Isosativenediol

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Isosativenediol
Category Others
Catalog number BBF-04399
CAS 57079-92-2
Molecular Weight 236.35
Molecular Formula C15H24O2
Purity 98.5%

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Description

Isosativenediol is produced from the culture filtrates of a Bipolaris species pathogenic to Johnson grass.

Specification

Synonyms 2,4-Methano-1H-indene-3,8-diol, octahydro-7a-methyl-1-methylene-5-(1-methylethyl)-, (2R,3R,3aR,4R,5S,7aS,8R)-rel-(-)-; 2,4-Methano-1H-indene-1,3-diol, octahydro-4-methyl-8-methylene-7-(1-methylethyl)-, (1α,2α,3β,3aβ,4α,7α,7aβ)-(-)-
Storage Store at -20°C
IUPAC Name (1S,2S,3S,4R,7R,8S,9S)-7-methyl-10-methylidene-4-propan-2-yltricyclo[5.2.1.03,8]decane-2,9-diol
Canonical SMILES CC(C)C1CCC2(C3C1C(C(C3O)C2=C)O)C
InChI InChI=1S/C15H24O2/c1-7(2)9-5-6-15(4)8(3)10-13(16)11(9)12(15)14(10)17/h7,9-14,16-17H,3,5-6H2,1-2,4H3/t9-,10+,11+,12-,13-,14-,15+/m1/s1
InChI Key JKWAVUHQXGRTII-AYECITQQSA-N

Properties

Appearance Powder
Boiling Point 347.7±30.0°C at 760 mmHg
Density 1.1±0.1 g/cm3
Solubility Soluble in Chloroform

Reference Reading

1. Bioactive seco-Sativene Sesquiterpenoids from an Artemisia desertorum Endophytic Fungus, Cochliobolus sativus
Yuan-Yuan Li, Xiang-Mei Tan, Yan-Duo Wang, Jian Yang, Yong-Gang Zhang, Bing-Da Sun, Ting Gong, Lan-Ping Guo, Gang Ding J Nat Prod. 2020 May 22;83(5):1488-1494. doi: 10.1021/acs.jnatprod.9b01148. Epub 2020 Apr 17.
A series of seco-sativene sesquiterpenoids (1-11) including two new natural products (2 and 3), four new analogues (4-7), and six known analogues, helminthosporic acid (1), drechslerine A (8), drechslerine B (9), helminthosporol (10), helminthosporal acid (11), and isosativenediol (12), were purified from the endophytic fungus Cochliobolus sativus isolated from a desert plant, Artemisia desertorum. The stereochemistry of helminthosporic acid (1) was established for the first time by X-ray diffraction, and the structures including relative and absolute configurations of these new compounds were determined by NMR and CD spectra together with biosynthetic considerations. Compounds 5-7 are the first seco-sativene sesquiterpenoids possessing a glucose group on C-15, C-15, and C-14, respectively. Compounds 1, 7, 9, and 11 displayed strong phytotoxic effects on corn leaves by producing visible lesions, and helminthosporic acid (1) was shown to promote division of leaves and roots of Arabidopsis thaliana with a dose-dependent relationship.

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