Immunomodulatory Polyketides from a Phoma-like Fungus
Isolated from a Soft Coral
Posted on 2017-10-19 - 18:48
Fourteen new polyketides with a trans-fused decalin
ring system, libertalides A–N (3–16), together with two known analogues, aspermytin A and its
acetate (1, 2), were isolated from the fermentation
extract of a coral-derived Libertasomyces sp. fungus.
Their relative configurations were elucidated on the basis of detailed
spectroscopic analysis, and the absolute configurations were determined
by TDDFT-ECD and optical rotation (OR) calculations. The OR of 1 and 2 were found to have opposite signs in
CH3CN and CHCl3, which was in agreement with
the OR calculations producing alternating signs for the optical rotation
depending on the applied conditions. Because the signs of the OR for 1 and 2 showed high solvent dependence, they
may not be used alone to correlate the absolute configurations. Compound 16 displayed structural novelty characterized by an α-enol
ether bridge conjugated with an aldehyde group. In in vitro immunomodulatory screening, compounds 1, 4, and 10 significantly induced the proliferation of
CD3+ T cells, while compounds 2, 7, 11, and 14 significantly increased the
CD4+/CD8+ ratio at 3 μM. A preliminary
structure–activity analysis revealed a crucial role of Δ7 and a terminal OH group in the regulation of CD3+ T cell proliferation. This is the first report of immunoregulatory
activity for metabolites of this kind.
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Sun, Yi-Zhe; Kurtán, Tibor; Mándi, Attila; Tang, Hua; Chou, Yalan; Soong, Keryea; et al. (2017). Immunomodulatory Polyketides from a Phoma-like Fungus
Isolated from a Soft Coral. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.7b00463
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AUTHORS (10)
YS
Yi-Zhe Sun
TK
Tibor Kurtán
AM
Attila Mándi
HT
Hua Tang
YC
Yalan Chou
KS
Keryea Soong
LS
Li Su
PS
Peng Sun
CZ
Chun-Lin Zhuang
WZ
Wen Zhang