Two New Anti-Tumor Promoting Serratane-Type Triterpenoids from the Stem Bark of<i>Picea jezoensis</i>var.<i>jezoensis</i>

Ultraviolet light is the major cause of skin cancers in human, and several effects of ultraviolet light B (UVB) are thought to contribute to skin photocarcinogenesis. 3Beta-methoxy-13alpha,14alpha-epoxyserratan-21beta-ol (PJJ-34; 1) isolated from Picea jezoensis Carr. var. jezoensis showed the strongest antitumor-promoting activity among naturally occurring triterpenoids in the in vivo two-stage mouse skin-carcinogenesis test. To investigate the anti-initiating activity, we further studied mouse models initiated with ultraviolet-B (UVB) and promoted with 12-O-tetradecanoylphorbol-13-acetate (TPA). Oral administration of the PJJ-34 (1) during a period before and after the three times of UVB irradiation led to a remarkable effect: oral administration of a 0.0025% solution of 1 only to the test group, which started one week before and ended one week after the irradiation, showed less than half papillomas, and inhibition of tumor incidence and tumor multiplicity in comparison to the control group. Therefore, it was recognized that PJJ-34 (1) showed strong anti-initiating activity as well as anti-promoting activity. After all, 1 seems to be useful as cancer-chemopreventive agent.

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Anti‐Initiating Activity of 3β‐Methoxy‐13α,14α‐epoxyserratan‐21β‐ol (PJJ‐34) from the Stem Bark of Picea jezoensis Carr. var. jezoensis

Tanaka

Minami

Tokuda

2006

Chemistry & Biodiversity

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Anti‐Tumor‐Initiating Effects of Spiro‐biflavonoids from Abies sachalinensis

Wada

Hitomi

Tokuda

et al. 2010

Chemistry & Biodiversity

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Cancer chemoprevention, the prevention of cancer by ingestion of chemical agents that reduce the risk of carcinogenesis, is one of the potent ways to reduce morbidity and mortality. We have been searching for cancer chemopreventive agents from the leaves and barks of coniferous trees that have been treated as waste in the forestry industry. We have previously reported the isolation of spiro-biflavonoids, named as abiesinols, and a neolignan from the MeOH extract of the bark of Abies sachalinensis. These compounds were tested for their inhibitory effects on the activation of (±)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxyhex-3-enamide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for anti-tumor initiators. All compounds tested exhibited potent inhibitory effects on NOR 1 activation. Furthermore, abiesinol A, bearing a spiro-biflavonoid skeleton, showed remarkable anti-tumor-initiating activity in the in vivo two-stage mouse skin carcinogenesis test using peroxynitrite (ONOO(-); PN) as the initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as the promoter.

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Three New Serratane Triterpenoids from Phlegmariurus squarrosus

Jian

Cheng

Zhang

et al. 2006

Helvetica Chimica Acta

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Three new serratane triterpenoids, (3α,14α,15α,21α)‐3,14,15,21,29‐pentahydroxyserratan‐24‐oic acid (1), (3α,21β)‐serrat‐14‐ene‐3,21,24,30‐tetraol (2), and (3α,21α)‐serrat‐14‐ene‐3,21,24,29‐tetraol (3), were isolated from Phlegmariurus squarrosus, together with eight known compounds. Their chemical structures were elucidated on the basis of in‐depth spectroscopic analyses.

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Two New Anti-Tumor Promoting Serratane-Type Triterpenoids from the Stem Bark ofPicea jezoensisvar.jezoensis

Cited by 17 publications

References 10 publications

Anti‐Initiating Activity of 3β‐Methoxy‐13α,14α‐epoxyserratan‐21β‐ol (PJJ‐34) from the Stem Bark of Picea jezoensis Carr. var. jezoensis

Anti‐Initiating Activity of 3β‐Methoxy‐13α,14α‐epoxyserratan‐21β‐ol (PJJ‐34) from the Stem Bark of Picea jezoensis Carr. var. jezoensis

Anti‐Tumor‐Initiating Effects of Spiro‐biflavonoids from Abies sachalinensis

Three New Serratane Triterpenoids from Phlegmariurus squarrosus

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