Five novel phenanthroindolizidine alkaloids, namely tylohirsutinine, 13a-methyltylohirsutine, 13a-methyltylohirsutinidine, tylohirsutinidine and 13a-hydroxysepticine, isolated from Tylophora hirsuta together with two unidentified bases are described. Structural studies indicate that the first four alkaloids possess the dibenzo [f, h]-pyrrolo-[1,2b]isoquinoline skeleton present in other Tylophora species, but differ in the presence of unsaturation in ring E or in the presence of an angular methyl function. The fifth alkaloid has been shown to be the 13a-hydroxy analogue of septicine.
Various alkaloids from Adhatoda vasica (Acanthaceae) were found to be responsible for the antifertility and antifeedant activity of the extracts of the plant against insects. Among the major alkaloids vasicine, vasicinol and vasicinone severe antifertility effects were exhibited by vasicinol against Dysdercus koenigii and Tribolium castaneum due to blocking of oocytes in the oviduct. Feeding deterrence was observed against Aulacophora foveicollis and Epilachna vijintioctopunctata at 0.05 and 0.1% levels of these compounds. These allelochemics appear to show a dual activity vis-à-vis a species specificity.
A diterpene lactone was isolated from the cold petrol (60−80°) extract of rhizomes of Euphorbia acaulis, a plant material used by a tribe of central India for curing various inflammatory disorder. The diterpene, which was observed to be identical to caudicifolin on the basis of its physical constants, was subjected to high resolution NMR spectroscopy and X-ray crystallography examination. This paper reports the salient features of the 2D 1H NMR, 13C NMR and X-ray crystallography data of the compound. 13C NMR assignments were made by the use of proton noise decoupling, SFORD, APT and automatic spectral editing techniques. 1H NMR assignments were made with the aid of a COSY experiment for long range couplings and NOE correlated 2D-experiments. The 1H and 13C NMR spectral assignments have been further corroborated by H/C correlation experimental results.
A new sapogenin 14beta, 26-epoxy serratane-3beta, 21alpha-diol has been isolated and characterized in addition to glucose, galactose and rhamnose from PRIMULA ROSEA.
AbstractDie Bromierung der Pyrido‐pyrimidinone (I) mit NBS (II) führt zu den Kernbromierungsprodukten (I11a)‐(1llc) und (IVa).
13a-hydroxytylophorine isolated from Tylophora hirsuta on heating with concentrated hydrochloric acid gave a quaternized salt which was reduced with sodium borohydride to (+)-tylophorine. An amine and a ketoamine having a seco[10–13a] bond were formed after lithium aluminium hydride reduction and chromium trioxide oxidation, respectively.
AbstractDie Alkylierung von 2‐Mercaptobenzimidazol (Ia) F′‐ (Ib) zu den isomeren Disubstitutionsprodukten (II) und (III) wird untersucht.
Two new unsymmetric tetracyclic triterpenoids onocer-7-ene-3α,21β-diol and onocer-7-ene-3β,21α-diol together with sitosterol, δ-amyrin and δ-amyrone have been isolated from Cissus quadrangularis. The structures of the new compounds were elucidated on the basis of 1H NMR, mass spectral and chemical evidence.
Epiafzelechin 5-glucoside was characterized from the bark of Crataeva religiosa together with other known compounds.
AbstractAus dem Pyrrolizidin (Ia) wird durch Ozonolyse das Keton (Ib) hergestellt, das als Pikrat isoliert und in die Derivate (IIIa)‐(IIId) übergeführt wird.
The hexane extract of dried root bark of M. champaca, on chromatography over silica gel, afforded four sesquiterpene lactones identified as costunolide, parthenolide, dihydroparthenolide and micheliolide (3) with the help of spectral studies. The structure (1) for micheliolide was further confirmed by its partial synthesis from parthenolide which on BF3-etherate treatment at —10° C for 24 h afforded a mixture which on chromatography over a silica gel column gave a major product (35 %) identified as micheliolide. Three more new compounds present in traceable amounts were also isolated and characterised as:
Three new bridged 14β,26-epoxy-C-homo-pentacyclic triterpenes isolated from Primula rosea have been shown to be 14β,26-epoxy-serratane-3,21-dione, 21α-hydroxy-14β,26-epoxy-serratane-3-one and 21β-hydroxy-14β,26-epoxy-serratane-3-one, respectively, on the basis of 1 H NMR, 13 C NMR and mass spectral and chemical evidence.
Embelin, a p-quinone, is derived from Embelia ribes Burm. The analgesic effect of potassium embelate has been studied in rats and mice. The test drug was found to be effective by oral, i.m. and i.c.v. routes and the results compared well with morphine. Although potassium embelate acts centrally to produce analgesia, its effect is not antagonized by naloxone indicating a different central site of action. There is no precipitation of abstinence syndrome as observed with morphine. Peripheral site of action of the drug is ruled out as it lacks any demonstrable anti-inflammatory action. It can be concluded that high oral efficacy and non-narcotic properties of the test drug make it more acceptable than morphine. In addition, lack of any adverse effects, high therapeutic index and absence of abstinence syndrome confers a long term safety on potassium embelate for use as an analgesic.
Further chromatography of an ethanolic extract of Vitex negundo resulted in the isolation of another new iridoid glucoside which was characterized as 6′- p -hydroxybenzoylmussaenosidic acid.
Three new isoflavone glycosides have been characterized from the leave of Juniperus macropoda: 5,7-dihydroxy-6,3′,4′-trimethoxyisoflavone 7-glucoside; 5,7,4′-trihydroxy-6,3′,5′-trimethoxyisoflavone 7-glucoside and 5,7,3′-trihydroxy-6,4′-dimethoxyisoflavone 7-diglucoside.
Further chromatography of an ethanolic extract of Vitex negundo resulted in the isolation of another new iridoid glucoside which was characterized as 6′-p-hydroxybenzoylmussaenosidic acid.