Two New Morphinane Alkaloids from Stephania cepharantha Hayata(Menispermaceae).

Kashiwaba, Noriaki; Morooka, Shigeo; Kimura, Michiko; Murakoshi, Y.; Toda, Jun; Sano, Takehiro

doi:10.1248/cpb.42.2452

Cited by 23 publications

(15 citation statements)

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“…Stephaoxocanine, stephaoxocanidine, romorphinane, cepharanthine, cepharanoline, steponine, isotetrandrine, berbamine, stecepharine, dehydroreticuline (11), magnoflorine, menisperine, oblongine, cyclanoline, cis-N-methylcapaurine, sinomenine, cephamerphinanine, D-glucopyranoside, 2 -N-methylisotetrandrine, N-methyl stesakine chloride (12), stesakine 9-O-␤-Dglucoside (13), N-methylasimilobine-2-O-␤-D-glucopyranoside (14), cephamonine, aromoline, zippelianine, cepharamine, aknadinine (15), aknadicine (16), cephatonine, (−)-cycleanine (28), obamegine, berbamine, isocorydine, anolobine, cotypalline, stepharine (9), (+)-reticuline (17), obaberine, homoaromoline, fangchinoline, tetrandrine (18), cephamuline Nakamura et al, 1992;Sugimoto et al, 1993Sugimoto et al, , 1988Kashiwaba et al, 1996Kashiwaba et al, , 1997Kashiwaba et al, , 2000Kashiwaba et al, , 1998Kashiwaba et al, , 1994Nakaoji et al, 1997;Tanahashi et al, 2000), berbamine and aromorine (Akasu et al, 1976).…”

Section: Stephania Cepharantha Hayatamentioning

confidence: 99%

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

Semwal¹,

Badoni

Semwal

et al. 2010

Journal of Ethnopharmacology

134

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Section: Stephania Cepharantha Hayatamentioning

confidence: 99%

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

Semwal¹,

Badoni

Semwal

et al. 2010

Journal of Ethnopharmacology

134

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“…By comparison of the spectral data with those reported in the literature [7], compound 5 was identified as cephamonine.…”

mentioning

confidence: 71%

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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“…2) displayed cross-peaks of H-14/H5a, H-14/H-15a, H-5b/H-15b, which indicated that H-14 and the N-containing ring of subunit 'a' were on the same side, having an a-orientation. 11 The ROESY correlations of H-12 0 /H-7 0 b and H-8 0 /H-7 0 a, were used to fix the spatial disposition of the two nonequivalent sides of the cyclohexadienone ring. The additional ROESY correlation of H-6 0 a/H-12 0 indicated that H-6 0 a and H-12 0 were a syn-periplanar relationship and H-6 0 a was the b-orientation.…”

Section: Resultsmentioning

confidence: 99%

New alkaloids sinomacutines A–E, and cephalonine-2-O-β-d-glucopyranoside from rhizomes of Sinomenium acutum

et al. 2014

Tetrahedron

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Two New Morphinane Alkaloids from Stephania cepharantha Hayata(Menispermaceae).

Cited by 23 publications

References 0 publications

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

Alkaloids from Stephania macrantha

New alkaloids sinomacutines A–E, and cephalonine-2-O-β-d-glucopyranoside from rhizomes of Sinomenium acutum

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