Phenolic Compound, Triterpene and Steroids From The Leaves and Bark of Dysoxylum Macrocarpum
Keywords:
TheAbstract
The bark and leaves of Dysoxylum macrocarpum (Meliaceace) yielded four compounds, two compounds from the leaves; 5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one (Eugenin) DM1, which was new as crystal and squalene DM2, while two more compounds were found from the bark; stigmasterol DM3 and sitosterol DM4.
The present work involves extraction, isolation and purification of compounds by using column chromatography followed by preparative TLC. Structural elucidation has been done through several spectroscopic methods, notably UV, IR, MS (HRMS, GCMS, and LCMS), 1D, 2D-NMR 1H NMR, 13CNMR, COSY, DEPT, HMQC, HMBC, and single crystal X-ray diffraction analysis.
References
Aalbersberg W., Singh Y. (1991) Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 30:921-6.
Barrero A.F., Oltra J.E., Poyatos J.A. (1996) Acidic metabolites from Phycomyces blakesleeanus. Phytochemistry 42:1427-1433.
Bhat S.V., Shah V., Dohadwalla A.N., Mandrekar S.S., De S.N.J. (1986) Isolation of a pharmacologically active substance having the structure of a chromone alkaloid from plant(s) belonging to the Meliaceae family, Hoechst India Ltd. pp. 21 pp.
Cui B.-S., Ma X.-Q., Yang D.-H., Hu X.-Q., Cai S.-Q. (2008) Purification method of rohitukine from the stem bark of Dysoxylum binectariferum. J. Chin. Pharm. Sci. 17:153-157.
De-Eknamkul W., Potduang B. (2003) Biosynthesis of [beta]-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 62:389-398.
Duh C.-Y., Wang S.-K., Chen I.-S. (2000a) Cytotoxic Prenyleudesmane Diterpenes from the Fruits of Dysoxylum kuskusense. J. Nat. Prod. 63:1546-1547. DOI: 10.1021/np000264z.
Duh C.Y., Wang S.K., Chen I.S. (2000b) Cytotoxic prenyleudesmane diterpenes from the fruits of Dysoxylum kuskusense. J Nat Prod 63:1546-7.
Forgo P., Kövér K.E. (2004) Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids 69:43-50.
Fujioka T., Yamamoto M., Kashiwada Y., Fujii H., Mihashi K., Ikeshiro Y., Chen I.-S., Leed K.-H. (1998a) Antitumor agents. 182. Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Bioorg. Med. Chem. Lett. 8:3479-3482.
Fujioka T., Yamamoto M., Kashiwada Y., Fujii H., Mihashi K., Ikeshiro Y., Chen I.S., Lee K.H. (1998b) Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Bioorg Med Chem Lett 8:3479-82.
Govindachari T.R., Suresh G., Kumari G.N.K. (1994) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 37:1127-9.
Govindachari T.R., Kumari G.N.K., Suresh G. (1996) Ergosta-5,24(24')-diene-3β,4β,20S-triol, an ergostane steroid from Dysoxylum malabaricum. Phytochemistry 44:153-155.
Govindachari T.R., Suresh G., Kumari G.N.K., Rajamannar T., Partho P.D. (1999) Nymania-3: a bioactive triterpenoid from Dysoxylum malabaricum. Fitoterapia 70:83-86.
He K., Timmermann B.N., Aladesanmi A.J., Zeng L. (1996) A biflavonoid from Dysoxylum lenticellare gillespie. Phytochemistry 42:1199-1201.
He X.-F., Wang X.-N., Yin S., Dong L., Yue J.-M. (2009) Ring A Modified Novel Triterpenoids from Dysoxylum hainanense. Eur. J. Org. Chem.:4818-4824. DOI: 10.1002/ejoc.200900609.
He X.-F., Wang X.-N., Gan L.-S., Yin S., Dong L., Yue J.-M. (2008a) Two Novel Triterpenoids from Dysoxylum hainanense. Org. Lett. 10:4327-4330. DOI: 10.1021/ol801834y.
