Chemistry of Fijian Plants. XIV  An Unsaturated Aryl Keto Acid from Xylocarpus moluccensis

Bercich, M. G.; Cambie, R. C.; Lal, Allick R.; Sidwell, David

doi:10.1071/c97195

Cited by 9 publications

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“…[86][87][88] Two phenolic acid, (5E)-4-oxo-19-phenylnonadec-5-enoic acid (174) and (5E)-4-oxo-19-phenylnonadec-5-enoic acid, methyl ester (175), were identified from the wood of the Fijian X. moluccensis. 89 Two alkaloids, N-methylflindersine (176), acetonyldihydrochelerythrine (177), were isolated as insect antifeedants from the east African X. granatum. 90 Recently, xylogranatinin (178), a new pyrido[1,2-a]pyrazine alkaloid, has been identified by our group from the fruit of the Chinese mangrove Xylocarpus granatum, 91 together with (+)-catechin (179) and daucosterol (180).…”

Section: Andirobins Methyl Angolensate (87) Was Identified Bymentioning

confidence: 99%

Natural products from true mangrove flora: source, chemistry and bioactivities

et al. 2008

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Section: Andirobins Methyl Angolensate (87) Was Identified Bymentioning

confidence: 99%

Natural products from true mangrove flora: source, chemistry and bioactivities

et al. 2008

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“…Wood : Triterpenoids : limonoids [247,248,249]; Fatty acid : 4-oxo-19-phenylnonadec-5-enoic acid [250]. …”

Section: Traditional Antidiarrhoeal Plants From Bangladeshmentioning

confidence: 99%

Can Scientific Evidence Support Using Bangladeshi Traditional Medicinal Plants in the Treatment of Diarrhoea? A Review on Seven Plants

et al. 2013

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Diarrhoea is a common disease which causes pain and may be deadly, especially in developing countries. In Bangladesh, diarrhoeal diseases affect thousands of people every year, and children are especially vulnerable. Bacterial toxins or viral infections are the most common cause of the disease. The diarrhoea outbreaks are often associated with flood affected areas with contaminated drinking water and an increased risk of spreading the water-borne disease. Not surprisingly, plants found in the near surroundings have been taken into use by the local community as medicine to treat diarrhoeal symptoms. These plants are cheaper and more easily available than conventional medicine. Our question is: What is the level of documentation supporting the use of these plants against diarrhoea and is their consumption safe? Do any of these plants have potential for further exploration? In this review, we have choosen seven plant species that are used in the treatment of diarrhoea; Diospyros peregrina, Heritiera littoralis, Ixora coccinea, Pongamia pinnata, Rhizophora mucronata, Xylocarpus granatum, and Xylocarpus moluccensis. Appearance and geographical distribution, traditional uses, chemical composition, and biological studies related to antidiarrhoeal activity will be presented. This review reveals that there is limited scientific evidence supporting the traditional use of these plants. Most promising are the barks from D. peregrina, X. granatum and X. moluccensis which contain tannins and have shown promising results in antidiarrhoeal mice models. The leaves of P. pinnata also show potential. We suggest these plants should be exploited further as possible traditional herbal remedies against diarrhoea including studies on efficacy, optimal dosage and safety.

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“…The mangroves Xylocarpus moluccensis and X. granatum are known for producing antifeedant limonoids, especially phragmalins and mexicanolides. Previous investigations on the mangrove, X. moluccensis, yielded a gedunin, 1) a monoterpene, 2) an andirobin, 3) two phenolic acids, 4) two phragmalins, 3,5) and 15 mexicanolides. 1,3,[5][6][7] Previously, eight unique 8,9,30-phragmalin orthoesters and 13 limonoids with a new carbon skeleton were identified by us from the bark and seeds of a Chinese mangrove, X. granatum.…”

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Mexicanolides from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

Zhang

Yang

et al. 2010

Chem. Pharm. Bull.

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Limonoids, derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton, are tetranortriterpenoids with a b-furyl ring substituent located at C-17. They are classified by the type of four rings, which are usually oxidized and designated as A, B, C, and D, in the intact triterpene nucleus. The mangroves Xylocarpus moluccensis and X. granatum are known for producing antifeedant limonoids, especially phragmalins and mexicanolides. Previous investigations on the mangrove, X. moluccensis, yielded a gedunin, 1) a monoterpene,2) an andirobin, 3) two phenolic acids, 4) two phragmalins, 3,5) and 15 mexicanolides. 1,3,5-7) Previously, eight unique 8,9,30-phragmalin orthoesters and 13 limonoids with a new carbon skeleton were identified by us from the bark and seeds of a Chinese mangrove, X. granatum. [8][9][10] In the continuing search for potential drug leads from mangrove plants, two new mexicanolides, named xylomexicanolides A and B (1, 2), were isolated from the seeds of an Indian mangrove, X. moluccensis (LAM.) M. ROEM. (Meliaceae), collected in the mangrove wetlands in Krishna estuary, Andhra Pradesh, together with four known limonoids, khayasin, 11) angolensic acid methyl ester, khayasin T, 12) and 2ЈS-methylbutanoylproceranolide.13) The complete assignments of NMR data for xylomexicanolides A, B and khayasin were achieved by means of 2D NMR techniques, including 1 H-1 H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOSEY) spectra. The 13 C-NMR data of khayasin were reported for the first time. Results and DiscussionXylomexicanolide A (1) was obtained as a white, amorphous powder. Its molecular formula of C 31 H 38 O 8 was established by a quasi-molecular ion peak in the HR-time of flight (TOF)-MS at m/z 561.2491 (Calcd for [MϩNa] ϩ 561.2464), indicating that 1 had 13 degrees of unsaturation. From the 1 H-and 13 C-NMR data (Table 1) of 1, it was clear that eight of the 13 elements of unsaturation came from a ketone, three ester functionalities, and four carbon-carbon double bonds. Therefore, the molecule was pentacyclic. The 13 C-NMR data and distortionless enhancement by polarization transfer (DEPT) experiments revealed that 1 had seven methyls (a methoxy, two secondary methyls, and four methyls of the mexicanolide nucleus), three methylenes, eleven methines (five olefinic) and ten quaternary carbons (four carbonyls). The NMR data of 1 (Table 1) 1 H-1 H COSY crosspeak to H-2 and HMBC correlations to C-2, C-4, and C-30 (Table 1), was assigned to CH-3. An olefinic methine group [d H 6.29 (dd, Jϭ6.0,3.0 Hz), d C 128.9 CH], showing a 1 H-1 H COSY correlation to H-2 and HMBC correlations to C-9 and C-14, was attributed to CH-30. The NMR data of 1 (Table 1) were similar to those of tigloylseneganolide A, 13) except for the presence of a different substituted group at C-3. The strong HMBC correlation from H-3 to the carbonyl Two new mexicanolides, named xylomexicanolides A and B, ...

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Chemistry of Fijian Plants. XIV An Unsaturated Aryl Keto Acid from Xylocarpus moluccensis

Abstract: A new unsaturated aryl keto acid (1) and its methyl ester (2) have been isolated from the wood of FijianXylocarpus moluccensis and their structures determined by spectroscopic examination.

Cited by 9 publications

References 0 publications

Natural products from true mangrove flora: source, chemistry and bioactivities

Natural products from true mangrove flora: source, chemistry and bioactivities

Can Scientific Evidence Support Using Bangladeshi Traditional Medicinal Plants in the Treatment of Diarrhoea? A Review on Seven Plants

Mexicanolides from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

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