Ginsenosides in <i>Panax</i> genus and their biosynthesis

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Abstract

Ginsenosides are a series of glycosylated triterpenoids which belong to protopanaxadiol (PPD)-, protopanaxatriol (PPT)-, ocotillol (OCT)- and oleanane (OA)-type saponins known as active compounds of Panax genus. They are accumulated in plant roots, stems, leaves, and flowers. The content and composition of ginsenosides are varied in different ginseng species, and in different parts of a certain plant. In this review, we summarized the representative saponins structures, their distributions and the contents in nearly 20 Panax species, and updated the biosynthetic pathways of ginsenosides focusing on enzymes responsible for structural diversified ginsenoside biosynthesis. We also emphasized the transcription factors in ginsenoside biosynthesis and non-coding RNAs in the growth of Panax genus plants, and highlighted the current three major biotechnological applications for ginsenosides production. This review covered advances in the past four decades, providing more clues for chemical discrimination and assessment on certain ginseng plants, new perspectives for rational evaluation and utilization of ginseng resource, and potential strategies for production of specific ginsenosides.

Graphical abstract

Ginsenosides are produced mainly via MVA pathway. Functional genes are regulated by multiple elicitors through different transcriptional factors, which together play pivotal roles in ginsenoside structure diversities.

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Most cited references 239

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High-level semi-synthetic production of the potent antimalarial artemisinin.

C J Paddon, P J Westfall, D J Pitera … (2013)

In 2010 there were more than 200 million cases of malaria, and at least 655,000 deaths. The World Health Organization has recommended artemisinin-based combination therapies (ACTs) for the treatment of uncomplicated malaria caused by the parasite Plasmodium falciparum. Artemisinin is a sesquiterpene endoperoxide with potent antimalarial properties, produced by the plant Artemisia annua. However, the supply of plant-derived artemisinin is unstable, resulting in shortages and price fluctuations, complicating production planning by ACT manufacturers. A stable source of affordable artemisinin is required. Here we use synthetic biology to develop strains of Saccharomyces cerevisiae (baker's yeast) for high-yielding biological production of artemisinic acid, a precursor of artemisinin. Previous attempts to produce commercially relevant concentrations of artemisinic acid were unsuccessful, allowing production of only 1.6 grams per litre of artemisinic acid. Here we demonstrate the complete biosynthetic pathway, including the discovery of a plant dehydrogenase and a second cytochrome that provide an efficient biosynthetic route to artemisinic acid, with fermentation titres of 25 grams per litre of artemisinic acid. Furthermore, we have developed a practical, efficient and scalable chemical process for the conversion of artemisinic acid to artemisinin using a chemical source of singlet oxygen, thus avoiding the need for specialized photochemical equipment. The strains and processes described here form the basis of a viable industrial process for the production of semi-synthetic artemisinin to stabilize the supply of artemisinin for derivatization into active pharmaceutical ingredients (for example, artesunate) for incorporation into ACTs. Because all intellectual property rights have been provided free of charge, this technology has the potential to increase provision of first-line antimalarial treatments to the developing world at a reduced average annual price.

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(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate.

Sandra Fonseca, Andrea Chini, Mats Hamberg … (2009)

Hormone-triggered activation of the jasmonate signaling pathway in Arabidopsis thaliana requires SCF(COI1)-mediated proteasome degradation of JAZ repressors. (-)-JA-L-Ile is the proposed bioactive hormone, and SCF(COI1) is its likely receptor. We found that the biological activity of (-)-JA-L-Ile is unexpectedly low compared to coronatine and the synthetic isomer (+)-JA-L-Ile, which suggests that the stereochemical orientation of the cyclopentanone-ring side chains greatly affects receptor binding. Detailed GC-MS and HPLC analyses showed that the (-)-JA-L-Ile preparations currently used in ligand binding studies contain small amounts of the C7 epimer (+)-7-iso-JA-L-Ile. Purification of each of these molecules demonstrated that pure (-)-JA-L-Ile is inactive and that the active hormone is (+)-7-iso-JA-L-Ile, which is also structurally more similar to coronatine. In addition, we show that pH changes promote conversion of (+)-7-iso-JA-L-Ile to the inactive (-)-JA-L-Ile form, thus providing a simple mechanism that can regulate hormone activity through epimerization.

