Abietane diterpenoids from suspension cultured cells of Torreya nucifera var. radicans

Orihara, Yutaka; Yang, Jin; Komiya, Noriko; Koge, Kenji; Yoshikawa, Takafumi

doi:10.1016/s0031-9422(01)00390-9

Cited by 28 publications

(10 citation statements)

References 10 publications

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“…The abietatriene 25 has been obtained 50 from callus tissues of Taxus baccata and from cultured cells of Torreya nucifera. 51 The biosynthesis of the abietanes in these cells by both the mevalonic acid and nonmevalonoid pathways has been examined. 52 A number of abietane quinones have been isolated including 12-deoxyroyleanone 26 from the roots of Salvia cilicica, 53 and its 7-ketone, cryptoquinone, from Cryptomeria japonica.…”

Section: Tricyclic Diterpenoidsmentioning

confidence: 99%

Diterpenoids

Hanson

2004

Nat. Prod. Rep.

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Section: Tricyclic Diterpenoidsmentioning

confidence: 99%

Diterpenoids

Hanson

2004

Nat. Prod. Rep.

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“…The F4 fraction was then purified via repeated semipreparative HPLC to yield 1 [solvent: CH 3 OH–H 2 O, 81/19; obtained amount: 113.8 mg; titer (obtained amount/plant amount): 0.01138 g/1 kg], 2 [solvent: CH 3 OH–H 2 O, 81/19; obtained amount: 121.2 mg; titer (obtained amount/plant amount): 0.01212 g/1 kg], and 3 [solvent: CH 3 OH–H 2 O, 90/10; obtained amount: 91.1 mg; titer (obtained amount/plant amount): 0.00911 g/1 kg]. The structures of 1 and 2 were identified by the HRESIMS, NMR spectroscopic analysis, single-crystal X-ray crystallography, and electronic circular dichroism (ECD) calculations, while the structure of the known compound, (3 S ,5 R ,10 S )-7-oxo-12-methoxyabieta-8,11,13-triene-3,11,14-triol ( 3 ), was confirmed by careful analysis of its NMR data …”

Section: Resultsmentioning

confidence: 99%

Bioassay-Guided Isolation of an Abetiane-Type Diterpenoid from Prunella vulgaris That Protects against Concanavalin A-Induced Autoimmune Hepatitis

et al. 2021

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Prunella vulgaris is a widely used edible Chinese medicinal plant. In the present study, two new abietane-type diterpenoids, abietoquinones A (1) and B (2), were isolated from this plant by an immunosuppressive bioassay-guided isolation procedure. Their structures were elucidated unambiguously by NMR spectroscopic analysis, single-crystal X-ray crystallography, and electronic circular dichroism calculations. Compounds 1 and 2 bear a cyclohex-2-ene-1,4-dione moiety, which is uncommon among abietane diterpenes. Also, abietoquinone A (1) suppressed murine splenocyte proliferation and decreased the production of proinflammatory cytokines induced by concanavalin A (Con A) in vitro. In Con A-challenged mice, preinjection with 1 significantly ameliorated liver injury. Additionally, abietoquinone A (1) exhibited inhibitory activities against the proliferation of murine splenocytes and human T cells induced by anti-CD3/anti-CD28 monoclonal antibodies (mAbs).Prunella vulgaris, a perennial plant, is distributed widely in East Asia, Europe, North Africa, and North America and was first recorded in the Chinese pharmacy document "Shennongbencaojing" approximately 2000 years ago. 1,2 For thousands of years, P. vulgaris has been regarded as a foodstuff and a folk medicine all over the world. 3 As a foodstuff, this herb has been used to make soup or tea in southern mainland China. Elsewhere in China, the spring buds of P. vulgaris are used to produce steamed glutinous rice cakes. 4,5 In the modern food industry, P. vulgaris is used to make functional beverages, such as the well-known "Wanglaoji-Liang-Cha" and "Jiaduobao-Liang-Cha". 6 As a folk medicine, P. vulgaris has been used to relieve sore throats, alleviate fever, accelerate wound healing, improve eyesight, and dissipate lumps. 7−10 Additionally, P. vulgaris is used often for the treatment of autoimmune diseases, including autoimmune hepatitis and autoimmune thyroiditis. It has been reported that the extracts of this plant possess antibacterial, antioxidative, hypoglycemic, antitumor, antiviral, and immunosuppressive effects. 11−18 However, most of these investigations focused on extracts of P. vulgaris rather than the specific active compounds present. 19,20 The immunosuppressive constituents of this plant and relevant pharmacological mechanism are still unknown.Autoimmune hepatitis (AIH) is a chronic inflammatory disease of the liver characterized by the loss of immunological self-tolerance. 21 It is accompanied by the emergence of

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“…The structural elucidation and identification of these compounds were based on spectral data analysis including MS, 1D and 2D NMR. The seven abietane diterpenoids included one new abietane diterpenoid, 20(10!5)-abeo-4,5-seco-5(10), 6,8,11,13-abietapentaene-3-one (1), and six known abietane diterpenoids, 12-hydroxyabieta-6,8,11,13-tetraene-3-one (2), abieta-8,11,13-triene-3b,12-diol (hinokiol) (3) (Zhao et al, 1998), abietatriene-3b-ol (4) (Urones et al, 1988;Chamy et al, 1991), 11,12-dihydroxy-8,11,13-abietatriene-3,7-dione (5) (Li et al, 2003), 11-hydroxy-12-methoxyabieta-8,11,13-triene-3,7-dione (6) (Yang et al, 1998), and 3b,11-dihydroxy-12-methoxyabieta-8,11,13-triene-7-one (7) (Li et al, 2002;Orihara et al, 2002;Monacelli et al, 2002) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%