Nortriterpenoids from <i>Chukrasia tabularis</i> var. <i>velutina</i>

Zhang, Chuan‐Rui; Yang, Sheng‐Ping; Zhu, Qiao; Liao, Shang‐Gao; Wu, Yan; Yue, Jian‐Min

doi:10.1021/np070345w

Cited by 33 publications

(17 citation statements)

References 16 publications

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“…[8][9][10][11] In our longstanding project of chemical studies on the Meliaceae family, [12][13][14] three new limonoids (1-3), and two new triterpenes (4) and (5), together with twelve known compounds, were further isolated from the ethanolic extract of the seeds of M. azedarach. The ethoxyl bearing compound 5 is likely an artifact formed by the involvement of ethanol in the extraction process.…”

Section: Regular Articlementioning

confidence: 99%

Limonoids and Triterpenoids from the Seeds of Melia azedarach

Liu

Zhang

Dong

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticlePlants of the Meliaceae family have been well documented for the ability to metabolize structurally diverse and biologically significant limonoids and triterpenes. [1][2][3][4][5] Plants of Melia azedarach LINN. (Meliaceae) are tall trees widely distributed in the tropical and subtropical areas of Asia, such as India, Indonesia, and Southern China. It has been applied for ascaricidal and antifeedant purposes. 6) In particular, the extract of the fruits of M. azedarach showed in vitro pediculicidal and ovicidal activities.7) Previous chemical investigations of M. azedarach have led to the isolation of a series of limonoids, triterpenes, steroids and flavonoids. [8][9][10][11] In our longstanding project of chemical studies on the Meliaceae family, [12][13][14] three new limonoids (1-3), and two new triterpenes (4) and (5), together with twelve known compounds, were further isolated from the ethanolic extract of the seeds of M. azedarach. The ethoxyl bearing compound 5 is likely an artifact formed by the involvement of ethanol in the extraction process. Herein we report the isolation and structural elucidation of these compounds, and their antimicrobial activity. Results and DiscussionCompound 1, a white powder, gave a molecular formula of C 36 H 44 O 9 , as established on the basis of high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) ([MϩNa] ϩ at m/z 643.2878, Calcd 643.2883). The IR spectrum revealed the presence of hydroxyl (3435 cm (Table 1) showed the presence of five tertiary methyls (d 1.01, 1.22, 1.37, 1.60, 1.76, each 3H, s) and one methoxy (d 2.41, 3H, s). In accord with the molecular formula, the 13 C-NMR spectrum resolved 36 carbon resonances, which were classified by chemical shifts and the heteronuclear singlequantum coherence (HSQC) spectrum as six methyls (one oxygenated), four methylenes (one oxygenated), seventeen methines (six oxygenated and eight olefinic ones), and nine quaternary carbons (two ester carbonyls and four olefinics). The characteristics of the b-furan ring and a benzoyl group were readily identified by NMR analysis (Tables 1 and 2). These functionalities accounted for ten out of the fifteen degrees of unsaturation, and the remaining degrees of unsaturation thus required compound 1 to be pentacyclic in the limonoid core. (Tables 1 and 2). The aforementioned data indicated that the structure of 1 was a C-seco nimbolinin type limonoid. [15][16][17] The extensive analysis of 1D-and 2D-NMR spectral data allowed the assignment of compound 1. The methoxyl group was placed at C-12 by the heteronuclear multiple-bond correlations (HMBC) between C-12 and OMe. The presence of a 6,28-oxygen bridge formed between C-6 and C-28 via an oxygen atom was evident from H-28 to C-6 in the HMBC experiment, as in the case of nimbolinin C.16) The difference was the presence of a benzoyloxyl group at C-1 of 1 instead of a cinnamoyloxyl group of nimbolinin C, as judged from the HMBC correlation between H-1 and C-1Ј (d C 165.3) of 1 (Fig. 1A), and 26 mass units less in t...