He X.-F., Wang X.-N., Gan L.-S., Yin S., Dong L., Yue J.-M. (2008b) Two novel triterpenoids from Dysoxylum hainanense. Org Lett 10:4327-30.
Hisham A., Bai M.D.A., Fumimoto Y., Hara N., Shimada H. (1996) Complete 1H and 13C NMR spectra assignment of cabraleadiol, a dammarane triterpene from Dysoxylum malabaricum Bedd. Magn. Reson. Chem. 34:146-50.
Hisham A., Ajitha B.M.D., JayaKumar G., Nair M.S., Fujimoto Y. (2001) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 56:331-334.
Huang R., Harrison L.J., Sim K.-Y. (1999) A triterpenoid with a novel abeo-dammarane skeleton from Dysoxylum cauliflorum. Tetrahedron Lett. 40:1607-1610.
Huang X., Kong L. (2006) Steroidal saponins from roots of Asparagus officinalis. Steroids 71:171-176.
Ismail I.S., Nagakura Y., Hirasawa Y., Hosoya T., Lazim M.I.M., Lajis N.H., Morita H. (2009) Acutaxylines A and B, two novel triterpenes from Dysoxylum acutangulum. Tetrahedron Lett. 50:4830-4832. DOI: 10.1016/j.tetlet.2009.05.110.
Jogia M.K., Andersen R.J. (1987) Dysoxylin, a limonoid from Dysoxylum richii. Phytochemistry 26:3309-11.
Jogia M.K., Andersen R.J. (1989) Limonoids from the Fijian medicinal plant Dysoxylum richii. Can. J. Chem. 67:257-60.
Jogia M.K., Andersen R.J., Mantus E.K., Clardy J. (1989) Dysoxysulfone, a sulfur rich metabolite from the Fijian medicinal plant Dysoxylum richii. Tetrahedron Lett. 30:4919-20.
Lakdawala A.D., Shirole M.V., Mandrekar S.S., Dohadwalla A.N. (1988) Immunopharmacological potential of rohitukine: a novel compound isolated from the plant Dysoxylum binectariferum. Asia Pac. J. Pharmacol. 3:91-8.
Lendl A., Werner I., Glasl S., Kletter C., Mucaji P., Presser A., Reznicek G., Jurenitsch J., Taylor D.W. (2005) Phenolic and terpenoid compounds from Chione venosa (sw.) urban var. venosa (Bois Bandé). Phytochemistry 66:2381-2387.
Luo X.-D., Wu S.-H., Wu D.-G., Ma Y.-B., Qi S.-H. (2002a) Novel antifeeding limonoids from Dysoxylum hainanense. Tetrahedron 58:7797-7804.
Luo X.-D., Wu S.-H., Wu D.-G., Ma Y.-B., Qi S.-H. (2002b) Three new apo-tirucallols with six-membered hemiacetal from Meliaceae. Tetrahedron 58:6691-6695.
Luo X.-D., Wu S.-H., Yang X.-S., Teng R.-W., Ma Y.-B., Wu D.-G., Hao X.-J., Lu Y., Liu X.-Y., Zheng Q.-T. (2000a) Prieurianin-type tetranortriterpenoids from the bark of Dysoxylum hainanense. Heterocycles 53:2225-2232.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2000b) Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54:801-805.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2000c) Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54:801-5.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2001a) Ent-pimarane derivatives from Dysoxylum hainanense. Phytochemistry 57:131-134.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2001b) ent-Pimarane derivatives from Dysoxylum hainanense. Phytochemistry 57:131-4.
Mabberly D.J., Pannell C.M. (1989) Meliaceae in Tree Flora of Malaya, Kuala Lumpur
Manoharan K.P., Benny T.K.H., Yang D. (2005) Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta. Phytochemistry 66:2304-2308.
Miyazawa M., Nankai H., Kameoka H. (1996) Biotransformation of acyclic terpenoid (2E,6E)-farnesol by plant pathogenic fungus Glomerella cingulata. Phytochemistry 43:105-109.
Mohamad K., Martin M.-T., Litaudon M., Gaspard C., Sevenet T., Pais M. (1999) Tirucallane triterpenes from Dysoxylum macranthum. Phytochemistry 52:1461-1468.
