Isolation of 4.BETA.-hydroxywithanolide E, a new withanolide from Physalis peruvianaL.

Sakurai, Kensuke; Ishii, Hiroshi; Kobayashi, Shinobu; Iwao, Toru

doi:10.1248/cpb.24.1403

Cited by 45 publications

(22 citation statements)

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“…Withanolides bearing hydroxyl groups at C-17 and C-20 positions undergo facile cleavage into two halves on Jones oxidation (148). The reaction was fully utilised in the structure determinations of physalolactone (147) and the withaperuvins isolated from Physalis peruviana (134,142).…”

Section: X-ray Crystallographic Methodsmentioning

confidence: 99%

“…Besides withaferin A and withacnistin, several other structurally related withanolides have been reported to have cytotoxic activity. Compounds that deserve mention are 4~-hydroxywithanolide E (151), withanolide E (150), withanolide D (68) and the trans-diequatorial chlorohydrin ofwithaferin A (3,13,148,(243)(244)(245). Of the different withanolides tested for antineoplastic activity, 4~-hydroxywithanolide E (151) was the most promising on the basis of its activity on B-16 melanosarcoma and L-121O leukemia (148,243) but its activity was less than necessary for clinical investigation (13).…”

Section: Biological Activity Of Withasteroidsmentioning

confidence: 99%

See 1 more Smart Citation

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

Ray¹,

Gupta²

1994

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Section: X-ray Crystallographic Methodsmentioning

confidence: 99%

Section: Biological Activity Of Withasteroidsmentioning

confidence: 99%

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

Ray¹,

Gupta²

1994

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Compounds 1-3 and 5 were identified as 4b-hydroxywithanolide E [14,15], withanolide S [16], 5a-methoxywithanolide S [16], and (3b,4b,5b,6b,17a,22R)-5,6-epoxy-4,14, 17,20,22-pentahydroxy-3-methoxy-1-oxo-ergost-24-en-26-oic acid-d-lactone [17], respectively, by comparison of their physical data with those reported previously. …”

Section: Identification Of Compoundsmentioning

confidence: 99%

Screening of promising chemotherapeutic candidates against human adult T-cell leukemia/lymphoma from plants: active principles from Physalis pruinosa and structure–activity relationships with withanolides

et al. 2011

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Adult T-cell leukemia/lymphoma (ATL) is a peripheral T-cell malignancy caused by human T-cell lymphotropic virus type I (HTLV-1). Clinical manifestations of ATL range from smoldering to chronic, lymphoma and acute subtypes. Patients with acute and lymphoma-type ATL require therapeutic intervention. Conventional chemotherapeutic regimens used against other malignant lymphoma have been administered to ATL patients, but the therapeutic outcomes of acute and lymphoma-type ATL remain very poor. In this study, 214 extracts from 162 plants belonging to 65 families were screened for the purpose of elucidating the anti-proliferative effect against HTLV-1-infected T-cell lines. Extracts from aerial parts of Physalis pruinosa showed potent inhibitory effect. We isolated five withanolides from the extracts by activity-guided fractionation and examined the structure-activity relationships. The presence of a 5β,6β-epoxy function is suggested to be essential for the activity, and the most active principle showed selective toxicity to HTLV-1-infected T-cell lines.

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“…4β‐Hydroxywithanolide E (4HWE) (Fig. ) has been identified as a component of P. peruviana , P. cinerascens , P. angulate , and P. pruinosa . The compound is reported to inhibit the proliferation of various human cancer cell lines derived from breast (MCF‐7 , T‐47D , MDA‐MB‐231 , and SK‐Br‐3 ), pancreas (Panc‐1 ), gingiva (Ca9‐22 ), liver (Hep G2 , Hep 3B ), and lung (A549 ).…”

Section: Introductionmentioning

confidence: 99%