,6″-dimethylchromeno-[2″,3′′:4′,3′]-β-hydroxychalcone (24) [Xia and Lee (2013), 2′-methoxy-6″,6″-dimethylchromeno-[2″,3′′:4′,3′]-β-hydroxychalcone (25) (Magalhães et al., 1996), praecansone B (26) (Tarus et al., 2002), (−)-12α-hydroxyrotenone (27) (Magalhães et al., 1996; Van Puyvelde et al., 1987), (−)-villosinol (28) (Krupadanam et al., 1977), (−)-tephrosin (29) (Ahmad et al., 1999; Belofsky et al., 2014; Lou et al., 2016), (−)-medicarpin (30) (Goel et al., 2012), and (−)-maackiain (31) (Suginome, 1962; Chaudhuri et al., 1995). This represents the first isolation of compound 24 as a natural product (Xia and Lee, 2013).
The phytochemical investigation for the constituents of the roots of Millettia brandisiana, using bioassay guided fractionation, resulted in the isolation of five previously undescribed (namely brandisianones A-E) and twenty-six known flavonoids. Their chemical structures were determined using a combination of NMR, MS, IR, optical rotation and CD analysis, as well as comparison with the literature data. The crude extract as well as the isolated compounds were evaluated in various biological assays for their cytotoxicity against a panel of human cancer cell lines, potential inhibitory activity against aromatase, and antioxidant property using the oxygen radical absorbance capacity (ORAC) with an aim to search for leads and develop them to drug candidates in our drug discovery effort, we identified three bioactive flavonoids from M. brandisiana which could be further developed into a potential chemopreventive (antiaromatase) agent against breast cancer.
Anti-inflammatory flavone and chalcone derivatives from the roots of Pongamia pinnata (L.) Pierre
2018, Phytochemistry
A phytochemical study on the roots of Pongamia pinnata (L.) Pierre yielded 52 flavonoids, including four previously undescribed flavone and four previously undescribed chalcone derivatives. The structures of the isolated compounds were determined on the basis of the 1D, 2D NMR, and mass spectroscopic data. The absolute configurations of the compounds were assigned via the specific rotation, Mosher's method, as well as the electronic circular dichroism (ECD) spectra. All the isolates were evaluated for their inhibitory effects on NO production in LPS-stimulated BV-2 microglial cells. Ten compounds showed significant inhibitory effects against NO production, comparable to the positive control, dexamethasone.

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Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra

Abstract

Indian J. Chem.

Aust. J. Chem.

Indian J. Chem.

Indian J. Chem.

Indian J. Chem.

Indian J. Chem.

Indian J. Chem.