Two New Alkaloids from the Bark of <i>Sarcomelicope megistophylla</i>

Papageorgiou, Magdalene; Fokialakis, Nikolas; Mitaku, Sofia; Skaltsounis, Alexios‐Léandros; Tillequin, François; Sévenet, Thierry

doi:10.1021/np9904096

Cited by 20 publications

(10 citation statements)

References 13 publications

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“…The carbon bearing this proton (C-10) was correlated with the OCH 3 group at 3.80 ppm, completing the structure of the side chain. As in the case of 1, the last OCH 3 group (3.89) showed a nOe correlation with the aromatic singlet (H-6), which additionally showed a weak 2 J correlation with the carbonyl carbon C-5 and two 3 J strong correlations with the carbonyl carbon C-8 and with the bridge carbon C-4a (110.8). The only carbon that did not show any correlation in the HMBC spectrum was the carbon at 145.2, which was assigned to C-8a.…”

Section: )mentioning

confidence: 69%

Megistoquinones I and II, Two Quinoline Alkaloids with Antibacterial Activity from the Bark of Sarcomelicope megistophylla.

Fokialakis

Magiatis

Chinou

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sarcomelicope megistophylla HARTLEY (Rutaceae) is a small to medium sized tree, endemic to the region of Néaoua, New Caledonia.1) Recently, we described the chemical constituents of its leaves 2) and the major alkaloids of the bark.3)In a continuation of our studies of the genus Sarcomelicope, 4) we report here the isolation and structure determination of two alkaloids, megistoquinone I (1) and megistoquinone II (2) from the bark of Sarcomelicope megistophylla. Both of them derive from a quinoline basic skeleton. Megistoquinone I (1) was obtained as a yellow amorphous compound, and its molecular formula was determined by high resolution (HR)-MS as C 13 H 9 NO 5 . The 1 H-, 13 C-NMR, and heteronuclear multiple bond coherence (HMBC) (Fig. 1) spectra agreed with structure 1, corresponding to that of a pquinone derived from the furo[2,3-b]quinoline basic skeleton. Compound 1 had been previously obtained by Lahey et al. 5) by nitric acid oxidation of acronycidine, in the course of a series of degradation experiments which led to the structure elucidation of this latter alkaloid. Reproduction of this reaction permitted to confirm the identity of megistoquinone I, which is isolated here for the first time from a natural source. Previous characterization of this compound only relied on melting point and elemental analysis to which we now add MS, UV, IR, and NMR spectroscopic data.Megistoquinone II (2) was obtained as a purple amorphous compound, and its molecular formula was determined by HR-MS as C 14 H 13 NO 6 . From the IR spectrum (nϭ1643, 1625 cm Ϫ1 ), it was obvious that this molecule also contained in its structure a p-quinone system. The 1 H-NMR spectrum indicated two conjugated olefinic protons, three OCH 3 groups (all placed on sp 2 carbons), one aromatic proton (d 5.94) and one N-H group (broad singlet at d 9.53). As in the case of 1 the 13 C-NMR spectrum confirmed the above observations and showed the presence of two carbonyl groups, corresponding to a p-quinone system (173.8, 181.2) but also an additional carbonyl group (160.3). It also showed the presence of five quaternary aromatic carbons, and three protonated olefinic or aromatic carbons. The five quaternary aromatic carbons together with the three carbonyl groups and one protonated aromatic carbon constituted a quinolone ring.From the HMBC spectrum ( Fig. 1) it was clear that the OCH 3 group at 3.85 ppm was correlated with an aromatic carbon at 158.2 ppm, which was identified as C-4 by its 3 J correlation with the olefinic proton H-9. That proton was also correlated with the carbonyl carbon C-2, confirming the placement of the side chain at C-3. That carbon was identified by its 3 J correlation with the second olefinic proton H-10. The carbon bearing this proton (C-10) was correlated with the OCH 3 group at 3.80 ppm, completing the structure of the side chain. As in the case of 1, the last OCH 3 group (3.89) showed a nOe correlation with the aromatic singlet (H-6), which additionally showed a weak 2 J correlation with the carbonyl carbon C-5 and two...

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Section: )mentioning

confidence: 69%

Megistoquinones I and II, Two Quinoline Alkaloids with Antibacterial Activity from the Bark of Sarcomelicope megistophylla.

Fokialakis

Magiatis

Chinou

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Further phytochemical studies on the chemical constituents of the New Caledonian tree Sarcomelicope megistophylla have brought to light two minor alkaloids with unprecedented skeletons. 22 The structures of (ϩ)-megistosarcimine 45 and (ϩ)-megistosarconine 46, elucidated on the basis of spectroscopic data and molecular modelling, incorporate a fused cyclopentanone ring that is clearly derived from a uniquely modified prenyl unit attached to C-5 of the furoquinoline nucleus. The cis ring junction was inferred from NOE interactions between the methoxy and hydrogen substituents at C-5 and C-6, respectively, as well as Monte Carlo conformational searches carried out to rationalise observed NMR spectroscopic correlations.…”

Section: Furoquinoline Alkaloidsmentioning

confidence: 99%

Quinoline, quinazoline and acridone alkaloids (July 1999 to June 2000)

Michael

2001

Nat. Prod. Rep.

140

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“…From 1948 to 2007, 53 alkaloids were isolated from the genus Sarcomelicope, belonging to 5 chemical classes: 3 pyranofuroquinolines, 10 quinolinones, 11 pyranoacridones, 14 furoquinolines and 15 acridones [4][5][6][7][8][9][10][11][12][13][14][15].…”

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confidence: 99%

Cytotoxic evaluation of sarcodifurines A and B, two novel dihydrofuroquinolines from Sarcomelicope follicularis (Rutaceae)

Chosson

Guguen‐Guillouzo

Glaise

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Sarcodifurines A and B are two original dihydrofuroquinolines isolated from Sarcomelicope follicularis, a New Caledonian tree. The cytotoxicity and antiproliferative activity of these two alkaloids were investigated against 8 distinct cell lines representative of the most frequent solid tumors developing in human. Cytotoxicity of sarcodifurines was low on the 8 cell lines, with, for example, less than 10% of the total cells killed after 24 h exposure at 10 mM and IC 50 < 7.10 25 M (MCF-7 and MDA MB 231 cell lines). Proliferation studies confirmed that sarcodifurines had a weak effect on cancer cells growth, with less than 5% growth inhibition at 10 mM. Sarcodifurine A activity was comparable to that of Sarcodifurine B, in term of cytotoxicity and antiproliferative activity on all cell lines. In spite of the weak activity of sarcodifurines and furoquinolines, rationalized pharmacomodulations to obtain planar analogs could lead to efficient topoisomerases inhibitors and DNA intercalants.

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Two New Alkaloids from the Bark of Sarcomelicope megistophylla

Abstract: Two new alkaloids, megistophylline I (1) and megistophylline II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data.

Cited by 20 publications

References 13 publications

Megistoquinones I and II, Two Quinoline Alkaloids with Antibacterial Activity from the Bark of Sarcomelicope megistophylla.

Megistoquinones I and II, Two Quinoline Alkaloids with Antibacterial Activity from the Bark of Sarcomelicope megistophylla.

Quinoline, quinazoline and acridone alkaloids (July 1999 to June 2000)

Cytotoxic evaluation of sarcodifurines A and B, two novel dihydrofuroquinolines from Sarcomelicope follicularis (Rutaceae)

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