Biotransformation of 1?,11?-dihydroxyisopimara-8(14),15-diene by Cunninghamella echinulata NRRL 1386 and their neuroprotective activity

被引：5

作者：

Chokchaisiri, Ratchanaporn ^{[1
]}

Chaichompoo, Waraluck ^{[2
,3
]}

Pabuprapap, Wachirachai ^{[2
,3
]}

Sukcharoen, Oratai ^{[4
]}

Tocharus, Jiraporn ^{[5
]}

Ganranoo, Lucksagoon ^{[1
]}

Bureekaew, Sareeya ^{[6
]}

Sangvichien, Ek ^{[7
]}

Suksamrarn, Apichart ^{[2
,3
]}

机构：

[1] Univ Phayao, Sch Sci, Dept Chem, Phayao 56000, Thailand

[2] Ramkhamhang Univ, Fac Sci, Dept Chem, Bangkok 10240, Thailand

[3] Ramkhamhang Univ, Fac Sci, Ctr Excellence Innovat Chem, Bangkok 10240, Thailand

[4] Ramkhamhang Univ, Fac Sci, Dept Biotechnol, Bangkok 10240, Thailand

[5] Chiang Mai Univ, Fac Med, Dept Physiol, Chiang Mai 50200, Thailand

[6] Vidyasirimedhi Inst Sci & Technol VISTEC, Dept Energy Sci & Engn, Wangchan 21210, Rayong, Thailand

[7] Ramkhamhang Univ, Fac Sci, Dept Biol, Bangkok 10240, Thailand

来源：

BIOORGANIC CHEMISTRY | 2021年 / 110卷

关键词：

Kaempferia marginata; Microbial transformation; Cunninghamella echinulata; Neuroprotective activity; ALZHEIMERS-DISEASE; AMYLOID CASCADE; HYPOTHESIS;

D O I：

10.1016/j.bioorg.2021.104799

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The isopimarane diterpene, 1?,11?-dihydroxyisopimara-8(14),15-diene (1), is the major constituents from the rhizomes of Kaempferia marginata (Zingiberaceae), a Thai medicinal plant. The microbial transformation of parent compound 1 by the fungus Cunninghamella echinulata NRRL 1386 gave five new metabolites, 7?,11?dihydroxy-1-oxoisopimara-8(14),15-diene (2), 3fl,7?,11?-trihydroxy-1-oxoisopimara-8(14),15-diene (3), 7fl,11?-dihydroxy-1-oxoisopimara-8(14),15-diene (4), 7?-hydroxy-1,11-dioxoisopimara-8(14),15-diene (5) and 1?,7fl,11?-trihydroxyisopimara-8(14),15-diene (6), together with three known metabolites, 7?9. The structures of the new metabolites were elucidated by spectroscopic techniques. The known compounds were identified by comparison of the spectroscopic and physical data with those of reported values. The parent compound 1 and the metabolites have been neuroprotective activities evaluated against A?25-35-induced damage in human neuroblastoma cells (SK-N-SH). Among them, compounds 1?3, 5 and 7?9 had significant neuroprotective activities at a concentration of 2.5 ?M. The results demonstrated that these compounds might be worth for further development into therapeutic agents for the treatment of neurodegenerative diseases.

引用

页数：6

共 3 条

[1] (1R,2R,5R,6R,9S,10S,13S,14S)-1,6,7,8,9,14,15,16,17,17-decachloropentacyclo[12.2.1.16,9.02,13.05,10]octadeca-7,15-diene
Riddell, Nicole
McCrindle, Robert
Arsenault, Gilles
Lough, Alan J.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1249 - U1767
[2] (1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-undecachloropentacyclo[12.2.1.16,9.02,13.05,10]octadeca-7,15-diene
Riddell, Nicole
McCrindle, Robert
Arsenault, Gilles
Lough, Alan J.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1250 - U1776
[3] 14-membered macrocyles: methyl trans-(10E)-5-methyl-8-methylene-11, 15-dioxobicyclo[12.3.0]-heptadec-4-ene-14-carboxylate, (I), and methyl trans-(2E,10E)-10-methyl-7-methylene-4,17-dioxobicyclo [12.3.0]heptadeca-2,10-diene-1-carboxylate, (II)
Acta Crystallogr Sect C Cryst Struct Commun, pt 1 (107):

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