Compositacins A–K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada

Xiao Qing Yu, Chang Sheng Jiang, Yi Zhang, Pan Sun, T. Kurtán, Attila Mándi, Xiao Lu Li, Li Gong Yao, Ai Hong Liu, Bin Wang, Yue Wei Guo, Shui Chun Mao

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A–K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C–L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC80 value of 4 μg/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC50 values ranging from 48.6 to 85.2 μM.

Original languageEnglish
Pages (from-to)81-93
Number of pages13
JournalPhytochemistry
Volume136
DOIs
Publication statusPublished - Apr 1 2017

Fingerprint

Laurencia
Microsporum
Rhodophyta
Cytotoxicity
Algae
sesquiterpenoids
Ether
Inhibitory Concentration 50
Bearings (structural)
Cell Line
Spectroscopic analysis
cytotoxicity
Cells
Microsporum gypseum
adenocarcinoma
inhibitory concentration 50
ethers
lungs
cell lines
Adenocarcinoma of lung

Keywords

  • Antifungal activity
  • Chamigrane sesquiterpenoid
  • Compositacins A–K
  • Cytotoxicity
  • ECD calculation
  • Laurencia composita
  • Rearranged chamigrane sesquiterpenoid
  • Rhodomelaceae
  • X-ray diffraction

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Compositacins A–K : Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada. / Yu, Xiao Qing; Jiang, Chang Sheng; Zhang, Yi; Sun, Pan; Kurtán, T.; Mándi, Attila; Li, Xiao Lu; Yao, Li Gong; Liu, Ai Hong; Wang, Bin; Guo, Yue Wei; Mao, Shui Chun.

In: Phytochemistry, Vol. 136, 01.04.2017, p. 81-93.

Research output: Contribution to journalArticle

Yu, XQ, Jiang, CS, Zhang, Y, Sun, P, Kurtán, T, Mándi, A, Li, XL, Yao, LG, Liu, AH, Wang, B, Guo, YW & Mao, SC 2017, 'Compositacins A–K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada', Phytochemistry, vol. 136, pp. 81-93. https://doi.org/10.1016/j.phytochem.2017.01.007
Yu, Xiao Qing ; Jiang, Chang Sheng ; Zhang, Yi ; Sun, Pan ; Kurtán, T. ; Mándi, Attila ; Li, Xiao Lu ; Yao, Li Gong ; Liu, Ai Hong ; Wang, Bin ; Guo, Yue Wei ; Mao, Shui Chun. / Compositacins A–K : Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada. In: Phytochemistry. 2017 ; Vol. 136. pp. 81-93.
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abstract = "Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A–K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C–L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC80 value of 4 μg/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC50 values ranging from 48.6 to 85.2 μM.",
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AU - Yu, Xiao Qing

AU - Jiang, Chang Sheng

AU - Zhang, Yi

AU - Sun, Pan

AU - Kurtán, T.

AU - Mándi, Attila

AU - Li, Xiao Lu

AU - Yao, Li Gong

AU - Liu, Ai Hong

AU - Wang, Bin

AU - Guo, Yue Wei

AU - Mao, Shui Chun

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AB - Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A–K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C–L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC80 value of 4 μg/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC50 values ranging from 48.6 to 85.2 μM.

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