Biocatalyzed Cross-Coupling of Sinomenine and Guaiacol by <i>Antrodiella semisupina</i>

Deng, Zhangshuang; Li, Jianxin; Teng, P. K.; Sun, Xiaoru

doi:10.1021/ol800024u

Cited by 23 publications

(15 citation statements)

References 24 publications

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“…Each molecule of disinomenine is bonded to four crystal water molecules. Here, it crystallized as the tetrahydrate from methanol, while the monohydrate, crystallized from chloroform/methanol/ethyl acetate (80: 15:5), has been reported earlier [14]. It is likely that water more easily permeates into the polar solvent of methanol than in the non-polar solvent of chloroform/methanol/ethyl acetate (80:15:5); as the result, the permeated water molecules can strengthen interaction of disinomenine and crystal water by more intermolecular hydrogen bonds.…”

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confidence: 76%

Crystal structure of 1,1′-disinomenine tetrahydrate, C38H44N2O8 · 4H2O

Wang¹,

Liu²

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialSinomenine is the main pharmacologically active alkaloid in the traditional Chinese plant medicine of Sinomenium acutum.Itwas produced from the powder of the plant roots by the BaojiYongjia Plant Medicine Extracting Limited Company, Baoji, P. R. China, under the patent technology [1], and crystallized from the concentratedb enzene extract of thep owder. Ther emaining sticky mother liquor (3 kg) after the extraction of sinomenine was obtained from the company. Thesticky residue was fractionated by columnchromatography on silica gel (100 mesh) eluted gradually with chloroform to chloroform/methanol (30:1; 10:1 and 4:1) to afford 7fractions, QT1 to QT7.The QT4 (5.5 g) was subjected to columnchromatography on silica gel (300-400 mesh) eluted with chloroform/methanol (20:1 to 5:1) to give 7s ubfractions, QT4-1 to QT4-7. The QT4-6 was crystallized repeatedly from methanol to yield the colorless crystals of the title compound (25 mg) suitable for single crystal X-ray diffraction analysis at room temperature. Experimental detailsOnly theeight Hatoms from four crystalwater molecules have been refined; they were determined from Fouriermap.All other Hatoms attached to Catoms and Oatoms of the title compound molecule were calculated by theoretical method and were not refined. The Flack parameter was 0(10). Discussion S. acutum is distributed mainly in hilly regions of southwest, northwest and southeast China. The dried stemsand roots of the planta re at raditional Chinesem edicine to cure rheumatism, arthralgia,dropsyand dermatophytosisrecordedinthe Chinese Pharmacopoeia [2]. The plant is ar ich source of alkaloids of bisbenzylisoquinoline, aporphine, isoaporphine, protoberberine and morphinane types. The diversity of the alkaloids and activities of this medicinal plant motivated our research work, we have studied the remaining mother benzene liquor of roots of S. acutum and obtained nearly 20 alkaloidal compounds, including the title compound. We once obtained them as the amorphous powder from thestems of thesameplant [3]. We have already reported thei solation andc rystal structureso fc heilanthifoline [ 4], 8-oxotetrahydropalmatine [5], tetrahydroepiberberine [6],8 -oxocanadine [7], sinoacutine [8], 8-demethoxyrunanine [9,10], sinoracutine [11,12], N-formylanonaine [13] and two new morphinane alkaloid dimers [3]. The title compound disinomenine tetrahydrate is ad imer of sinomenine, in which the two monomers are interconnected at C1 position. The two benzene rings from each monomer are perpendicular to each other in order to decrease the steric hindrance. Each monomer is composed of rings A, B, Cand D. The two methoxy groups at each C3 are basically coplanar to their attached benzene rings A, the rings Band Cadopt half-chair conformations whereas the rings Dadopt chair conformations. Z. Kristallogr. NCS 227 (2012) 93-95

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confidence: 76%

Crystal structure of 1,1′-disinomenine tetrahydrate, C38H44N2O8 · 4H2O

Wang¹,

Liu²

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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“…In particular, previous studies on S. acutum have led to the isolation of a series of unique dimers of sinomenine analogues, which have significant effects on synthesis and biological evaluation. 6,7 Our current phytochemical investigation on S. acutum lead to the isolation of six new alkaloids, sallisonines AeE (1e5), and cephatonine-2-O-b-D-glucopyranoside (6), along with three known ones, sinomenine (7), 8 sinoacutine (8), 9 and (À)-N-methylcoclaurine (9). 10 We herein report the isolation, structural elucidation, anti-inflammatory, and cytotoxic biological evaluation of the new isolates.…”

Section: Introductionmentioning

confidence: 95%

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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“…Previous studies of genus Antrodiella manily focused on taxonomy [1,2], biodegradation [3,4] and biotransformation [5]. However, few researches were carried on the investigation of secondary metabolites from cultural broth or fruiting bodies of this genus.…”

Section: Introductionmentioning

confidence: 99%

A new bisabolane-type sesquiterpenoid from the fermentation broth of fungus Antrodiella gypsea

Zhao

Chen

et al. 2015

Journal of Asian Natural Products Research

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Studies of the fermentation broth of fungus Antrodiella gypsea led to the isolation of a new bisabolane-type sesquiterpenoid that was named gypseatriol (1), together with the known compound 2,10-dodecadiene-1,6,7-triol (2). The structure of this new metabolite was assigned by analysis of 2D NMR and HR-EI-MS. Absolute configuration was assigned by single crystal X-ray diffraction analysis. Compound 1 was evaluated for its antifungal activity on Candida albicans.

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Biocatalyzed Cross-Coupling of Sinomenine and Guaiacol by Antrodiella semisupina

Cited by 23 publications

References 24 publications

Crystal structure of 1,1′-disinomenine tetrahydrate, C38H44N2O8 · 4H2O

Crystal structure of 1,1′-disinomenine tetrahydrate, C38H44N2O8 · 4H2O

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

A new bisabolane-type sesquiterpenoid from the fermentation broth of fungus Antrodiella gypsea

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