Mohanakumara P., Sreejayan N., Priti V., Ramesha B.T., Ravikanth G., Ganeshaiah K.N., Vasudeva R., Mohan J., Santhoshkumar T.R., Mishra P.D., Ram V., Shaanker R.U. (2010) Dysoxylum binectariferum Hook.f (Meliaceae), a rich source of rohitukine. Fitoterapia 81:145-148. DOI: 10.1016/j.fitote.2009.08.010.
Mulholland D.A., Naidoo N. (2000) Dammarane triterpenoids from Dysoxylum muellerii. Biochem. Syst. Ecol. 28:295-297.
Mulholland D.A., Nair J.J., Taylor D.A.H. (1996) Glabretal triterpenoids from Dysoxylum muelleri. Phytochemistry 42:1667-1671.
Mulholland D.A., Iourine S., Taylor D.A.H. (1998) Sesquiterpenoids from Dysoxylum schiffneri. Phytochemistry 47:1421-1422.
Mulholland D.A., Monkhe T.V., Pegel K.H., Taylor D.A.H. (1999) Limonoids and diterpenoids from Dysoxylum spectabile (Meliaceae). Biochem. Syst. Ecol. 27:313-315.
Naik R.G., Kattige S.L., Bhat S.V., Alreja B., De S.N.J., Rupp R.H. (1988) An antiinflammatory and immunomodulatory piperidinylbenzopyranone from Dysoxylum binectariferum: isolation, structure and total synthesis. Tetrahedron 44:2081-6.
Najmuldeen I.A., Hadi A.H.A., Awang K., Mohamad K., Ng S.W. (2008) 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E64:o2163, o2163/1-o2163/16. DOI: 10.1107/s1600536808033163.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010a) 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1883. DOI: 10.1107/s1600536810025146.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010b) 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1883. DOI: 10.1107/s1600536810025146.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010c) 14-Deoxyxyloccensin K from Chisocheton ceramicus (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1927. DOI: 10.1107/s160053681002564x.
Najmuldeen I.A., Hadi A.H.A., Awang K., Mohamad K., Ketuly K.A., Mukhtar M.R., Chong S.-L., Chan G., Nafiah M.A., Weng N.S., Shirota O., Hosoya T., Nugroho A.E., Morita H. (2011) Chisomicines A-C, Limonoids from Chisocheton ceramicus. J. Nat. Prod. 74:1313-1317. DOI: 10.1021/np200013g.
Nishiyama Y., Moriyasu M., Ichimaru M., Tachibana Y., Kato A., Mathenge S.G., Nganga J.N., Juma F.D. (1996) Acyclic triterpenoids from Ekebergia capensis. Phytochemistry 42:803-807.
Russell G.B., Hunt M.B., Bowers W.S., Blunt J.W. (1994) A sesquiterpenoid ant repellent from Dysoxylum spectabile. Phytochemistry 35:1449-53.
Säynäjoki S., Sundberg S., Soupas L., Lampi A.-M., Piironen V. (2003) Determination of stigmasterol primary oxidation products by high-performance liquid chromatography. Food Chemistry 80:415-421.
Singh Y., Aalbersberg W. (1992) Dammarane triterpenoids from a Fijian medicinal plant, Dysoxylum richii. Part 2. Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 31:4033-5.
Tsui W.-Y., Brown G.D. (1996) Chromones and chromanones from Baeckea frutescens. Phytochemistry 43:871-876. DOI: 10.1016/0031-9422(96)00360-3.
Xie B.-J., Yang S.-P., Yue J.-M. (2008a) Terpenoids from Dysoxylum densiflorum. Phytochemistry (Elsevier) 69:2993-2997. DOI: 10.1016/j.phytochem.2008.09.017.
Xie B.-J., Yang S.-P., Yue J.-M. (2008b) Terpenoids from Dysoxylum densiflorum. Phytochemistry 69:2993-7.
Xu W.L., Huang Y.B., Qian J.H., Sha O., Wang Y.Q. (2005) Separation and purification of stigmasterol and [beta]-sitosterol from phytosterol mixtures by solvent crystallization method. Separation and Purification Technology 41:173-178.
