Carpusin: a novel 2-hydroxy-2-benzylcoumaranone from Pterocarpus marsupium

Mathew, Jose; Rao, A. V. Subba

doi:10.1016/s0031-9422(00)86994-0

Cited by 29 publications

(10 citation statements)

References 3 publications

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“…Due to MS data, the presence of a second hydroxy group at C-2¢ was excluded, and ring closure from C-2¢ to C-7 was supposed, building a furanocoumarin. The NMR shifts of this furan ring region were nearly identical to data found in literature (16), (17). From the presence of the ion at m/z 294 [M ± 122] + , it could be supposed, that they have the same basic structure as the other compounds isolated.…”

Section: Resultssupporting

confidence: 85%

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

Quadri-Spinelli

Heilmann²,

Rali³

et al. 2000

Planta med

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Three new coumarin derivatives, compounds 1-3, three new furanocoumarins, compounds 4-6, and a novel dioxocane derivative, compound 7, were isolated from the fern Cyclosorus interruptus (Willd.) H. Itô. Based on spectrometric and spectroscopic analysis (FAB or El mass spectrometry as well as 1D and 2D NMR experiments) their structures were characterised as 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenylpropionyl)-1-benzopyran-2-one (1), 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenyl-trans-acryloyl)-1- benzopyran-2-one (2), 5,7-dihydroxy-8-(2-hydroxy-3-phenylpropionyl)-6-methyl-4-phenyl-1- benzopyran-2-one (3), 8-benzyl-5,8-dihydroxy-6-methyl-4-phenylfuro[2,3-h]-1-benzopyran-2,9- dione (4), 8-benzyl-5,8 beta,9 beta-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (5), 8-benzyl-5,8 beta,9 alpha-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (6) and 5,11-dihydroxy-6-methyl-4-phenyl-11-(1-phenylmethyl)-7,10-dioxocane [5,6-h]-1-benzopyran-2,12-dione (7). For these compounds we propose the trivial names interruptins A-F. Compounds 1, 5/6 and 7 showed antibacterial activity while compounds 1 and 2 were cytotoxic to a KB cell line.

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Section: Resultssupporting

confidence: 85%

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

Quadri-Spinelli

Heilmann²,

Rali³

et al. 2000

Planta med

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“…For instance, to the carbons C-5 and C-9 was assigned the same chemical shift (δ 155.50). A value of δ 171.91 was assigned to the C-3 carbonyl, which is in complete disagreement with the values observed for maesopsin (C-3 carbonyl; δ 196.9 ppm), for compound 2 (C-3 carbonyl; δ 195.4 ppm), and for several other similar compounds isolated by Yoshikawa et al [12] The deuterated solvent used for carpusin [11] is not mentioned, but C-2 (δ 101.32) and C-9 (δ 105.44) have different chemical shifts relative to maesopsin [10] (MeOD): C-2, δ 107.7 and C-9, δ 103.1. This is of considerable importance since maesopsin is indeed the 4-hydroxyl derivative of carpusin.…”

Section: Resultsmentioning

confidence: 46%

“…A survey in the literature, looking for model compounds for comparison, revealed a few examples of 2-auranonols (dihydroauron-2-ols) to which the NMR data have been assigned. Mathew and Rao [11] have isolated carpusin from Pterocarpus marsupium, but questions about what seems to be a series of misassignments can be raised. For instance, to the carbons C-5 and C-9 was assigned the same chemical shift (δ 155.50).…”

Section: Resultsmentioning

confidence: 99%

¹H and ¹³C NMR assignments of new methoxylated furanoflavonoids from Lonchocarpus araripensis

Lima

Mileo

Andrade‐Neto

et al. 2008

Magnetic Reson in Chemistry

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Two new polymethoxylated flavonoids, 2',5',6'-trimethoxy-[2'',3'' : 3',4']furano dihydrochalcone and 2,4',4,5-tetramethoxy-[2'',3'' : 6,7]-furanodihydroaurone, were isolated from the root barks of Lonchocarpus araripensis, along with the known compounds 3,4,5,6-tetramethoxy-[2'',3'' : 7,8]-furanoflavan, 3,6-dimethoxy-1'',1''-dimethylcromene-[2'',3'' : 7,8]-flavone, 3',4'-methylenodioxy-5,6-dimethoxy-[2'',3'' : 7,8]-furanoflavone, 3,5,6-trimethoxy-[2'',3'' : 7,8]-furanoflavanone, 3,5,6-trimethoxy-[2'',3'' : 7,8]-furanoflavone, and 6alpha-hydroxy-medicarpin. The complete (1)H and (13)C NMR assignments of the new furan flavonoids were performed using 1D and 2D pulse sequences, including COSY, HSQC, and HMBC experiments, and comparison with spectral data for analog compounds from the literature, particularly for the new furanodihydroaurone because of several inconsistencies on the carbonyl chemical shifts from the literature.

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“…The major phytoconstituents of Pterocarpus Marsupium are pterostilbene and marsupin. [13,14] Others are liquirtigenin, iso liquirtigenin, pterosupin, p-hydroxybenzaldehyde, 7, 4'dihydroxyflavone [14] , propterol carsupin [17] and so on. Different plant parts of Pterocarpus Marsupium have been used for various diseases like leaves for boils, sores, skin diseases and stomach pain; flowers for fever; Gum Kino for diarrhea, dysentery, leucorrhoea etc.…”

Section: Phytochemicalmentioning

confidence: 99%

Pterocarpus Marsupium Importance in Various Activities - A Review

E¹

2018

IJTSRD

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Extracts of Pterocarpus Marsupium were prepared using methods like infusion, maceration, decoction and percolation. Several chemical constituents like pterostilbene, epicatechin, pterosupin, marsupin, tannins, pentosan, propterol, isoflavonoid glycol, liquiritigenin etc. were identified an Pterocarpus Marsupium Roxb. (Fabaceae) is one such herbal drug which finds its place in AYUSH. Nature has bestowed this herb with a high versatility due to which it exhibits a wide range of Pharmacological actions. Pterocarpus marsupium commonl Indian Kino tree or Asana or Vijayasar is a large deciduous tree found in the subtropical regions of the world.

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Carpusin: a novel 2-hydroxy-2-benzylcoumaranone from Pterocarpus marsupium

Cited by 29 publications

References 3 publications

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

¹H and ¹³C NMR assignments of new methoxylated furanoflavonoids from Lonchocarpus araripensis

Pterocarpus Marsupium Importance in Various Activities - A Review

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Carpusin: a novel 2-hydroxy-2-benzylcoumaranone from Pterocarpus marsupium

Cited by 29 publications

References 3 publications

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

1H and 13C NMR assignments of new methoxylated furanoflavonoids from Lonchocarpus araripensis

Pterocarpus Marsupium Importance in Various Activities - A Review

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¹H and ¹³C NMR assignments of new methoxylated furanoflavonoids from Lonchocarpus araripensis