Bioactive sesterterpenoids from a Korean sponge monanchora sp.

Weihong Wang; Bora Mun; Yehee Lee; Mallepally Venkat Reddy; Youngmin Park; Jihye Lee; Hiyoung Kim; Dongyup Hahn; Jungwook Chin; Merrick Ekins; Sang Jip Nam; Heonjoong Kang

doi:10.1021/np300573m

Bioactive sesterterpenoids from a Korean sponge monanchora sp.

Weihong Wang, Bora Mun, Yehee Lee, Mallepally Venkat Reddy, Youngmin Park, Jihye Lee, Hiyoung Kim, Dongyup Hahn, Jungwook Chin, Merrick Ekins, Sang Jip Nam, Heonjoong Kang

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.

Original language	English
Pages (from-to)	170-177
Number of pages	8
Journal	Journal of Natural Products
Volume	76
Issue number	2
DOIs	https://doi.org/10.1021/np300573m
State	Published - 22 Feb 2013

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title = "Bioactive sesterterpenoids from a Korean sponge monanchora sp.",

abstract = "Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.",

author = "Weihong Wang and Bora Mun and Yehee Lee and Reddy, {Mallepally Venkat} and Youngmin Park and Jihye Lee and Hiyoung Kim and Dongyup Hahn and Jungwook Chin and Merrick Ekins and Nam, {Sang Jip} and Heonjoong Kang",

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doi = "10.1021/np300573m",

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T1 - Bioactive sesterterpenoids from a Korean sponge monanchora sp.

AU - Wang, Weihong

AU - Mun, Bora

AU - Lee, Yehee

AU - Reddy, Mallepally Venkat

AU - Park, Youngmin

AU - Lee, Jihye

AU - Kim, Hiyoung

AU - Hahn, Dongyup

AU - Chin, Jungwook

AU - Ekins, Merrick

AU - Nam, Sang Jip

AU - Kang, Heonjoong

PY - 2013/2/22

Y1 - 2013/2/22

N2 - Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.

AB - Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.

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SP - 170

EP - 177

JO - Journal of Natural Products

JF - Journal of Natural Products

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ER -

Bioactive sesterterpenoids from a Korean sponge monanchora sp.

Abstract

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