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The oxylipin signal jasmonic acid is activated by an enzyme that conjugates it to isoleucine in Arabidopsis.

Paul E Staswick, Iskender Tiryaki (2004)

Despite its importance in a variety of plant defense responses, our understanding of how jasmonic acid (JA) functions at the biochemical level is limited. Several amino acid conjugates of JA were tested for their ability to complement the JA-insensitive Arabidopsis thaliana mutant jar1-1. Unlike free JA, JA-Ile inhibited root growth in jar1-1 to the same extent as in the wild type, whereas JA-Val, JA-Leu, and JA-Phe were ineffective inhibitors in both genotypes. Thin-layer chromatography and gas chromatography-mass spectrometry (GC-MS) analysis of products produced in vitro by recombinant JAR1 demonstrated that this enzyme forms JA-amido conjugates with several amino acids, including JA-Ile. JA-Val, -Leu, -Ile, and -Phe were each quantified in Arabidopsis seedlings by GC-MS. JA-Ile was found at 29.6 pmole g(-1) fresh weight (FW) in the wild type but was more than sevenfold lower in two jar1 alleles. JA-Leu, -Val, and -Phe were present at only low levels in both genotypes. Expression of wild-type JAR1 in transgenic jar1-1 plants restored sensitivity to JA and elevated JA-Ile to the same level as in the wild type. The ethylene precursor 1-aminocyclopropane-1-carboxylic acid (ACC) conjugated to JA was also found in plant tissue at 18.4 pmole g(-1) FW. JA-ACC was determined not be an effective jasmonate root inhibitor, and surprisingly, was twofold higher in the mutants than in the wild type. This suggests that another JA-conjugating enzyme(s) is present in Arabidopsis. Synthesis of JA-ACC might provide a mechanism to coregulate the availability of JA and ACC for conversion to the active hormones JA-Ile and ethylene, respectively. We conclude that JAR1 is a JA-amino synthetase that is required to activate JA for optimal signaling in Arabidopsis. Plant hormone activation by conjugation to amino acids and the enzymes involved in their formation were previously unknown.

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Author and article information

Contributors

Shujuan Zhao

Zhengtao Wang

Journal

Journal ID (nlm-ta): Acta Pharm Sin B

Journal ID (iso-abbrev): Acta Pharm Sin B

Title: Acta Pharmaceutica Sinica. B

Publisher: Elsevier

ISSN (Print): 2211-3835

ISSN (Electronic): 2211-3843

Publication date PMC-release: 02 January 2021

Publication date (Print): July 2021

Publication date (Electronic): 02 January 2021

Volume: 11

Issue: 7

Pages: 1813-1834

Affiliations

[1]The SATCM Key Laboratory for New Resources & Quality Evaluation of Chinese Medicine, The MOE Key Laboratory for Standardization of Chinese Medicines and Shanghai Key Laboratory of Compound Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

Author notes

[∗ ]Corresponding author. Tel: 86 21 51322576, fax: +86 21 51322495 (Shujuan Zhao); Tel.: +86 21 51322507, fax: +86 21 51322505 (Zhengtao Wang). zhaoshujuan@ 123456126.com zhaoshujuan@ 123456shutcm.edu.cn ztwang@ 123456shutcm.edu.cn

Article

Publisher Item ID: S2211-3835(20)30851-0

DOI: 10.1016/j.apsb.2020.12.017

PMC ID: 8343117

PubMed ID: 34386322

SO-VID: 34f97964-56a7-4f38-b0ae-e7275ea85383

License:

