Tigliane Type Diterpene-esters with Epstein–Barr Virus-inducing Activity from<i>Sapium sebiferum</i>

Ohigashi, Hajime; Ohtsuka, Takanao; Hirota, Mitsuru; Koshimįzu, Koichi; Tokuda, Harukuni; Itô, Yôhei

doi:10.1080/00021369.1983.10865799

Cited by 9 publications

(13 citation statements)

References 4 publications

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“…Thus, the structure of S1 is ascertained to be 12-O-hexadecanoylphorbol-13-acetate (2b). It is identi- Table! cal with Croton oil factor A4 from Croton oil [13] and with one of three tigliane type diterpene esters obtained from leaves of the Chinese tallow tree [9]. By mass and NMR data factor S2 is assumed to be 12-0octadecenoylphorbol-13-acetate (2c).…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, it is known, that phorbol esters are converted under storage conditions to autoxidation products, especially to 63,7f3-epoxides [22]. Two of the three tigliane derivatives isolated from leaves [9], i.e. L\56-7-hydroperoxide of 2b and A56-7-ketone of 2b, are most probably artifacts, too [22,23].…”

Section: Discussionmentioning

confidence: 99%

“…A number of common plant constituents have been obtained from the tallow [1,5], the roots [6], the stem [7] and the leaves [7] of the tree. Moreover, three tigliane type diterpene esters with Epstein-Barr Virus-Inducing activity [8] have been isolated recently from the leaves [9]; however, they were not assayed for further biological activities.…”

Section: Introductionmentioning

confidence: 99%

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Skin Irritant and Tumor Promoting Diterpene Esters of the Tigliane Type from the Chinese Tallow Tree (Sapium sebiferum)*

Seip¹,

Ott²,

Hecker³

1983

Planta Med

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From seed oil of the Chinese tallow tree skin irritant principles could be enriched; their diterpene parent was recognized as 12-deoxyphorbol (la). Skin irritant Sapium factors S1 to S8 were isolated from roots; they represent 13-monoesters of 12-deoxyphorbol (Ia) (S4-S8), 12,13-diesters of phorbol (2a) (S and S2) and of 63,713-epoxyphorbol (3a) (S3). The factors S1. S5 and a homologue of S3 are known as tumor promoters.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Skin Irritant and Tumor Promoting Diterpene Esters of the Tigliane Type from the Chinese Tallow Tree (Sapium sebiferum)*

Seip¹,

Ott²,

Hecker³

1983

Planta Med

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“…TPA (12-0-tetradecanoylphorbol-13-acetate; Funakoshi Chemicals, Tokyo) was used as a promoter for in vitro and in vivo assays. ΗΡΑ (12-0-hexadecanoylphorbol-13-acetate) and teleocidin B-4, also used as promoters, were isolated from the plant Sapium sebiferum (18) and an actinomycete Streptoverticillium blastmyceticum (19) in our laboratory. Because of sample availability, ΗΡΑ and teleocidin B-4 were used for screening tests in place of TPA.…”

Section: Methodsmentioning

confidence: 99%

Antitumor Promoters from Edible Plants

Ohigashi

Murakami

Koshimįzu

1994

ACS Symposium Series

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Possible inhibitory properties against tumor promotion (anti-tumor promoting activity) food items as well as their active constituents have been studied by an in vitro assay detecting inhibition of tumor promoter-induced Epstein-Barr virus (EBV) activation. In screening tests of 121 edible plants, 12% of the methanol extracts exhibited strong activity, and 6 and 10% showed moderate and weak activities, respectively. Oleanolic acid (OA) from a green perilla, mokko lactone (ML) and arctic acid from an edible burdock, and gingerol from a ginger were isolated as inhibitors of EBV activation in Raji cells. OA and ML were proven to be anti-tumor promoters by in vivo tests using a mouse skin model. Similar screening tests of marine algae showed that the algae in the genus Phaeophyta, which contains many edible species such as wakame seaweed and sea tangles, in particular possess significant activities. An in vivo test of an extract of wakame seaweed, an important daily food in Japan, indicated strong anti-tumor promoting activity. Further screening tests of tropical plants used as condiments and occasionally medicines suggested that the Zingiberaceae plants possess highly effective anti-tumor promotion activities. (1'S)-1'-Acetoxychavicol acetate (ACA), isolated from Languas galanga, inhibited EBV activation greater than 10 times more potently than other inhibitors from edible plants. On the basis of this investigation, the combination of food constituents is suggested to be a significant source of anti-tumor promoting activity. The two step model of carcinogenesis involving initiation and promotion, first proposed by Berenblum (1,2), has recently been accepted as occurring in a variety of organs (1-8). Thus, chemical inhibition of either process would result in prevention of cancer. While inhibition of tumor initiation has hitherto been extensively studied (9), less attention has been given to the inhibitors of the promotion process, called anti-tumor promoters. This may provide a challenging

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“…Sheng-Quan Liu, activity. Other workers have isolated ellagic acid, friedelin, sitosterol, and three phorbol esters from this plant part (4,5).…”

Section: Additional Biologically Active Constituents Of the Chinese T...mentioning

confidence: 98%

Additional Biologically Active Constituents of the Chinese Tallow Tree (Sapium sebiferum)

Liu¹,

Pezzuto²,

Kinghorn³

et al. 1988

J. Nat. Prod.

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Tigliane Type Diterpene-esters with Epstein–Barr Virus-inducing Activity fromSapium sebiferum

Cited by 9 publications

References 4 publications

Skin Irritant and Tumor Promoting Diterpene Esters of the Tigliane Type from the Chinese Tallow Tree (Sapium sebiferum)*

Skin Irritant and Tumor Promoting Diterpene Esters of the Tigliane Type from the Chinese Tallow Tree (Sapium sebiferum)*

Antitumor Promoters from Edible Plants

Additional Biologically Active Constituents of the Chinese Tallow Tree (Sapium sebiferum)

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