Voluhemins, new inhibitors of sterol O-acyltransferase, produced by Volutella citrinella BF-0440

Taichi Ohshiro^{1

2

3}, Haruka Morita⁴, Elyza Aiman Azizah Nur⁴, Kanji Hosoda^{4

5}, Ryuji Uchida⁶, Hiroshi Tomoda^{7

8}

Affiliations

¹ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tohshiro@med.nagoya-u.ac.jp.
² Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tohshiro@med.nagoya-u.ac.jp.
³ Graduate School of Medicine, Nagoya University, 65 Tsurumai-cho, Showa-ku, Nagoya, Aichi, 466-8550, Japan. tohshiro@med.nagoya-u.ac.jp.
⁴ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
⁵ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
⁶ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan.
⁷ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.
⁸ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.

PMID: 32467602
DOI: 10.1038/s41429-020-0327-0

Voluhemins, new inhibitors of sterol O-acyltransferase, produced by Volutella citrinella BF-0440

Taichi Ohshiro et al. J Antibiot (Tokyo). 2020 Nov.

. 2020 Nov;73(11):748-755.

doi: 10.1038/s41429-020-0327-0. Epub 2020 May 29.

Authors

Taichi Ohshiro^{1

2

3}, Haruka Morita⁴, Elyza Aiman Azizah Nur⁴, Kanji Hosoda^{4

5}, Ryuji Uchida⁶, Hiroshi Tomoda^{7

8}

Affiliations

¹ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tohshiro@med.nagoya-u.ac.jp.
² Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tohshiro@med.nagoya-u.ac.jp.
³ Graduate School of Medicine, Nagoya University, 65 Tsurumai-cho, Showa-ku, Nagoya, Aichi, 466-8550, Japan. tohshiro@med.nagoya-u.ac.jp.
⁴ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
⁵ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
⁶ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan.
⁷ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.
⁸ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.

PMID: 32467602
DOI: 10.1038/s41429-020-0327-0

Abstract

New compounds, designated voluhemins A (1) and B (2), are isolated from the culture broth of the fungal strain Volutella citrinella BF-0440 along with structurally related known NK12838 (3). Spectroscopic data, including 1D and 2D NMR, elucidated their structures. Compounds 1-3 have a common indoline-diterpene core and two additional isoprenyl moieties. Compounds 1 and 3 contain a hemiaminal unit, while 2 is O-methylated 1. Their inhibitory activities toward sterol O-acyltransferase (SOAT) 1 and 2 isozymes in SOAT1- and SOAT2-expressing Chinese hamster ovary (CHO) cells show that 2 selectively inhibits the SOAT2 isozyme.

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References

1. Anderson RA, Joyce C, Davis M, Reagan JW, Clark M, Shelness GS, et al. Identification of a form of acyl-CoA: cholesterol acyltransferase specific to liver and intestine in nonhuman primates. J Biol Chem. 1998;273:26747–54. - DOI
1. Cases S, Novak S, Zheng YW, Myers HM, Lear SR, Sande E, et al. ACAT-2, a second mammalian acyl-CoA: cholesterol acyltransferase. Its cloning, expression, and characterization. J Biol Chem. 1998;273:26755–64. - DOI
1. Oelkers P, Behari A, Cromley D, Billheimer JT, Sturley SL. Characterization of two human genes encoding acyl coenzyme A: cholesterol acyltransferase-related enzymes. J Biol Chem. 1998;273:26765–71. - DOI
1. Rudel LL, Lee RG, Cockman TL. Acyl coenzyme A: cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis. Curr Opin Lipidol. 2001;12:121–7. - DOI
1. Parini P, Davis M, Lada AT, Erickson SK, Wright TL, Gustafsson U, et al. ACAT2 is localized to hepatocytes and is the major cholesterol-esterifying enzyme in human liver. Circulation. 2004;110:2017–23. - DOI

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Voluhemins, new inhibitors of sterol O-acyltransferase, produced by Volutella citrinella BF-0440

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Voluhemins, new inhibitors of sterol O-acyltransferase, produced by Volutella citrinella BF-0440

Authors

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Abstract

References

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Full Text Sources

Miscellaneous