Yang D.-H., Cai S.-Q., Zhao Y.-Y., Liang H. (2004) A new alkaloid from Dysoxylum binectariferum. J. Asian Nat. Prod. Res. 6:233-236. DOI: 10.1080/10286020310001608930.
Barrero A.F., Oltra J.E., Poyatos J.A. (1996) Acidic metabolites from Phycomyces blakesleeanus. Phytochemistry 42:1427-1433.
Bhat S.V., Shah V., Dohadwalla A.N., Mandrekar S.S., De S.N.J. (1986) Isolation of a pharmacologically active substance having the structure of a chromone alkaloid from plant(s) belonging to the Meliaceae family, Hoechst India Ltd. pp. 21 pp.
Cui B.-S., Ma X.-Q., Yang D.-H., Hu X.-Q., Cai S.-Q. (2008) Purification method of rohitukine from the stem bark of Dysoxylum binectariferum. J. Chin. Pharm. Sci. 17:153-157.
De-Eknamkul W., Potduang B. (2003) Biosynthesis of [beta]-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 62:389-398.
Duh C.-Y., Wang S.-K., Chen I.-S. (2000a) Cytotoxic Prenyleudesmane Diterpenes from the Fruits of Dysoxylum kuskusense. J. Nat. Prod. 63:1546-1547. DOI: 10.1021/np000264z.
Duh C.Y., Wang S.K., Chen I.S. (2000b) Cytotoxic prenyleudesmane diterpenes from the fruits of Dysoxylum kuskusense. J Nat Prod 63:1546-7.
Forgo P., Kövér K.E. (2004) Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids 69:43-50.
Fujioka T., Yamamoto M., Kashiwada Y., Fujii H., Mihashi K., Ikeshiro Y., Chen I.-S., Leed K.-H. (1998a) Antitumor agents. 182. Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Bioorg. Med. Chem. Lett. 8:3479-3482.
Fujioka T., Yamamoto M., Kashiwada Y., Fujii H., Mihashi K., Ikeshiro Y., Chen I.S., Lee K.H. (1998b) Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Bioorg Med Chem Lett 8:3479-82.
Govindachari T.R., Suresh G., Kumari G.N.K. (1994) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 37:1127-9.
Govindachari T.R., Kumari G.N.K., Suresh G. (1996) Ergosta-5,24(24')-diene-3β,4β,20S-triol, an ergostane steroid from Dysoxylum malabaricum. Phytochemistry 44:153-155.
Govindachari T.R., Suresh G., Kumari G.N.K., Rajamannar T., Partho P.D. (1999) Nymania-3: a bioactive triterpenoid from Dysoxylum malabaricum. Fitoterapia 70:83-86.
He K., Timmermann B.N., Aladesanmi A.J., Zeng L. (1996) A biflavonoid from Dysoxylum lenticellare gillespie. Phytochemistry 42:1199-1201.
He X.-F., Wang X.-N., Yin S., Dong L., Yue J.-M. (2009) Ring A Modified Novel Triterpenoids from Dysoxylum hainanense. Eur. J. Org. Chem.:4818-4824. DOI: 10.1002/ejoc.200900609.
He X.-F., Wang X.-N., Gan L.-S., Yin S., Dong L., Yue J.-M. (2008a) Two Novel Triterpenoids from Dysoxylum hainanense. Org. Lett. 10:4327-4330. DOI: 10.1021/ol801834y.
He X.-F., Wang X.-N., Gan L.-S., Yin S., Dong L., Yue J.-M. (2008b) Two novel triterpenoids from Dysoxylum hainanense. Org Lett 10:4327-30.
Hisham A., Bai M.D.A., Fumimoto Y., Hara N., Shimada H. (1996) Complete 1H and 13C NMR spectra assignment of cabraleadiol, a dammarane triterpene from Dysoxylum malabaricum Bedd. Magn. Reson. Chem. 34:146-50.
Hisham A., Ajitha B.M.D., JayaKumar G., Nair M.S., Fujimoto Y. (2001) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 56:331-334.
