Studies on the biosynthesis of pentalenolactone, part II isolation of pentalehic acid and pentalenolactone H

Seto, Haruo; Sasaki, Tōru; Uzawa, Jun; Takeuchi, Setsuo; Yonehara, Hiroshi

doi:10.1016/s0040-4039(01)95238-4

Cited by 45 publications

(28 citation statements)

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“…8) Therefore long-range selective proton-decoupling (LSPD) 14) method was applied to 1 and 2. Selective irradiation at H-8 in 2 collapsed the carbon signals for C-4Ј, which became significantly sharper, thereby indicating that compound 2 has a hydroxymethyl group and a chatechol unit attaching to C-8 and C-7, respectively.…”

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Structures of 1,4-Benzodioxane Derivatives from the Seeds of Phytolacca americana and Their Neuritogenic Activity in Primary Cultured Rat Cortical Neurons

Takahasi

Yanagi

Nakade

2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Phytolacca americana L. (Phytolaccaceae) is a plant originating in North America, and its dried roots have been used as a diuretic drug in place of the Chinese medicinal plant Phytolacca esuclenta. A number of triterpenes, their glycosides, and neolignans have been isolated from the roots of P. americana.1-7) Previously, we reported the structures of americanol A (6) and isoamericanol A (7) isolated from seeds of P. americana, 8,9) as well as those of triterpene glycosides produced from the cultures of P. americana. 10) Americanol A (6) and isoamericanol A (7) in particular showed interesting neurite outgrowth-promoting activity in primary cultured rat cortical neurons. 9) Their significant biological properties stimulated our interest in developing the preparative synthesis of 6 and 7, resulting in the successful one-step syntheses of 6 and 7 through horseradish peroxidase (HRP)-catalyzed oxidative coupling of 3,4-dihydroxycinnamyl alchohol.11,12) The methanol extract of the seeds of P. americana showed antioxidant activities, i.e., free radical-scavenging activity of the a,a-diphenyl-b-picrylhydrazyl radical (DPPH) 13) and superoxide anion-scavenging activity (O 2 Ϫ ).This result encouraged us to reinvestigate the chemical constituents in P. americana.In this paper, we describe the structures of three new 1,4-benzodioxane compounds 1-3 named americanoic acid A methyl ester, isoamericanoic acid A methyl ester, and 9Ј-Omethylamericanol A, and their neuritogenic activity together with neuritogenesis of dicarboxilic acids 6 and 7 11,12) in primary cultured rat cortical neurons. Results and DiscussionThe methanol extract of the seeds of P. americana was subjected to silica gel chromatography and then purified by reverse-phase HPLC to yield compounds 1-3 along with the previously isolated neolignans, isoamericanol A (7), americanin A (8), and isoamericanin A (9) (Fig. 1), and the triterpenes glycoside esculentoside B and esculentside S. 10)Compounds 1 and 2 not only had the same molecular formula C 17 H 16 O 7 determined by high-resolution (HR) electron impact (EI)-MS, but also similar 1 H-and 13 C-NMR spectral data. Their IR spectra showed the presence of hydroxyl Yamashiro-cho, Tokushima 770-8514, Japan. Received July 24, 2003; accepted September 17, 2003 The methanol extract of the seeds of Phytolacca americana was reinvestigated to yield three new 1,4-benzodioxane-type compounds, americanoic acid methyl ester (1), isoamericanoic acid A methyl ester (2), and 9-Omethylamericanol A (3) along with the previously isolated neolignans 6-9. The structures of 1-3 were characterized by 2D NMR and long-range selective proton-decoupling (LSPD) techniques. The neuritogenic effects of compounds 1-3, and dicarboxilic acids 4 and 5, which had been previously synthesized with horseradish peroxidase-catalyzed oxidative coupling of caffeic acid, were examined in primary cultured rat cortical neurons. Americanoic acid A methyl ester (1) exhibited neurite outgrowth-promoting activity at concentration of 0.01-1.0 m mM, whereas d...

