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New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata).

ABSTRACT: Eighteen compounds including new caryophyllene-type sesquiterpene and flavonol tetraglycoside were purified and isolated from sword beans (Canavalia gladiata). Two new compounds, (Z,1R,7S,9S)-7-hydroxy-11,11-dimethyl-8-methylenebicyclo[7.2.0]undec-4-ene-4-carboxylic acid (2) and kaempferol-7-O-α-l-dirhamnopyranosyl(1 → 2;1 → 6)-O-β-d-glucopyranosyl(1 → 2)-O-α-l-rhamnopyranoside (9), were identified. Other known compounds including methyl gallate (1), (2S,3S,4E,8E)-2-aminooctadeca-4,8-diene-1,3-diol 1-O-β-d-glucopyranoside (3), (2S,3S,4E,8Z)-2-aminooctadeca-4,8-diene-1,3-diol 1-O-β-d-glucopyranoside (4), lupeol (5), trilinolein (6), 1,6-di-O-galloyl β-d-glucopyranoside (7), N-(2-methoxybenzoyl)homoserine (8), dihydrophaseic acid (10), dillenetin (11), kaempferol-7-O-[2-O-β-d-glucopyranosyl-6-O-α-l-rhamnopyranosyl]-α-l-rhamnopyranoside (12), canavalioside (13), kaempferol-3-O-[2-O-β-d-glucopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (14), kaempferol-3-O-(2,6-O-α-l-dirhamnopyranosyl)-β-d-glucopyranoside (15), kaempferol-3-O-rutinoside (16), gladiatoside A₁ (17), and gladiatoside B₁ (18) were identified. The chemical structures of these compounds were determined by ESI-MS and NMR analyses.

SUBMITTER: An HJ

PROVIDER: S-EPMC7492346 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata).

An Hyun Jeong HJ Kim Eun Hee EH Lee Hyoung Jae HJ Cho Jeong-Yong JY Moon Jae-Hak JH

Food science and biotechnology 20200801 10

Eighteen compounds including new caryophyllene-type sesquiterpene and flavonol tetraglycoside were purified and isolated from sword beans (Canavalia gladiata). Two new compounds, (Z,1R,7S,9S)-7-hydroxy-11,11-dimethyl-8-methylenebicyclo[7.2.0]undec-4-ene-4-carboxylic acid (2) and kaempferol-7-O-α-l-dirhamnopyranosyl(1 → 2;1 → 6)-O-β-d-glucopyranosyl(1 → 2)-O-α-l-rhamnopyranoside (9), were identified. Other known compounds inclu ...[more]

PMID: 32999741

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Project description:Backgroundβ-Caryophyllene, a kind of bicyclic sesquiterpene, is mainly used as a spice in the food and cosmetic industries. Furthermore, it also has significant value in the pharmaceutical industry and is now considered to be used as a new fuel. As a chemical energy heterotrophic microorganism, Escherichia coli can produce a large amount of acetyl-CoA through aerobic respiration, and acetyl-CoA is the common precursor substance in the biosynthesis of all terpenoids. Therefore, E. coli has the potential to be a cell factory to produce terpenoids.ResultsA new gene of β-caryophyllene synthase (TPS7) was found by analyzing the genome of Nicotiana tabacum L. using bioinformatics methods. The gene was overexpressed in engineered E. coli with a heterogeneous mevalonate (MVA) pathway to build a recombinant strain CAR1. Subsequent cultivation experiments in shake flask of engineered strain CAR1 verified that 16.1 mg/L β-caryophyllene was detected from the fermentation broth in the shake flask after induction for 24 h with IPTG. The toxic by-product of farnesyl acetate was detected during the process, and CAR1 showed a heavily cellular accumulation of product. We constructed an engineered strain CAR2, in which the downstream genes of the MVA pathway were integrated into the E. coli chromosome, successfully increasing β-caryophyllene production to 100.3 mg/L. The highest production of β-caryophyllene during the fed-batch fermentation was 4319 mg/L. Then we employed in situ extraction fermentation to successfully increase the production of β-caryophyllene by 20% to 5142 mg/L.ConclusionA new sesquiterpene synthase, TPS7, from tobacco was found to be able to produce β-caryophyllene with high efficiency. Based on this, an engineered E. coli was constructed to produce a much higher concentration of β-caryophyllene than the previous studies. During the fermentation process, we observed that β-caryophyllene tends to accumulate in intracellular space, which will eventually influence the activity of engineered E. coli. As a result, we solved this by metabolism regulation and in situ extractive fermentation.

Dataset Information

New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (Canavalia gladiata).

Publications

New caryophyllene-type sesquiterpene and flavonol tetraglycoside with sixteen known compounds from sword bean (<i>Canavalia gladiata</i>).

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