JPS6320822B2 - - Google Patents
Info
- Publication number
- JPS6320822B2 JPS6320822B2 JP13842979A JP13842979A JPS6320822B2 JP S6320822 B2 JPS6320822 B2 JP S6320822B2 JP 13842979 A JP13842979 A JP 13842979A JP 13842979 A JP13842979 A JP 13842979A JP S6320822 B2 JPS6320822 B2 JP S6320822B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- silica gel
- hexane
- chloroform
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229930004069 diterpene Natural products 0.000 claims description 5
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012156 elution solvent Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- REIZGKBBDMCFBK-UHFFFAOYSA-N Sarcophytonin A Natural products C1CC(C)=CCCC(C)=CCCC(C)=CC2OCC(C)=C21 REIZGKBBDMCFBK-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- REIZGKBBDMCFBK-KQZOUPBZSA-N (6E,10E,14E)-3,6,10,14-tetramethyl-2,4,5,8,9,12,13,15a-octahydrocyclotetradeca[b]furan Chemical compound C1C\C(C)=C\CC\C(C)=C\CC\C(C)=C\C2OCC(C)=C21 REIZGKBBDMCFBK-KQZOUPBZSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000124001 Alcyonacea Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700108 Ctenophora <comb jellyfish phylum> Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000567 diterpene group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- 241000243321 Cnidaria Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 description 1
- 241000512743 Sarcophyton <anthozoan> Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000063 antileukemic agent Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CGAKBBMRMLAYMY-BUHUPKIQSA-N sarcophine Chemical compound C1C\C(C)=C\CC[C@]2(C)O[C@H]2CC\C(C)=C\[C@@H]2OC(=O)C(C)=C21 CGAKBBMRMLAYMY-BUHUPKIQSA-N 0.000 description 1
- CGAKBBMRMLAYMY-UHFFFAOYSA-N sarcophine Natural products C1CC(C)=CCCC2(C)OC2CCC(C)=CC2OC(=O)C(C)=C21 CGAKBBMRMLAYMY-UHFFFAOYSA-N 0.000 description 1
- 229930189376 sarcophytonin Natural products 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は、センブラン型ジテルペンに関するも
のである。
センブラン型ジテルペンは、ヤギ目
(Gorgonacea)およびウミトサカ目
(Alcyonacea)に属する腔腸動物に見出され、ま
た最近抗腫瘍活性のあることがわかり、注目され
ている。〔例えばトウルシユ(B.Tursch)ら、テ
トラヘドロン(Tetrahedron)31巻、129頁、
1975年、イギリス国およびワインハイマー(A.J.
Weinheimer)ら、テトラヘドロンレタース
(Tetrahedron Letters)2923頁、1977年、イギ
リス国参照〕
本発明者等は、この様な事情に鑑み、ウミトサ
カ目に属する腔腸動物オオウミキノコ
(Sarcophyton glaucun)に注目し鋭意研究した
結果、新規なセンブラン型ジテルペンを見出し、
本発明に到達した。
以下に本発明を詳細に説明する。
本発明に係わる化合物は、一般式()
で示されるセンブラン型ジテルペンである。な
お、本発明においては、一般式()で示される
化合物をサルコフイトニン(Sarcophytonin)−
Aと命名する。
本発明に係わる化合物は、例えばオオウミキノ
コから抽出することができる。本発明に係わる化
合物は、オオウミキノコの抽出物の脂質画分よ
