Kaemtakols A-D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

被引：4

作者：

Jongsomjainuk, Orawan ^{[1
]}

Boonsombat, Jutatip ^{[1
,4
]}

Thongnest, Sanit ^{[1
,4
]}

Prawat, Hunsa ^{[1
,4
]}

Batsomboon, Paratchata ^{[2
]}

Charoensutthivarakul, Sitthivut ^{[5
,6
]}

Ruchisansakun, Saroj ^{[7
]}

Chainok, Kittipong ^{[8
]}

Sirirak, Jitnapa ^{[9
]}

Mahidol, Chulabhorn ^{[1
,3
]}

Ruchirawat, Somsak ^{[2
,3
,4
]}

机构：

[1] Chulabhorn Res Inst, Lab Nat Prod, Bangkok, Thailand

[2] Chulabhorn Res Inst, Lab Med Chem, Bangkok, Thailand

[3] Chulabhorn Royal Acad, Chulabhorn Grad Inst, Program Chem Sci, Bangkok, Thailand

[4] MHESI, Ctr Excellence Environm Hlth & Toxicol EHT, OPS, Bangkok, Thailand

[5] Mahidol Univ, Excellent Ctr Drug Discovery ECDD, Sch Bioinnovat & Biobased Prod Intelligence, Bangkok, Thailand

[6] Mahidol Univ, Fac Sci, Ctr Neurosci, Bangkok, Thailand

[7] Mahidol Univ, Fac Sci, Dept Plant Sci, Bangkok, Thailand

[8] Thammasat Univ, Thammasat Univ Res Unit Multifunct Crystalline Mat, Fac Sci & Technol, Bangkok, Pathum Thani, Thailand

[9] Silpakorn Univ, Dept Chem, Fac Sci, Nakhon Pathom, Thailand

来源：

NATURAL PRODUCTS AND BIOPROSPECTING | 2023年 / 13卷 / 01期

关键词：

Kaempferia takensis; Diterpenoid; Structure elucidation; Anti-inflammatory; DP4+; Molecular docking; BASIS-SETS; INHIBITION; RHIZOMES; DESIGN; CELLS; INOS;

D O I：

10.1007/s13659-023-00420-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Four highly oxidized pimarane diterpenoids were isolated from Kaempferia takensis rhizomes. Kaemtakols A-C possess a tetracyclic ring with either a fused tetrahydropyran or tetrahydrofuran motif. Kaemtakol D has an unusual rearranged A/B ring spiro-bridged pimarane framework with a C-10 spirocyclic junction and an adjacent 1-methyltricyclo[3.2.1.02,7]octene ring. Structural characterization was achieved using spectroscopic analysis, DP4 + and ECD calculations, as well as X-ray crystallography, and their putative biosynthetic pathways have been proposed. Kaemtakol B showed significant potency in inhibiting nitric oxide production with an IC50 value of 0.69 mu M. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein.

引用

页数：13

共 34 条

[1]

BIOVIA Dassault Systmes, 2019, Discovery studio visualizer

[2] NATURALLY-OCCURRING TERPENE DERIVATIVES .293. GERMACRANOLIDES AND DITERPENES FROM VIGUIERA SPECIES [J].

BOHLMANN, F ;

JAKUPOVIC, J ;

AHMED, M ;

GRENZ, M ;

SUDING, H ;

ROBINSON, H ;

KING, RM .

PHYTOCHEMISTRY, 1981, 20 (01) :113-116

[3] Roscotanes and roscoranes: Oxygenated abietane and pimarane diterpenoids from Kaempferia roscoeana [J].

Boonsombat, Jutatip ;

Mahidol, Chulabhorn ;

Chawengrum, Pornsuda ;

Reuk-Ngam, Nanthawan ;

Chimnoi, Nitirat ;

Techasakul, Supanna ;

Ruchirawat, Somsak ;

Thongnest, Sanit .

PHYTOCHEMISTRY, 2017, 143 :36-44

[4] Diterpenoids and p-methoxycinnamic acid diol esters from Kaempferia saraburiensis Picheans. (Zingiberaceae): Structural assignment of saraburol and their biological activities [J].

Booranaseensuntorn, Pornpuk ;

Boonsombat, Jutatip ;

Mahidol, Chulabhorn ;

Reuk-Ngam, Nanthawan ;

Khlaychan, Panita ;

Batsomboon, Paratchata ;

Techasakul, Supanna ;

Thongnest, Sanit ;

Ruchirawat, Somsak .

PHYTOCHEMISTRY, 2022, 199

[5]

Bruhn T, 2017, SpecDis

[6] SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra [J].

Bruhn, Torsten ;

Schaumloeffel, Anu ;

Hemberger, Yasmin ;

Bringmann, Gerhard .

CHIRALITY, 2013, 25 (04) :243-249

[7] Diterpenoids with Aromatase Inhibitory Activity from the Rhizomes of Kaempferia elegans [J].

Chawengrum, Pornsuda ;

Boonsombat, Jutatip ;

Mahidol, Chulabhorn ;

Eurtivong, Chatchakorn ;

Kittakoop, Prasat ;

Thongnest, Sanit ;

Ruchirawat, Somsak .

JOURNAL OF NATURAL PRODUCTS, 2021, 84 (06) :1738-1747

[8] Inhibition of Nitric Oxide (NO) Production in Lipopolysaccharide (LPS)-Activated Murine Macrophage RAW 264.7 Cells by the Norsesterterpene Peroxide, Epimuqubilin A [J].

Cheenpracha, Sarot ;

Park, Eun-Jung ;

Rostama, Bahman ;

Pezzuto, John M. ;

Chang, Leng Chee .

MARINE DRUGS, 2010, 8 (03) :429-437

[9] Marginaols G-M, anti-inflammatory isopimarane diterpenoids, from the rhizomes of Kaempferia marginata [J].

Chokchaisiri, Ratchanaporn ;

Thothaisong, Teerawut ;

Chunglok, Warangkana ;

Chulrik, Wanatsanan ;

Yotnoi, Bunlawee ;

Chokchaisiri, Suwadee ;

Ganranoo, Lucksagoon ;

Cheenpracha, Sarot ;

Thepmalee, Chutamas ;

Suksamrarn, Apichart .

PHYTOCHEMISTRY, 2022, 200

[10] Isopimarane Diterpenoids from the Rhizomes of Kaempferia marginata and Their Potential Anti-inflammatory Activities [J].

Chokchaisiri, Ratchanaporn ;

Chaichompoo, Waraluck ;

Chunglok, Warangkana ;

Cheenpracha, Sarot ;

Ganranoo, Lucksagoon ;

Phutthawong, Nathaporn ;

Bureekaew, Sareeya ;

Suksamrarn, Apichart .

JOURNAL OF NATURAL PRODUCTS, 2020, 83 (01) :14-19

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