Withanolides from Physalis coztomatl

Zhang, Huaping; Cao, Cong-Mei; Gallagher, Robert J.; Day, Victor W.; Kindscher, Kelly; Timmermann, Barbara N.

doi:10.1016/j.phytochem.2014.10.012

Cited by 16 publications

(28 citation statements)

References 16 publications

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“…and Sessé ex Dunal (Solanaceae) and in vitro evaluation of withanolides (3-5, and 8-33) against a panel of prostate cancer and renal carcinoma cell lines, and normal human fibroblast cells. Previous studies on P. coztomatl, a plant native to South America, has resulted in the isolation of 13 withanolides in two independent studies [27,28], including six 17-BHWs (3, 4, 25, 26, 30, and 32), all of which were also encountered in the biomass obtained from aeroponic cultivation of this plant.…”

Section: Refs and Notesmentioning

confidence: 99%

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Production and Structural Diversification of Withanolides by Aeroponic Cultivation of Plants of Solanaceae: Cytotoxic and Other Withanolides from Aeroponically Grown Physalis coztomatl

Wijeratne

Liu

et al. 2022

Molecules

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Withanolides constitute one of the most interesting classes of natural products due to their diversity of structures and biological activities. Our recent studies on withanolides obtained from plants of Solanaceae including Withania somnifera and a number of Physalis species grown under environmentally controlled aeroponic conditions suggested that this technique is a convenient, reproducible, and superior method for their production and structural diversification. Investigation of aeroponically grown Physalis coztomatl afforded 29 withanolides compared to a total of 13 obtained previously from the wild-crafted plant and included 12 new withanolides, physacoztolides I−M (9–13), 15α-acetoxy-28-hydroxyphysachenolide C (14), 28-oxophysachenolide C (15), and 28-hydroxyphysachenolide C (16), 5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (17), 15α-acetoxy-5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (18), 28-hydroxy-5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (19), physachenolide A-5-methyl ether (20), and 17 known withanolides 3–5, 8, and 21–33. The structures of 9–20 were elucidated by the analysis of their spectroscopic data and the known withanolides 3–5, 8, and 21–33 were identified by comparison of their spectroscopic data with those reported. Evaluation against a panel of prostate cancer (LNCaP, VCaP, DU-145, and PC-3) and renal carcinoma (ACHN) cell lines, and normal human foreskin fibroblast (WI-38) cells revealed that 8, 13, 15, and 17–19 had potent and selective activity for prostate cancer cell lines. Facile conversion of the 5,6-chlorohydrin 17 to its 5,6-epoxide 8 in cell culture medium used for the bioassay suggested that the cytotoxic activities observed for 17–19 may be due to in situ formation of their corresponding 5β,6β-epoxides, 8, 27, and 28.

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Section: Refs and Notesmentioning

confidence: 99%

“…b Since 2 is a prodrug of 1 [15], total % yield of withaferin A (1) in aeroponicallygrown plant is 0.93. c Yield not reported. d Not encountered in wild-crafted plants [27,28].…”

Section: Introductionmentioning

confidence: 99%

Production and Structural Diversification of Withanolides by Aeroponic Cultivation of Plants of Solanaceae: Cytotoxic and Other Withanolides from Aeroponically Grown Physalis coztomatl

Wijeratne

Liu

et al. 2022

Molecules

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“…)-14α,17β,20trihydroxy-18-acetoxy-3α,5α-cyclo-1-oxowitha-24-enolide, named physacoztolide F (93), was found in the CH 2 Cl 2 /MeOH extract of the aerial parts of Physalis coztomatl (family Solanaceae) [117]. Withanolide-type steroids named cilistols P (94), PM (95) and U (96) were isolated from the leaves of Solanum cilistum [118].…”

Section: Glycoside 6β-o-[β-d-glucopyranosyl-(1->6)-β-d-glucopyranosyl]-(20s22rmentioning

confidence: 99%

“…The steroid, (3β,4α,5α)-4-methylgorgostan-3-ol (117), is synthesized by marine algae and invertebrates, and it has been found in dinoflagellates Peridinium foliaceum and Glenodinium foliaceum, corky sea finger Briareum asbestinum, rough leather coral Sarcophyton glaucum, and soft coral Lobophytum sp. [133][134][135].…”