り、シリカゲルカラムクロマトグラフイーにより
分離しうる。
オオウミキノコは、通常インド洋および太平洋
の珊瑚礁に生息し、例えば紅海に生息するオオウ
ミキノコはサルコフイン(Sarcophine)および
16−デオキソサルコフインを含むことが知られて
いる。〔バーンスタイン(J.Bernstein)ら、テト
ラヘドロン30巻、2817頁、1974年、イギリス国お
よびカシユマン(Y.Kashman)ら、テトラヘド
ロン30巻、3615頁、1974年、イギリス国参照〕
オオウミキノコに含まれる成分は、その採集時
期や採集場所により相違することがあるので、適
宜選択決定する必要がある。
抽出の際、表面の粘稠性がなくなる程度に脱
水、細断しておくことが好ましい。
抽出溶剤は、例えばメタノール、エタノール、
イソプロパノール等のアルコール類;クロロホル
ム等のハロゲン化炭化水素類;ベンゼン、ヘキサ
ン、ヘプタン等の炭化水素類;エチルエーテル、
イソプロピルエーテル、ジオキサン等のエーテル
類;アセトン、メチルエチルケトン等のケトン
類;酢酸エチル等のエステル類等の有機溶剤また
はこれらの混合溶剤が挙げられる。
抽出操作中は、含有成分の分解を避けるため、
なるべく空気との接触面積が小さくなる様にする
か、不活性ガス雰囲気下とすることが好ましい。
抽出は常温でも可能であるが、抽出を早めるた
めには、加温下に行つてもよい。
常法により残渣と分離して得られた抽出液は、
常法により溶媒を留去して、粗留出物を得ること
ができる。
粗抽出物は常法〔例えばフオルシユ(J.Folch)
の方法−フオルシユら、ジヤーナル オブ バイ
オロジカル ケミストリー(J.Biol.Chem.)226
巻、497頁、1957年、アメリカ国参照〕により、
脂質画分に分画することができる。
かくして得られたオオウミキノコの抽出物の脂
質画分の性状は、粘稠性の茶褐色の油状である。
更に精製するには、クロマトグラフイーによれ
ばよい。クロマトグラフイーは、カラムクロマト
グラフイーおよび調製用薄層クロマトグラフイー
の何れでもよい。
カラムクロマトグラフイーの充填剤としては、
シリカゲル、アルミナ、セルロースパウダー、活
性炭等が用いられる。溶出溶剤としては、充填剤
に応じて適宜選択決定すれば良いが、充填剤とし
てシリカゲルを用いた場合には、ベンゼンまたは
ヘキサン−ベンゼンの混合溶媒が好適である。ヘ
キサンとベンゼンの混合比は、3:1〜1:1
(容積比)程度が好適である。また、ここで得ら
れた粗分画は、充填剤や溶出溶媒を変えて、更に
カラムクロマトグラフイーにより精製・単離する
こともできる。
調製用薄層クロマトグラフイーのゲルとして
は、シリカゲル、アルミナ、セルロースパウダー
等が用いられる。展開溶媒としては、クロロホル
ムまたはクロロホルム−エーテル混合溶媒が好適
である。
本発明に係わる化合物は空気酸化を受けやすい
ので、取扱い、保存等には注意が必要である。
本発明に係わる化合物は、医薬として有用なも
のである。すなわち、本発明に係わる化合物はマ
ウスの白血病−P−388腫瘍細胞に対して効果が
あり、抗白血病薬として大いに期待できるもので
ある。
さらに、本発明に係わる化合物は、医薬および
農薬等の中間体としても有用である。
以下に実施例を挙げて、本発明を更に詳細に説
明するが、本発明はその要旨を超えない限り、以
下の実施例により限定を受けるものではない。
実施例 1
沖縄県石垣島にて昭和52年6月に採取したオオ
ウミキノコ17Kgを細かく刻み、最初は40のメタ
ノール、次いで30のクロロホルム−メタノール
(容積比2:1)で、充分に室温にて抽出する。
抽出液を、減圧下溶媒を留去する。抽出残の乾燥
重量は、約5.5Kgであつた。次いでフオルシユら
の方法〔J.Folchら、ジヤーナル オブ バイオ
ロジカル ケミストリー(J.Biol.Chem.)226巻、
497頁、1957年、アメリカ国参照〕により、脂質
画分に分画した。かくして、粘稠の茶褐色の油状
の脂質部1.6Kgを得る。脂質画分の400gをヘキサ
ンに溶かし、シリカゲル(メルク社製、70〜230
メツシユ)2.5Kgのカラムクロマトグラフイーで
分離した。
溶出溶媒と、各分画の関係は表1の通りであ
る。
The present invention relates to Semblan-type diterpenes. Sembran-type diterpenes are found in coelenterates belonging to the orders Gorgonacea and Alcyonacea, and have recently been found to have antitumor activity, and have attracted attention. [For example, B. Tursch et al., Tetrahedron, Vol. 31, p. 129,
1975, United Kingdom and Weinheimer (A.J.
Weinheimer et al., Tetrahedron Letters, p. 2923, 1977, United Kingdom.] In view of these circumstances, the present inventors focused on the coelenterate Sarcophyton glaucun, which belongs to the order Cylindriformes. As a result of intensive research, we discovered a new Sembran-type diterpene.
