Novel meliacins (limonoids) from the wood of

Ekong, D. E. U.; Olagbemi, E. O.

doi:10.1016/s0040-4039(01)89835-x

Cited by 25 publications

(27 citation statements)

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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.…”

supporting

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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supporting

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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“…The NMR data of 5 were similar to those of 4, except for the presence of one more 2S-methylbutyryl group [δ H 0.88 (t, J ) 7.5 Hz), 1.14 (d, J ) 7.0 Hz), 1 Tables 1 and 2) and the absence of an isobutyryl group (3 -isobutyryl group in 4). The second 2-methylbutyryl group in 5 was corroborated by 1 H-1 H COSY correlations between H 3 -4′/H 2 -3′, H 2 -3′/H-2′, and H-2′/H 3 -5′ and HMBC crosspeaks between H 3 -4′/C-3′, H 3 -4′/C-2′, H 3 -5′/C-2′, H 3 -5′/C-1′, and H-2′/C-1′.…”

Section: Resultsmentioning

confidence: 67%

“…Since isobutanoic acid is optically inactive, the absolute configuration at C-2 in 2-methylbutyric acid was suggested as S by the [R] 25 D +10 (c 0.06, Me 2 CO) of the above mixture. In the same way, the absolute configuration of C-2 in the 2-methylbutyryl group of moluccensins I-L (2-5) was indicated to be S. Supporting Information Available: Figures S1-S9 and Scheme S1; copies of HR-MS (HR-TOFMS or HR-ESIMS), 1 H and 13 C NMR spectra of compounds 1-5 and 7-10; copies of RP-HPLC preparative chromatogram, ESI-MS, HRTOF-MS, HRTOF-MS-MS, 1D and 2D NMR spectra of 6. This material is available free of charge via the Internet at http://pubs.acs.org.…”

Section: Methodsmentioning

confidence: 92%

“…They are classified by the type of foursusually highly oxidizedsrings (designated as A, B, C, and D) in the intact triterpene. Phragmalins, such as pseudrelones A 1 and A 2 1 isolated from Pseudocedrela kotschyii and khayanolides A-C 2 from Khaya senegalensis, have characteristic tricyclo[3.3.1 2,10 .1 1,4 ]decane or tricyclo[4.2.1 10,30 .1 1,4 ]decane ring systems. The family Meliaceae has proved to produce a variety of antifeedant limonoids, such as azadirachtin 3 from the neem tree, Azadiracha indica, and harrisonin 4 from Harrisonnia abyssinica.…”

mentioning

confidence: 99%

“…In the current paper, we present the isolation and characterization of five additional phragmalins (1)(2)(3)(4)(5), each with a C-30 carbonyl group, and a unique ring-D-opened 16-norphragmalin (6), from seeds of the same Indian mangrove, X. moluccensis (Lam.) M Roem.…”

mentioning

confidence: 99%

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Limonoids and Tirucallane Derivatives from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

Yang

et al. 2010

J. Nat. Prod.

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Six new phragmalins, moluccensins H-M (1-6), two new andirobin-type limonoids, moluccensins N and O (7, 8), and two new tirucallane derivatives, moluccensins P and Q (9, 10), were isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, together with the known compound 3 ,22S-dihydroxytirucalla-7,24-dien-23-one. The structures of these compounds were established on the basis of spectroscopic data. Moluccensins H-L were phragmalins with a C-30 carbonyl group, and moluccensin M was a unique ring-D-opened 16-norphragmalin. Moluccensins H-J possess conjugated ∆ 8,9 and ∆ 14,15 double bonds, moluccensins K and L contain a ∆ 8,14 double bond, and moluccensin M has a characteristic C 15 -C 30 linked five-membered lactone ring. Moluccensins H and I showed moderate insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L. ]decane ring systems. The family Meliaceae has proved to produce a variety of antifeedant limonoids, such as azadirachtin 3 from the neem tree, Azadiracha indica, and harrisonin 4 from Harrisonnia abyssinica. Two meliaceous mangroves, Xylocarpus granatum and X. moluccensis, are known for producing antifeedant limonoids, especially phragmalins and mexicanolides. Previous investigations on seeds of these two species yielded an andirobin, two phragmalins, three gedunins, and 14 mexicanolides, including xyloccensins A-K. 5-9Previously we have reported the isolation and identification of eight unique 8,9,30-phragmalin ortho esters and 13 limonoids with a new carbon skeleton from the bark and seeds of a Chinese mangrove, X. granatum. [10][11][12] To date, 42 mexicanolides and 23 phragmalins, including three 1,8,9-phragmalin ortho esters, eight 8,9,30-phragmalin ortho esters, and 12 polyhydroxylated phragmalins, have been isolated from the wood, seeds, and fruits of X. granatum and X. moluccensis. 13 We recently identified seven phragmalins, moluccensins A-G, 14 from seeds of an Indian mangrove, X. moluccensis, collected in the mangrove wetlands of Krishna estuary, AndhraPradesh. In the current paper, we present the isolation and characterization of five additional phragmalins (1-5), each with a C-30 carbonyl group, and a unique ring-D-opened 16-norphragmalin (6), from seeds of the same Indian mangrove, X. moluccensis (Lam.) M Roem. (Meliaceae), together with two new andirobin-type limonoids (7, 8), two new tirucallane derivatives (9, 10), and the known compound 3 , 22S-dihydroxytirucalla-7,24-dien-23-one. 15 The structures of these compounds were established on the basis of spectroscopic data or comparison with data in the literature. The new compounds were tested for insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L. (Tables 1 and 2) indicated that nine of the 15 elements of unsaturation came from a conjugated ketone group, four carbon-carbon double bonds, and four ester functionalities. Therefore, the molecule Results and Discussion

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Trichiliton A, a Novel Limonoid from Trichilia connaroides

Fang

Geng

et al. 2010

Eur J Org Chem

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Trichiliton A (1), a novel limonoid with an unprecedented bicyclo[5.2.14,10]decane motif in the tetranortriterpenoid core, has been isolated from the leaves of Trichilia connaroides. Its structure and absolute configuration have been elucidated by spectroscopic analysis and computational methods. The biosynthetic pathway of compound 1 is discussed and involves an alternative new routine from mexicanolide to phragmalin.

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Novel meliacins (limonoids) from the wood of

Cited by 25 publications

References 1 publication

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

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

Limonoids and Tirucallane Derivatives from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

Trichiliton A, a Novel Limonoid from Trichilia connaroides

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