Abstract
Pinoresinol diglucoside (PDG) and pinoresinol (Pin) are normally produced by plant cells via the phenylpropanoid pathway. This study reveals the existence of a related pathway in Phomopsis sp. XP-8, a PDG-producing fungal strain isolated from the bark of the Tu-chung tree (Eucommiaulmoides Oliv.). After addition of 0.15 g/L glucose to Phomopsis sp. XP-8, PDG and Pin formed when phenylalanine, tyrosine, leucine, cinnamic acid, and p-coumaric acid were used as the substrates respectively. No PDG formed in the absence of glucose, but Pin was detected after addition of all these substrates except leucine. In all systems in the presence of glucose, production of PDG and/or Pin and the accumulation of phenylalanine, cinnamic acid, or p-coumaric acid correlated directly with added substrate in a time- and substrate concentration- dependent manner. After analysis of products produced after addition of each substrate, the mass flow sequence for PDG and Pin biosynthesis was defined as: glucose to phenylalanine, phenylalanine to cinnamic acid, then to p-coumaric acid, and finally to Pin or PDG. During the bioconversion, the activities of four key enzymes in the phenylpropanoid pathway were also determined and correlated with accumulation of their corresponding products. PDG production by Phomopsis sp. exhibits greater efficiency and cost effectiveness than the currently-used plant-based system and will pave the way for large scale production of PDG and/or Pin for medical applications.
Highlights
Pinoresinol diglucoside, (+)-1-pinoresinol 4, 40-di-O-β-D-glucopyranoside ((+)-PDG) is a glycoside lignan compound having various pharmacological functions, including antihypertensionPLOS ONE | DOI:10.1371/journal.pone.0137066 September 2, 2015Bioconversion of Pinoresinol Diglucoside and Pinoresinol [1], [2] and prevention of osteoporosis [3]
In the absence of glucose, only biosynthesis of Pin was found only when Phe and tyrosine (Tyr) were used as the sole substrates (Table 2). This was consistent with the biosynthesis pathway reported in plants, Pin and PDG are synthesized via the phenylpropanoid pathway from Phe or Tyr
It was deduced that Phe and Tyr acted as phenyl donors in the biosynthesis of PDG and Pin
Summary
Pinoresinol diglucoside, (+)-1-pinoresinol 4, 40-di-O-β-D-glucopyranoside ((+)-PDG) is a glycoside lignan compound having various pharmacological functions, including antihypertensionPLOS ONE | DOI:10.1371/journal.pone.0137066 September 2, 2015Bioconversion of Pinoresinol Diglucoside and Pinoresinol [1], [2] and prevention of osteoporosis [3]. As with PDG, Pin has been identified as an enterolactone precursor [8] with a preventive effect against breast cancer [9] and endometrial cancer [10]. XP-8 produced PDG, PMG, and Pin during submerged liquid cultivation in defined medium [15] and in the bioconversion system containing whole mung bean or polysaccharides and starch isolated from mung bean [16]. These results indicated a possible way to produce Pin and PDG in dependence of plant growth. It is necessary to understand the intrinsic mechanisms for this strain to produce PDG and Pin
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