Two new polyprenylated acylphloroglucinols from Hypericum scabrum

Rang-Dong Liu; Jie Ma; Jian-Bo Yang; Ai-Guo Wang; Ya-Lun Su

doi:10.1080/10286020.2014.917083

Two new polyprenylated acylphloroglucinols from Hypericum scabrum

J Asian Nat Prod Res. 2014;16(7):717-23. doi: 10.1080/10286020.2014.917083. Epub 2014 May 14.

Authors

Rang-Dong Liu¹, Jie Ma, Jian-Bo Yang, Ai-Guo Wang, Ya-Lun Su

Affiliation

¹ a State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.

PMID: 24827084
DOI: 10.1080/10286020.2014.917083

Abstract

Two new polyprenylated acylphloroglucinols, (1S,32R,5S,6R,7R)-6-((R)-3,4-di-hydroxy-4-methylpentyl)-2-(2-hydroxypropan-2-yl)-7-isobutyryl-6-methyl-5,9-bis(3-methylbut-2-en-1-yl)-4,5,6,7-tetrahydro-2H-32,7-methanocycloocta[b]furan-8,10(3H)-dione (1) and (4R,5R,7R)-4-((R)-3,4-dihydroxy-4-methylpentyl)-2,2,4-trimethyl-5,7-bis(3-methyl-but-2-en-1-yl)-7-(5-methylhex-4-enoyl)-4,5,6,7-tetrahydrobenzofuran-3(2H)-one (2) were isolated from Hypericum scabrum. The structures were elucidated by means of spectroscopic methods, including MS, IR, NMR, OR, and CD.

Keywords: Guttiferae; Hypericum scabrum; polyprenylated acylphloroglucinols.

MeSH terms

Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification*
Hypericum / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Phloroglucinol / analogs & derivatives*
Phloroglucinol / chemistry
Stereoisomerism

Substances

(1S,32R,5S,6R,7R)-6-((R)-3,4-di-hydroxy-4-methylpentyl)-2-(2-hydroxypropan-2-yl)-7-isobutyryl-6-methyl-5,9-bis(3-methylbut-2-en-1-yl)-4,5,6,7-tetrahydro-2H-32,7-methanocycloocta(b)furan-8,10(3H)-dione
(4R,5R,7R)-4-((R)-3,4-dihydroxy-4-methylpentyl)-2,2,4-trimethyl-5,7-bis(3-methyl-but-2-en-1-yl)-7-(5-methylhex-4-enoyl)-4,5,6,7-tetrahydrobenzofuran-3(2H)-one
Drugs, Chinese Herbal
Phloroglucinol