Section: Sterols and Triterpenoids With Cyclopropane Ring In The Side Chainmentioning

confidence: 99%

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

2021

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This review focuses on the rare group of carbon-bridged steroids (CBS) and triterpenoids found in various natural sources such as green, yellow-green, and red algae, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in amoebas, fungi, fungal endophytes, and plants. For convenience, the presented CBS and triterpenoids are divided into four groups, which include: (a) CBS and triterpenoids containing a cyclopropane group; (b) CBS and triterpenoids with cyclopropane ring in the side chain; (c) CBS and triterpenoids containing a cyclobutane group; (d) CBS and triterpenoids containing cyclopentane, cyclohexane or cycloheptane moieties. For the comparative characterization of the antitumor profile, we have added several semi- and synthetic CBS and triterpenoids, with various additional rings, to identify possible promising sources for pharmacologists and the pharmaceutical industry. About 300 CBS and triterpenoids are presented in this review, which demonstrate a wide range of biological activities, but the most pronounced antitumor profile. The review summarizes biological activities both determined experimentally and estimated using the well-known PASS software. According to the data obtained, two-thirds of CBS and triterpenoids show moderate activity levels with a confidence level of 70 to 90%; however, one third of these lipids demonstrate strong antitumor activity with a confidence level exceeding 90%. Several CBS and triterpenoids, from different lipid groups, demonstrate selective action on different types of tumor cells such as renal cancer, sarcoma, pancreatic cancer, prostate cancer, lymphocytic leukemia, myeloid leukemia, liver cancer, and genitourinary cancer with varying degrees of confidence. In addition, the review presents graphical images of the antitumor profile of both individual CBS and triterpenoids groups and individual compounds.

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“…It's a tropical plant with hairy, soft, heart-shaped, slender-pointed leaves and edible orange fruits. They are protected from birds and bugs by a thin protective covering that resembles a Chinese lantern [5].…”

Section: Introductionmentioning

confidence: 99%

Chemical and Biological Studies on the Goldenberry (Physalis peruviana L.) on Hyperglycemic Rats

Eman

Boriy

Lamiaa

2021

IJBcRR

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The aim this investigate was to see if the medicine goldenberry fruits (Physalis peruviana L.) could help lower blood sugar, cholesterol, and triglycerides. The results of the chemical composition of goldenberry fruits were found to be a high source of antioxidants and which contain a high level of hypoglycemic and hypocholesterolemic such as phenolic compounds, ascorbic acid and ꞵ-carotenoid. The results showed that dried goldenberry fruits powder could be added to replace up to 5 and 10 % of hyperglycemic -diet respectively. Experimental hyperglycemic rats were fed for six weeks on diet contain dried goldenberry at extent 5% or 10% except normal control (G1) was fed on basal diet. Hyperglycemic rats fed on diets substituted in a part with 5% and10 % dried goldenberry the results showed that supplementing the hyperglycemic-producing diets with the additive goldenberry had significant decrease in serum glucose, lipid profile (cholesterols, triglyceride, low density lipoprotein LDL and very low density lipoprotein vLDL-cholesterol). Meanwhile, high density lipoprotein HDL cholesterol increased with all treatments, significant reduction in alanine aminotransferase ALT, aspartate aminotransferase AST, alkaline phosphatase ALP, and total bilirubin values, in respect to positive control were also observed.

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Withanolides from Physalis coztomatl

Cited by 16 publications

References 16 publications

Production and Structural Diversification of Withanolides by Aeroponic Cultivation of Plants of Solanaceae: Cytotoxic and Other Withanolides from Aeroponically Grown Physalis coztomatl

Production and Structural Diversification of Withanolides by Aeroponic Cultivation of Plants of Solanaceae: Cytotoxic and Other Withanolides from Aeroponically Grown Physalis coztomatl

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

Chemical and Biological Studies on the Goldenberry (Physalis peruviana L.) on Hyperglycemic Rats

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