Alkaloids. Plants, structures, properties

Shakirov, R.; Telezhenetskaya, M. V.; Bessonova, I. A.; Aripova, S. F.; Israilov, I. A.; Sultankhodzhaev, M. N.; Виноградова, В. И.; Akhmedzhanova, V. I.; Tulyaganov, T. S.; Salimov, B. T.; Tel'nov, V. A.

doi:10.1007/bf01375127

Cited by 17 publications

(12 citation statements)

References 6 publications

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“…Column chromatography of the phenolic CHCl 3 part of the total bases isolated serotonin hydrochloride [4] and a new base with mp 193-195°C that we named schobericine (1a).…”

Section: Alkaloids From Plants Of the Genus Nitrariamentioning

confidence: 98%

Alkaloids from plants of the genus Nitraria

2006

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Acetylkomaroidine (1c). Fractions 8-15 were combined. Solvent was distilled off. The residual was crystallized from ethanol:acetone to afford 1c (34 mg), mp 229-230°C.Extraction and separation of the total bases from N. komarovii has been described in detail [8,9]. The benzene part of the total bases was separated by chromatography over a silica-gel column with elution by CHCl 3 :CH 3 OH (20:1, 10:1, 4:1). Fractions (15-20 mL) were collected.Komaroidine (1b). Fractions 14-16 were combined and separated by chromatography over a silica-gel column with elution by CHCl 3 :CH 3 OH (10:1). Fractions (8-10 mL) were collected. Fractions 17-23 were combined and worked up by crystallization from ethanol:acetone to afford 1b (56 mg), mp 207-208°C.Acetylkomaroidine (1c). Fractions 11-16 were combined and worked up by crystallization from ethanol:acetone to afford 1c (51 mg), mp 229-230°C.Hydrolysis of 1c. Komaroidine. Base 1c (0.05 g) was dissolved in HCl (5 mL, 1 N) and heated at 90°C for 2 h. After the reaction was complete, the solution was cooled, made basic with KOH solution (10%), and extracted with CHCl 3 . Solvent was distilled off. The residual was crystallized from acetone:ethanol to afford komaroidine (0.027 g), mp 207-208°C.Acetylation of Komaroidine (Acetylkomaroidine). A mixture of 1b (0.04 g), pyridine (1 mL), and acetic anhydride (1 mL) was left at room temperature for 5 d. After the reaction was complete, the excesses of anhdyride and pyridine were removed in vacuo. The dry residual was treated with water (2 mL) and made basic with conc. aqueous NH 3 . The product was extracted with ether. The ether extract was dried over anhydrous Na 2 SO 4 . Solvent was distilled off. The residual was crystallized from acetone:ethanol to afford N-acetylkomaroidine (0.031 g), mp 229-230°C.Synthesis of Komaroidine. A mixture of tryptamine hydrochloride (1 g, 0.005 mol) in water (15 mL), ethanol (25 mL), H 2 SO 4 (3 mL, 2 N), and butyraldehyde (3 mL) was gradually heated to boiling on a sand bath and held at this temperature for 5 h. The alcohol was distilled off in vacuo. The solution was made basic with conc. aqueous NH 3 . The product was extracted with CHCl 3 . The CHCl 3 was distilled off. The solid was crystallized from acetone:alcohol to afford 1b (0.91 g), mp 207-208°C.Synthesis of Schobericine. Schobericine was synthesized by condensation of serotonin and butyraldehyde by the method described above for the synthesis of komaroidine to afford 1a (0.87 g), mp 193-194°C.

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“…Column chromatography of the phenolic CHCl 3 part of the total bases isolated serotonin hydrochloride [4] and a new base with mp 193-195°C that we named schobericine (1a).…”

Section: Alkaloids From Plants Of the Genus Nitrariamentioning

confidence: 98%

Alkaloids from plants of the genus Nitraria

2006

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“…( 10 ), reported from Colchicaceae have structures not completely consistent with any of the previous groups. They are all isolated from different species of Colchicum [110, 127, 128, 129]. …”

Section: Alkaloid Diversitymentioning

confidence: 99%

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Larsson¹,

Rønsted

2013

CTMC

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The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways.

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“…By comparison of the spectral data with those reported in the literature [4], compund 1 was identified to be (-)-roemerine.…”

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Alkaloids from Stephania macrantha

Zuo

Rao

2013

Chem Nat Compd

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The genus Stephania belonging to the family Menispermaceae includes about 60 species worldwide and occurs mainly in the tropical and semitropical zones of Asia and Africa. There are about 39 species grown in China, and most of them are distributed in Yunnan and Guangxi Provinces [1]. Stephania macrantha, one of these 39 species, is an endemic species in China and is mainly distributed in the Yang-Bi District of Yunnan Province, China [2]. Large tubers of this plant have been used in traditional medicine as a substitute for Stephania epilogue, which is locally named "Shan-Wu-Gui" and is employed as an antirheumatic drugs. Phytochemical studies reveal that alkaloids are the main consitituent in S. macrantha. To date, only several alkaloids, including l-tetrahydropalmatine, isocorydine, corydine, corydalmine, stepholidine, palmatine, and laudanidine have been reported from this medicinal plant [3]. To further explore the chemical constituents of this plant, we investigated the plant, which resulted in the isolation of nine alkaloids.S. macrantha was collected from Gengma County of Yunnan, China, in October, 2005. The fresh tubers of S. macrantha (12 kg) were powdered and extracted under reflux with hot MeOH three times (30 L u 3); the extract was concentrated under vacuum to give a residue (980 g, Fr. A). The residue was extracted with 2% aq. HCl at room temperature three times (2 L u 3). The acid-soluble fraction was alkalinized to pH 9.5 with 25% aq. NH 3 , then extracted with CHCl 3 (2 L u 3) and n-BuOH (2 L u 3) in succession. The CHCl 3 and n-BuOH extracts were concentrated under vacuum to give the CHCl 3 fraction (Fr. B, 380 g) and the n-BuOH fraction (Fr. C, 74 g), respectively. Fraction B was chromatographed over silica gel eluted with petroleum ether-acetone-diethylamine (30:2:1-15:8:1) and then chromatographed on Al 2 O 3 eluted with petroleum ether-acetone (15:1-12:1) to yield compounds 4 (9 mg), 5 (28 mg), 6 (61 mg), 7 (47 mg), 3 (23 mg), 1 (13 mg), and 2 (27 mg). Fraction C (74 g) was subjected to silica gel column chromatography with an eluent of petroleum ether-acetone-diethylamine (20:1:1) and further purified by Al 2 O 3 column chromatography eluted with petroleum ether-acetone (4:1) to afford compounds 8 (14 mg) and 9 (8 mg).Based on the spectral data, including PMR and 13 C NMR, compounds 1-9 were determined to be (-)-roemerine (1), (-)-crebanine (2), isocorydine (3), sinomenine (4), cephamonine (5), tetrahydrocolumbamine (6), tetrahydropalmatine (7), jatrorrhizine (8), and palmatine (9).

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Alkaloids. Plants, structures, properties

Cited by 17 publications

References 6 publications

Alkaloids from plants of the genus Nitraria

Alkaloids from plants of the genus Nitraria

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Alkaloids from Stephania macrantha

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