This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

History

Date received : 8 September 2020

Date revision received : 3 December 2020

Date accepted : 11 December 2020

Categories

Subject: Review

Keywords: ginsenoside,panax species,biosynthetic pathway,transcription factors,non-coding rnas,biotechnological approach,α-as, α-amyrin synthase,aba, abscisic acid,adp, adenosine diphosphate,atcpr (atr), arabidopsis thaliana cytochrome p450 reductase,bars, baruol synthase,β-as, β-amyrin synthase,cas, cycloartenol synthase,cdp, cytidine diphosphate,cpq, cucurbitadienol synthase,cyp, cytochrome p450,dds, dammarenediol synthase,dm, dammarenediol-ii,dmapp, dimethylallyl diphosphate,fpp, farnesyl pyrophosphate,fpps (fps), farnesyl diphosphate synthase,gdp, guanosine diphosphate,heja, 2-hydroxyethyl jasmonate,hmgr, hmg-coa reductase,ipp, isopentenyl diphosphate,its, internal transcribed spacer,ja, jasmonic acid,ja-ile, (+)-7-iso-jasmonoyl-l-isoleucine,jar, ja-amino acid synthetase,jaz, jasmonate zim-domain,kcms, kandelia candel multifunctional triterpene synthases,las, lanosterol synthase,lup, lupeol synthase,mep, methylerythritol phosphate,meja, methyl jasmonate,mva, mevalonate,mvd, mevalonate diphosphate decarboxylase,ndp, nucleotide diphosphate,oa, oleanane or oleanic acid,oas, oleanolic acid synthase,oct, ocotillol,osc, oxidosqualene cyclase,ppd, protopanaxadiol,ppds, ppd synthase,ppt, protopanaxatriol,ppts, ppt synthase,rnai, rna interference,sa, salicylic acid,se (sqe), squalene epoxidase,ss (sqs), squalene synthase,spl, squamosa promoter-binding protein-like,sus, sucrose synthase,tdp, thymine diphosphate,udp, uridine diphosphate,ugpase, udp-glucose pyrophosphosphprylase,ugt, udp-dependent glycosyltransferase,wgd, whole genome duplication

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Keywords: ginsenoside, panax species, biosynthetic pathway, transcription factors, non-coding rnas, biotechnological approach, α-as, α-amyrin synthase, aba, abscisic acid, adp, adenosine diphosphate, atcpr (atr), arabidopsis thaliana cytochrome p450 reductase, bars, baruol synthase, β-as, β-amyrin synthase, cas, cycloartenol synthase, cdp, cytidine diphosphate, cpq, cucurbitadienol synthase, cyp, cytochrome p450, dds, dammarenediol synthase, dm, dammarenediol-ii, dmapp, dimethylallyl diphosphate, fpp, farnesyl pyrophosphate, fpps (fps), farnesyl diphosphate synthase, gdp, guanosine diphosphate, heja, 2-hydroxyethyl jasmonate, hmgr, hmg-coa reductase, ipp, isopentenyl diphosphate, its, internal transcribed spacer, ja, jasmonic acid, ja-ile, (+)-7-iso-jasmonoyl-l-isoleucine, jar, ja-amino acid synthetase, jaz, jasmonate zim-domain, kcms, kandelia candel multifunctional triterpene synthases, las, lanosterol synthase, lup, lupeol synthase, mep, methylerythritol phosphate, meja, methyl jasmonate, mva, mevalonate, mvd, mevalonate diphosphate decarboxylase, ndp, nucleotide diphosphate, oa, oleanane or oleanic acid, oas, oleanolic acid synthase, oct, ocotillol, osc, oxidosqualene cyclase, ppd, protopanaxadiol, ppds, ppd synthase, ppt, protopanaxatriol, ppts, ppt synthase, rnai, rna interference, sa, salicylic acid, se (sqe), squalene epoxidase, ss (sqs), squalene synthase, spl, squamosa promoter-binding protein-like, sus, sucrose synthase, tdp, thymine diphosphate, udp, uridine diphosphate, ugpase, udp-glucose pyrophosphosphprylase, ugt, udp-dependent glycosyltransferase, wgd, whole genome duplication

Ginsenosides in Panax genus and their biosynthesis

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Abstract

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Plant MYBs

Most cited references 239

High-level semi-synthetic production of the potent antimalarial artemisinin.

(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate.

The oxylipin signal jasmonic acid is activated by an enzyme that conjugates it to isoleucine in Arabidopsis.

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Contributors

Journal

Affiliations

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History

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