New Cytotoxic Nor- and Bisnorditerpene Dilactones, Makilactones A-D, from Podocarpus macrophyllus D. Don

Sato, Kimihiko; Sugawara, Keito; Takeuehi, Hirono; Park, Hye-Jin; Akiyama, Tsuyoshi; Koyama, Tetsuo; Fukaya, Haruhiko; Aoyagi, Yutaka; Takeya, Koichi

doi:10.3987/com-08-11624

Cited by 6 publications

References 12 publications

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Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus

Zhang

et al. 2018

Chemistry & Biodiversity

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Activity-guided fractionation strategy was used to investigate chemical constituents from the roots of Podocarpus macrophyllus. Successfully, two new norditerpenes, 2β-hydroxymakilactone A (1) and 3β-hydroxymakilactone A (2), along with ten known analogues (3 - 12) were isolated. The structures of 1 and 2 were elucidated by spectroscopic analysis including 1D-, 2D-NMR, and HR-ESI-MS data. The previously reported structure of 2,3-dihydro-2α-hydroxypodolide was revised as 2,3-dihydro-2β-hydroxypodolide (3) by spectroscopic analysis, and was further confirmed by X-ray crystallographic analysis. Cytotoxic activities of all isolated compounds against five human solid tumour cell lines (AGS, HeLa, MDA-MB-231, HepG-2, and PANC-1) were evaluated. All of them exhibited anti-proliferative activities (IC = 0.3 - 27 μm), except for 10. Compounds 1, 4, 5, 6, and 8 exhibited potent inhibitory activities with IC < 1 μm against HeLa and AGS cells.

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Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus

Zhang

et al. 2018

Chemistry & Biodiversity

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ChemInform Abstract: New Cytotoxic Nor‐ and Bisnorditerpene Dilactones, Makilactones A‐D, from Podocarpus macrophyllus D. Don.

et al. 2009

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Terpenes U 0200New Cytotoxic Nor-and Bisnorditerpene Dilactones, Makilactones A-D, from Podocarpus macrophyllus D. Don. -Makilactones (Ib) and (II)-(IV), having a 7:8,9:11-dienolide moiety, are isolated from the bark and root of the title plant. Diterpenes (I) display strong cytotoxic activities against leukemia cells. -(SATO, K.; SUGAWARA, K.; TAKEUCHI, H.; PARK, H.-S.; AKIYAMA, T.; KOYAMA, T.; FUKAYA, H.; AOYAGI, Y.; TAKEYA*, K.; Heterocycles 78 (2009) 6, 1453-1462; Sch. Pharm., Univ. Pharm. Life Sci., Hachioji, Tokyo 192, Japan; Eng.) -H. Hoennerscheid 44-180

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Naturally Occurring Organohalogen Compounds—A Comprehensive Review

Gribble

2023

Progress in the Chemistry of Organic Natural Products

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New Cytotoxic Nor- and Bisnorditerpene Dilactones, Makilactones A-D, from Podocarpus macrophyllus D. Don

Cited by 6 publications

References 12 publications

Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus

Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus

ChemInform Abstract: New Cytotoxic Nor‐ and Bisnorditerpene Dilactones, Makilactones A‐D, from Podocarpus macrophyllus D. Don.

Naturally Occurring Organohalogen Compounds—A Comprehensive Review

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New Cytotoxic Nor- and Bisnorditerpene Dilactones, Makilactones A-D, from Podocarpus macrophyllus D. Don

Cited by 6 publications

References 12 publications

Two New Anti‐Proliferative C18‐Norditerpenes from the Roots of Podocarpus macrophyllus

Two New Anti‐Proliferative C18‐Norditerpenes from the Roots of Podocarpus macrophyllus

ChemInform Abstract: New Cytotoxic Nor‐ and Bisnorditerpene Dilactones, Makilactones A‐D, from Podocarpus macrophyllus D. Don.

Naturally Occurring Organohalogen Compounds—A Comprehensive Review

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Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus

Two New Anti‐Proliferative C₁₈‐Norditerpenes from the Roots of Podocarpus macrophyllus