Steroidal Glycosides from the Fruits of Solanum viarum

Abstract

Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae) is a major source of steroidal raw material, and four glycosides of solasodine and diosgenin are reported to occur in its fruits and roots, respectively. 1) As part of a continuing study of the steroidal constituents of solanaceous plants, 2) we now describe the isolation and structural elucidation of three new steroidal glycosides and seven known steroidal glycosides from the fruits of S. viarum.The MeOH extract of the fruits of S. viarum was successively subjected to Diaion HP20, silica gel, Sephadex LH-20, and Chromatorex octadecyl silica (ODS) column chromatography as well as HPLC on ODS, to afford ten steroidal glycosides (1-10).Compounds 4-10 were identified as P-d [pregna-5,16-dien-3b-ol-20-one 4,7) anguivioside XV (9), 8,9) and aculeatiside A (10), 10) respectively, based on comparison with their physical and spectral data with authentic samples or those already reported ( Fig. 1 C-NMR signals were assigned in detail with the help of 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) spectra, and the planar structure of 1 was determined (Fig. 2). The 13 C-NMR data of the A and B rings of the aglycone moiety and the sugar moiety were considerably similar to those of 8, and nuclear Overhauser effect (NOE) correlations were observed between H-14 and H-17, H 3 -18 and H-20, and H 3 -18 and H 3 -21 in the nuclear Overhauser ef- Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.

In vitro evaluation of nematicidal properties of Solanum sisymbriifolium and S. nigrum extracts on Pratylenchus goodeyi

“…In fact, it is well known that plants of the family Solanaceae are sources of secondary metabolites which act as bioactivc compounds. such as alkaloids, flavonoids and saponins that have a broad spectrum of activity (Evans et al, 1984;Eltayeb et al, 1997;Zhou et al, 2006;Ono et al, 2009;Cai et al, 2010). Tbe water extracts obtained from dry and fresh plants demonstrated the same efficacy on P. goodeyi mortality as the water extracts from the sequential solvent extraction.…”

Observations on traditional usage of ethnomedicinal plants in humans and animals of Kangra and Chamba districts of Himachal Pradesh in North-Western Himalaya, India

“…Nerve sedative, hypertensive and analgesic (Choudhary et al, 2005) Coumarins (selinidin, vaginidin, angelicin, oroselol, lomatin), flavone derivative selinone (Chauhan, 1999) Solanum nigrum L., Solanaceae Antitumorigenic, antioxidant, antiinflammatory, emollient, hepatoprotective, diuretic, antipyretic, treat flu, cough, headache, stomachache, ophthalmic diseases, obesity, jaundice, constipation, hepatitis and diarrhea (Singh and Kumar, 2000;Lee and Lim, 2003;Acharya and Pokhrel, 2006;Ballabh and Chaurasia, 2009;Mahmood et al, 2013;Kayani et al, 2014;Khan et al, 2015) Alkaloids, saponins, tannins, glycosides, coumarins, terpenoids and flavonoids (Djaafar and Ridha, 2014) Solanum viarum Dunal, Solanaceae Piles, dysentery, toothache, influence central nervous system, remove blockage from teats Steroidal glycosides (Ono et al, 2009) of the animals and used in birth control pills (Chauhan, 1999;Singh and Kumar, 2000;Sharma et al, 2013a;Sharma et al, 2014b;Shah et al, 2015) Spilanthes acmella (L.) L., Asteraceae Toothache and oral sore (Ong and Nordiana, 1999;Kumar and Sharma, 2014) Spilanthol, β-sitosterol, stigmasterol, α-amyrin, β-amyrin, limonene, β-caryophyllene, β-ocimene, germacrene-D, myrecene, 3-acetylaleuritolic acid, vanillic acid, β-sitostenone, scopoletin, ferulic acid and isoferulic acid (Dubey et al, 2013) Tanacetum dolichophyllum (Kitam.) Kitam., Asteraceae…”

Chemical constituents from Solanum glabratum Dunal var. sepicula

“…The attachment of D-rhamnose and the second D-glucose moieties to carbons C-2 Gal and C-3 Gal, respectively, was confirmed from the long range correlations of their anomeric carbons (δ C 102.3, H-1 Rh and 105.9, H-1 Glc ) to the respective protons (δ H 3.77, H-2 Gal and 3.74, H-3 Gal ), respectively. The full assignment of the protons and carbons of compound 3 was further confirmed by the analysis of 2D NMR spectra ( 1 H-1 H gDQCOSY, gHSQCAD, gHMBCAD, ROESY and zTOCSY) and by comparison to the published data of the related glycosides [17,18,22,23]. Thus, the structure of compound 3 was identified as (25R)-spirost-5-en-3-…”