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New gingerdione from the rhizomes of Zingiber officinale
Fitoterapia 71 Ž2000. 716᎐718
Phytochemical communication
New gingerdione from the rhizomes of Zingiber officinale Reena Charles, S.N. GargU , Sushil Kumar Central Institute of Medicinal and Aromatic Plants, P.O. CIMAP, Lucknow-226015, India
Received 26 February 2000; accepted in revised form 2 May 2000
Abstract A new gingerdione has been isolated from the rhizomes of Zingiber officinale and identified as 1-dehydrogingerdione Ž1.. 䊚 2000 Elsevier Science B.V. All rights reserved. Keywords: Zingiber officinale; 1-Dehydrogingerdione
Plant. Fresh rhizomes of Zingiber officinale Roscoe ŽZingiberaceae. were purchased from a local market in December 1998 and identified by the Department of Taxonomy of our Institute. A voucher specimen has been deposited at the herbarium of Central Institute of Medicinal and Aromatic Plants Lucknow. Uses in traditional medicines. The rhizomes Žginger: commonly known as ‘adrak’. are frequently prescribed in Indian system of medicine for the treatment of cough, stomach-ache, asthma, worms, leprosy, skin, gastrointestinal and respiratory diseases. Ginger is a well-known spice, widely used for flavoring variety of foods and for the preparation of oleoresins and volatile oils. Gingerols are the constituents responsible for the taste of ginger, including the pungency of the oleoresins w1x. Antiulcer w2x, antifungal w3x, prostaglandin biosynthesis inhibiting w4x, antirhinoviral w5,6x, insecticidal w7x and antioxidant activities w8x have been reported from the rhizomes. U
Corresponding author. Tel.: q91-522-342676; fax: q91-522-342666. E-mail address: [email protected] ŽS.N. Garg.. 0367-326Xr00r$ - see front matter 䊚 2000 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 0 . 0 0 2 1 5 - X
R. Charles et al. r Fitoterapia 71 (2000) 716᎐718
717
Previously isolated classes of constituents. Gingerols and shogaols w9᎐11x, diarylheptanoids w3,12,13x, phenylbutenoids w14x, flavonoids w15,16x, glycosides and gingesulphonic acids w17x, cassumunaquinones w18x and sesquiterpenes w19,20x. New-isolated constituent. 1-Dehydrogingerdione Ž1. Žyield: 0.003% on fresh wt. basis..
1-Dehydrogingerdione Ž1.. Yellow crystals, Rf 0.50 Žbenzene., mp 84᎐85⬚C, w ␣ x15 q 20.1⬚ Žc 0.41, MeOH.; IR bands ŽKBr.; 3940, 3812,3612,1750, 1642, 1526, 1127, 1146, 968, 824 cmy1 ; 1 H-NMR Ž300 MHz, CDCl3 .: ␦ 7.52 Ž1H, d, J 16 Hz, H-1., 7.07 Ž1H, dd, J 8.5, 1.5 Hz, H-6⬘., 7.01 Ž1H, d, J 1.5 Hz, H-2⬘., 6.93 Ž1H, d, J 8.5 Hz, H-5⬘., 6.32 Ž1H, d, J 16 Hz, H-2., 5.62 Ž2H, s, H-4., 3.94 Ž3H, s, OMe., 2.37 Ž2H, m, H-6., 1.65 Ž2H, m, H-7., 1.32 Ž4H, m, H-8 and H-9., 0.91 Ž3H, t, J 7 Hz, H-10.; 13 C-NMR Ž75 MHz CDCl3 .: 197.50 ŽC-5., 177.50 ŽC-3., 149.5 ŽC-3⬘., 147.1 ŽC-4⬘., 140.24 ŽC-1. 126.14 ŽC-1⬘., 122.32 ŽC-6⬘., 120.42 ŽC-2., 115.34 ŽC-5⬘., 112.16 ŽC-2⬘., 100.12 ŽC-4., 56.82 ŽOCH3 ., 41.32 ŽC-6., 33.34 ŽC-7., 28.82 ŽC-8., 24.56 ŽC-9., 15.78 ŽC-10.; EI-MS mrz Žrel int..: 290 wMxq Ž36.2., 219 Ž33.3., 191 Ž45.7., 177 Ž100., 113 Ž30., 86 Ž60., 71 Ž25..
Acknowledgements The authors are grateful to Regional Sophisticated Instrumentation Centre, Central Drug Research Institute, Lucknow for providing 1 H-NMR, 13 C-NMR and mass spectra of the compound and also to Taxonomy Department of Central Institute of Medicinal and Aromatic Plants Lucknow for establishing the identity of the plant.
