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Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

JOURNAL OF NATURAL MEDICINES (2023)

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Isolation of cytotoxic daphnane-type and tigliane-type diterpenoids from Daphne genkwa using MetGem software

Si-Hui Mi et al.

Summary: The biological and chemical diversity of the flower buds of Daphne genkwa Sieb. et Zucc was investigated to discover diterpenoids that naturally possess chemical weapons against cancer. Eight diterpenoids, including four new compounds, were isolated and their structures were elucidated. Compounds 1 and 8 showed potent activity against A549 and Hep3B cells.

NEW JOURNAL OF CHEMISTRY (2023)

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Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents

Ahmed H. H. El-Desoky et al.

Summary: Three new diterpenes were isolated from the roots of Stellera chamaejasme L., and their structures were determined through NMR and mass spectroscopic analyses. Compounds 1 and 2 are the first derivatives containing a hydroxy group at C-2 in the family of daphnane and tigliane diterpenes. Compound 1, with a chlorine atom, and compound 3, with an odd-number acyl group, are unique plant metabolites.

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Total Synthesis of Resiniferatoxin Enabled by Photocatalytic Decarboxylative Radical Cyclization

Yuto Hikone et al.

Summary: This article reports a new synthetic route to resiniferatoxin, which involves 27 steps starting from a d-ribose derivative. The carbon spacer and A-ring are attached to the C-ring through radical allylation and Stille coupling reactions, respectively. The sterically hindered bond between the tetra- and trisubstituted carbons is formed through an Ir(III)-catalyzed photoinduced decarboxylative radical reaction to cyclize the central seven-membered B-ring.

ORGANIC LETTERS (2022)

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Review Biochemistry & Molecular Biology

Yuanhuacin and Related Anti-Inflammatory and Anticancer Daphnane Diterpenes from Genkwa Flos-An Overview

Christian Bailly

Summary: The dried flower buds of Daphne genkwa Sieb. et Zucc. have long been used in traditional Chinese medicine to treat inflammatory diseases. Various diterpenoids, including the yuanhuacin (YC) series and analogues, have been isolated from Genkwa Flos. These compounds have shown potential as anticancer agents, with YC being particularly effective against lung and breast cancers. Although protein kinase C has been identified as a key factor in YC's activity, the exact molecular targets of these compounds remain unclear. The pharmacological activity of each compound and the properties of Genkwa Flos extracts are discussed, along with the potential toxic effects associated with their use.

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A feruloylated acylglycerol isolated from Wikstroemia pilosa and its distribution in ten plants of Wikstroemia species

Mi Zhang et al.

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JOURNAL OF NATURAL MEDICINES (2022)

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Daphnepedunins A-F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from Daphne pedunculata

Lingjian Tan et al.

Summary: Twelve macrocyclic daphnane diterpenoids, including six new compounds, were isolated from the whole plant of Daphne pedunculata. Their structures were determined using various methods, and their anti-HIV activity was evaluated. The compounds showed significant activity against HIV, providing further insights into the structure-activity relationships of macrocyclic daphnane diterpenoids.

JOURNAL OF NATURAL PRODUCTS (2022)

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Targeted isolation of diterpenoids and sesquiterpenoids from Daphne gemmata E. Pritz. ex Diels using molecular networking together with network annotation propagation and MS2LDA

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Anti-HIV Tigliane-Type Diterpenoids from the Aerial Parts of Wikstroemia lichiangensis

Di Zhou et al.

Summary: Tigliane-type diterpenoids have significant biological effects, including antineoplastic and anti-HIV activities. In this study, new tigliane-type diterpenoids were isolated from Wikstroemia lichiangensis for the first time, and their structures were determined. These compounds exhibited potent anti-HIV activity against HIV-1 infection.

JOURNAL OF NATURAL PRODUCTS (2022)

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Target isolation of cytotoxic diterpenoid esters and orthoesters from Daphne tangutica maxim based on molecular networking

Rui Guo et al.

Summary: By using LC-MS/MS analysis and GNPS Molecular Networking, researchers discovered five new daphnane diterpenoids, tanguticanines A-E, and eleven known analogues from Daphne tangutica Maxim. Tanguticanine E showed promising cytotoxicity against HepG2 cell line, with further experiments indicating that various cytotoxic diterpenoids induce apoptosis in cells.

PHYTOCHEMISTRY (2022)

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Article Plant Sciences

Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from Edgeworthia chrysantha

Yoshihisa Asada et al.

Summary: Edgeworthianins A-E, a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring structure formed from a C14 aliphatic chain, were isolated from Edgeworthia chrysantha. Compounds 2, 4, and 5 showed potent anti-HIV activity against HIV-1 infection of MT4 cells, with EC50 values of 29.3, 8.4, and 2.9 nM, respectively.

