Alkaloids from the plant Haplophyllum griffithianum

Kodirova, D. R.; Rasulova, Kh. A.; Абдуллаев, Н. Д.; Бобакулов, Х. М.

doi:10.1007/s10600-011-0085-0

Cited by 5 publications

(2 citation statements)

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“…Alkaloids have been reported as the most representative compounds in the genus, and they are also of the utmost importance from a chemosystematic standpoint [ 114 ]. Skimmianine is the most reported compound of this class in the genus, followed by γ-fagarine [ 44 , 45 , 46 , 49 , 51 , 52 , 53 , 54 , 57 , 58 , 66 , 73 , 75 , 77 , 78 , 80 , 81 , 82 , 85 , 86 , 87 , 89 , 90 , 95 , 97 , 98 , 101 , 106 , 108 , 111 ]. Coumarins were also quite present in the Haplophyllum genus, in particular scopoletin [ 56 , 58 , 62 , 68 , 84 , 91 , 98 , 111 ].…”

Section: Phytochemistrymentioning

confidence: 99%

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

et al. 2021

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Herein, a comprehensive review is given focusing on the chemical profiles of the essential oils (EOs), non-volatile compounds, ethnobotany, and biological activities of different Haplophyllum (Rutaceae family) species. To gather the relevant data, all the scientific databases, including Scopus, ISI-WOS (Institute of Scientific Information-Web of Science), and PubMed and highly esteemed publishers such as Elsevier, Springer, Taylor and Francis, etc., were systematically retrieved and reviewed. A wide array of valuable groups of natural compounds, e.g., terpenoids, coumarins, alkaloids, lignans, flavonoids, and organic acids have been isolated and subsequently characterized in different organic extracts of a number of Haplophyllum species. In addition, some remarkable antimicrobial, antifungal, anti-inflammatory, anticancer, cytotoxic, antileishmanial, and antialgal effects as well as promising remedial therapeutic properties have been well-documented for some species of the genus Haplophyllum.

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Section: Phytochemistrymentioning

confidence: 99%

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

et al. 2021

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“…collected during flowering (Nilu village, Surkhandarcya Oblast) of the quinoline alkaloids skimmanine, dictamnine, dubinine, dubinidine, dubamine, and N-methylhaplofoline [5]. In continuation of studies of the alkaloid composition of the CHCl 3 total alkaloids, we isolated from the aerial part of the plant a new base with mp 93-95°C whose physicochemical properties and spectral data differed from quinoline bases that were previously reported and which we called gerphytine.…”

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confidence: 93%

Gerphytine, a new furanoquinoline alkaloid from Haplophyllum griffithianum

et al. 2011

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A series of known alkaloids and the new base gerphytine were isolated from total alkaloids from the aerial part of Haplophyllum griffithianum growing in Surkhandarcya Oblast, Republic of Uzbekistan. Gerphytin was identified based on spectral data and an x-ray crystal structure analysis as a furanoquinoline derivative and had the structure 7-O-allyl-4,8-dimethoxyfuranoquinoline.The plant genus Haplophyllum (Rutaceae) has for a long time been used in folk medicine as an anesthetic and woundhealing agent for burns and tumors, toothache, and stomach and skin diseases and as a treatment for respiratory organs and several types of cancer [1][2][3]. Extracts of several Haplophyllum species exhibit cytotoxic activity [4].We reported earlier on the isolation from the aerial part and roots of H. griffithianum Boiss. collected during flowering (Nilu village, Surkhandarcya Oblast) of the quinoline alkaloids skimmanine, dictamnine, dubinine, dubinidine, dubamine, and N-methylhaplofoline [5]. In continuation of studies of the alkaloid composition of the CHCl 3 total alkaloids, we isolated from the aerial part of the plant a new base with mp 93-95°C whose physicochemical properties and spectral data differed from quinoline bases that were previously reported and which we called gerphytine.Gerphytine (1) had formula C 16 H 15 NO 4 ([M] + 285), was soluble in CHCl 3 , poorly soluble in acetone and alcohol, and insoluble in water and base.The IR spectrum of the base exhibited absorption bands at 3139 and 3166 cm -1 due to a furan ring. Absorption bands of hydroxyl and carbonyl groups were missing.The UV spectrum showed two principal absorption maxima including a strong (short-wavelength) band at 249.64 nm (log H 4.7) and a weaker band at 318.91 nm (log H 3.8). The long-wavelength band was split into three peaks and was separated from the first maximum by a deep minimum at 278.0 nm (log H 3.00). This was characteristic of furanoquinoline alkaloids [6,7].The aromatic region of the PMR spectrum of gerphytine had two resonances for protons of a benzene ring at 7.87 and 7.11 ppm (1H each, d, J = 9.3 Hz) and resonances for protons of a furan ring at 7.48 (1H, d, J = 2.8 Hz, H-2) and 6.93 ppm (1H, d, J = 2.8, H-3) that were typical of furanoquinoline-type alkaloids.

