Spiro-gamma-lactone diterpenes from in vitro cultures of the liverwort, Heteroscyphus planus

被引:13
作者
Nabeta, K [1 ]
Oohata, T [1 ]
Ohkubo, S [1 ]
Sato, T [1 ]
Katoh, K [1 ]
机构
[1] SHIONOGI ABURAHI LABS,KOHGA,SHIGA 52034,JAPAN
关键词
Heteroscyphus planus; jungermanniales; suspension cultures; diterpenes; clerodanes; 3,4-epoxy-6,13-diacetoxy-5,10-trans-cleroda-14-en-20,12-olide; 3,4-epoxy-6-acetoxy-13-hydroxy-5,10-trans-cleroda-14-en-20,12-olide; 18-hydroxy-5,10-trans-cleroda-3,13E-dien-15-oic acid methyl ester;
D O I
10.1016/0031-9422(95)00420-3
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Two new C-9-spiro-gamma-lactones of clerodane-type diterpenes, named heteroscypholide A and B, and one new cleroda-15-oic acid methyl ester were isolated from the cells of suspension culture of the liverwort, Heteroscyphus planus. The structures of heteroscypholide A and B and the cleroda-15-oic acid methyl ester were established as 3,4-epoxy-6,13-diacetoxy-5,10-trans-cleroda-14-en-20,12-olide 3,4-epoxy-6-acetoxy-13-hydroxy-5,10-trans-cleroda- 14-en-20,12-olide and 18-hydroxy-5,10-trans-cleroda-3,13E-dien-15-oic acid methyl ester, respectively. Their relative stereochemistry was determined on the basis of spectral analyses including X-ray crystallography and chemical correlation.
引用
收藏
页码:581 / 587
页数:7
相关论文
共 17 条
[1]   ENT-LABDANES AND FURANODITERPENES FROM THE LIVERWORT JAMESONIELLA-AUTUMNALIS [J].
BLECHSCHMIDT, M ;
BECKER, H .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (01) :111-121
[2]   NATURALLY-OCCURRING TERPENE DERIVATIVES .323. 13 KOLAVANE DERIVATIVES FROM SYMPHYOPAPPUS SPECIES [J].
BOHLMANN, F ;
ZDERO, C ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1981, 20 (07) :1657-1663
[3]  
HASHIMOTO T, 1992, 36TH S CHEM TERP ESS, P260
[4]  
Hashimoto T., 1993, J HATTORI BOT LAB, V74, P121
[5]   GYMNOCOLIN, A NEW CIS-CLERODANE DITERPENOID FROM THE LIVERWORT GYMNOCOLEA-INFLATA - CRYSTAL-STRUCTURE ANALYSIS [J].
HUNECK, S ;
ASAKAWA, Y ;
TAIRA, Z ;
CAMERON, AF ;
CONNOLLY, JD ;
RYCROFT, DS .
TETRAHEDRON LETTERS, 1983, 24 (01) :115-116
[6]  
KATSUMOTO S, 1969, B CHEM SOC JPN, V42, P812
[7]   ISOLATION OF 7 VERRUCOSANE DITERPENOIDS FROM THE LIVERWORT SCAPANIA-BOLANDERI [J].
MATSUO, A ;
ATSUMI, K ;
NAKAYAMA, M .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1984, 39 (09) :1281-1285
[8]   CONSTITUENTS OF SOLIDAGO SPECIES .6. CONSTITUTION OF DITERPENOIDS FROM A CHEMICALLY DISTINCT VARIETY OF SOLIDAGO-SEROTINA [J].
MCCRINDLE, R ;
NAKAMURA, E .
CANADIAN JOURNAL OF CHEMISTRY, 1974, 52 (11) :2029-2036
[9]   CLERODANE DITERPENOIDS [J].
MERRITT, AT ;
LEY, SV .
NATURAL PRODUCT REPORTS, 1992, 9 (03) :243-287
[10]   DITERPENES OF THE CLERODANE-TYPE FROM CULTURED-CELLS OF HETEROSCYPHUS-PLANUS [J].
NABETA, K ;
OOHATA, T ;
IZUMI, N ;
KATOH, K .
PHYTOCHEMISTRY, 1994, 37 (05) :1263-1268