153. The alkaloids of Gelsemium sempervirens. Part I

Forsyth, W. G. C.; Marrian, S. F.; Stevens, T. S.

doi:10.1039/jr9450000579

Cited by 8 publications

(4 citation statements)

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“…I t melted a t 136-13g0, which was 32-35" lower than the reported melting point of gelsemicine and had [aID -150°, a value intermediate between the two figures previously reported (3,4,5). Fractional crystallization dicl not yield any higher melting crop, although some fractioils contained two distinct forms of crystals, i.e., large stout rhombs and elongated rhombs.…”

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confidence: 44%

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THREE MINOR ALKALOIDS OF GELSEMIUMSEMPERVIRENS AIT.

Schwarz¹,

Marion²

1953

Can. J. Chem.

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After the removal of gelsemine and sempervirine from the extract of the root of Gelsemizirn se7nperuirens Ait. the residual alkaloids left in the mother liq~lors were berizoylated. I t was thus possible to separate the tertiary bases from the secondary bases which were obtained as a rnixture of the neutral benzoyl derivatives. Puritication by chromatography yielded the benzoylated mixture in crystalli~ie form. This was hydrolyzed and the recovered secondary bases were separated by fractional crystallization of the perchlorates into alkaloid A and alkaloid B.Allcaloid A was shown by direct conlparison to be identical with the gelsemicinr

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“…227". I t is inert towards the usual carbony1 reagents (4). Raymond-Hamet (7) colnpared the ~~ltraviolet absorption spectrum of C~O L I ' S gelsemicine with the spectra of other alltaloids and concluded that gelsemicine contained an indole nucleus.…”

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THREE MINOR ALKALOIDS OF GELSEMIUMSEMPERVIRENS AIT.

Schwarz¹,

Marion²

1953

Can. J. Chem.

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“…Although the structural relationship to maremycins is not close, spiro-indole compounds have previously been reported as metabolites of plants and microorganisms. In gelsemine (8), [8] the spiro ring is constructed between an indole (C-3) and an isoindole moiety (C-7Ј) (Scheme 2). This metabolite, isolated from Gelsem-Scheme 2.…”

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confidence: 99%

Maremycins C and D, New Diketopiperazines, and Maremycins E and F, Novel Polycyclicspiro-Indole Metabolites Isolated fromStreptomycessp.

et al. 2001

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New diketopiperazines, named maremycins C 1 /C 2 (1a/1b) and D 1 /D 2 (2a/2b), as well as the novel spiro-indoles, maremycins E (3) and F (4), have been detected alongside the known maremycin B (6) in the culture broth of Streptomyces sp. (strain GT 051237) by chemical screening. The structures have been determined by detailed NMR spectroscopic investigations of the isolated metabolites. Maremycins C 1 /C 2 (1a/1b) as well as D 1 /D 2 (2a/2b) are diastereomers and were [a] Hans-Knöll-Institut für Naturstoff-Forschung e.V.,

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“…It was clain~ecl by filoore (7) that gelsemine contai~lecl a free h3 clrox>.l group \\rhich could l ~e acet).latecl with acetic anhydride. Howc\rer, all attempts to prepare 0-acet>lgelsernine have failed in our hands, and other in\-estigators (2,3) ha\-e been s i ~n ~l a r l y unsuccessful. Incleecl, Moore's claim is untenal~le in view of the facts that gelsenline contains onll.…”

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Gelsemine: Iii. Reduction With Lithium Aluminum Hydride

Kates¹,

Marion²

1951

Rev. can. chim.

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The infrarecl alrsorptinr~ spectrum of gelsemine inclicatcs the prcscncc o l a carbon)-l group. Recluction cf the alkaloid with lithiurn alurl~inuun hyclr-itlc converts the carbonyl no1 ra a r;ccontlar). alcohol, but to a 1uet11)-lene group, thus indicating hat thc carOo~l!-l is present irr a lactan~ic grouping. Ttlc I-ctl~~cetl base shoxvs thc properrics oi a s~ibstituted aniline. Since geiscnlinc has been s h o n r ~ to yielcl 3-erhylinclolc un clel~ytlrogenation with seleni~rnl ant1 since the N-atom involvctl in the l a c ~a r l ~i c group capnot be the strongly basic nitrogen, gclsen~ine ni~rst contain ;In nxinclole grouping. Furthern~ore, 3 -~n d n o s ~r h s t i t ~e c i orindoles are cor~vertctl by l i i h i ~r o ~ ~I U ~I I ~~L I I I I hyclride to 3 -s ~r b s t i ~u ~c d incloles, wl~ereas gelscrnine ~~n c l c r the same co~lclitions gives rise to a dihyclrointlole.'l'herefore, the alkaloitl m u s t contain a 3, 3-clisubstitutetl oxindolc grouping.

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153. The alkaloids of Gelsemium sempervirens. Part I

Cited by 8 publications

References 0 publications

THREE MINOR ALKALOIDS OF GELSEMIUMSEMPERVIRENS AIT.

THREE MINOR ALKALOIDS OF GELSEMIUMSEMPERVIRENS AIT.

Maremycins C and D, New Diketopiperazines, and Maremycins E and F, Novel Polycyclicspiro-Indole Metabolites Isolated fromStreptomycessp.

Gelsemine: Iii. Reduction With Lithium Aluminum Hydride

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