Stephania

Stephania cepharantha Hayata (Jap. name tamasaki-tsuzurafuji. ... 

Stephania japonica Miers. From the stems of this species, long used as a febrifuge in Japan, Kondo and Sanada have isolated eight alkaloids ... 

In the course of studies directed towards the structure elucidation of Rotundine from Stephania rotunda LOUREIO, the /3-piperidone 28, which is available starting from the keto ester 27, was treated with mercuric acetate in 10% acetic acid solution. Basification yields the betaine 29 as colorless prisms (Scheme 12). 

Bio-assay guided fractionation of the methanolic extract of the African climbing shrub Stephania dinklagei contains six bioactive alkaloids, among... 

Wu S et al. (2001) Cardiac effects of the extract and active components of Radix stephaniae tetrandrae. I. Electrically induced intracellular calcium transient and protein release during the calcium paradox. Life Sci 68(25) 2853-2861... 

Rubiandin-1-methyl ether Stephania verosa Murraya simensis SiOj T + AcOEt... 

Stephania abyssinica Walp. Metaphanine C19H23NOs(345) 233 -21° (CHC13) 14... 

Stephania cephalanta Hayata Cepharamine C19H23N04 (329) 186-187 -248° (CHC13) 39... 

Stephania delavayi Diels Delavaine C20H23NO5 (357) 140-150 -240° (CHClj) 40... 

Stephania hernandifolia Walp. Aknadicine C19H23NOs (345) 156 -200° (EtOH) 23-25... 

Stephania japonica Miers Metaphanine Ci9H23NOs (345) 232 -41°(CHC13) 15... 

During a search for physiologically active compounds in South African plants, a new hasubanan ester acetal alkaloid, methylstephavanine (6), was isolated from Stephania abyssinica (19). The H-NMR spectrum of the new alkaloid 6 exhibited signals for one methylenedioxy, one N-methyl, and four methoxyl groups (19) (Table II). Its mass spectrum revealed the most abundant ion peak at m/z 229, indicating a close resemblance to the known hasubanan alkaloid, stephavanine (18). 

Dihydroepistephamiersine 6-acetate (7) was isolated from Stephania abyssinica as a homogeneous oil. The UV spectrum showed an absorption maximum at 286 nm, and the IR spectrum exhibited a band corresponding to an aliphatic ester carbonyl group at 1725 cm-1 (20). The H-NMR data are summarized in Table II. In chemical investigations, hydrolysis of 7 with barium methoxide gave an alcohol identical with 6-dihydroepistephamiersine (17), which on further treatment with mineral acid gave the known alkaloid, stephasunoline (17). Thus structure 7 was proposed for 6-dihydroepistephamiersine 6-acetate (20). 

Longaninine (11) was isolated from the roots and stems of Stephania longa collected in Hainan Island, China (29-31). This alkaloid was once named longanine, but the name was soon changed to longaninine to avoid confusion... 

Oxostephasunoline (4) was isolated from the roots of Stephania japonica(4). The UV spectrum of oxostephasunoline (4) showed an absorption maximum at 286 nm, and the IR spectrum depicted bands at 3550,3500, and 1670 cm, indicating the presence of a hydroxyl group and a y-lactam. The mass spectrum (Table VI) exhibited the most abundant ion peak at m/z 258, and the H-NMR spectrum (Table II) revealed the presence of three methoxyl and one N-methyl group. The downfield shift (53.06) of the JV-methyl resonance indicated that oxostephasunoline (4) was a y-lactam, which was further supported by the IR band at 1670 cm 1, significant features of the mass spectrum (Table VI), and the 13C-NMR spectrum (Table III). On exhaustive H-NMR analysis similar to the case of stephasunoline (17), the structure of oxostephasunoline (4) including the stereochemistry was practically proved (4). 

Oxostephabenine (15) was isolated from the fruits of Stephania japonica (7). The UV spectrum of 15 showed absorption maxima at 294 and 230 nm, and the IR spectrum depicted bands at 1700, 1680, and 1600 cm-1. Its mass spectrum revealed a molecular ion peak at m/z 493 (17%), the most abundant ion peak at m/z 241 (C14HuN03), and another significant ion peak at m/z 242 (60%, C14H12N03). The H-NMR (Table II) and 13C-NMR (Table III) spectra exhibited close similarity to those of stephabenine (13) (10) except for W-methyl resonance (7). 

Stephadiamine (16) was isolated as a minor component from the ethanolic extract of the whole plant of Stephania japonica collected in Taiwan (6). The IR spectrum of stephadiamine (16) exhibited bands at 3375 (NH2) and 1720 cm 1 (5-lactone), and the H-NMR spectrum (Table II) showed the presence of one JV-methyl and two methoxyl groups. Its mass spectrum revealed a base ion peak at m/z 243 of stephamiersine-type cleavage (Table V) (6). 

Runanine (17) was isolated from the roots of Stephania sinica, a species found in the Chinese provinces of Heibei, Gueizhou, and Yunnan (35). The H-NMR spectrum of runanine (17) (Table II) revealed the presence of two aromatic protons, C-5 methylene protons, one N-methyl, and four methoxyl groups. An NOE effect (10% enhancement) was observed between the protons of two methoxyl groups (53.79 and 3.80) and the aromatic protons (56.47 and 6.64), but the same phenomenon was not observed for the other methoxyl protons (53.61 and 4.05). Therefore, the former methoxyls should be situated on ring A. From the further observation of an NOE (22.6% enhancement) between the aromatic C-4 proton (56.64) and one (53.00) of the C-5 methylene protons, it was assumed that the two methoxyl groups (53.79 and 3.80) should be located at C-2 and C-3, respectively. The absence of signals for olefinic... 

During the period 1976-1986, biosynthetic studies on hasubanan alkaloids were carried out by Battersby et al. (81-84) for hasubanonine (5) together with protostephanine (57). The two alkaloids, isolated from Stephania japonica, arise from the same precursor, and their unusual structures are of biosynthetic interest, namely, the vicinally trioxygenated ring C in 5 and the unique natural example of a dibenz d,f ] azonine skeleton in 57. 

Degradation of 5 and 57 revealed that both skeletons are built from two C6-C2 units derivable from tyrosine (81,82). Many 14C-labeled isoquinolines, which on biogenetic grounds could be possible late precursors of both alkaloids, were prepared and fed to Stephania japonica plants, after which the labeled alkaloids were isolated. Isoquinolines 59-64, lacking the... 

Fangchinoline (40), a 4> 5-benzylisoquinoline alkaloid isolated from Stephania tetrandra S. Moore (family Menispermaceae), was evaluated to possess significant antihyperglycemic activity studied in streptozotocin (STZ)-induced diabetic ddY mice in a dose-dependent manner the drug reduced the blood glucose level of diabetic mice by 52.7 6.7% when administered in 14 h-fasted diabetic mice at a dose of 1 mg/kg. Blood... 

Tsutsumi T, Kobayashi S, Liu YY, Kontani H. (2003) Anti-hyperglycemic effect of fangchinoline isolated from Stephania tetrandra radix in strepto-zotocin-diabetic mice. Biol Pharm Bull 26 313-317. 

Stephania dinklagei A-methyllirio dendronine 2-O-A-dimethyl liriodendronine Dicentrinone Cory dine Aloe-emodin... 

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