Huang R., Harrison L.J., Sim K.-Y. (1999) A triterpenoid with a novel abeo-dammarane skeleton from Dysoxylum cauliflorum. Tetrahedron Lett. 40:1607-1610.
Huang X., Kong L. (2006) Steroidal saponins from roots of Asparagus officinalis. Steroids 71:171-176.
Ismail I.S., Nagakura Y., Hirasawa Y., Hosoya T., Lazim M.I.M., Lajis N.H., Morita H. (2009) Acutaxylines A and B, two novel triterpenes from Dysoxylum acutangulum. Tetrahedron Lett. 50:4830-4832. DOI: 10.1016/j.tetlet.2009.05.110.
Jogia M.K., Andersen R.J. (1987) Dysoxylin, a limonoid from Dysoxylum richii. Phytochemistry 26:3309-11.
Jogia M.K., Andersen R.J. (1989) Limonoids from the Fijian medicinal plant Dysoxylum richii. Can. J. Chem. 67:257-60.
Jogia M.K., Andersen R.J., Mantus E.K., Clardy J. (1989) Dysoxysulfone, a sulfur rich metabolite from the Fijian medicinal plant Dysoxylum richii. Tetrahedron Lett. 30:4919-20.
Lakdawala A.D., Shirole M.V., Mandrekar S.S., Dohadwalla A.N. (1988) Immunopharmacological potential of rohitukine: a novel compound isolated from the plant Dysoxylum binectariferum. Asia Pac. J. Pharmacol. 3:91-8.
Lendl A., Werner I., Glasl S., Kletter C., Mucaji P., Presser A., Reznicek G., Jurenitsch J., Taylor D.W. (2005) Phenolic and terpenoid compounds from Chione venosa (sw.) urban var. venosa (Bois Bandé). Phytochemistry 66:2381-2387.
Luo X.-D., Wu S.-H., Wu D.-G., Ma Y.-B., Qi S.-H. (2002a) Novel antifeeding limonoids from Dysoxylum hainanense. Tetrahedron 58:7797-7804.
Luo X.-D., Wu S.-H., Wu D.-G., Ma Y.-B., Qi S.-H. (2002b) Three new apo-tirucallols with six-membered hemiacetal from Meliaceae. Tetrahedron 58:6691-6695.
Luo X.-D., Wu S.-H., Yang X.-S., Teng R.-W., Ma Y.-B., Wu D.-G., Hao X.-J., Lu Y., Liu X.-Y., Zheng Q.-T. (2000a) Prieurianin-type tetranortriterpenoids from the bark of Dysoxylum hainanense. Heterocycles 53:2225-2232.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2000b) Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54:801-805.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2000c) Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54:801-5.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2001a) Ent-pimarane derivatives from Dysoxylum hainanense. Phytochemistry 57:131-134.
Luo X.D., Wu S.H., Ma Y.B., Wu D.G. (2001b) ent-Pimarane derivatives from Dysoxylum hainanense. Phytochemistry 57:131-4.
Mabberly D.J., Pannell C.M. (1989) Meliaceae in Tree Flora of Malaya, Kuala Lumpur
Manoharan K.P., Benny T.K.H., Yang D. (2005) Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta. Phytochemistry 66:2304-2308.
Miyazawa M., Nankai H., Kameoka H. (1996) Biotransformation of acyclic terpenoid (2E,6E)-farnesol by plant pathogenic fungus Glomerella cingulata. Phytochemistry 43:105-109.
Mohamad K., Martin M.-T., Litaudon M., Gaspard C., Sevenet T., Pais M. (1999) Tirucallane triterpenes from Dysoxylum macranthum. Phytochemistry 52:1461-1468.
Mohanakumara P., Sreejayan N., Priti V., Ramesha B.T., Ravikanth G., Ganeshaiah K.N., Vasudeva R., Mohan J., Santhoshkumar T.R., Mishra P.D., Ram V., Shaanker R.U. (2010) Dysoxylum binectariferum Hook.f (Meliaceae), a rich source of rohitukine. Fitoterapia 81:145-148. DOI: 10.1016/j.fitote.2009.08.010.