JOURNAL OF NATURAL PRODUCTS (2022)

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Discovery of Highly Potent Daphnane Diterpenoids Uncovers Importin-β1 as a Druggable Vulnerability in Castration-Resistant Prostate Cancer

Jia-Luo Huang et al.

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Total Synthesis of Resiniferatoxin

Vasil H. Vasilev et al.

Summary: The large family of daphnane diterpene orthoesters (DDOs) represents a remarkable class of natural products both in terms of structure and function. They are potent lead compounds for the treatment of pain, neurodegeneration, HIV/AIDS, and cancer. However, the synthesis of DDO natural products remains rare.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Practical synthesis of the therapeutic leads tigilanol tiglate and its analogues

Paul A. Wender et al.

Summary: Tigilanol tiglate, a natural product diterpenoid, is being clinically tested as a treatment for various cancers. It shows promising selectivity for protein kinase C isoforms, making it a potential candidate for treating diseases like AIDS, cancer immunotherapy, Alzheimer's, and multiple sclerosis. With limited natural supply, researchers have developed a practical laboratory synthesis method to sustainably produce tigilanol tiglate.

NATURE CHEMISTRY (2022)

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Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes

Jason K. Cullen et al.

Summary: The study challenges the longstanding view of some Protein Kinase C (PKC) isoforms as oncogenes, suggesting that activation of certain isoforms may have tumor-suppressive effects. This research identified a group of novel phorboids related to a PKC-activating compound, with potential anticancer activity. The findings indicate that PKC activation could be a promising strategy for anticancer drug discovery in some cases.

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Phytochemistry and Pharmacological Activities of the Diterpenoids from the Genus Daphne

Yi-Wen Nie et al.

Summary: Plants of the genus Daphne contain abundant natural diterpenoids with various bioactivities such as anticancer, anti-inflammatory, and anti-HIV effects. Studies have also summarized the structure-activity relationship to facilitate the synthesis and optimization of drugs.

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Discovering the Mechanisms of Wikstroelide E as a Potential HIV-Latency-Reversing Agent by Transcriptome Profiling

Shi-Fei Li et al.

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JOURNAL OF NATURAL PRODUCTS (2021)

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Article Chemistry, Medicinal

Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC-MS analysis and phytochemical investigation

Kouharu Otsuki et al.

Summary: This study conducted the first chemical investigation on Wikstroemia ligustrina and identified several daphnane diterpenoids with potential anti-HIV activity, especially the MDOs. The MS/MS fragmentation pathway of the isolated MDO (1) was also elucidated in this study.

JOURNAL OF NATURAL MEDICINES (2021)

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Article Plant Sciences

LC-MS Identification, Isolation, and Structural Elucidation of Anti-HIV Tigliane Diterpenoids from Wikstroemia lamatsoensis

Mi Zhang et al.

Summary: Structurally diverse tigliane diterpenoids, including two new compounds, were isolated from the first phytochemical investigation on Wikstroemia lamatsoensis using LC-MS-guided fractionation and separation. The new structures were elucidated based on extensive physicochemical and spectroscopic analyses. Three compounds showed the most potent anti-HIV activity among the isolated tiglianes.

JOURNAL OF NATURAL PRODUCTS (2021)

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Article Oncology

Yuanhuacine Is a Potent and Selective Inhibitor of the Basal-Like 2 Subtype of Triple Negative Breast Cancer with Immunogenic Potential

Charles S. Fermaintt et al.

Summary: The study identified a class of plant-derived natural products, including yuanhuacine, that selectively kill cells representing a molecularly defined subtype of triple negative breast cancer (TNBC) and promote an antitumor immune response. Yuanhuacine exerts potent antitumor efficacy in a mouse TNBC model by activating protein kinase C.

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Review Chemistry, Medicinal

Daphnane-type diterpenes from genus Daphne and their anti-tumor activity

Zi-lin Hou et al.

Summary: Daphnane-type diterpenoids in the genus Daphne exhibit anti-tumor activity by potentially modulating cell signaling pathways and inhibiting protein and DNA synthesis. However, current research on these compounds mainly focuses on drug efficacy, lacking in-depth mechanistic studies, leaving ample room for further exploration.

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Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSn

Hua-Ding Zhao et al.

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Three new 1α-alkyldaphnane-type diterpenoids from the flower buds of Wikstroemia chamaedaphne

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Gnidimacrin, a Potent Anti-HIV Diterpene, Can Eliminate Latent HIV-1 Ex Vivo by Activation of Protein Kinase C β

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Stelleralides D-J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

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Neogenkwanines A-H: daphnane-type diterpenes containing 4,7 or 4,6-ether groups from the flower bud of Daphne genkwa

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