title: Lipidated steroid saponins from Dioscorea villosa (wild yam).
abstract: Two groups of lipidated steroid saponins including seven new compounds (2, 3, 5, and 7-10) were isolated from the widely used botanical, wild yam (Dioscorea villosa), employing a fractionation protocol of metabolomic mining. This methodology recently led to the isolation of 14 diarylheptanoids from the same plant. Together with these lipidated steroid saponins, they establish additional new markers for D. villosa. The lipidation of steroids with analog long-chain fatty acids containing different degrees of unsaturation generates an entire series of compounds which are difficult to purify and analyze. The structures of the two series of lipidated steroid saponins (series A and B) were established by a combination of 1D and 2D NMR as well as GC-MS after chemical modification. Series A was determined to be a mixture of lipidated spirostanol glycosides (1-5), while series B (6-10) was proved to be a mixture of five lipidated clionasterol glucosides. The latter group represents the first derivatives of clionasterol to be found in D. villosa. The discovery of this specific structural type of aliphatic esters of steroid saponins expands the characterization of the secondary metabolome of D. villosa. It may also inspire biological studies which take into account the lipophilic character and significantly altered physiochemical characteristics of these otherwise relatively polar phytoconstituents.
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Shi-Hui
authors: SH
authors: Dong
authors: Institute for Tuberculosis Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Geping
authors: G
authors: Cai
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States; Institute for Tuberculosis Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: José G
authors: JG
authors: Napolitano
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Dejan
authors: D
authors: Nikolić
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: David C
authors: DC
authors: Lankin
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: James B
authors: JB
authors: McAlpine
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Richard B
authors: RB
authors: van Breemen
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Djaja D
authors: DD
authors: Soejarto
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States; Institute for Tuberculosis Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
authors: Guido F
authors: GF
authors: Pauli
authors: UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States. Electronic address: sc4sa@uic.edu.
authors: Shao-Nong
authors: SN
authors: Chen
mesh_terms: D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification*; D027742:Dioscorea / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification; D055432:Metabolomics; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D012855:Sitosterols / Q000737:chemistry / Q000302:isolation & purification*; D013150:Spirostans / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D036381:Diarylheptanoids; D005227:Fatty Acids; D006027:Glycosides; D010936:Plant Extracts; D012503:Saponins; D012855:Sitosterols; D013150:Spirostans; C025473:gamma-sitosterol
keywords: Dioscorea villosa; Lipidated steroid saponins; Metabolomic mining; Residual complexity; Wild yam
references: J Nat Prod. 2013 Mar 22;76(3):413-9
references: 23356207
references: Steroids. 2005 Jul;70(8):525-30
references: 15894036
references: J Nat Prod. 2012 Feb 24;75(2):238-48
references: 22332915
references: Nat Prod Res. 2010 Mar;24(5):448-56
references: 20306367
references: J Chromatogr A. 2012 Jun 15;1242:26-34
references: 22579361
references: Biol Pharm Bull. 2013;36(1):36-40
references: 23302635
references: J Am Chem Soc. 1947 Sep;69(9):2167-2230
references: 20262743
references: J Agric Food Chem. 2011 Oct 12;59(19):10435-41
references: 21916514
references: Tuberculosis (Edinb). 2013 May;93(3):322-9
references: 23454100
references: Phytochem Anal. 2012 Sep-Oct;23(5):462-8
references: 22407490
references: Indian J Exp Biol. 1992 May;30(5):367-70
references: 1459613
references: J Pharm Biomed Anal. 2011 Nov 1;56(3):650-4
references: 21795000
references: Magn Reson Chem. 2007 Nov;45(11):1001-5
references: 17887511
references: Anal Chem. 2007 Aug 15;79(16):6102-10
references: 17636880
references: J Org Chem. 2013 Apr 5;78(7):2827-39
references: 23461697
references: Anal Chem. 2012 Jan 3;84(1):428-39
references: 22132738
references: J Nat Prod. 2012 Apr 27;75(4):834-51
references: 22482996
references: Int J Pharm. 2013 Jan 30;441(1-2):680-6
references: 23107795
references: J Pharm Biomed Anal. 2008 Dec 15;48(5):1411-6
references: 19027255
references: J Proteome Res. 2011 Aug 5;10(8):3660-73
references: 21671558
references: J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Mar 25;817(2):271-5
references: 15686995
references: J Sep Sci. 2008 Jul;31(13):2486-91
references: 18646278
references: Planta Med. 2005 Oct;71(10):960-1
references: 16254830
references: J Nat Prod. 2012 Dec 28;75(12):2168-77
references: 23245349