Terpendoles, Novel ACAT Inhibitors Produced by Albophoma yamanashiensis. III. Production, Isolation and Structure Elucidation of New Components.

Abstract

Eight new components of terpendoles E to L were isolated and characterized from the culture broth of Albophomayamanashiensis using a different production medium. All the structures were elucidated by spectroscopic analyses including various NMRexperiments, indicating that all the terpendoles have the same indoloditerpene core as terpendoles A to D. Terpendoles J, K and L showed the moderate inhibition against acyl-CoA : cholesterol acyltransferase (ACAT)activity with IC50 values of 38.8, 38.0 and.32.4//m in rat liver microsomes, respectively. But terpendoles E~I showed weak activities (IC50 145~388 /iM).

Functional analysis of an indole‐diterpene gene cluster for lolitrem B biosynthesis in the grass endosymbiont Epichloë festucae

“…Despite no direct evidence for the pathway leading to 11,12‐epoxides, terpendole B is proposed as the first 11,12‐epoxide based on the observation that it occurs in Albophoma yamanashiensis , along with other terpendoles, notably terpendoles E, F, and G [24,25], even though it was not identified in this study. The biosynthetic scheme proposed (Fig.…”

Molecular analysis of two cytochrome P450 monooxygenase genes required for paxilline biosynthesis in Penicillium paxilli, and effects of paxilline intermediates on mammalian maxi-K ion channels

“…They have been somewhat arbitrarily classified into six structural groups, namely the penitrems, janthitrems, lolitrems, aflatrem, paxilline and the paspaline/paspalinine/paspalitrems (Steyn and Vleggaar 1985). To these groups can be added the more recently discovered terpendoles (Huang et al 1995;Tomoda et al 1995;Gatenby et al 1999), shearinines (Belofsky et al 1995), sulpinines (Laakso et al 1992), nodulisporic acid (Ondeyka et al 1997) and thiersinines (Li et al 2002). All these compounds have a cyclic diterpene skeleton derived from four isoprene units, and an indole moiety derived from tryptophan or a tryptophan precursor (Acklin et al 1977;de Jesus et al 1983;Laws and Mantle 1989), but very little is known about the pathways for their biosynthesis.…”

Two New Prenylated Indole Diterpenoids from Tolypocladium sp. and Their Antimicrobial Activities

“…By detailed analyses of its NMR data, we found that the NMR data of 2 are very similar to those of the closely related compound, terpendole L, a known indole diterpenoid reported from Albophoma yamanashiensis. [13] The only difference is that the position of an isopentenyl group at C-20 in terpendole L was migrated at C-22 in 2, as confirmed by HMBC and COSY experiments ( Figure 2). The relative configuration of 2 was established as the same as that of terpendole L by comparing their NMR data, as well as analyses of the NOESY correlations of H-5α with H-7/H-25, H-7 with H-6α/H-9, H-10 with H-11/H-35, and H-26 with H-6β/H-11/H-16 ( Figure 3).…”