Holarrhena antidysenterica alkaloids

The stem bark of Holarrhena antidysenterica Wall. (Apocynaceae) yielded the known steroidal alkaloids holarrhimine, isoconessimine, and conimine (108). Leaves of Holarrhena curtisii King et Gamble yielded the known as well as new aminoglycosteroidal alkaloids holacurtine (102) and N-demethylholacurtine (103), respectively (109). 

Carbon source was found to be a significant factor in plant cell metabolism [34 - 39], which affected the accumulation of alkaloids by suspension cultures of Holarrhena antidysenterica [36], of anthocyanins by Vitis vinifera cell suspen-... 

Nitrogen source is also very important for plant cell metabolite formation, as reported in suspension cultures of Holarrhena antidysenterica for accumulation of alkaloids [36], in cell suspensions of Vitis vinifera for anthocyanin formation [37], and in shikonin production by Lithospermum erythrorhizon cell cultures [38]. 

A new alkaloid, holacetine (la), has been isolated in 0.04% yield from the root bark of Holarrhena antidysenterica, together with the known component cones-sine.1 Acetylation of holacetine gave an O-acetyl derivative (lb), vigorous acid-catalysed hydrolysis of which yielded the (20S)-20-amino-pregnane (lc). The identity of the latter, and hence of holacetine, was established by its conversion via standard methods into the known alkaloid funtumafrine C (2), and by its preparation from (20S)-3/3-hydroxypregn-5-ene-20-carboxylic acid.1 Conessine has been identified in tissue cultures of H. antidysenterica.2... 

An alkaloid obtained from the seeds of Holarrhena antidysenterica (Apocynaceae). 

Note added in proof The structures of neoconessine 240), epipachysandrine-A 241), several new alkaloids from Buxus microphylla 242), and of artifacts arising on methy-lation of the alkaloids from Holarrhena antidysenterica 24 ) have been established. The reactions of Eschweiler methylation productsof 16 S aininoparava]larine derivatives have been studied 244). 

In a study of toxicity of Sri Lankan traditional medicinal herbs, Arseculer-atne and co-workers evaluated 125 commonly used medicinal plants for the occurrence of hepatotoxic pyrrolizidine alkaloids (129,130). Crotolaria juncea, C. verrucosa, and Holarrhena antidysenterica were shown to contain pyrrolizidine alkaloids by TLC. When fed to rats, these plants produced hepatic lesions compatible with the action of pyrrolizidine alkaloids. 

Heble et al. (803) fed cholesterol to Holarrhena antidysenterica callus cultures. This sterol was among others incorporated into the alkaloid conessine. Ccdlus cultures of Holarrhena floribunda were reported to produce small amounts of conessine as well as some unidentified alkaloids (total alkaloids were 0.001% of the fresh weight) 894). 

Jokela and Lounasmaa presented and C-NMR exact spectral data for seven types of ajmaline-type alkaloids from various species of the Dogbane family. These alkaloids are as follows ajmaline, 17-O-acetylajmaline, iso-ajmaline, isosandwichine, rauflorine, vincamajine, and vincamedine. Four steroidal alkaloids (conessine, holadysenterine, isoconessimine, and kurchessine) were found in the stem bark of Holarrhena antidysenterica Eleven indole alkaloids were isolated from the stem bark of Kopsia hainanensis Tsiang, which is a species of Kopsia, endemic in China. They are (—)-kopsinine, (—)-kopsinnic acid, (—)-kopsinoline, kopsinilam, kopsanome, (-h)-5,22-dioxokopsane, ebumamenine, (-i-)-ebumamine, (—)-isoebumamine, (-i-)-tubotaiwine, and (-i-)-kopsoffine. Moreover, from... 

Holarrhena antidysenterica (Apocynaceae), an Indian plant, is used for treatment of dysentery. The steroidal alkaloid conessine (101) was the main antiamebic constituent (Bonis and Schaeffer, 1992). The same compound occurs in Wrightia tomentosa. Another Indian plant, Chonemorpha fragrans (Apocynaceae), afforded the alkaloid chonemor-phine (102) which had an MIC of 25 p.g/ml in vitro (Bonis and Schaeffer, 1992). 

The extracts of the plants of the genus Holarrhena have been used in the Ayurvedic medicine for over 1500 years in the Indian subcontinent for the treatment of parasitic infections. An important plant of this class is H. antidysenterica, whose bark has been used to treat amoebic dysentery in man. The extract of the bark of this plant, called kurchi, conessi or telicherry bark, contains several alkaloids of which the major one is conessine (8) [32,33]. This alkaloid has been used in the treatment of intestinal and extraintestinal amoebiasis in humans [34,35]. However, neither conessine nor its structural analogues find use in the modern therapy of human amoebiasis [36]. 

In 1858 Haines 1 isolated from the bark of Holarrhena (Wrightia) antidysenterica Wall., known in India as kurchi, the alkaloid conessine. It was prepared from the seeds of the same plant by Stenhouse, who named it wrightine, and by Warnecke, in a crystalline condition from the same source. It was also obtained by Polstorlf and Schirmer from the African species H. africana D.C., by Pyman from H. congolensis Stapf., together with a second alkaloid, holarrhenine, by Henry and Brown from H. Wulfsbergii, and by Siddiqui et from H. febrifuga Klotsch. 

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