Glycozolinine, a carbazole derivative from Glycosmis pentaphilla

Mukherjee, Samir Kumar; Mukherjee, Meghomukta; Ganguly, S.N.

doi:10.1016/0031-9422(83)85070-5

Cited by 22 publications

(14 citation statements)

References 3 publications

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“…The 1 H-NMR spectrum of 8 showed clearly two sets of signals in a ratio of ca. 2 : 1, except for protons H-5, H-6, H-7, and 8-CH 3 . The corresponding 13 C-NMR spectrum of 8 showed doubling of signals from C-2, C-1Ј, C-2Ј, C-3Ј, C-4Ј, C-4Јa, C-4Јb and 3-CH 3 .…”

Section: C-mentioning

confidence: 95%

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A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots

Cuong

Hung

Sung

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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The genus Glycosmis, family Rutaceae, is a rich source of alkaloids, including those of the quinolone, quinazoline, furoquinoline, acridone, sulphur-containing amides and carbazole types.1,2) Carbazole alkaloids were isolated from the seeds 3) and the roots 4,5) of G. pentaphylla, from the bark of G. mauritiana 6) and G. rupestris, 7) and from the roots of G. arborea. 8) Carbazole alkaloids have also been found in other Rutaceous genera, e.g., Micromelum, Murraya, and Clausena. From two genera, Murraya and Clausena, nearly four fifths of the natural carbazole alkaloids have been isolated.9,10) In a continuing search for bioactive natural products from Vietnamese plants, a number of plants, including species Glycosmis stenocarpa (DRAKE) TAN., have been screened for cytotoxic, antifungal, and antibacterial activities.11,12) G. stenocarpa, local name "com ruou trai hep," is a small shrub, 0.75-1 m high. It is an endemic plant, found in some provinces in north Vietnam.13) This paper reports the isolation and structural elucidation of a new dimeric pyranocarbazole alkaloid, named bisisomahanine (1), and two known monomeric carbazole alkaloids, viz. murrayafoline-A (2) 14) and murrayanine (3), 15) from the roots of G. stenocarpa. Results and DiscussionBisisomahanine (1) was obtained as a pale ivory powder, mp 130-140°C, [a] D 20 Ϫ13.1°. The UV spectrum showed the typical absorbances at 209, 224, and 245 nm, closely similar to those of 2 and 3, and indicative of the carbazole skeleton in 1. Furthermore, it exhibited absorbances at 298 (sharp, strong) and 335 nm (broad, weak), typical of an angular pyranocarbazole unit as described for isomahanine (4). (Table 1) and the peak at m/z 83 in the EI-MS spectrum were assignable to the isohexenyl side chain.16,17) The assignments of carbons at positions C-1Ј and C-2Ј of alkaloid 1 are different than those reported for isomahanine (4), 16) and were confirmed by data from HMQC and HMBC experiments ( Table 1). The HMQC spectrum of 1 showed the direct .1 (C-3Ј), and 22.7 (C-2Ј). The 1 H-1 H COSY and NOESY spectra of 1 also confirmed the above assignment of the isohexenyl side chain (Fig. 1).In the downfield region of the 1 H-NMR spectrum, two broad singlets at d 7.51 and 5.14 were assigned to an NH and a phenolic hydroxyl group, respectively; this was supported by the IR bands at 3470 and 3362 cm Ϫ1, and the fact that no carbons were attached to these proton signals, as shown by the HMQC spectrum. There were two isolated pairs of orthocoupled protons: the first pair at d 6.73 (H-5) and 7.71 (H-6), and the second at d 6.43 (H-1) and 5.54 (H-2). The COSY spectrum confirmed the two separate spin systems. The NMR spectral data of the latter pair were similar to those in some Murraya alkaloids such as isomahanine (4) and mahanine (5), 16) murrayamine C (7), 18) and pyrayafoline-D (6) (assigned the same structure as 4 by Ito et al.), 17) indicating the presence of a pyran ring double bond in the pyranocarbazoletype skeleton of 1.The position of fusion between the pyrano and carbazole ...

