Carbon-13 nuclear magnetic resonance spectral analysis of cycloartanol and related compounds

Khuong-Huu, Françoise; Sangare, M.; Chari, V. M.; Bekaert, A.; Devys, Michel; Barbier, Michel; Lukacs, Gabor

doi:10.1016/s0040-4039(00)75256-7

Cited by 64 publications

(25 citation statements)

References 9 publications

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“…Its physical data were found to be identical with that of cyclolaudanol which is the corresponding reduction product of cyclolaudenol reported from the alkaloid-free fraction of opium by Spring et al [8]. The melting point and optical rotation of cyclotirucananyl acetate agree with those reported for cyclolaudanyl acetate [8], Moreover, in the 13 C NMR spectrum of 1 the chemical shifts of the nucleus carbon atoms showed close agreement with the published spectrum of cyclolaudenol [9] but differed in the chemical shifts of the side chain carbon atoms. In view of these findings it may be concluded that 1 has the same basic skeleton and stereochemistry as cyclolaudenol, the former differing from the latter in having different position of double bond.…”

Section: Resultssupporting

confidence: 85%

The Structure and Absolute Configuration of Cyclotirucanenol, a New Triterpene from Euphorbia tirucalli Linn

Khan

Ahmed

Kazmi

et al. 1988

Zeitschrift Für Naturforschung B

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Section: Resultssupporting

confidence: 85%

The Structure and Absolute Configuration of Cyclotirucanenol, a New Triterpene from Euphorbia tirucalli Linn

Khan

Ahmed

Kazmi

et al. 1988

Zeitschrift Für Naturforschung B

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“…Their structures were elucidated by extensive 1D and 2D NMR spectroscopy and confirmed by comparison of their 13 C NMR data with those for cycloeucalenol [15], cycloartanol [16], lupeol [17], lupeol acetate [18], and betulin [19].…”

Section: Resultsmentioning

confidence: 98%

Hypoglycemic Potential of Triterpenes from Alstonia scholaris

et al. 2015

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A dichloromethane extract of air-dry leaves of Alstonia scholaris (L.) R. Br. contains a mixture of cycloeucalenol (1a), cycloartanol (1b) and lupeol (1c); lupeol acetate (2); and betulin (3). The structures of these triterpenes were elucidated by extensive 1D and 2D NMR spectroscopy and confirmed by comparison of their 13 C NMR data to those reported in the literature. A previous study reported that the powdered leaves of Alstonia scholaris produced a highly significant decrease in blood glucose and a mechanism of this action was upon insulin triggering and direct insulin-like effects. Betulin and lupeol acetate were reported to exhibit hypoglycemic activity. Thus, only a mixture of 1a -1c was tested for hypoglycemic potential using the oral glucose tolerance test (OGTT). A possible hypoglycemic activity was observed for a mixture of 1a -1c at a dose of 25 mg/kg BW administered orally to normoglycemic mice.

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“…The 13 C NMR spectrum (Table 2) (br s, 3H-11'), 2.28 (br t, 7.0, 2H-7'), and corroborated by the HMBC correlation between the methyl and methylene protons with the olefinic carbons at d C 132.7 (C-9') and 121.7 (C-8'). This was supported by the mass spectrum which showed fragment at m/z 211 [C 18 C signals for C-3' (d C 51.6) and C-5' (d C 71.5). As for compound 1, the relative stereochemistry of 2 was deduced from gNOESY experiments.…”

Section: Resultsmentioning

confidence: 68%

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

Rosas¹,

Veiga²,

Fernandes³

et al. 2011

J. Braz. Chem. Soc.

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O extrato diclorometano do caule de Raputia praetermissa levou ao isolamento de quatro compostos novos, 4-desóxi-raputindol C (1), raputimonoindol A-B (2, 3) e hexadecanil 2-hidróxi-4-metóxi-cinnamato (5), juntamente com os alcalóides 5-(4-metóxi-metilfuran-2-il)-1H-indol (raputimonoindol C), furoquinolinos maculosidine, robustine, evolitrine e dictamnine. O estudo do extrato hexano levou ao isolamento de N-metil-4-metóxi-quinolin-2(1H)-ona, skimmianina, cicloartenona, sitosterol, stigmasterol e sitostenona. Os alcalóides antranílicos isolados indicam que o gênero possui afinidade química relevante com aqueles da tribo Cusparieae, mas difere de Neoraputia devido à ausência de alcalóides prenilindois neste último, cujas espécies foram anteriormente incluídas em Raputia.The dichloromethane extract from the stems of Raputia praetermissa afforded four new compounds, 4-deoxyraputindole C (1), raputimonoindole A-B (2, 3), and hexadecanyl 2-hydroxy-4-methoxy-cinnamate (5), besides the alkaloids 5-(4-methoxymethylfuran-2-yl)-1H-indole (raputimonoindole C), furoquinolines maculosidine, robustine, evolitrine and dictamnine. The hexane extract yielded N-methyl-4-methoxyquinolin-2(1H)-one, skimmianine, cycloartenone, sitosterol, stigmasterol and sitostenone. The anthranilate alkaloid content indicates that the genus is strongly related to those included in Cusparieae tribe, but differs from Neoraputia by the absence of prenylindole alkaloids in the late, whose species have previously been placed in Raputia. Previous investigations of Neoraputia reported the presence of eleven polymethoxylated flavonoids, six flavones, three 5,6-(2",2"-dimethylpyrano)flavones, one 6,7-(2",2"-dimethylpyrano)flavone and one flavanone from N. alba (Engler) Emmerich; 6,7 five polymethoxylated flavones and two flavanones, 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone, three 5',6'-(2",2"-dimethylpyrano)-polymethoxylated chalcones from N. magnifica var. magnifica (Engler) Emmerich; 8,9 ten polymethoxylated flavonoids, six flavones, three 6,7-(2",2"-dimethylpyrano) flavones and one 6-(3"-hydroxy,3"-methyl-trans-but-1"-enyl)flavone from N. paraensis. Keywords10,11 A reinvestigation of N. paraensis searching for alkaloids afforded flindersine, skimmianine, 8-methoxyflindersine and dictamnine.12 Rosas et al. 1347 Vol. 22, No. 7, 2011 C-glycosylflavones were also reported from N. paraensis, 13 which was cited as Raputia paraensis, but this species was transferred to Neoraputia by Emmerich. 1The first investigation about the chemistry of Raputia reported the presence of cyclopentyl bisindole alkaloids raputiindoles A-D from R. simulans Kllunki. 14 In this paper we report a phytochemical study on R. praetermissa Pirani & Kallunki, and the chemosystematic significance of isolated compounds is discussed in order to clarify the relationships between Raputia and Neoraputia. Results and DiscussionThe dichloromethane extract from the stems of Raputia praetermissa afforded four prenylindole alkaloids (1-4), a cinnamic acid derivative (5) (Figure 1 -5b), a...

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Carbon-13 nuclear magnetic resonance spectral analysis of cycloartanol and related compounds

Cited by 64 publications

References 9 publications

The Structure and Absolute Configuration of Cyclotirucanenol, a New Triterpene from Euphorbia tirucalli Linn

The Structure and Absolute Configuration of Cyclotirucanenol, a New Triterpene from Euphorbia tirucalli Linn

Hypoglycemic Potential of Triterpenes from Alstonia scholaris

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

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