Planta Med 2010; 76(6): 635-639
DOI: 10.1055/s-0029-1240631
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Triterpenoids from Brazilian Ginseng, Pfaffia paniculata

Jing Li1 , Atul N. Jadhav2 , Ikhlas A. Khan1 , 2
  • 1Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS, USA
  • 2National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
Weitere Informationen

Publikationsverlauf

received June 23, 2009 revised September 28, 2009

accepted October 24, 2009

Publikationsdatum:
25. November 2009 (online)

Abstract

Two new nortriterpenoids, pfaffine A and B (12), were isolated from the roots of Pfaffia paniculata Kuntze, along with ten known compounds including four ecdysteroids, ecdysone (3), 20-hydroxyecdysone (4), pterosterone (5), rapisterone (6), five triterpenoids, pfaffic acid (7), pfameric acid (8), mesembryanthemoidigenic acid (9), calenduloside E 6′-methyl ester (10), oleanolic acid 28-O-β-D-glucopyranoside (11), and one monoterpene glycoside (+)-angelicoidenol-2-O-β-D-glucopyranoside (12). The structures of the new compounds were elucidated as 3β,16β-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid (1), and 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid-28-O-β-D-glucoside (2) through the extensive analysis of 1D- (1H, 13C, DEPT) and 2D‐NMR (COSY, HSQC, HMBC, NOESY) spectra, as well as by a chemical method.

References

  • 1 Vasconcelos J M O. Estudo taxonômico sobre Amaranthaceae no RS, Brasil. Porto Alegre; Universidade Federal do Rio Grande do Sul 1982: 151 Dissertação de Mestrado, Curso de Pós-Graduação em Botânica.
  • 2 Oliveira F. Pfaffia paniculata (Martius) Kuntze – O ginseng brasileiro.  Rev Bras Farmacogn. 1986;  1 86-92
  • 3 Wakunaga Pharmaceutical Co., Ltd., Japan (Assignee). β-Ecdysone from Pfaffia paniculata. JP 59010600. 
  • 4 Takemoto T, Nishimoto N, Nakai S, Takagi N, Hayashi S, Odashima S, Wada Y. Pfaffic acid, a novel nortriterpene from Pfaffia paniculata Kuntze.  Tetrahedron Lett. 1983;  24 1057-1060
  • 5 Nishimoto N, Nakai S, Takagi N, Hayashi S, Takemoto T, Odashima S, Kizu H, Wada Y. Pfaffosides and nortriterpenoid saponins from Pfaffia paniculata.  Phytochemistry. 1984;  23 139-142
  • 6 Chan Y Y, Wu T S, Kuoh C S, Damu Amooru G. A new phytoecdysteroid from Ajuga taiwanensis.  Chem Pharm Bull. 2005;  53 836-838
  • 7 Wang T, Cui S Y, Suo Y R, Lu R H. Studies on water-soluble chemical constituents in root of Achyranthes bidentata.  China J Chin Mater Med. 2004;  29 649-652
  • 8 Coll J, Reixach N, Sánchez-Baeza F, Casas J, Camps F. New ecdysteroids from Polypodium vulgare.  Tetrahedron. 1994;  50 7247-7252
  • 9 Baltaev U A, Abubakirov N K. Phytoecdysteroids of Rhaponticum carthamoides.  Khimiya Prirodnykh Soedinenii. 1987;  5 681-684
  • 10 Shiobara Y, Inoue S S, Kato K, Nishiguchi Y, Oishi Y, Nishimoto N, De Oliveira F, Akisue G, Akisue M K, Hashimoto G. A nortriterpenoid, triterpenoids and ecdysteroids from Pfaffia glomerata.  Phytochemistry. 1993;  32 1527-1530
  • 11 Ikuta A, Itokawa H. Triterpenoids of Akebia quinata callus tissue.  Phytochemistry. 1986;  25 1625
  • 12 Melek F R, Miyase T, El-Gindi O D, Abdel-Khalik S M, Haggag M Y. Saponins from Fagonia mollis.  Phytochemistry. 1996;  42 1405-1407
  • 13 Gupta A, Singh R, Purwar C, Chauhan D, Singh J. Two pentacyclic triterpenes from the stem of Calotropis procera.  Indian J Chem. 2003;  42 B 2030-2033
  • 14 Inoshiri S, Saiki M, Kohda H, Otsuki H, Yamasaki K. Monoterpene glucosides from Berchemia recemosa.  Phytochemistry. 1988;  27 2869-2871
  • 15 Mahato S B, Kundu A P. 13C NMR spectra of pentacyclic triterpenoids-a compilation and some salient features.  Phytochemistry. 1994;  37 1517-1575
  • 16 Woldemichael G M, Wink M. Identification and biological activities of triterpenoid saponins from Chenopodium quinoa.  Agric Food Chem. 2001;  49 2327-2332
  • 17 Hara S, Okabe H, Mihashi K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates.  Chem Pharm Bull. 1987;  35 501-506

Ikhlas A. Khan

School of Pharmacy
National Center for Natural Products Research
The University of Mississippi

University, MS 38677

USA

Telefon: + 1 66 29 15 78 21

Fax: + 1 66 29 15 79 89

eMail: ikhan@olemiss.edu