Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities

Phytochemistry

Volumn 93, Issue , 2013, Pages 203-209

  Chen, Si ^a   Huang, Hung Yi ^a   Cheng, Ming Jen ^b   Wu, Chin Chung ^a   Ishikawa, Tsutomu ^c   Peng, Chien Fang ^a   Chang, Hsun Shou ^a   Wang, Chyi Jia ^a   Wong, Su Ling ^a   Chen, Ih Sheng ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b FOOD INDUSTRY RESEARCH AND DEVELOPMENT INSTITUTE   (Taiwan)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

Antiplatelet activity; Antitubercular activity; Neolignan; Phenylpropanoid; Piper taiwanense; Piperaceae; Root

Indexed keywords

MYCOBACTERIUM TUBERCULOSIS; PIPER TAIWANENSE; PIPERACEAE;

ANTICOAGULANT AGENT; LIGNAN; NEOLIGNAN; PHENYLPROPANOID; PHENYLPROPIONIC ACID DERIVATIVE; TUBERCULOSTATIC AGENT;

ANTIPLATELET ACTIVITY; ANTITUBERCULAR ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; HUMAN; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM TUBERCULOSIS; PIPER (PLANT); PIPER TAIWANENSE; PIPERACEAE; PLANT ROOT; ROOT; STRUCTURE ACTIVITY RELATION; THROMBOCYTE; THROMBOCYTE AGGREGATION;

ANTIPLATELET ACTIVITY; ANTITUBERCULAR ACTIVITY; NEOLIGNAN; PHENYLPROPANOID; PIPER TAIWANENSE; PIPERACEAE; ROOT;

ANTICOAGULANTS; ANTITUBERCULAR AGENTS; BLOOD PLATELETS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; LIGNANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PHENYLPROPIONATES; PIPER; PLANT ROOTS; PLATELET AGGREGATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84884900818     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.03.008     Document Type: Article

References (27)

