New Amides and Gastroprotective Constituents from the Fruit of Piper chaba

Toshio Morikawa; Hisashi Matsuda; Itadaki Yamaguchi; Yutana Pongpiriyadacha; Masayuki Yoshikawa

doi:10.1055/s-2004-815493

Planta Medica, Table of Contents

Planta Med 2004; 70(2): 152-159
DOI: 10.1055/s-2004-815493

Original Paper

Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Amides and Gastroprotective Constituents from the Fruit of Piper chaba

Toshio Morikawa¹ , Hisashi Matsuda¹ , Itadaki Yamaguchi¹ , Yutana Pongpiriyadacha¹ , Masayuki Yoshikawa¹

¹Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, Japan

Abstract

The 80 % aqueous acetone extract from the fruit of Piper chaba was found to show protective effects on ethanol- and indomethacin-induced gastric lesions in rats. From the aqueous acetone extract, four new amides named piperchabamides A (1), B (2), C (3), and D (4) were isolated, and their structures were determined on the basis of chemical and physicochemical evidence. In addition, the gastroprotective effects of the principal constituents, piperine (5), piperanine (6), pipernonaline (7), dehydropipernonaline (8), piperlonguminine (9), retrofractamide B (10), guineensine (11), N-isobutyl-(2E,4E)-octadecadienamide (12), N-isobutyl-(2E,4E,14Z)-eicosatrienamide (13), and methyl piperate (14), were examined. As a result, compounds 5 - 10 and 12 - 14 significantly inhibited ethanol-induced gastric lesions at a dose of 25 mg/kg, p. o., while 5, 7, 8, 10, 12, and 13 also significantly inhibited indomethacin-induced gastric lesions at the same dose.

Key words

Piper chaba - Piperaceae - piperchabamide - amide - gastroprotection - piperine

Full Text

References

1 Tewtrakul S, Hase K, Kadota S, Namba T, Komatsu K, Tanaka K. Fruit oil composition of Piper chaba Hunt., P. longum L. and P. nigrum L. J Essent Oil Res. 2000; 12 603-8
2 Matsuda H, Pongpiriyadacha Y, Morikawa T, Ochi M, Yoshikawa M. Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action. Eur J Pharmacol. 2003; 471 59-67
3 Kikuchi F, Nakamura N, Tsuda Y, Kondo K, Yoshimura H. Studies on crude drugs effective on visceral larva migrans. IV. Isolation and identification of larvicidal principles in pepper. Chem Pharm Bull. 1988; 36 2452-65
4 Narui T, Takeuchi M, Ishii R, Ishida T, Okuyama T. Studies on the constituents of Piper hancei of spice from Okinawa. Nat Med. 1995; 49 438-41
5 Addae-Mensah I, Torto F G, Oppong I V, Baxter I, Sanders J KM. N-Isobutyl-trans-2-trans-4-eicosadienamide and other alkaloids of fruits of Piper guineense . Phytochemistry. 1977; 16 483-5
6 Navickiene H MD, Alecio A C, Kato M J, Bolzani V S, Young M CM, Cavalheiro A J, Furlan M. Antifungal amides from Piper hispidum and Piper tuberculatum . Phytochemistry. 2000; 55 621-6
7 Tabuneng W, Bando H, Amiya T. Studies on the constituents of the crude drug ”Piperis Longi Fructus” on the alkaloids of fruits of Piper longum L. Chem Pharm Bull. 1983; 31 3562-5
8 Shoji N, Umeyama A, Saito N, Takemoto T, Kajiwara A, Ohizumi Y. Dehydropipernonaline, an amide possessing coronary vasodilating activity, isolated from Piper longum L. J Pharm Sci. 1986; 75 1188-9
9 Koul S K, Taneja S C, Agarwal V K, Dhar K L. Minor amides of Piper species. Phytochemistry. 1988; 27 3523-7
10 Okogun J I, Ekong D EU. Extracts from the fruits of Piper guineense Schum. and Thonn. J Chem Soc Perkin Trans. 1974; 1 2195-8
11 Stöhr J R, Xiao P G, Bauer R. Isobutylamides and a new methylbutylamide from Piper sarmentosum . Planta Med. 1999; 65 175-7
12 Kikuzaki H, Kawabata M, Ishida E, Akazawa Y, Takei Y, Nakatani N. LC-MS analysis and structural determination of new amides from Javanese long pepper (Piper retrofractum). Biosci Biotech Biochem. 1993; 57 1329-33
13 Kijjoa A, Pinto M MM, Tantisewie B, Herz W. A new linalool derivative and other constituents from Piper ribesoides . Planta Med. 1989; 55 193-4
14 Parmar V S, Jain S C, Bisht K S, Jain R, Taneja P, Jha A, Tyagi O D, Prasad A K, Wengel J, Olsen C E, Boll P M. Phytochemistry of the genus Piper . Phytochemistry. 1997; 46 597-673
15 Atal C K, Dubey R K, Singh J. Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism. J Pharmacol Exp Ther. 1985; 232 258-62
16 Singh J, Dubey R K, Atal C K. Piperine-mediated inhibition of glucuronidation activity in isolated epithelial cells of the guinea-pig small intestine: evidence that piperine lowers the endogeneous UDP-glucuronic acid content. J Pharmacol Exp Ther. 1986; 236 488-93
17 Bajad S, Bedi K L, Singla A K, Johri R K. Antidiarrhoeal activity of piperine in mice. Planta Med. 2001; 67 284-7
18 Unchern S, Nagata K, Saito H, Fukuda J. Reduction of neurite extension by piperine, examined on hippocampal and septal neurons in serum-free cultures. Boil Pharm Bull. 1994; 17 898-901
19 Takaki M, Jin J G, Lu Y F, Nakayama S. Effects of piperine on the motility of the isolated guinea-pig ileum: comparison with capsaicin. Eur J Pharmacol. 1990; 186 71-7
20 Capasso R, Izzo A A, Borrelli F, Russo A, Sautebin L, Pinto A, Capasso F, Mascolo N. Effect of piperine, the active ingredient of black pepper, on intestinal secretion in mice. Life Sci. 2002; 71 2311-7
21 Szolcsanyi J, Bartho L. Capsaicin-sensitive afferents and their role in gastroprotection: an update. J Physiol Paris. 2001; 95 181-8

Masayuki Yoshikawa

Kyoto Pharmaceutical University

Misasagi

Yamashina-ku

Kyoto 607-8412

Japan

Phone: +81-75-595-4633

Fax: +81-75-595-4768

Email: shoyaku@mb.kyoto-phu.ac.jp.