A New Metabolite with a Unique 4-Pyranone-γ-Lactam-1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus

Chun Shun Li; Yuanqing Ding; Bao Jun Yang; Gabriella Miklossy; Hong Quan Yin; Larry A. Walker; James Turkson; Shugeng Cao

doi:10.1021/acs.orglett.5b01650

A New Metabolite with a Unique 4-Pyranone-γ-Lactam-1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus

Chun Shun Li
, Yuanqing Ding
, Bao Jun Yang
, Gabriella Miklossy
, Hong Quan Yin
, Larry A. Walker
, James Turkson
, Shugeng Cao^*

^*Corresponding author for this work

University of Hawai'i at Mānoa
University of Mississippi
University of Hawai'i at Hilo

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

58 Citations (Scopus)

Abstract

An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone-γ-lactam-1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1-3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.

Original language	English
Pages (from-to)	3556-3559
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.5b01650
Publication status	Published - 17 Jul 2015
Externally published	Yes

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title = "A New Metabolite with a Unique 4-Pyranone-γ-Lactam-1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus",

abstract = "An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone-γ-lactam-1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1-3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.",

author = "Li, \{Chun Shun\} and Yuanqing Ding and Yang, \{Bao Jun\} and Gabriella Miklossy and Yin, \{Hong Quan\} and Walker, \{Larry A.\} and James Turkson and Shugeng Cao",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.orglett.5b01650",

language = "English",

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AU - Li, Chun Shun

AU - Ding, Yuanqing

AU - Yang, Bao Jun

AU - Miklossy, Gabriella

AU - Yin, Hong Quan

AU - Walker, Larry A.

AU - Turkson, James

AU - Cao, Shugeng

PY - 2015/7/17

Y1 - 2015/7/17

N2 - An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone-γ-lactam-1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1-3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.

AB - An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone-γ-lactam-1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1-3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.

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A New Metabolite with a Unique 4-Pyranone-γ-Lactam-1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus

Abstract

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