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Griffithine, a New Furanoquinolone Alkaloid from Haplophyllum griffithianum

et al. 2015

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The new alkaloid griffithine (1) was isolated from total alkaloids from the aerial part of Haplophyllum griffithianum (Rutaceae). Spectral data established it as a furanoquinolin-4-one derivative with the structure N-methyl-7-O-(1c-dimethyl-2c,3c-dihydroxypropyl)-8-methoxyfuranoquinolin-4-one.The alkaloids dubamine, dubinine, dubinidine, dictamnine, skimmianine, N-methylhaplofoline, and gerphytine were isolated from the aerial part of Haplophyllum griffithianum Boiss. collected in Surkhandarya Province (Nilu village), Republic of Uzbekistan, during flowering [1,2]. Further separation of the total alkaloids produced a new alkaloid with mp 158-159°C that we called griffithine (1).Griffithine, C 18 H 21 NO 6 , was very soluble in MeOH and CHCl 3 , less soluble in alcohol, and insoluble in H 2 O, base, and benzine.The UV spectrum of 1 showed absorption bands at 201, 235, 259, 293, and 331 nm. The absorption maxima did not change after acidification or basicification. The IR spectrum of 1 contained absorption bands for hydroxyls (3362 cm -1 , broad), carbonyl (1623), and an aromatic ring (1591, 1538, 1518). A resonance in the 13 C NMR spectrum at 173.04 ppm corresponded to a ketone carbonyl.The structure of 1 was elucidated by analyzing PMR and 13 C NMR spectral data and results from DEPT (Table 1) and HETCOR experiments (Fig. 1).The strong-field region of the PMR spectrum showed resonances for two methyls at G 1.26 and 1.30 ppm. Resonances of CH 2 -OH and CH-OH protons geminal to hydroxyls were observed in the aliphatic region of the spectrum as three doublets of doublets at 4.31 (J = 9.8, 3.0 Hz, H-3c), 4.14 (J = 9.8, 7.4 Hz, H-3c), and 3.82 ppm (J = 7.4, 3.0 Hz, H-2c), respectively. The lack of other through-space couplings with resonances of aromatic protons indicated that a CH 2 (OH)-CH(OH) side chain was present.Resonances of aromatic H-2 and H-3 of the furan ring formed an AB-system at G 7.21 and 6.96 ppm and appeared as two doublets (J = 2.4 Hz), which were analogous to those of isofuranoquinoline alkaloids [3]. Resonances of aromatic H-5 and H-6 appeared as two doublets at 8.15 (J = 8.9 Hz) and 6.93 ppm (J = 8.9 Hz), respectively. Resonances for o-aromatic protons H-5 and H-6 indicated that the C-7 and C-8 positions were substituted.An analysis of the 13 C NMR and DEPT spectra of griffithine showed 18 resonances for C atoms as 8 quaternary, 5 methine, 1 methylene, and 4 methyl C atoms. Resonances of furan C atoms C-2 and C-3 appeared at 137.99 and 107.86 ppm; of quaternary C-2a, C-3a, C-4a, and C-8a, at 157.92, 106.04, 121.90, and 133.94 ppm, respectively. Resonances of C-5 and C-6 were observed at stronger field at 123.75 and 110.10 ppm, indicating that C-7 and C-8 were substituted. The C-4 carbonyl C atom resonated at the weakest field near 173.04 ppm. Resonances of methyl C atoms were found at 62.13 (8-OCH 3 ) and 35.77 ppm (N-CH 3 ), respectively ( Table 1). The C-8 methoxy group shifted the N-CH 3 resonance to weaker field by ~5 ppm [4].

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Alkaloids from the plant Haplophyllum griffithianum

Cited by 5 publications

References 1 publication

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review

Gerphytine, a new furanoquinoline alkaloid from Haplophyllum griffithianum

Griffithine, a New Furanoquinolone Alkaloid from Haplophyllum griffithianum

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