Mulholland D.A., Naidoo N. (2000) Dammarane triterpenoids from Dysoxylum muellerii. Biochem. Syst. Ecol. 28:295-297.
Mulholland D.A., Nair J.J., Taylor D.A.H. (1996) Glabretal triterpenoids from Dysoxylum muelleri. Phytochemistry 42:1667-1671.
Mulholland D.A., Iourine S., Taylor D.A.H. (1998) Sesquiterpenoids from Dysoxylum schiffneri. Phytochemistry 47:1421-1422.
Mulholland D.A., Monkhe T.V., Pegel K.H., Taylor D.A.H. (1999) Limonoids and diterpenoids from Dysoxylum spectabile (Meliaceae). Biochem. Syst. Ecol. 27:313-315.
Naik R.G., Kattige S.L., Bhat S.V., Alreja B., De S.N.J., Rupp R.H. (1988) An antiinflammatory and immunomodulatory piperidinylbenzopyranone from Dysoxylum binectariferum: isolation, structure and total synthesis. Tetrahedron 44:2081-6.
Najmuldeen I.A., Hadi A.H.A., Awang K., Mohamad K., Ng S.W. (2008) 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E64:o2163, o2163/1-o2163/16. DOI: 10.1107/s1600536808033163.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010a) 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1883. DOI: 10.1107/s1600536810025146.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010b) 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1883. DOI: 10.1107/s1600536810025146.
Najmuldeen I.A., Abdul H.A.H., Awang K., Mohamad K., Ng S.W. (2010c) 14-Deoxyxyloccensin K from Chisocheton ceramicus (Meliaceae). Acta Crystallogr., Sect. E: Struct. Rep. Online E66:o1927. DOI: 10.1107/s160053681002564x.
Najmuldeen I.A., Hadi A.H.A., Awang K., Mohamad K., Ketuly K.A., Mukhtar M.R., Chong S.-L., Chan G., Nafiah M.A., Weng N.S., Shirota O., Hosoya T., Nugroho A.E., Morita H. (2011) Chisomicines A-C, Limonoids from Chisocheton ceramicus. J. Nat. Prod. 74:1313-1317. DOI: 10.1021/np200013g.
Nishiyama Y., Moriyasu M., Ichimaru M., Tachibana Y., Kato A., Mathenge S.G., Nganga J.N., Juma F.D. (1996) Acyclic triterpenoids from Ekebergia capensis. Phytochemistry 42:803-807.
Russell G.B., Hunt M.B., Bowers W.S., Blunt J.W. (1994) A sesquiterpenoid ant repellent from Dysoxylum spectabile. Phytochemistry 35:1449-53.
Säynäjoki S., Sundberg S., Soupas L., Lampi A.-M., Piironen V. (2003) Determination of stigmasterol primary oxidation products by high-performance liquid chromatography. Food Chemistry 80:415-421.
Singh Y., Aalbersberg W. (1992) Dammarane triterpenoids from a Fijian medicinal plant, Dysoxylum richii. Part 2. Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 31:4033-5.
Tsui W.-Y., Brown G.D. (1996) Chromones and chromanones from Baeckea frutescens. Phytochemistry 43:871-876. DOI: 10.1016/0031-9422(96)00360-3.
Xie B.-J., Yang S.-P., Yue J.-M. (2008a) Terpenoids from Dysoxylum densiflorum. Phytochemistry (Elsevier) 69:2993-2997. DOI: 10.1016/j.phytochem.2008.09.017.
Xie B.-J., Yang S.-P., Yue J.-M. (2008b) Terpenoids from Dysoxylum densiflorum. Phytochemistry 69:2993-7.
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2013-06-30
How to Cite
Najmuldeen, I. A., Ketuly, K. A., & Hadi, A. H. A. (2013). Phenolic Compound, Triterpene and Steroids From The Leaves and Bark of Dysoxylum Macrocarpum. Science Journal of University of Zakho, 1(1), 227–245. Retrieved from https://sjuoz.uoz.edu.krd/index.php/sjuoz/article/view/79
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Science Journal of University of Zakho
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