Withanolides and Sucrose Esters from <i>Physalis neomexicana</i>

Cao, Cong-Mei; Wu, Xiaoqing; Kindscher, Kelly; Xu, Liang; Timmermann, Barbara N.

doi:10.1021/acs.jnatprod.5b00698

Cited by 24 publications

(19 citation statements)

References 15 publications

(35 reference statements)

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“…In the past 50 years, approximately 900 withanolides falling into 24 diverse structural types have been discovered [1,3]. Withanolides are mainly distributed in various genera of Solanaceae, which includes Acnistus, Aureliana, Brachistus, Browallia, Datura, Deprea, Discopodium, Dunalia, Exodeconus, Hyoscyamus, Iochroma, Jaborosa, Larnax, Lycium, Mandragora, Nicandra, Physalis, Salpichroa, Saracha, Solanum, Trechonaetes, Tubocapsicum, Vassobia, Withania, and Witheringia [1][2][3][7][8][9]. A minor population of withanolides has been isolated from other plant sources such as Dioscoreaceae, Fabaceae, Labiatae, Lamiaceae, Leguminosae, Myrtaceae, and Taccaceae [1][2][3] and interestingly from marine sources of Alcyoniidae family [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Natural Withanolides in the Treatment of Chronic Diseases

White

Subramanian

Motiwala

et al. 2016

Advances in Experimental Medicine and Biology

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Withanolides, and in particular extracts from Withania somnifera, have been used for over 3,000 years in traditional Ayurvedic and Unani Indian medical systems as well as within several other Asian countries. Traditionally, the extracts were ascribed a wide range of pharmacologic properties with corresponding medical uses, including adaptogenic, diuretic, anti-inflammatory, sedative/anxiolytic, cytotoxic, antitussive, and immunomodulatory. Since the discovery of the archetype withaferin A in 1965, approximately 900 of these naturally occurring, polyoxygenated steroidal lactones with 28-carbon ergostane skeletons have been discovered across 24 diverse structural types. Subsequently, extensive pharmacologic research has identified multiple mechanisms of action across key inflammatory pathways. In this chapter we identify and describe the major withanolides with anti-inflammatory properties, illustrate their role within essential and supportive inflammatory pathways (including NF-κB, JAK/STAT, AP-1, PPARγ, Hsp90 Nrf2, and HIF-1), and then discuss the clinical application of these withanolides in inflammation-mediated chronic diseases (including arthritis, autoimmune, cancer, neurodegenerative, and neurobehavioral). These naturally derived compounds exhibit remarkable biologic activity across these complex disease processes, while showing minimal adverse effects. As novel compounds and analogs continue to be discovered, characterized, and clinically evaluated, the interest in withanolides as a novel therapeutic only continues to grow.

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Section: Introductionmentioning

confidence: 99%

Natural Withanolides in the Treatment of Chronic Diseases

White

Subramanian

Motiwala

et al. 2016

Advances in Experimental Medicine and Biology

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“…Cong-Mei Cao et al isolated four new withanolides, 35 – 38 ( Figure 5 ), which were evaluated for anti-proliferative activity against MDA-MB-231 and MCF-7 breast cancer cell lines using WA (IC 50 0.5 and 1.3 µM, respectively) and withaloglide B (IC 50 0.2 and 0.8 μM, respectively) as references compounds. Among all the four new isolated withanolides, compound 36 was most active against MDA-MB-231 and MCF-7 cell lines, with IC 50 values of 1.7 and 6.3 µM, respectively [ 74 ], being less effective than the two reference compounds.…”

Section: Withanolides As Anti-cancer Agentsmentioning

confidence: 99%

Recent Advances in the Chemistry and Therapeutic Evaluation of Naturally Occurring and Synthetic Withanolides

et al. 2022

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Natural products are a major source of biologically active compounds that make promising lead molecules for developing efficacious drug-like molecules. Natural withanolides are found in many flora and fauna, including plants, algae, and corals, that traditionally have shown multiple health benefits and are known for their anti-cancer, anti-inflammatory, anti-bacterial, anti-leishmaniasis, and many other medicinal properties. Structures of these withanolides possess a few reactive sites that can be exploited to design and synthesize more potent and safe analogs. In this review, we discuss the literature evidence related to the medicinal implications, particularly anticancer properties of natural withanolides and their synthetic analogs, and provide perspectives on the translational potential of these promising compounds.

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“…peruviana , and electronic circular dichroism (ECD) spectrum was used for confirming the 22 R configuration and cis linkage of rings A/B in their structures . Withaneomexolide B ( 5 ) is a novel withanolide isolated from the aerial parts of P. neomexicana , and its structure was elucidated by the analysis of the spectroscopic data . Recently, peruvianolide D ( 7 ) was obtained from the whole plants of P. peruviana …”

Section: The Phytochemical Classificationmentioning

confidence: 99%

“…Withaneomexolide A ( 17 ) is a new withanolide derived of P . neomexicana , which is a structural analogue of withanolide D and determined as 15α‐acetoxy‐16α‐hydroxy‐withanolide D . Compounds 18–32 are 5β,6β‐epoxy withanolides lacking a Δ 24,25 double bound in ring E. Of which, 18–24 have a 24β‐hydroxy substituent group in their structures.…”

Section: The Phytochemical Classificationmentioning

confidence: 99%

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Withanolides from the genus Physalis: a review on their phytochemical and pharmacological aspects

Huang

et al. 2019

Journal of Pharmacy and Pharmacology

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Objectives Withanolides are a group of modified C28 ergostane‐type steroids with a C‐22, C‐26 δ‐lactone side chain or a C‐23, C‐26 γ‐lactone side chain. They enjoy a limited distribution in the plant kingdom and predominantly occur in several genera of Solanaceae. Of which, the genus Physalis is an important resource for this type of natural molecules. The present review aims to comprehensively illustrate the structural characteristics and classification of withanolides, and particularly focus on the progression on phytochemical and pharmacological aspects of withanolides from Physalis ranging from January 2015 to June 2019. Key findings Approximately 351 natural withanolides with novel and unique structures have so far been identified from genus Physalis, mainly isolated from the species of P. angulata and P. peruviana. Withanolides demonstrated diverse biological activity, such as anticancer, anti‐inflammatory, antimicrobial, immunoregulatory, trypanocidal and leishmanicidal activity. Their observed pharmacological functions supported the uses of Physalis species in traditional or folk medicines. Summary Due to their unique structure skeleton and potent bioactivities, withanolides are regarded to be promising drug candidates, particularly for developing anticancer and anti‐inflammatory agents. Further investigations for discovering novel withanolides of genus Physalis, exploiting their pharmacological values and evaluating their potency as therapeutic agents are significant work.

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Withanolides and Sucrose Esters from Physalis neomexicana

Cited by 24 publications

References 15 publications

Natural Withanolides in the Treatment of Chronic Diseases

Natural Withanolides in the Treatment of Chronic Diseases

Recent Advances in the Chemistry and Therapeutic Evaluation of Naturally Occurring and Synthetic Withanolides

Withanolides from the genus Physalis: a review on their phytochemical and pharmacological aspects

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