References w1x Anonymous. The wealth of India 1948, XI. New Delhi, India: CSIR, 1989. w2x Yoshikawa M, Hatakeyame S, Taniguchi K, Matuda H, Yamahara J. Chem Pharm Bull 1992;40:2239.
718 w3x w4x w5x w6x w7x w8x w9x w10x w11x w12x w13x w14x w15x w16x w17x w18x w19x w20x
R. Charles et al. r Fitoterapia 71 (2000) 716᎐718 Endo K, Kanno E, Oshima Y. Phytochemistry 1990;29:797. Kiuchi F, Iwakami S, Shobuya M, Hanaoka F, Sankawa US. Chem Pharm Bull 1992;40:387. Denyer CV, Jackson P, Loaker DM. J Nat Prod 1994;57:658. Toshiya M, Akiko J. J Food Agric Chem 1994;42:1850. Nugroho BW, Schwarz B, Wray V, Proksch P. Phytochemistry 1996;41:129. Jitoe A, Masuda T, Tengoh IGP, Suprapta ND, Gara IW, Nakatani N. J Agric Food Chem 1992;40:1337. Wu TS, Wu YC, Wu PL, Chern CY, Leu Y, Chan Y. Phytochemistry 1998;48:889. Kiuchi P, Iwakami S, Masaaki S, Hanaoka F, Sankawa U. Chem Pharm Bull 1992;40:387. Kikuzaki H, Tsai SM, Nakatani N. Phytochemistry 1992;31:1783. Kikuzaki H, Kobayashi M, Nakatani N. Phytochemistry 1991;30:3347. Kikuzaki H, Usuguchi J, Nakatani N. Chem Pharm Bull 1991;39:120. Masuda T, Jitoe A. Phytochemistry 1993;32:357. Nakatani N, Jitoe A, Masuda T, Yonemori S. Agric Bio Chem 1991;55:455. Masuda T, Jitoe A, Kato S, Nakatani N. Phytochemistry 1991;30:239. Yoshikawa M, Yamaguchi S, Kumini K et al. Chem Pharm Bull 1994;42:1226. Hildegard D, Rudolf H, Andrew P. Naturforsch Z Biosci 1980;35:154. Akhila A, Tewari R. CROMAP 1994;6:143. Terhune SJ, Hogg JW, Bromstein AC, Lawrence BM. Can J Chem 1975;53:3285.
Phytochemical communication
New gingerdione from the rhizomes of Zingiber officinale Reena Charles, S.N. GargU , Sushil Kumar Central Institute of Medicinal and Aromatic Plants, P.O. CIMAP, Lucknow-226015, India
Received 26 February 2000; accepted in revised form 2 May 2000
Abstract A new gingerdione has been isolated from the rhizomes of Zingiber officinale and identified as 1-dehydrogingerdione Ž1.. 䊚 2000 Elsevier Science B.V. All rights reserved. Keywords: Zingiber officinale; 1-Dehydrogingerdione
Plant. Fresh rhizomes of Zingiber officinale Roscoe ŽZingiberaceae. were purchased from a local market in December 1998 and identified by the Department of Taxonomy of our Institute. A voucher specimen has been deposited at the herbarium of Central Institute of Medicinal and Aromatic Plants Lucknow. Uses in traditional medicines. The rhizomes Žginger: commonly known as ‘adrak’. are frequently prescribed in Indian system of medicine for the treatment of cough, stomach-ache, asthma, worms, leprosy, skin, gastrointestinal and respiratory diseases. Ginger is a well-known spice, widely used for flavoring variety of foods and for the preparation of oleoresins and volatile oils. Gingerols are the constituents responsible for the taste of ginger, including the pungency of the oleoresins w1x. Antiulcer w2x, antifungal w3x, prostaglandin biosynthesis inhibiting w4x, antirhinoviral w5,6x, insecticidal w7x and antioxidant activities w8x have been reported from the rhizomes. U
Corresponding author. Tel.: q91-522-342676; fax: q91-522-342666. E-mail address: [email protected] ŽS.N. Garg.. 0367-326Xr00r$ - see front matter 䊚 2000 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 0 . 0 0 2 1 5 - X
R. Charles et al. r Fitoterapia 71 (2000) 716᎐718
717
Previously isolated classes of constituents. Gingerols and shogaols w9᎐11x, diarylheptanoids w3,12,13x, phenylbutenoids w14x, flavonoids w15,16x, glycosides and gingesulphonic acids w17x, cassumunaquinones w18x and sesquiterpenes w19,20x. New-isolated constituent. 1-Dehydrogingerdione Ž1. Žyield: 0.003% on fresh wt. basis..