1. Achenbach, H., Fietz, W., Worth, J., Waibel, R., Portecop, J., 1986. Constituents of tropical medicinal plants: IXX. GC/MS-investigations of the constituents of Piper amalago: 30 new amides of the piperine-type. Planta Med. 52, 12-18. (Pubitemid 16129315)
2. Anjaneyulu, A.S.R., Sagar, K.S., Venugopal, M.J.R.V., 1995. Terpenoid and steroid constituents of the Indian Ocean soft coral Sinularia maxima. Tetrahedron 51, 10997-11010.
3. Badheka, L.P., Prabhu, B.R., Mulchandani, N.B., 1987. Lignans of Piper cubeba. Phytochemistry 26, 2033-2036.
4. Barbosa-Filho, J.M., Yoshida, M., Gottlieb, O.R., Barbosa, R.C.S.B.C., Giesbrecht, A.M., Young, M.C.M., 1987. Benzoyl esters and amides, styrylpyrones and neolignans from the fruits of Aniba riparia. Phytochemistry 26, 2615-2617.
5. Brown, G.R., Mallion, K.B., Whittamore, P.R.O., Brittain, D.R., 1997. Quinuclidine derivatives as squalene synthase inhibitors. United States Patent: US005691349
6. A. Chen, I.S., Chen, Y.C., Liao, C.H., 2007. Amides with anti-platelet aggregation activity from Piper taiwanense. Fitoterapia 78, 414-419.
7. Chen, Y.C., Chen, J.J., Chang, Y.L., Teng, C.M., Lin, W.Y., Wu, C.C., Chen, I.S., 2004. A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense. Planta Med. 70, 174-177.
8. Chia, Y.C., Chang, F.R., Teng, C.M., Wu, Y.C., 2000. Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii. J. Nat. Prod. 63, 1160-1163.
9. Chiji, H., Tanaka, S., Izawa, M., 1980. Phenolic germination inhibitors in the seed balls of red beet (Beta vulgaris L. var. rubra). Agric. Biol. Chem. 44, 205-207.
10. Coolen, H.K.A.C., Meeuwis, J.A.M., van Leeuwen, P.W.M.N., Nolte, R.J.M., 1995. Substrate selective catalysis by rhodium metallohosts. J. Am. Chem. Soc. 117, 11906-11913. (Pubitemid 126634916)
11. Crohare, R., Priestap, H.A., Farina, M., Cedola, M., Ruveda, E.A., 1974. Aristololactams of Aristolochia argentina. Phytochemistry 13, 1957-1962.
12. Desai, S.J., Chaturvedi, R., Mulchandani, N.B., 1990. Piperolactam D, a new aristolactam from Indian Piper species. J. Nat. Prod. 53, 496-497. (Pubitemid 20202697)
13. Desai, S.J., Prabhu, B.R., Mulchandani, N.B., 1988. Aristolactams and 4,5-dioxoaporphines from Piper longum. Phytochemistry 27, 1511-1515.
14. Ee, G.C.L., Lim, C.M., Lim, C.K., Rahmani, M., Shaari, K., Bong, C.F.J., 2009. Alkaloids from Piper sarmentosum and Piper nigrum. Nat. Prod. Res. 23, 1416-1423.
15. Evans, P.H., Bowers, W.S., Funk, E.J., 1984. Identification of fungicidal and nematocidal components in the leaves of Piper betle (Piperaceae). J. Agric. Food Chem. 32, 1254-1256.
16. Kojima, H., Sato, N., Hatano, A., Ogura, H., 1990. Sterol glucosides from Prunella vulgaris. Phytochemistry 29, 2351-2355.
17. Ley, J.P., Blings, M., Paetz, S., Krammer, G.E., Bertram, H.J., 2006. New bitter-masking compounds: hydroxylated benzoic acid amides of aromatic amines as structural analogues of homoeriodictyol. J. Agric. Food Chem. 54, 8574-8579. (Pubitemid 44753106)
18. Liao, S.G., Wu, Y., Yue, J.M., 2006. Lignans from Wikstroemia hainanensis. Helv. Chim. Acta 54, 73-80. (Pubitemid 43145535)
19. Lin, T.T., Lu, S.Y., 1996. Piperaceae in Flora of Taiwan, second ed., vol. 2. Editorial Committee of the Flora of Taiwan, Taipei, Taiwan, pp. 624-631.
20. Liu, H.J., Wu, C.L., Becker, H., Zapp, J., 2000. Sesquiterpenoids and diterpenoids from the Chilean liverwort Lepicolea ochroleuca. Phytochemistry 53, 845-849. (Pubitemid 30233110)
21. Morimoto, T., Nagai, H., Achiwa, K., 2005. Lipase-catalyzed esterification of a (±)-2,3-di(arylmethyl)-1,4-butanediol and its application to the synthesis of (S, S)-(+)-hinokinin. Synth. Commun. 35, 857-865. (Pubitemid 40434701)
22. Nagabhushan, M., Amonkar, A.J., Nair, U.J., D'Souza, A.V., Bhide, S.V., 1989. Hydroxychavicol: a new anti-nitrosating phenolic compound from betel leaf. Mutagenesis 4, 200-204. (Pubitemid 19128781)
23. Rohmann, C., Wilm, H.D., 1942. Über Konstitution und wirkung substituierter Benzoesäuren. Arch. Pharm. 280, 76-85.
24. Sakakibara, N., Nakatsubo, T., Suzuki, S., Shibata, D., Shimada, M., Umezawa, T., 2007. Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method. Org. Biomol. Chem. 5, 802-815.
25. Takahashi, S., Kurabayashi, M., Ogiso, A., Mishima, H., 1969. The structure of futoamide: a constituent of Piper futokadzura Sieb. et Zucc. Chem. Pharm. Bull. 17, 1225-1228.
26. Trikojus, V.M., White, D.E., 1949. The synthesis of myristicin. J. Chem. Soc. 27, 436-439.
27. Xia, Y., You, J., Zhang, Y., Su, Z., 2009. Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues. J. Chem. Res. 2009, 565-569.