We have arrived at the present invention. The present invention will be explained in detail below. The compound according to the present invention has the general formula () It is a Semblan-type diterpene represented by In addition, in the present invention, the compound represented by the general formula () is used as Sarcophytonin-
Name it A. The compound according to the present invention can be extracted from, for example, the giant sea mushroom. The compound according to the present invention can be separated from the lipid fraction of the extract of the Oriental seaweed mushroom by silica gel column chromatography. Giant sea mushrooms usually live in the coral reefs of the Indian and Pacific Oceans, for example, the giant sea mushrooms that live in the Red Sea contain sarcophine and
It is known to contain 16-deoxosarcofin. [See J. Bernstein et al., Tetrahedron Vol. 30, p. 2817, 1974, UK and Y. Kashman et al., Tetrahedron, vol. 30, p. 3615, 1974, UK]] The components contained may differ depending on the collection time and collection location, so it is necessary to select them appropriately. During extraction, it is preferable to dehydrate and shred to such an extent that the surface loses its viscosity. Extraction solvents include, for example, methanol, ethanol,
Alcohols such as isopropanol; halogenated hydrocarbons such as chloroform; hydrocarbons such as benzene, hexane, heptane; ethyl ether,
Examples include organic solvents such as ethers such as isopropyl ether and dioxane; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate; or mixed solvents thereof. During the extraction operation, to avoid decomposition of the contained components,
It is preferable to minimize the contact area with air or to use an inert gas atmosphere. Extraction can be carried out at room temperature, but in order to speed up the extraction, it may be carried out under heating. The extract obtained by separating the residue by a conventional method is
A crude distillate can be obtained by distilling off the solvent by a conventional method. Crude extracts can be prepared using conventional methods [e.g. J.Folch].
Methods - Fourciu et al., Journal of Biological Chemistry (J.Biol.Chem.) 226
Vol. 497, 1957, United States Reference]
It can be fractionated into lipid fractions. The property of the lipid fraction of the extract of the giant sea mushroom thus obtained is a viscous brown oil. Further purification may be achieved by chromatography. The chromatography may be either column chromatography or preparative thin layer chromatography. As a packing material for column chromatography,
Silica gel, alumina, cellulose powder, activated carbon, etc. are used. The elution solvent may be appropriately selected depending on the filler, but when silica gel is used as the filler, benzene or a mixed solvent of hexane-benzene is suitable. The mixing ratio of hexane and benzene is 3:1 to 1:1
(volume ratio) is suitable. Further, the crude fraction obtained here can be further purified and isolated by column chromatography by changing the packing material and elution solvent. Silica gel, alumina, cellulose powder, etc. are used as the gel for preparative thin layer chromatography. As the developing solvent, chloroform or a chloroform-ether mixed solvent is suitable. Since the compounds related to the present invention are susceptible to air oxidation, care must be taken when handling and storing them. The compounds according to the present invention are useful as pharmaceuticals. That is, the compound according to the present invention is effective against murine leukemia-P-388 tumor cells, and has great promise as an anti-leukemia drug. Furthermore, the compounds according to the present invention are useful as intermediates for pharmaceuticals, agricultural chemicals, and the like. EXAMPLES The present invention will be described in more detail with reference to Examples below, but the present invention is not limited by the Examples unless it exceeds the gist thereof. Example 1 17 kg of giant sea mushrooms collected in June 1972 from Ishigaki Island, Okinawa Prefecture were finely chopped and thoroughly mixed with 40 parts methanol and then 30 parts chloroform-methanol (volume ratio 2:1) at room temperature. Extract.
The solvent of the extract was distilled off under reduced pressure. The dry weight of the extraction residue was approximately 5.5 kg. Next, the method of Folch et al. [J. Folch et al., Journal of Biological Chemistry (J. Biol. Chem.) vol. 226,
497, 1957, United States of America]. In this way, 1.6 kg of viscous brown oily lipid fraction is obtained. Dissolve 400 g of the lipid fraction in hexane and add silica gel (manufactured by Merck & Co., Ltd., 70-230
Separated using 2.5Kg column chromatography. The relationship between the elution solvent and each fraction is shown in Table 1.
