A limonoid from Neobeguea mahafalensis

Randrianarivelojosia, Milijaona; Kotsos, Maria; Mulholland, Dulcie A.

doi:10.1016/s0031-9422(99)00290-3

Cited by 18 publications

(16 citation statements)

References 5 publications

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“…The C-15-acyl 16-norphragmalins isolated in this investigation and reported previously [11][12][13][14] could be correlated well by the plausible biosynthetic pathway, and we think that the origin of carbonate moiety in 16-norphragmalin limonoids (1)(2)(3)(4)(5)(6)(7)(8) maybe comes from the 16-carbonyl of phragmalin skeleton which degradated through decarboxylation. Herein, the isolation, structural elucidation, the anti-inflammatory activity, as well as the proposed biosynthetic pathway of these novel compounds were reported.…”

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confidence: 83%

Twelve Novel and Diverse 16-Norphragmalin-Type Limonoids from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2012

Chem. Pharm. Bull.

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A series of novel and structurally related C-15-acyl 16-norphragmalin-type limonoids, chuktabrins C-J (1-8) and chuktabularins U-X (9-12), were isolated from the stem bark of Chukrasia tabularis var. velutina. Their structures were established on the basis of detailed spectroscopic analysis, and the absolute configuration of compound 1 was determined by a single-crystal X-ray study using a mirror CuKα radiation. Compounds 7 and 8 were unprecedent C-15-acyl 16-norphragmalins with ketonic alkyl appendage at C-15, and compounds 4 and 8 were first examples of limonoid with a characteristic carbonate moiety esterified at OH-9/OH-8 or OH-1/OH-8 respectively. A biosynthetic pathway of these limonoids was reasonably presumed based on the novel and diverse structures isolated, which provides a new insight into the plausible biosynthesis of C-15-acyl 16-norphragmalin-type limonoids. The anti-inflammatory activity of major isolates were evaluated for inhibitory activity against lipopolysaccharide (LPS) induced nitric oxide (NO) production in macrophage (RAW264.7) cell line, with IC 50 value ranging from 2.40 to 16.90 μM.

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confidence: 83%

Twelve Novel and Diverse 16-Norphragmalin-Type Limonoids from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2012

Chem. Pharm. Bull.

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“…Swietenitin V (9), a white amorphous powder, gave a molecular formula of C 35 H 38 O 13 Comprehensive analysis of its NMR data (Tables 2, 3) indicated that 10 is a phragmalin-type limonoid bearing biosynthetically extended C2 unit at C-15 and forming enol moiety between C-15 and C-31, which is similar to the case of neobeguin. 13) This was confirmed by the HMBC correlations from H-14 to C-13, C-15, C-16 and C-31, and from Me-32 to C-31 and C-15. The tigloyloxyl group was located at C-3 by HMBC correlation between H-3 and C-1Ј.…”

Section: )mentioning

confidence: 85%

“…Swietenitin T (7) was yielded as a white amorphous powder, and had a molecular formula of C 36 H 42 O 13 O] ϩ (Calcd 650.2363). The NMR spectra of 8 showed high similarity to those of 7 except for the absence of one -CH 2 -unit, and this was supported by its molecular formula, which showed 14 mass units less than that of 7.…”

Section: )mentioning

confidence: 99%

“…The IR absorption peaks at 3537 and 1743 cm Ϫ1 implied the presence of hydroxyl and ester carbonyl groups. 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra displayed 39 carbon resonances comprising nine methyl (one methoxyl), six methylenes, six sp 3 methines (four oxygenated), nine sp 3 quaternary carbons (six oxygenated), five carbonyl and two double bonds. Furthermore, a combined analysis of its 1 H-and 13 C-NMR data (Tables 1, 2) revealed the presence of one acetyl, an orthoacetate group, a b-furyl ring, a propionyloxy group and an 2,3-epoxy-2-methyl-butyryl moiety.…”

