Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum.

@article{Tanabe2018TotalSO,
  title={Total Synthesis of $\gamma$-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum.},
  author={Genzoh Tanabe and Yoshiaki Manse and Teppei Ogawa and Naoki Sonoda and Shinsuke Marumoto and Fumihiro Ishikawa and Kiyofumi Ninomiya and Saowanee Chaipech and Yutana Pongpiriyadacha and Osamu Muraoka and Toshio Morikawa},
  journal={The Journal of organic chemistry},
  year={2018},
  volume={83 15},
  pages={
          8250-8264
        }
}
A hitherto unreported member of γ-alkylidenebutenolides in Melodorum fruticosum (Annonaceae), (4 E)-6-benzoyloxy-7-hydroxy-2,4-heptadiene-4-olide, named as isofruticosinol (4) was isolated from the methanol extract of flowers, along with the known related butenolides, namely, the (4 Z)-isomer (3) of 4, melodrinol (1), and its (4 E)-isomer (2). To unambiguously determine the absolute configuration at the C-6 position in these butenolides, the first total syntheses of both enantiomers of 2-4 were… Expand
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References

SHOWING 1-10 OF 63 REFERENCES
Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua.
The first total synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by theExpand
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit.
TLDR
An aqueous acetone extract from the fruit of Alpinia galanga demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells, and the active compounds 1-3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions could be the mechanism of melanogenesis inhibitory activity. Expand
Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis
A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells.Expand
Bioactive butenolides from Melodorum fruticosum
TLDR
All butenolides showed cytotoxic activities in several tumour cell lines and the structures of the isolated compounds were elucidated by spectroscopic methods. Expand
Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora
TLDR
Results indicated that the methanol extract from the rhizomes of Kaempferia parviflora Wall was reproducible, precise, and could be readily utilized for the quality evaluation of the plant materials. Expand
Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves.
TLDR
Thirteen new metabolites, including the polyoxygenated cyclohexenoids and heptenolides in C. kirkii are of biogenetic and chemotaxonomic significance, and none of the compounds investigated exhibited translational inhibitory activity in vitro at 20 μM. Expand
Nitric Oxide Inhibitory Activity and Absolute Configurations of Arylalkenyl α,β-Unsaturated δ/γ-Lactones from Cryptocarya concinna.
TLDR
Compounds 4-6 and 8-10 showed inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages, particularly compounds 4-8-10, with IC50 values of 3.2, 4.4, and 7.5 μM, respectively. Expand
Anti-Dengue Virus Constituents from Formosan Zoanthid Palythoa mutuki
TLDR
Peridinin (9) exhibited strong antiviral activity, which is better than that of the positive control, 2′CMC, and is the first carotene-like substance possessing anti-dengue virus activity. Expand
Alkaloids from Pandanus amaryllifolius: Isolation and Their Plausible Biosynthetic Formation.
TLDR
The purification of the ethanolic extract of the aerial parts of P. amaryllifolius exhibited antioxidant, antibiofilm, and anti-inflammatory activities in previous studies yielded nine new compounds, including N-acetylnorpandamarilactonines A and B, and pandalizines A, 3, and B. Expand
Potent cytotoxicity against human small cell lung cancer cells of the heptenes from the stem bark of Xylopia pierrei Hance
Phytochemical investigation of the stem bark of Xylopia pierrei Hance led to the isolation of one triterpene, polycarpol (1), three heptenes, (7R)-acetylmelodorinol (2), (7R)-melodorinol (3), andExpand
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