Xyloccensins Q–V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum

Wu, Jun; Xiao, Qiang; Zhang, Si; Li, Xiang; Xiao, Zhihui; Ding, Haixin; Li, Qingxin

doi:10.1016/j.tet.2005.06.099

Cited by 78 publications

(69 citation statements)

References 17 publications

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“…Recently, we have reported the isolation and identification of eight unique 8,9,30-phragmalin ortho esters and eight new mexicanolides from the bark and fruit of a Chinese mangrove X. granatum [6 -12]. Five new phragmalins [13], among which four were the same as we have reported [9], were obtained from the bark of the same plant. In the current paper, we present the isolation and characterization of a mixture of four new butyrospermol and two known β -sitosterol fatty acid esters from the fruit of X. granatum.…”

Section: Introductionmentioning

confidence: 86%

Butyrospermol Fatty Acid Esters from the Fruit of a Chinese Mangrove Xylocarpus granatum

Xiao

et al. 2006

Zeitschrift Für Naturforschung B

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A mixture of four new butyrospermol and two known β -sitosterol fatty acid esters, was obtained from the fruit of a Chinese mangrove Xylocarpus granatum. The structures of these compounds were established on the basis of spectroscopic data and chemical means. The butyrospermol fatty acid esters were characterized as mainly comprising butyrospermol 3β -O-palmitate (1), butyrospermol 3β -O-oleate (2), butyrospermol 3β -O-stearate (3) and butyrospermol 3β -O-linoleate (4). The β -sitosterol fatty acid esters were identified as mainly containing β -sitosterol 3β -O-myristate and β -sitosterol 3β -O-oleate.

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Section: Introductionmentioning

confidence: 86%

Butyrospermol Fatty Acid Esters from the Fruit of a Chinese Mangrove Xylocarpus granatum

Xiao

et al. 2006

Zeitschrift Für Naturforschung B

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“…The presence of the OH group at C-1, the weak HMBC correlation from H-30 (d H 4.51) to the orthoester carbon, and the chemical shifts of C-2 (d C 75.2), C-8 (d C 83.8), C-9 (d C 85.4) and C-30 (d C 78.0) confined the location of the orthoester group to C-8/C-9/C-30. 13,16) The ROESY correlations (Fig. 2), from H-5 to H-11 and H-12, from H-17 to H-12, from H-15 to H-30, from H-3 to H-29a, from Me-19 to H-29b, indicated the basic skeleton of 1 to be the same as that of xyloccensin O-V which had been unequivocally been elucidated by X-ray analysis.…”

Section: Resultsmentioning

confidence: 87%

“…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.…”

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confidence: 99%

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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“…[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, Andhra…”

Section: -9mentioning

confidence: 99%

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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Xyloccensins Q–V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum

Cited by 78 publications

References 17 publications

Butyrospermol Fatty Acid Esters from the Fruit of a Chinese Mangrove Xylocarpus granatum

Butyrospermol Fatty Acid Esters from the Fruit of a Chinese Mangrove Xylocarpus granatum

Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

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

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