【表】
溶出溶媒の混合比は、容積で示した。(以下同
様)
かくして得られた分画BおよびCの部分を、シ
リカゲルを用いたカラムクロマトグラフイーによ
り精製する。30倍量のシリカゲルを用い、分画B
およびCを最少量のヘキサンに溶解し、ヘキサン
−クロロホルムの混合溶媒で溶出する。ヘキサン
−クロロホルム(1:1)でサルコフイトニン−
Aが溶出する。
サルコフイトニン−Aの収率は、それぞれ脂質
画分の5〜10%である。
サルコフイトニン−A
無色油状
〔α〕D+92゜(C=2.3、CHCl3)
赤外スペクトルνneat naxcm-1:1660、1450、1040、
860、840
質量分析
m/e:281(M+)、271(M+−CH3)、135(ベース
ピーク)
PMRスペクトル(CDCl3)、(100MHz)δ1.59(3H
×2、br.s)、1.64(3H、br.s)、1.69(3H、br.
s)、2.0〜2.5(12H、br.)、4.48(2H、br.d、J
=4.5Hz)、5.48(1H、dt、J=10、4.5Hz)、5.06
(1H、br.d、J=10Hz)
CMRスペクトル(ppm)140.3(C1)、78.4(C2)、
124.0、125.5、125.8(C3、C7、C11)、127.1
(C4)、39.2、40.4(C5、C9)、23.5、24.8(C6、
C10)、133.2、134.0、135.4(C8、C12、C15)、
37.2(C13)、84.0(C16)、10.2(C17)、15.0、15.2
、
15.6(C18、C19、C20)
Rf0.31(シリカゲルHF254メルク社製−クロロホ
ルム、リンモリブデン試薬で検出)[Table] The mixing ratio of elution solvents is shown by volume. (Similarly below) The thus obtained fractions B and C are purified by column chromatography using silica gel. Fraction B using 30 times the amount of silica gel
and C are dissolved in a minimum amount of hexane and eluted with a mixed solvent of hexane-chloroform. Sarcophytonin in hexane-chloroform (1:1)
A is eluted. The yield of sarcophytonin-A is 5-10% of the lipid fraction, respectively. Sarcophytonin-A Colorless oil [α] D +92° (C = 2.3, CHCl 3 ) Infrared spectrum ν neat nax cm -1 : 1660, 1450, 1040,
860, 840 Mass spectrometry m/e: 281 (M + ), 271 (M + -CH 3 ), 135 (base peak) PMR spectrum (CDCl 3 ), (100MHz) δ1.59 (3H
×2, br.s), 1.64 (3H, br.s), 1.69 (3H, br.
s), 2.0-2.5 (12H, br.), 4.48 (2H, br.d, J
= 4.5Hz), 5.48 (1H, dt, J = 10, 4.5Hz), 5.06
(1H, br.d, J=10Hz) CMR spectrum (ppm) 140.3 (C 1 ), 78.4 (C 2 ),
124.0, 125.5, 125.8 ( C3 , C7 , C11 ), 127.1
( C4 ), 39.2, 40.4 ( C5 , C9 ), 23.5, 24.8 ( C6 ,
C10 ), 133.2, 134.0, 135.4 ( C8 , C12 , C15 ),
37.2 ( C13 ), 84.0 ( C16 ), 10.2 ( C17 ), 15.0, 15.2
,
15.6 (C 18 , C 19 , C 20 ) Rf0.31 (Silica gel HF 254 manufactured by Merck - detected with chloroform and phosphomolybdenum reagent)
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13842979A JPS5661372A (en) | 1979-10-26 | 1979-10-26 | Cembrane type diterpene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13842979A JPS5661372A (en) | 1979-10-26 | 1979-10-26 | Cembrane type diterpene |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5661372A JPS5661372A (en) | 1981-05-26 |
JPS6320822B2 true JPS6320822B2 (en) | 1988-04-30 |
Family
ID=15221754
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13842979A Granted JPS5661372A (en) | 1979-10-26 | 1979-10-26 | Cembrane type diterpene |
Country Status (1)
Country | Link |
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JP (1) | JPS5661372A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6317823A (en) * | 1986-07-10 | 1988-01-25 | Mitsubishi Chem Ind Ltd | Antisolid tumor agent |
JP4880421B2 (en) * | 2006-10-24 | 2012-02-22 | トッパン・フォームズ株式会社 | Sample catalog booklet set and booklet |
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1979
- 1979-10-26 JP JP13842979A patent/JPS5661372A/en active Granted
Also Published As
Publication number | Publication date |
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JPS5661372A (en) | 1981-05-26 |
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