mentioning

confidence: 99%

“…13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra displayed 39 carbon resonances comprising nine methyl (one methoxyl), six methylenes, six sp 3 methines (four oxygenated), nine sp 3 quaternary carbons (six oxygenated), five carbonyl and two double bonds. Furthermore, a combined analysis of its 1 H-and 13 C-NMR data (Tables 1, 2) revealed the presence of one acetyl, an orthoacetate group, a b-furyl ring, a propionyloxy group and an 2,3-epoxy-2-methyl-butyryl moiety. There are sixteen unsaturations in the molecule of 1, of which, nine degrees are occupied by five ester carbonyls, 2,3-epoxy-2-methyl-butyryl moiety and the b-furyl ring, and the remaining seven degrees required 1 being heptacyclic at the central core.…”

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confidence: 99%

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Phragmalin-Type Limonoid Orthoesters from the Twigs of Swietenia macrophylla

Lin

Zhang

Yang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Swietenia species of family Meliaceae are mainly found in Malaysia, India and Southeast Asia, and many of them have been applied in traditional medicine. [1][2][3][4][5][6] Recently, we reported the isolation and characterization of sixteen D-ring opened phragmalin-type limonoid orthoesters from the twigs and leaves of Swietenia macrophylla which were collected in Hainan Province of People's Republic of China. 7) In a continuation, eleven new phragmalin-type limonoid orthoesters, swietenitins N-X (1-11), as well as a known one epoxyfebrinin B (12), were further isolated from the same plant sample. The stereochemistry of epoxyfebrinin B (12) was completely assigned in the current study. The antimicrobial activities of these isolates against a small panel of microbes were evaluated, but none of them were active. Herein, we report the isolation and structure elucidation of 1-12. Results and DiscussionSwietenitins N-Q (1-4) and Epoxyfebrinin B (12) Swietenitin N (1), a colorless crystal, had the molecular formula C 39 H 48 O 15 as determined by high resolution-electron ionization-mass spectra (HR-EI-MS) at m/z 756.2970 [M] ϩ (Calcd 756.2993), which was supported by the protonated and sodiated molecular ions at m/z 756 [MϩH] ϩ and 779 [MϩNa] ϩ in the positive mode of electrospray ionization (ESI)-MS, respectively. The IR absorption peaks at 3537 and 1743 cm Ϫ1 implied the presence of hydroxyl and ester carbonyl groups. 13C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra displayed 39 carbon resonances comprising nine methyl (one methoxyl), six methylenes, six sp 3 methines (four oxygenated), nine sp 3 quaternary carbons (six oxygenated), five carbonyl and two double bonds. Furthermore, a combined analysis of its 1 H-and 13 C-NMR data (Tables 1, 2) revealed the presence of one acetyl, an orthoacetate group, a b-furyl ring, a propionyloxy group and an 2,3-epoxy-2-methyl-butyryl moiety. There are sixteen unsaturations in the molecule of 1, of which, nine degrees are occupied by five ester carbonyls, 2,3-epoxy-2-methyl-butyryl moiety and the b-furyl ring, and the remaining seven degrees required 1 being heptacyclic at the central core. The aforementioned data suggested that 1 was a phragmalin-type limonoid orthoester.Extensive analysis of 2D-NMR spectra, especially heteronuclear multiple bond correlation (HMBC), allowed the assignment of the most functional groups to the limonoid core and confirmed the framework of a phragmalin-type limonoid for 1. In the HMBC (Fig. 1A), the key correlations of H 2 -29/C-1, C-2, C-4, C-28 and C-10, and H-30/C-3, C-2, C-8 and C-9 revealed 1 being a B-seco phragmalin-type limonoid. The carbon resonances at d 170.4 and 78.8 were assignable to C-16 and C-17 by the HMBC correlations between H 2 -15 and C-16, and between H 3 -18 and C-17, respectively, indicating the existence of the ring D of a six-membered lactone.8) The quaternary carbon at d 118.8 (C-31) correlating with a methyl at d 1.67 (s) revealed the presence of a typical orthoacetate moiety. The HMBC...

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