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Section: C-mentioning

confidence: 95%

“…2 : 1, except for protons H-5, H-6, H-7, and 8-CH 3 . The corresponding 13 C-NMR spectrum of 8 showed doubling of signals from C-2, C-1Ј, C-2Ј, C-3Ј, C-4Ј, C-4Јa, C-4Јb and 3-CH 3 . Thus this evidence suggests that compound 1 is a mixture of two diastereomers, in a ratio of ca.…”

Section: C-mentioning

confidence: 99%

A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots

Cuong

Hung

Sung

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[9][10] In 1983, compound 5 was isolated by Mukherjee et al from the benzene extract of the seeds of Glycosmis pentaphylla and named glycozolinine (5). 11 One year later, Bhattacharyya et al isolated the same compound from the petroleum ether extract of the roots of the same plant and named it glycozolinol (5). 12 They confirmed their structural assignment by synthesis.…”

Section: Introductionmentioning

confidence: 98%

Total synthesis of glycomaurrol and eustifoline-C by DIBAL-H promoted reductive ring opening of pyrano[2,3-c]carbazoles

2015

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“…Roots pounded and mixed with sugar are given in low fever and wood is used in snake bite (Chopra et al, 1956). It is reported to contain arborinine (Quader et al, 1999), glycozolicine, 3-formyl carbazole, glycosinine (Jash et al, 1992), mupamine (Kamaruzzman and Chakraborty 1989), varbazole, 3methyl carbazole (Chowdhury et al, 1987), glycolone (Bhattacharyya and Chowdhury, 1985), glycozolidol (Bhattacharyya et al, 1985), glycozolinine (Mukherjee et al, 1983), glycophymoline (Sarka and Chakraborty 1979), glycophymine, glycomide (Sarka and Chakraborty, 1977), glycozoline (Chakraborty, 1969), noracronycine, des-Nmethylacrocynine and des-N-methylnoracronycine (Govindachari et al, 1966). Eugenia fruticosa (Myrtaceae), a small to medium sized evergreen tree is well known as bon jam, puti jam, khudi jam and traditionally has been used for the treatment of anemia, blood dysentery, dysentery .…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive activity of the methanol extracts of leaves of Eugenia fruticosa (Roxb.) and Glycosmis pentaphylla (Retz.) in Swiss albino mice

Shams-Ud-Doha¹,

Apu²,

Howlader³

et al. 2012

J. App. Pharm. Sci

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The present study was designed to evaluate analgesic potential of the methanolic extracts of the leaves of the both Glycosmis pentaphylla (Rutaceae) and Eugenia fruticosa (Myrtaceae). The analgesic activity was evaluated using the acetic acid (0.7% i.p.)-induced writhing inhibition method in swiss albino mice. The methanolic extract of leaves of Glycosmis pentaphylla, at the dose of 200 and 400 mg/kg body weight significantly (p<0.001) reduced the number of writhes with 31.97% and 44.21% of inhibition, respectively compared to control group. The methanolic extracts of leaves of Eugenia fruticosa significantly and dose dependently reduced the pain threshold (p<0.001) with 51.02 and 72.1% of writhing inhibition when compared to the control group at the dose of 200 and 400 mg/kg body weight, respectively which were comparable to that of the standard drug Diclofenac Na (65.31% inhibition of writhing, p<0.001). The results of the study demonstrated the potential antinociceptive activity of the methanolic extracts of the leaves of Glycosmis pentaphylla and Eugenia fruticosa which validated the traditional uses of the both plants in painful diseases and further investigations to elucidate the mechanism of action are required.

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Glycozolinine, a carbazole derivative from Glycosmis pentaphilla

Cited by 22 publications

References 3 publications

A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots

A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots

Total synthesis of glycomaurrol and eustifoline-C by DIBAL-H promoted reductive ring opening of pyrano[2,3-c]carbazoles

Antinociceptive activity of the methanol extracts of leaves of Eugenia fruticosa (Roxb.) and Glycosmis pentaphylla (Retz.) in Swiss albino mice

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