Marine Natural Products. XXXII. Absolute Configurations of C-4 of the Manoalide Family, Biologically Active Sesterterpenes from the Marine Sponge Hyrtions erecta

Motomasa KOBAYASHI; Takumi OKAMOTO; Kozo HAYASHI; Norio YOKOYAMA; Takuma SASAKI; Isao KITAGAWA

doi:10.1248/cpb.42.265

Marine Natural Products. XXXII. Absolute Configurations of C-4 of the Manoalide Family, Biologically Active Sesterterpenes from the Marine Sponge Hyrtions erecta

Motomasa KOBAYASHI, Takumi OKAMOTO, Kozo HAYASHI, Norio YOKOYAMA, Takuma SASAKI, Isao KITAGAWA

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Keywords: marine sponge, Hyrtios erecta, sesterterpene, manoalide, neomanoalide, antitumor activity

JOURNAL FREE ACCESS

1994 Volume 42 Issue 2 Pages 265-270

DOI https://doi.org/10.1248/cpb.42.265

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Abstract

Cytotoxic sesterterpenes, manoalide 25-acetals (1a, 1b), seco-manoalide (2), (E)-neomanoalide (3), (Z)-neomanoalide (4), and heteronemin (6), were isolated from the marine sponge Hyrtios erecta (collected at Amami Island, Kagoshima Prefecture, Japan) by bioassay-guided separation and the absolute configrations of these manoalide family members have been determined. Manoalide 25-acetals (1a, 1b) were shown to exhibit in vivo antitumor activity and to inhibit the DNA-relaxing activity of mouse DNA topoisomerase I and the DNA-unknotting activity of calf thymus DNA topoisomerase II.

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