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Structures of 1,4-Benzodioxane Derivatives from the Seeds of Phytolacca americana and Their Neuritogenic Activity in Primary Cultured Rat Cortical Neurons

Takahasi

Yanagi

Nakade

2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Pentalenic acid 43 is an angular triquinane sesquiterpene that was first isolated as a shunt pathway product of pentalenolactone biosynthesis (Seto et al 1978), and later was obtained from many Streptomyces spp. as a co-metabolite of the pentalenolactone sesquiterpene family of natural products (Takamatsu et al 2011).…”

Section: Aminoheptosyl Glycosidesmentioning

confidence: 99%

Natural product diversity of actinobacteria in the Atacama Desert

Rateb

Ebel

Jaspars

2018

Antonie van Leeuwenhoek

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The Atacama Desert of northern Chile is considered one of the most arid and extreme environment on Earth. Its core region was described as featuring "Mars-like" soils that were at one point deemed too extreme for life to exist. However, recent investigations confirmed the presence of diverse culturable actinobacteria. In the current review, we discuss a total of 46 natural products isolated to date representing diverse chemical classes characterized from different actinobacteria isolated from various locations in the Atacama Desert. Their reported biological activities are also discussed.

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“…The first step in pentalenolactone biosynthesis is the cyclization of farnesyl diphosphate, the universal precursor of all sesquiterpenes, to pentalenene ( 2 ), which is the parent hydrocarbon of the pentalenolactone family of metabolites. From the results of feeding experiments for pentalenolactone biosynthesis, a variety of plausible intermediates in the conversion of pentalenene to pentalenolactone have been isolated, including 1-deoxypentalenic acid ( 5 ; as glucuronate ester) [4] as well as pentalenic acid ( 1 ) [8, 9], a demonstrated shunt metabolite of the main pentalenolactone biosynthetic pathway. The fact that tritium label from (1 R )-[1- 3 H] pentalenene ( 2 ) was lost upon formation of pentalenic acid ( 1 ) but was retained in the derived pentalenolactone has definitively ruled out 1 as an intermediate in the formation of pentalenolactone [9].…”

Section: Introductionmentioning

confidence: 99%

Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis

Takamatsu

Fushinobu

et al. 2010

J Antibiot

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Pentalenic acid (1) has been isolated from many Streptomyces sp. as a co-metabolite of the sesquiterpenoid antibiotic pentalenolactone and related natural products. We have previously reported the identification of a 13.4-kb gene cluster in the genome of Streptomyces avermitilis implicated in the biosynthesis of the pentalenolactone family of metabolites consisting of 13 open reading frames. Detailed molecular genetic and biochemical studies have revealed that at least seven genes are involved in the biosynthesis of the newly discovered metabolites, neopentalenoketolactone, but no gene specifically dedicated to the formation of pentalenic acid (1) was evident in the same gene cluster. The wild-type strain of S. avermitilis, as well as its derivatives, mainly produce pentalenic acid (1), together with neopentalenoketolactone (9). Disruption of the sav7469 gene encoding a cytochrome P450 (CYP105D7), members of which class are associated with the hydroxylation of many structurally different compounds, abolished the production of pentalenic acid (1). The sav7469-deletion mutant derived from SUKA11 carrying pKU462Hptl-clusterDptlH accumulated 1-deoxypentalenic acid (5), but not pentalenic acid (1). Reintroduction of an extra-copy of the sav7469 gene to SUKA11 Dsav7469 carrying pKU462Hptl-clusterDptlH restored the production of pentalenic acid (1). Recombinant CYP105D7 prepared from Escherichia coli catalyzed the oxidative conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1) in the presence of the electron-transport partners, ferredoxin (Fdx) and Fdx reductase, both in vivo and in vitro. These results unambiguously demonstrate that CYP105D7 is responsible for the conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1), a shunt product in the biosynthesis of the pentalenolactone family of metabolites.

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Studies on the biosynthesis of pentalenolactone, part II isolation of pentalehic acid and pentalenolactone H

Cited by 45 publications

References 1 publication

Structures of 1,4-Benzodioxane Derivatives from the Seeds of Phytolacca americana and Their Neuritogenic Activity in Primary Cultured Rat Cortical Neurons

Structures of 1,4-Benzodioxane Derivatives from the Seeds of Phytolacca americana and Their Neuritogenic Activity in Primary Cultured Rat Cortical Neurons

Natural product diversity of actinobacteria in the Atacama Desert

Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis

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