Deacetyl 19,20-epoxycytochalasin Q

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Deacetyl 19,20-epoxycytochalasin Q
Category Mycotoxins
Catalog number BBF-04984
CAS 156616-84-1
Molecular Weight 481.58
Molecular Formula C28H35NO6

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Description

Deacetyl 19,20-epoxycytochalasin Q is a cytotoxic agent obtained from Xylaria obovata, which is a plant growth regulator.

Specification

Synonyms 3H-Oxireno[f]oxireno[9,10]cycloundec[1,2-d]isoindole-3,12(4H)-dione, 1a,2,5,7a,7b,8a,9,9a,10,11,13,13a-dodecahydro-2,13-dihydroxy-2,4,8a,9-tetramethyl-10-(phenylmethyl)-, (1aR,2R,4S,6E,7aR,7bS,8aR,9S,9aR,10S,12aR,13S,13aS)-; 2H-Oxireno[f]oxireno[9,10]cycloundec[1,2-d]isoindole-3,12(1aH,4H)-dione, 5,5a,6,6a,7a,7b,10,11,13,13a-decahydro-2,13-dihydroxy-6,6a,11,13-tetramethyl-5-(phenylmethyl)-, [1aS-(1aR*,2R*,2aS*,5R*,5aS*,6R*,6aS*,7aR*,7bS*,8E,11R*,13S*,13aS*)]- (9CI); [11]Cytochalas-13-ene-1,17-dione, 6,7:19,20-diepoxy-18,21-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19R,20S,21R)-; (1aR,2R,4S,6E,7aR,7bS,8aR,9S,9aR,10S,12aR,13S,13aS)-1a,2,5,7a,7b,8a,9,9a,10,11,13,13a-Dodecahydro-2,13-dihydroxy-2,4,8a,9-tetramethyl-10-(phenylmethyl)-3H-oxireno[f]oxireno[9,10]cycloundec[1,2-d]isoindole-3,12(4H)-dione; Deacetyl 19,20-epoxycytochalasin Q
IUPAC Name (4S,6R,6aR,7aR,8R,8aR,11S,11aR,12S,12aR,13aS,13bR,E)-11-benzyl-6,8-dihydroxy-4,6,12,12a-tetramethyl-3,6,6a,7a,8,10,11,11a,12,12a,13a,13b-dodecahydro-5H-oxireno[2,3-f]oxireno[2',3':9,10]cycloundeca[1,2-d]isoindole-5,9(4H)-dione

Properties

Boiling Point 713.4±60.0°C (Predicted)
Melting Point 119-121°C
Density 1.32±0.1 g/cm3 (Predicted)

Reference Reading

1. Six 19,20-epoxycytochalasans from endophytic Diaporthe sp. RJ-47
Qiong Zhang, Zhi-Pu Huang, Yu-Ying Zhao, Qing Zhao, Jian-Hong Chen, Wei-Guang Ma, Xiao-Mei Zhang Nat Prod Res. 2022 Jul;36(13):3375-3380. doi: 10.1080/14786419.2020.1859504. Epub 2020 Dec 16.
Two new cytochalasins, deacetyl-19-epi-cytochalasin P1 (1), deacetyl-19,20-epoxycytochalasin D (2) were isolated from the endophytic fungus Diaporthe sp. RJ-47, along with four known compounds deacetyl-5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (3), 19,20-epoxycytochalasin Q (4), 19,20-epoxycytochalasin C (5) and deacetyl-19,20-epoxy cytochalasin C (6). Their structures were unambiguously elucidated on the basis of the comprehensive analysis of extensive spectroscopic data. The antimicrobial effects of these compounds were evaluated.

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