Novel Fusicoccins R and S, and the fusicoccin S aglycon (phomopsiol) from Phomopsis amygdali niigata 2-A, and their seed germination-stimulating activity in the presence of abscisic acid.

نویسندگان

  • Naoto Tajima
  • Manabu Nukina
  • Nobuo Kato
  • Takeshi Sassa
چکیده

Our search for new 3-hydroxyfusicoccins structurally related to cotylenin A from a culture of Phomopsis amygdali Niigata 2-A resulted in the isolation of novel 3-hydroxy fusicoccins, called fusicoccins R and S, and the fusicoccin S aglycon, called phomopsiol, together with known 3alpha-hydroxyfusicoccin J. The structure of phomopsiol was identified as that of O-demethyl-3-epicotylenol based on spectroscopic evidence. The structures of fusicoccins R and S were also determined to be those of 3'-deacetyl-3alpha-hydroxyfusicoccin A and 3beta-hydroxy-3-epifusicoccin H. The lettuce seed germination-stimulating activity of fusicoccins R and S, phomopsiol and 3alpha-hydroxyfusicoccin J was examined in the presence of ABA; fusicoccin R and 3alpha-hydroxyfusicoccin J were highly active, while fusicoccin S and phomopsiol were inactive. The possible biosynthetic relationships among these novel fusicoccins having a 3alpha- or 3beta-hydroxy group in their diterpene moiety are briefly discussed.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

16-O-Demethyl Fusicoccin J and Its 3-Epimer from Fusicoccum amygdali, and Their Seed Germination-stimulating Activity in the Presence of Abscisic Acid.

Our search for new metabolites biosynthetically related to fusicoccin with potent plant growth-stimulating activity from the culture filtrate of Fusicoccum amygdali F6 resulted in the isolation of a new derivative of fusicoccin J, as well as fusicoccin J and 16-O-demethyl 3-epifusicoccin J. Its structure was analyzed by 600 MHz NMR spectrometry and identified as 16-O-demethyl fusicoccin J. The ...

متن کامل

FusicQccins P and Q , and 3 - from Isolate Niigata 2 - A ofEpifusicoccins H and Q , New Polar a Peach Fusicoccum Canker

Our search for new polar f"siceccins biosynthetically related to fusicoccin A from the culture filtrate of isolate Niigata 2-A of a peach Fusicoccum canker fungus resutted in the iso]atiofi of new fusicoccins named fusicocci"s P and Q, and 3-epifusicoccins H and Q, together with 3'-deacetylf"sicoccin A and 16-Odemethyl-3-epifusicoccin J. The structures of fusicoccins P and Q, and of 3-epifuslco...

متن کامل

Identification of (+)-phyllocladene, (--)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6.

A chemical analysis of the diterpene hydrocarbons produced by fusicoccin-producing fungus Phomopsis amygdali F6 identified five phyllocladene-related tri- and tetracyclic diterpene hydrocarbons. The presence of (+)-phyllocladene, (--)-sandaracopimaradiene, (+)-isopimara-8,15-diene, and (+)-pimara-8(14),15-diene in the fungus was demonstrated by GC-MS, 1H-NMR, and [alpha]D measurements. (+)-Kaur...

متن کامل

Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi.

Fusicoccins are a class of diterpene glucosides produced by the plant-pathogenic fungus Phomopsis amygdali. As modulators of 14-3-3 proteins, fusicoccins function as potent activators of plasma membrane H(+)-ATPase in plants and also exhibit unique biological activity in animal cells. Despite their well studied biological activities, no genes encoding fusicoccin biosynthetic enzymes have been i...

متن کامل

Purification and Characterization of Two Acid Phosphatases from Germinating Peanut (Arachis hypogaea) Seed

The maximum acid phosphatasic activity was detected in peanut seed at the 5th day of germination. At least, two acid phosphatases were purified by successive chromatography separations on DEAE-Sepharose CL-6B, CM-Sepharose CL-6B, Sephacryl S-100 HR, and Phenyl-Sepharose HP to apparent homogeneity from five days old cotyledon of peanut after germination. These isoenzymes, designated peanut cotyl...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Bioscience, biotechnology, and biochemistry

دوره 68 5  شماره 

صفحات  -

تاریخ انتشار 2004