1-Dehydrogingerdione Ž1.. Yellow crystals, Rf 0.50 Žbenzene., mp 84᎐85⬚C, w ␣ x15 q 20.1⬚ Žc 0.41, MeOH.; IR bands ŽKBr.; 3940, 3812,3612,1750, 1642, 1526, 1127, 1146, 968, 824 cmy1 ; 1 H-NMR Ž300 MHz, CDCl3 .: ␦ 7.52 Ž1H, d, J 16 Hz, H-1., 7.07 Ž1H, dd, J 8.5, 1.5 Hz, H-6⬘., 7.01 Ž1H, d, J 1.5 Hz, H-2⬘., 6.93 Ž1H, d, J 8.5 Hz, H-5⬘., 6.32 Ž1H, d, J 16 Hz, H-2., 5.62 Ž2H, s, H-4., 3.94 Ž3H, s, OMe., 2.37 Ž2H, m, H-6., 1.65 Ž2H, m, H-7., 1.32 Ž4H, m, H-8 and H-9., 0.91 Ž3H, t, J 7 Hz, H-10.; 13 C-NMR Ž75 MHz CDCl3 .: 197.50 ŽC-5., 177.50 ŽC-3., 149.5 ŽC-3⬘., 147.1 ŽC-4⬘., 140.24 ŽC-1. 126.14 ŽC-1⬘., 122.32 ŽC-6⬘., 120.42 ŽC-2., 115.34 ŽC-5⬘., 112.16 ŽC-2⬘., 100.12 ŽC-4., 56.82 ŽOCH3 ., 41.32 ŽC-6., 33.34 ŽC-7., 28.82 ŽC-8., 24.56 ŽC-9., 15.78 ŽC-10.; EI-MS mrz Žrel int..: 290 wMxq Ž36.2., 219 Ž33.3., 191 Ž45.7., 177 Ž100., 113 Ž30., 86 Ž60., 71 Ž25..
Acknowledgements The authors are grateful to Regional Sophisticated Instrumentation Centre, Central Drug Research Institute, Lucknow for providing 1 H-NMR, 13 C-NMR and mass spectra of the compound and also to Taxonomy Department of Central Institute of Medicinal and Aromatic Plants Lucknow for establishing the identity of the plant.
References w1x Anonymous. The wealth of India 1948, XI. New Delhi, India: CSIR, 1989. w2x Yoshikawa M, Hatakeyame S, Taniguchi K, Matuda H, Yamahara J. Chem Pharm Bull 1992;40:2239.
718 w3x w4x w5x w6x w7x w8x w9x w10x w11x w12x w13x w14x w15x w16x w17x w18x w19x w20x
R. Charles et al. r Fitoterapia 71 (2000) 716᎐718 Endo K, Kanno E, Oshima Y. Phytochemistry 1990;29:797. Kiuchi F, Iwakami S, Shobuya M, Hanaoka F, Sankawa US. Chem Pharm Bull 1992;40:387. Denyer CV, Jackson P, Loaker DM. J Nat Prod 1994;57:658. Toshiya M, Akiko J. J Food Agric Chem 1994;42:1850. Nugroho BW, Schwarz B, Wray V, Proksch P. Phytochemistry 1996;41:129. Jitoe A, Masuda T, Tengoh IGP, Suprapta ND, Gara IW, Nakatani N. J Agric Food Chem 1992;40:1337. Wu TS, Wu YC, Wu PL, Chern CY, Leu Y, Chan Y. Phytochemistry 1998;48:889. Kiuchi P, Iwakami S, Masaaki S, Hanaoka F, Sankawa U. Chem Pharm Bull 1992;40:387. Kikuzaki H, Tsai SM, Nakatani N. Phytochemistry 1992;31:1783. Kikuzaki H, Kobayashi M, Nakatani N. Phytochemistry 1991;30:3347. Kikuzaki H, Usuguchi J, Nakatani N. Chem Pharm Bull 1991;39:120. Masuda T, Jitoe A. Phytochemistry 1993;32:357. Nakatani N, Jitoe A, Masuda T, Yonemori S. Agric Bio Chem 1991;55:455. Masuda T, Jitoe A, Kato S, Nakatani N. Phytochemistry 1991;30:239. Yoshikawa M, Yamaguchi S, Kumini K et al. Chem Pharm Bull 1994;42:1226. Hildegard D, Rudolf H, Andrew P. Naturforsch Z Biosci 1980;35:154. Akhila A, Tewari R. CROMAP 1994;6:143. Terhune SJ, Hogg JW, Bromstein AC, Lawrence BM. Can J Chem 1975;53:3285.