Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells

Sultan Pulat; Prima F. Hillman; Sojeong Kim; Ratnakar N. Asolkar; Haerin Kim; Rui Zhou; İsa Taş; Chathurika D.B. Gamage; Mücahit Varlı; So Yeon Park; Sung Chul Park; Inho Yang; Jongheon Shin; Dong Chan Oh; Hangun Kim; Sang Jip Nam; William Fenical

doi:10.3390/md21030153

Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells

Sultan Pulat, Prima F. Hillman, Sojeong Kim, Ratnakar N. Asolkar, Haerin Kim, Rui Zhou, İsa Taş, Chathurika D.B. Gamage, Mücahit Varlı, So Yeon Park, Sung Chul Park, Inho Yang, Jongheon Shin, Dong Chan Oh, Hangun Kim, Sang Jip Nam, William Fenical

Department of Chemistry & Nanoscience

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

9 Scopus citations

Abstract

Marinobazzanan (1), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus Acremonium. The chemical structure of 1 was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of 1 were determined by the modified Mosher’s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6R, 7R, 9R, and 10R. It was found that compound 1 was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound 1 was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound 1 suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, 1 also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model.

Original language	English
Article number	153
Journal	Marine Drugs
Volume	21
Issue number	3
DOIs	https://doi.org/10.3390/md21030153
State	Published - Mar 2023

Bibliographical note

Publisher Copyright:
© 2023 by the authors.

Keywords

Acremoniumsp
anticancer
bazzanane-type sesquiterpenoid
cytotoxicity
marinobazzanan

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md21030153

Cite this

Pulat, S., Hillman, P. F., Kim, S., Asolkar, R. N., Kim, H., Zhou, R., Taş, İ., Gamage, C. D. B., Varlı, M., Park, S. Y., Park, S. C., Yang, I., Shin, J., Oh, D. C., Kim, H., Nam, S. J., & Fenical, W. (2023). Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells. Marine Drugs, 21(3), Article 153. https://doi.org/10.3390/md21030153

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title = "Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells",

abstract = "Marinobazzanan (1), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus Acremonium. The chemical structure of 1 was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of 1 were determined by the modified Mosher{\textquoteright}s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6R, 7R, 9R, and 10R. It was found that compound 1 was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound 1 was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound 1 suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, 1 also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model.",

keywords = "Acremoniumsp, anticancer, bazzanane-type sesquiterpenoid, cytotoxicity, marinobazzanan",

author = "Sultan Pulat and Hillman, {Prima F.} and Sojeong Kim and Asolkar, {Ratnakar N.} and Haerin Kim and Rui Zhou and İsa Ta{\c s} and Gamage, {Chathurika D.B.} and M{\"u}cahit Varlı and Park, {So Yeon} and Park, {Sung Chul} and Inho Yang and Jongheon Shin and Oh, {Dong Chan} and Hangun Kim and Nam, {Sang Jip} and William Fenical",

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T1 - Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells

AU - Pulat, Sultan

AU - Hillman, Prima F.

AU - Kim, Sojeong

AU - Asolkar, Ratnakar N.

AU - Kim, Haerin

AU - Zhou, Rui

AU - Taş, İsa

AU - Gamage, Chathurika D.B.

AU - Varlı, Mücahit

AU - Park, So Yeon

AU - Park, Sung Chul

AU - Yang, Inho

AU - Shin, Jongheon

AU - Oh, Dong Chan

AU - Kim, Hangun

AU - Nam, Sang Jip

AU - Fenical, William

PY - 2023/3

Y1 - 2023/3

N2 - Marinobazzanan (1), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus Acremonium. The chemical structure of 1 was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of 1 were determined by the modified Mosher’s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6R, 7R, 9R, and 10R. It was found that compound 1 was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound 1 was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound 1 suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, 1 also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model.

AB - Marinobazzanan (1), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus Acremonium. The chemical structure of 1 was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of 1 were determined by the modified Mosher’s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6R, 7R, 9R, and 10R. It was found that compound 1 was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound 1 was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound 1 suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, 1 also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model.

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KW - anticancer

KW - bazzanane-type sesquiterpenoid

KW - cytotoxicity

KW - marinobazzanan

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DO - 10.3390/md21030153

M3 - Article

C2 - 36976200

AN - SCOPUS:85151167993

SN - 1660-3397

VL - 21

JO - Marine Drugs

JF - Marine Drugs

IS - 3

M1 - 153

ER -

Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells

Abstract

Bibliographical note

Keywords

UN SDGs

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