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Section: Regular Articlementioning

confidence: 99%

Limonoids and Triterpenoids from the Seeds of Melia azedarach

Liu

Zhang

Dong

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[11][12][13][14][17][18][19][20][21][22][23] In our present research, a series of novel and structurally related 16-norphragmain-type limonoids with alkyl appendage at C-15 ( Fig. 1), chuktabrins C-J (1-8) and chuktabularins U-X (9-12), were isolated from chloroform extract of the stem bark of title plant.…”

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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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“…1,2) The genus chukrasia (Meliaceae) 3) was revealed to be a rich resource of structure diversified phragmalin-type limonoids as well as orthoesters. [4][5][6][7][8][9] Our previous study on phragmalin-type limonoids from Chukrasia tabularis var. velutina afforded a series of 16-norphragmalin limonoids 10,11) and a new class of C-15-acyl phragmalin-type limonoids orthoesters.…”

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Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleThe orthoester group contains a carbon atom bearing three alkoxy or aryloxy groups, and, combined with additional attachments and/or rings, constructs often various structural skeletons of stereochemical complexity, such as daphnane diterpenoids, phragmalin-type limonoids, and bufadienolide and ergostanoid steroids, some of which showed anticancer, antifeedant, and insecticidal activities. 1)Phragmalin-type limonoid orthoester is an important branch of orthoesters with phragmalin limonoid as the basic skeleton, discovered exclusively from the genera of Meliaceae.1,2) The genus chukrasia (Meliaceae) 3) was revealed to be a rich resource of structure diversified phragmalin-type limonoids as well as orthoesters. [4][5][6][7][8][9] Our previous study on phragmalin-type limonoids from Chukrasia tabularis var. velutina afforded a series of 16-norphragmalin limonoids 10,11) and a new class of C-15-acyl phragmalin-type limonoids orthoesters.12) In our present research, nine new phragmalintype limonoid orthoesters, tabulalides F-N (1-9), together with three known compounds, tabulalides C and D and tabularisin N (10-12), were isolated from the ethanol extract of this plant. The structures of these new compounds ( Fig. 1) were elucidated using extensive 2D spectroscopic technologies, and the absolute configurations of 1 and 2 were determined by circular dichroism (CD) exciton chirality method.1,13) Tabulalide F (1) possesses a rare orthoisobutylate moiety in phragmalin limonoid orthoesters.Anticancer activity is the important aspect of limonoids from Meliaceae, and a precursor of phragmalin limonoid was found to be a novel Hsp90 inhibitor.14,15) So, we evaluated cytotoxic activity of compounds 2-12 against five human cancer cell lines, MCF-7 (human breast cancer), Hela (human cervical cancer), SGC-7901 and BGC-823 (human gastric cancer), HepG2 (human liver cancer). The preliminary results indicated that compund 2 exhibts moderate cytotoxic activity against MCF-7 with IC 50 value of 20.4 mmol/l and weak cytotoxic activity against SGC-7901 with IC 50 value of 63.4 mmol/l. The other isolates show weak cytotoxic activity or noncytotoxic (IC 50 Ͼ100 mmol/l) anainst other cancer cell lines. Herein, the isolation, structural elucidation, and cytotoxic activity of these isolates were reported. Results and DiscussionTabulalide F (1) was isolated as white amorphous powder. Its molecular formula was established to be C 38 H 44 O 17 by the high resolution-electrospray ionization (HR-ESI)-MS ion at m/z 783.2470 [MϩNa] ϩ (Calcd: C 36 H 44 O 16 Na, 783.2471). The IR absorption bands at 3499, 1737 and 1641 cm Ϫ1 suggested the presence of hydroxyl, ester, and a,b-unsaturated ester carbonyl groups. The data from decoupling and subsequent 1D-and 2D-NMR studies ( 1 H, 13 C, heteronuclear multiple bond connectivity (HMBC), heteronuclear single quantum coherence (HSQC), and rotating frame Overhauser enhancement spectroscopy (ROESY)) (Fig. 2) Nine new phragmalin-type limonoid orthoesters, tabulalides F-N (1-9), together with th...

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Nortriterpenoids from Chukrasia tabularis var. velutina

Cited by 33 publications

References 16 publications

Limonoids and Triterpenoids from the Seeds of Melia azedarach

Limonoids and Triterpenoids from the Seeds of Melia azedarach

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

Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

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