Genkwadaphnin, a potent antileukemic diterpene from Daphne genkwa

doi:10.1016/0031-9422(81)83105-6

Phytochemistry

Volume 20, Issue 11, 1981, Pages 2592-2594

https://doi.org/10.1016/0031-9422(81)83105-6 Get rights and content

Abstract

In vivo P-388 assay-directed fractionation of an active extract of Daphne genkwa (Yuán Huā) has led to the isolation and characterization of a new antileukemic principle. genkwadaphnin.

References (18)

S.M. Kupchan et al.
J. Org. Chem.
(1976)
W. Adolf et al.
Terashedron Letters
(1975)
W.S. Kan
M. Sugi et al.M. Sugi et al.M. Sugi et al.
M. Nakao et al.
Yakugaku Zasshi
(1932)
M. Nakao et al.
Yakugaku Zasshi
(1932)
R.I. Geran et al.
Cancer Chemother. Rep.
(1972)
G.H. Stout et al.
J. Am. Chem. Soc.
(1970)

There are more references available in the full text version of this article.

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Tigliane-and daphnane-type diterpenoids from the buds of Daphne genkwa with their cytotoxic activities
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Two new tigliane- and daphnane-type diterpenoids, given the trivial names daphnegens A–B (1–2) were isolated from the buds of Daphne genkwa. Their structures were assigned on the basis of extensive spectroscopic. The absolute configurations of both compounds were determined by comparison of their calculated and experimental CD curves. In addition, compounds 1–2 were tested for their cytotoxic activities against MCF-7 and HepG-2 human cancer cell lines, and compound 2 showed remarkable cytotoxic activity against HepG-2 cell line with the IC₅₀ value of 11.5 μM.
Daphnane-type diterpenes from genus Daphne and their anti-tumor activity
2021, Chinese Herbal Medicines
Daphnane-type diterpenenoids are the major biologically active constituents in the genus Daphne. We find that there are about 101 Daphnane-type diterpenes in this genus, most of those compounds show different degrees of inhibitory effect on various cancer cell. Some of them have been studied in depth and the potent molecular mechanisms might be associated with modulation of different cell-signaling pathways. In addition, some compounds of this type also can inhibit the synthesis of protein and DNA. Absolutely, the anti-tumor activity of Daphnane-type diterpenes is worthy of attention. Unfortunately, most of the current research on the activity of these compounds is focused on simple drug efficacy, and its in-depth mechanism research is far from enough. On the other point of view, there still exists wide growing space on the depth of these compounds.
The genus Daphne: A review of its traditional uses, phytochemistry and pharmacology
2020, Fitoterapia
The genus Daphne belongs to the Thymeleaceae family and contains over 90 species that are distributed in Asia, Europe and parts of North Africa. The species of the genus Daphne are used in the traditional medicine of China, Tibet, Korea, and the Middle East for the treatment of various conditions. A broad range of studies has shown the significant biological potential of these species as sources of biologically and pharmacologically active compounds. Daphne species are a source of several classes of valuable phytochemicals such as coumarins, flavonoids, lignans, steroids and different classes of terpenes. The phytochemical diversity of this genus is demonstrated by over 350 secondary metabolites isolated from various species. The genus possesses a broad spectrum of biological activities including antibacterial, antifungal, antioxidant, analgesic, anti-inflammatory, cytotoxic, antiviral, abortive and haemostatic effects. A variety of bioactive secondary metabolites found in this genus may have potential use in pharmaceutical, cosmetic and food industries. Thus, species belonging to the genus Daphne can be considered an important source both for the treatment of various disorders, due to the presence of a plethora of bioactive constituents with potent bioactivities, and as possible leads in the discovery and synthesis of new medications.
Genkwalathins A and B, new lathyrane-type diterpenes from Daphne genkwa
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Screening for new natural anti-neuroinflammatory compounds was performed with the traditional folk medicine Genkwa Flos, which potently inhibited nitric oxide (NO) production by LPS-activated microglial BV-2 cells. Two new lathyrane-type diterpenes, genkwalathins A (1) and B (2), and 14 known daphnane-type diterpenes (3–16) were isolated. The lathyrane-type diterpenes were isolated for the first time from the Thymelaeaceae family in this study. Compounds 1 and 2 moderately inhibited LPS-induced NO production in BV-2 cells without affecting cell viability, while six daphnane-type diterpenes (3, 4, 6, 7, 9 and 10) potently reduced NO production with IC₅₀ values less than 1 μM, although they did display weak cytotoxicity. A structure–activity relationship study on the daphnane-type diterpenes indicated that the stereochemistry at C-19, the benzoate group at C-20, and the epoxide moiety could be important for their anti-neuroinflammatory effects.
Phytochemistry of Daphne oleoides
2016, Natural Product Research
Genus Daphne belongs to the Thymelaeaceae family and consists of 70 species. Its various species exist in Europe, Philippine Islands, temperate and subtropical Asia, North Africa, Australia and Pacific. In Pakistan, Daphne is represented by three species. Our focused Daphne oleoides is widely found in diverse climatic conditions from northern cold to central hot regions which creates a rich diversity and novelty in biosynthetic levels of its chemical constituents and hence is a great opportunity. Daphne oeloides is a proven rich source of a variety of unique and interesting nature-made skeletons with a wide range of therapeutic properties. D. oleoides possesses effective therapeutic properties, therefore, has been used in herbal medicines and is still being used to treat various diseases. The modern research by various groups, including ourselves, has resulted in the isolation of a number of natural molecules including some novel tris- and bis- coumarins, daphnane diterpenoids and lignoids. Therefore, due to novelty and richness of the nature-made molecules, and their therapeutic potential combined with our significant work on D. oleoides, this report covers chemical constituents isolated from D. oleoides. The pharmacological activities of the isolated compounds and use of this species in folk medicine have also been reviewed.
Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa
2013, Bioorganic and Medicinal Chemistry Letters
Two new daphnane-type diterpene esters, daphneresiniferins A (1) and B (2), along with seven known diterpenes, yuanhuacine (3), yuanhuadine (4), yuanhuahine (5), genkwadaphnin (6), genkwanine A (7), genkwanine F (8), and genkwanine H (9), were isolated from the methanol extract of the flower buds of Daphne genkwa. Their structures were elucidated on the basis of spectroscopic methods, especially 2D NMR spectra such as HMQC, HMBC, and NOESY. All the isolates were evaluated for their inhibitory effects of the melanogenesis against α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells.

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^☆: Part 40 in the series “Antitumor Agents”. For Part 39 see Lee, K.H., Tagahara, K., Suzuki, H. Wu, R.Y., Haruna, M., Hall, I.H., Huang, H.C., Itoh, K. Iida, T. and Lai, J.S. J. Nat. Prod. (in press).

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Short reportGenkwadaphnin, a potent antileukemic diterpene from Daphne genkwa☆

Abstract

J. Org. Chem.

Terashedron Letters

Yakugaku Zasshi

Yakugaku Zasshi

Cancer Chemother. Rep.

J. Am. Chem. Soc.

Short report
Genkwadaphnin, a potent antileukemic diterpene from Daphne genkwa☆