The Structure of Physalin P, a Neophysalin from <i>Physalis Alkekengi</i>

Kawai, Maki; Matsumoto, Akihide; Makino, Bunsho; Mori, Hideyuki; Ogura, Tomohito; Butsugan, Yasuo; Ogawa, Kiyoshi; Hayashi, Masahito

doi:10.1246/bcsj.66.1299

Cited by 30 publications

(9 citation statements)

References 7 publications

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“…angulata were separated by silica gel, Sephadex LH-20, ODS open column chromatography, preparative TLC, and preparative HPLC to yield five new physalins, including an uncommon 1,10- seco one, physalin V ( 1 ), physalins VI ( 2 ), VII ( 4 ), and VIII ( 5 ), and a novel 11,15- cyclo one, physalin IX ( 6 ), together with eleven known analogues, 25 β -hydroxyphysalin D ( 7 ) 19 , physalins D 1 ( 3 ), D ( 8 ) 20 , B ( 9 ) 21 , F ( 10 ) 22 , G ( 11 ) 23 , P ( 12 ) 24 , H ( 13 ) 25 , I ( 14 ) 20 , and R ( 15 ) 26 , and isophysalin B ( 16 ) 25 (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities

Sun

Qiu

Zhao

et al. 2017

Sci Rep

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Five new physalins, including a novel 1,10-seco one, physalin V (1), a tricarboxylic acid cycle one, physalin VIII (5), a rare 11,15-cyclo one, physalin IX (6), and two new ones, physalins VI (2) and VII (4) were isolated from stems and leaves of Physalis angulata together with eleven known analogues (3 and 7–16). Their structures were established by MS, IR, UV, and NMR spectroscopic analysis, together with the X-ray diffraction analysis of neophysalin, physalin P (12), and the structure of physalin D1 (3) has been revised here. These isolated compounds were evaluated for their antiproliferative activities against human cancer cells (C4-2B, 22Rv1, 786-O, A-498, ACHN, and A375-S2) and inhibitory effects on nitric oxide production. Compounds 9 and 10 showed antiproliferative activities against all tested human cancer cells with IC50 values of 0.24–3.17 μM. Compounds 1, 3, 4, 9, 10, 13, 14, and 16 exhibited inhibitory activities against NO production. The IC50 values of compounds 9, 10, 13, and 16 were between 0.32 and 4.03 μM, while compounds 1, 3, 4, and 14 had IC50 values of 12.83–34.19 μM. Herein, plausible biosynthetic pathways for rare structures 1 and 6 and structure−activity relationships on the inhibition of NO production for all isolated compounds are discussed.

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Section: Resultsmentioning

confidence: 99%

Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities

Sun

Qiu

Zhao

et al. 2017

Sci Rep

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“…franchetii in 1992. 101 All the neophysalins, up to now, have been isolated exclusively from P. alkekengi var. franchetii.…”

Section: Neophysalinsmentioning

confidence: 99%

Natural withanolides: an overview

2011

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Withanolides are a group of naturally occurring C28 steroids built on an ergostane skeleton functionalized at carbons 1, 22 and 26, commonly known as the withanolide skeleton. Over the period of August 1996 to March 2010, 360 new naturally occurring withanolides were isolated and identified. This review provides a comprehensive summary of the structural classification and distribution of these new compounds. The diverse biological and pharmacological activities of natural withanolides are also discussed based on their structural features. A total of 211 references are cited in this review.

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“…8 Phytochemical studies on the aerial parts of Physalis plants have led to the identification of about thirty physalins. [9][10][11][12][13] The unusual steroids and variety of biological activities of this plant prompted us to extend our studies to the calyces of P. alkekengi var. franchetii, which resulted in the isolation of 15 physalins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) and eight flavonoids (16)(17)(18)(19)(20)(21)(22)(23).…”

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confidence: 99%

Steroids and Flavonoids from Physalis alkekengi var. franchetii and Their Inhibitory Effects on Nitric Oxide Production

et al. 2008

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Four new steroidal compounds possessing a rare 13,14-seco-16,24-cycloergostane skeleton, physalin Y ( 1), physalin Z ( 2), physalin I ( 6), and physalin II ( 7), were isolated from the 80% EtOH extract of calyces from Physalis alkekengi var. franchetii together with 11 known steroids ( 3- 5 and 8- 15) and eight flavonoids ( 16- 23). The structures of the new compounds were elucidated primarily on the basis of 1D and 2D NMR and mass spectroscopic studies. The relative configuration of the 3-OH group of 3, 4, and 5 was also established or re-established. The inhibitory effects of compounds 1- 23 on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.

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The Structure of Physalin P, a Neophysalin from Physalis Alkekengi

Abstract: The structure of physalin P, a constituent of Physalis alkekengi var. francheti, was determined to be 5α-hydroxy-6,7-didehydro-5,6-dihydroneophysalin B by spectroscopic study and chemical correlation with a known compound.

Cited by 30 publications

References 7 publications

Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities

Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities

Natural withanolides: an overview

Steroids and Flavonoids from Physalis alkekengi var. franchetii and Their Inhibitory Effects on Nitric Oxide Production

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