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

Zhao, Junping; Nakamura, Norio; Hattori, Masao; Kuboyama, Tomoharu; Tohda, Chihiro; Komatsu, Kenshi

doi:10.1248/cpb.50.760

Cited by 178 publications

(140 citation statements)

References 15 publications

(16 reference statements)

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“…A less common cleavage is that occurring in a transdiequatorial manner, as found in 9 and 10 (14), later reported as new by Kuroyanagi et al (19), and in 4-deoxywithaperuvin (11) (20). Compound 12 represents an unusual variant of the above, with a 3a,6a-epoxy bridge (21), which could derive from the cyclization of 10 also present in the same extract. While Michael-type addition of alcohols to the D 2 -1-keto system of withanolides is well known, intramolecular addition is rare.…”

Section: B6b-epoxywithanolides and Related Compoundsmentioning

confidence: 90%

“…The configurations at positions 24 and 25 of the latter compound were not elucidated. Also within this group are three withanolides with an additional sugar moiety at C-27 (21), withanosides VIII (35), IX (36), and X (37) (this structure was reported again as new, one year later (15)), an analogue of withanoside VI with a monosacharide at C-3 named withanoside XI (38) (21), and an analogue of withanoside IV with a trisacharide moiety at C-3 (39) (15 Glucosomniferanolide (57), isolated from W. somnifera, contains a glucose unit at the tertiary hydroxy group at C-20 (39). This compound was described as having a (22S) configuration, opposite to that found in all withanolides with a d-lactone side chain.…”

Section: B6b-epoxywithanolides and Related Compoundsmentioning

confidence: 99%

“…Several withanolides isolated from the methanolic extract of W. somnifera roots as well as the extract itself, have been shown to possess neurite outgrowth activity (21,261). Withanoside IV (31) and VI (32) predominantly induced dendritic outgrowth in normal cortical neurons, while withanolide A (504) predominantly induced axon outgrowth (262).…”

Section: Synaptogenesis and Neuritic Outgrowthmentioning

confidence: 99%

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Withanolides and Related Steroids

Misico

Nicotra

Oberti

et al. 2011

Progress in the Chemistry of Organic Natural Products Vol. 94

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Section: B6b-epoxywithanolides and Related Compoundsmentioning

confidence: 90%

Section: B6b-epoxywithanolides and Related Compoundsmentioning

confidence: 99%

Section: Synaptogenesis and Neuritic Outgrowthmentioning

confidence: 99%

See 1 more Smart Citation

Withanolides and Related Steroids

Misico

Nicotra

Oberti

et al. 2011

Progress in the Chemistry of Organic Natural Products Vol. 94

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“…To date, up to 19 withanolide derivatives have been isolated from Withania roots [174]. Recently, Withania and its active components were shown to scavenge free radicals and to inhibit lipid peroxydation [175].…”

Section: Other Anti-glycative Compoudsmentioning

confidence: 99%

Plant-Derived Agents with Anti-Glycation Activity

Odjakova¹,

Popova²,

Sharif³

et al. 2012

Glycosylation

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“…Furthermore, the orientation of the hydroxy group at C-3 was determined as α due to the small coupling constant (J = 2.2 Hz) between H-3 (δ 4.33, brs)/H-4β (δ 2.81, dd, J = 2.2, 15.8 Hz) and the NOESY correlations of H-3/H-1β, H-2β, and H-4β. Thus, the structure of 14 (withalongolide N) was assigned as 28-O-β-D-glucopyranosyl-3α-hydroxy-6-oxo-19-norwitha-5(10), 24-dienolide. Eight known compounds were identified by comparison of their data with those published in the literature, as seven withanolides, sitoindoside IX (15), 18 withaferin A (16), 1,13 2,3-dihydro-3β-methoxywithaferin A (17), 15 viscosalactone B (18), 22 2,3-dihydro-3β-O-sulfate withaferin A (19), 17 2,3-dihydrowithaferin A (20), 15 and 3α,6α-epoxy-4β,5β,27-trihydroxy-1-oxowitha-24-enolide (21), 23 and a flavonoid glucoside, rutin (22). 24 The full assignments of the NMR data of 15, 16, 17, 18, and 19 are listed in Tables 2−5, as these data were either unavailable, incomplete, or in need of revision within the published literature.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Cytotoxic withanolide constituents of Physalis longifolia

Zhang¹,

Samadi²,

Gallagher³

et al. 2012

Planta Med

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Fourteen new withanolides, 1−14, named withalongolides A−N, respectively, were isolated from the aerial parts of Physalis longifolia together with eight known compounds (15−22). The structures of compounds 1−14 were elucidated through spectroscopic techniques and chemical methods. In addition, the structures of withanolides 1, 2, 3, and 6 were confirmed by X-ray crystallographic analysis. Using a MTS viability assay, eight withanolides (1, 2, 3, 7, 8, 15, 16, and 19) and four acetylated derivatives (1a, 1b, 2a, and 2b) showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal fibroblast (MRC-5) cells with IC 50 values in the range between 0.067 and 9.3 μM.C lassically defined withanolides are a group of C 28 ergostane-type steroids with a C-22,26 δ-lactone group, first isolated from the genus Withania. 1 They are present primarily in the Solanaceae family, which includes the genera Acnistus, Datura, Dunalia, Jaborosa, Nicandra, Physalis, Withanolides have attracted interest in recent years mainly due to their exhibition of significant biological activities, inclusive of antimicrobial, antitumor, anti-inflammatory, immunomodulatory, and insect-antifeedant activities. 2,3,6 It has been reported that those withanolides displaying the most promising antitumor characteristics contain an α,β-unsaturated ketone in ring A, a 5β,6β-epoxy group in ring B, and a nine-carbon side chain with an α,β-unsaturated δ-lactone group. 10 The typical withanolide withaferin A (16) (Figure 1) contains these three moieties and has been shown in vitro and in vivo to suppress the growth of an array of tumor cells, including breast, pancreatic, prostate, lung, leukemia, and head and neck squamous cell carcinoma (HNSCC), by inducing apoptosis, 11 thus possessing potential application as an antiproliferative agent. As part of an ongoing study of withanolides from plant sources, 11,12 a library of 224 native plant extracts from the U.S. Great Plains was evaluated for cytotoxic activities against HNSCC and melanoma cell lines using the MTS viability assay. One of the most promising leads, Physalis longifolia Nutt. (Solanaceae), commonly known as "long leaf groundcherry", was subjected to a phytochemical investigation, and the results are presented herein, including the details of the isolation and structure elucidation of 14 new withanolides (1−14), four acetylated derivatives (1a, 1b, 2a, and 2b), and eight known compounds (15−22). Their cytotoxicity was determined against HNSCC (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal fibroblast (MRC-5) cells. This constitutes the first report of a phytochemical and bioactivity study of P. longifolia. ■ RESULTS AND DISCUSSIONThe CH 2 Cl 2 −MeOH (1:1) extract of the aerial parts of the title plant and the EtOAc-soluble and n-BuOH-soluble fractions showed cytotoxicity against the above-mentioned cells with IC 50 values in the range between 0.7 and 9.8 μg/mL using a MTS assay. All ...

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

Cited by 178 publications

References 15 publications

Withanolides and Related Steroids

Withanolides and Related Steroids

Plant-Derived Agents with Anti-Glycation Activity

Cytotoxic withanolide constituents of Physalis longifolia

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