Planta Med 2010; 76(15): 1758-1761
DOI: 10.1055/s-0030-1249807
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Cucurbitane-Type Triterpenoids from Momordica charantia

Jun Ma1 , Paul Whittaker1 , Amy C. Keller2 , Eugene P. Mazzola1 , Rahul S. Pawar1 , Kevin D. White1 , John H. Callahan1 , Edward J. Kennelly2 , Alexander J. Krynitsky1 , Jeanne I. Rader1
  • 1Office of Regulatory Science, Center for Food Safety and Applied Nutrition, U. S. Food and Drug Administration, College Park, MD, USA
  • 2Department of Biological Sciences, Lehman College and The Graduate Center, The City University of New York, Bronx, NY, USA
Further Information

Publication History

received January 15, 2010 revised March 5, 2010

accepted March 9, 2010

Publication Date:
08 April 2010 (online)

Abstract

One new cucurbitane-type triterpenoid glycoside, momordicoside X (1), together with five known cucurbitane-type triterpenoids and related glycosides, 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al (2), momordicine I (3), momordicine II (4), 3-hydroxycucurbita-5,24-dien-19-al-7,23-di-O-β-glucopyranoside (5), and kuguaglycoside G (6), were isolated from the whole plant of Momordica charantia. Their structures were determined by chemical and spectroscopic methods. Momordicoside X (1) was evaluated for insulin secretion activity in an in vitro insulin secretion assay and displayed moderate activity.

References

  • 1 Basch E, Gabardi S, Ulbricht C. Bitter melon (Momordica charantia): a review of efficacy and safety.  Am J Health Syst Pharm. 2003;  60 356-359
  • 2 Li Q Y, Chen H B, Liu Z M, Wang B, Zhao Y Y. Cucurbitane triterpenoids from Momordica charantia.  Magn Reson Chem. 2007;  45 451-456
  • 3 Akihisa T, Higo N, Tokuda H, Ukiya M, Akazawa H, Tochigi Y, Kimura Y, Suzuki T, Nishino H. Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects.  J Nat Prod. 2007;  70 1233-1239
  • 4 Wang Y H, Avula B, Liu Y, Khan I A. Determination and quantitation of five cucurbitane triterpenoids in Momordica charantia by reversed-phase high-performance liquid chromatography with evaporative light scattering detection.  J Chromatogr Sci. 2008;  46 133-136
  • 5 Liu Y, Ali Z, Khan I A. Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.  Planta Med. 2008;  74 1291-1294
  • 6 Okabe H, Miyahara Y, Yamaguchi T, Miyahara K, Kawasaki T. Studies on the constituents of Momordica charantia L. I. Isolation and characterization of momordicosides A and B, glycosides of a pentahydroxy-cucurbitane triterpene.  Chem Pharm Bull. 1980;  28 2753-2762
  • 7 Miyahara Y, Okabe H, Yamaguchi T. Studies on the constituents of Momordica charantia L. II. Isolation and characterization of minor seed glycosides, momordicosides C, D and E.  Chem Pharm Bull. 1981;  29 1561-1566
  • 8 Yasuda M, Iwamoto M, Okabe H, Yamaguchi T. Structures of momordicines I, II and III, the bitter principles in the leaves and vines of Momordica charantia.  Chem Pharm Bull. 1984;  32 2044-2047
  • 9 Fatope M O, Takeda Y, Yamashita H, Okabe H, Yamaguchi T. New cucurbitane triterpenoids from Momordica charantia.  J Nat Prod. 1990;  53 1491-1497
  • 10 Chang C I, Chen C R, Liao Y W, Cheng H L, Chen Y C, Chou C H. Cucurbitane-type tripterpenoids from Momordica charantia.  J Nat Prod. 2006;  69 1168-1171
  • 11 Chang C I, Chen C R, Liao Y W, Cheng H L, Chen Y C, Chou C H. Cucurbitane-type triterpenoids from the stems of Momordica charantia.  J Nat Prod. 2008;  71 1327-1330
  • 12 Chen J, Tian R, Qiu M, Lu L, Zheng Y, Zhang Z. Trinocucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia.  Phytochemistry. 2008;  69 1043-1048
  • 13 Chen J C, Lu L, Zhang X M, Zhou L, Li Z R, Qiu M H. Eight new cucurbitane glycosides, kuguaglycosides A–H, from the root of Momordica charantia L.  Helv Chim Acta. 2008;  91 920-929
  • 14 Harinantenaina L, Tanaka M, Takaoka S, Oda M, Mogami O, Uchida M, Asakawa Y. Momordica charantia constituents and antidiabetic screening of the isolated major compounds.  Chem Pharm Bull. 2006;  54 1017-1021
  • 15 Tan M J, Ye J M, Turner N, Hohnen-Behrens C, Ke C Q, Tang C P, Chen T, Weiss H C, Gesing E R, Rowland A, James D E, Ye Y. Antidiabetic activities of triterpenoids isolated from bitter melon associated with activation of the AMPK pathway.  Chem Biol. 2008;  15 263-273
  • 16 Mekuria D B, Kashiwagi T, Tebayashi S, Kim C S. Cucurbitane triterpenoid oviposition deterrent from Momordica charantia to the leafminer, Liriomyza trifolii.  Biosci Biotechnol Biochem. 2005;  69 1706-1710
  • 17 Yasui H, Kato A, Yazawa M J. Antifeedants to armyworms, Spodoptera litura and Pseudaletia separate, from bitter gourd leaves, Momordica charantia.  Chem Ecol. 1998;  24 803-813
  • 18 Kashiwagi T, Mekuria D B, Dekebo A, Sato K, Tebayashi S, Kim C S. A new oviposition deterrent to the leafminer, Liriomyza trifolii: cucurbitane glucoside from Momordica charantia.  Z Naturforsch C. 2007;  62C 603-607
  • 19 Zhao J, Pawar R S, Ali Z, Khan I A. Phytochemical investigation of Turnera diffusa.  J Nat Prod. 2007;  70 289-292
  • 20 Persaud S J, Al-Majed H, Raman A, Jones P M. Gymnema sylvestre stimulates insulin release in vitro by increased membrane permeability.  J Endocrinol. 1999;  163 207-212

Dr. Jun Ma

U. S. Food and Drug Administration
Center for Food Safety and Applied Nutrition

5100 Paint Branch Parkway

20740 College Park, Maryland

United States

Phone: + 1 30 14 36 17 77

Fax: + 1 30 14 36 30 77

Email: jun.ma@fda.hhs.gov