New Withanolides from Withania sp.

Abstract

l-oxo-(22I?)-witha-3,5,24-trienolide] [1] and withasomidienone [27-hydroxy-3-oxo-(22R)witha-1,4,24-trienolide] [2] have been isolated from Withania coagulante and Withania somnífera, respectively. The structures have been determined on the basis of spectroscopic studies.Withania coagulante Dun. (Solanaceae) is widely distributed throughout the drier parts of the South Asian subcontinent (1). The fruit of the plant is commonly used in Sind (Pakistan), North India, and Afghanistan instead of rennet to coagulate milk (2). It is also used as an emetic and in smaller doses as a remedy for dyspepsia arising from chronic liver diseases (3).Withania somnífera Dun., a perennial plant, is widely distributed along the shores of the Mediterranean sea, as well as in India, South Africa, Pakistan and other countries (4). Various therapeutic properties have been attributed to this plant and it has been used in the indigenous system of medicine for the treatment of ulcers, rheumatism, cough, dropsy, consumption, and sensile debility (5).A number of withanolides have been isolated previously from Withania spp. Some of these compounds have shown interesting biological activities. For instance, withaferin A has shown antibactérica! properties against acid-fast bacilli and Gram-positive microorganisms (6-8). 3 ß-Hyd oxy-2,3-dihydrowithanolide F has hepatoprotective activity against CCl4-induced hepatotoxicity in adult albino rats (9). We now describe the isolation and structure elucidation of two new withanolides, coagulin [1] and withasomidienone [2],RESULTS AND DISCUSSION Coagulin [1], C28H36Oé, isolated from W. coagulance, showed a uv spectrum with an absorption at 226 nm characteristic of an ,ß-unsaturated lactone chromophore (10). The ir spectrum displayed bands at 3350,1705, and 1690 cm 1 indicative of a hydroxyl, a six-membered cyclic ketone, and an ,ß-unsaturated lactone, respectively. Positive

Withanolide Derivatives from the Roots of Withania somnifera and Their Neurite Outgrowth Activities.

“…Consequently, compound 1 was designated as (20S,22R)-3a ,6a -epoxy-4b ,5b ,27-trihydroxy-1-oxowitha-24-enolide. Although there have been several reports on isolation of 14,20-epoxy withanolides from Withania spp., 12,14) to the best of our knowledge, compound 1 was the first example of a withanolide with an ether bridge between C-3 and C-6. Withanoside VIII (9) was isolated as a white amorphous powder.…”

“…By comparison with the reported data, fourteen known compounds were identified as withanolide A (2), 4) (20S,22R)-5a,27-dihydroxy-6a,7a-epoxy-1-oxowitha-2,24-dienolide (3), 5) lycium substance B (4), 6) withacoagin (5), 7) (20S,22R)-4b,5b,6a,27-tetrahydroxy-1-oxowitha-2,24-dienolide (6), 8) withanolide D (7), 9) and withaferin A (8), 10) withanosides V (13), 8,11) IV (14), 11) VI (15), 11) III (18), 11) and II (19), 11) coagulin Q (16), 12) and physagulin D (17). 13) Compound 1 was obtained as a white powder.…”

Cholinesterase Inhibiting Withanolides from Withania somnifera

“…10) Previous phytochemical investigations of this plant resulted in the isolation of more than 70 compounds. [10][11][12][13][14] We report here the isolation of two new (1, 2) and four known (3)(4)(5)(6) withanolides from the whole plant of W. somnifera, along with their cholinesterase [acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)] inhibitory activity. AChE is a key component of cholinergic brain synapses and neuromuscular junctions.…”

Biochemical study of root extract of Withania somnifera (L.)plant through HPLC analysis

“…have been identified, extracted, and isolated (Kapoor, 2001;Atta-ur-Rahman, et.al., 1991, 1993Choudary, et.al., 1996;Rastogi and Mehrotra, 1998;Bandyopadhyay and Jha, 2007). At present, knowledge indicated that more than twelve (12) alkaloids, fourty (40) to 0.5% dry weight (DW) (Kapoor, 2001;Anonymous, 2004).…”