Abstract
Three new macrocyclic trichothecenes, named 12′-hydroxyroridin E (1), roridin Q (2), and 2′,3′-deoxyroritoxin D (3), were isolated from the marine-derived fungus Myrothecium roridum TUF 98F42, and a new macrocyclic trichothecene, named roridin R (4), was isolated from Myrothecium sp. TUF 02F6 together with roridins A and H and isororidin E. The structures of new compounds were determined on the basis of their spectral data. Compound 2 possessed a unique ether moiety at the 13′ position of 1. Compound 4 was a 2′,3′-dihydro-2′-hydroxy derivative of roridin H. The IC50 values of compounds 1, 2, and 4 against the murine leukemia cell line L1210 were 0.19, 31.2, and 0.45 μM, respectively. Compound 3 showed antiyeast activity to Saccharomyces cerevisiae at 1 μg/disc (inhibition zone: 12.2 mm), which was about 10 time more active than roritoxin D (10.2 mm at 10 μg/disc).
References
- 1
Cole R, Cox RH . Handbook of Toxic Fungal Metabolites. Academic Press, New York, pp. 152–263 (1981)
- 2
Namikoshi M, Akano K, Meguro S, Kasuga I, Mine Y, Takahashi T, Kobayashi H . A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau. J Nat Prod 64: 396–398 ( 2001)
- 3
Wagenaar MM, Clardy J . Two new roridins isolated from Myrothecium sp. J Antibiot 54: 517–520 ( 2001)
- 4
Murakami Y, Okuda T, Shindo K . Roridin L, M and verrucarin M, new macrocyclic trichothecene group antitumor antibiotics, from Myrothecium verrucaria. J Antibiot 54: 980–983 ( 2001)
- 5
Alvi KA, Rabenstein J, Woodard J, Baker DD, Bergthold JD, Lynch J, Lieu KL, Braude IA . 14′-Hydroxymytoxin B and 16-hydroxyroridin E, two new cytotoxic trichothecenes from Myrothecium roridum. J Nat Prod 65: 742–744 ( 2002)
- 6
Wang T, Zhang Y, Pei YH, Hua HM, Feng BM . A new macrocyclic trichothecene from soil fungus. Chinese Chem Lett 13: 67–68 ( 2002)
- 7
(a) Kobayashi M, Kanasaki R, Ezaki M, Sakamoto K, Takase S, Fujie A, Hino M, Hori Y . FR227244, a novel antifungal antibiotic from Myrothecium cinctum No. 002. I. Taxonomy, fermentation, isolation and physico-chemical properties. J Antibiot 57: 780–787 ( 2004)
- 8
(b) Kobayashi M, Sato I, Abe F, Nitta K, Hashimoto M, Fujie A, Hino M, Hori Y . FR227244, a novel antifungal antibiotic from Myrothecium cinctum No. 002. II. Biological properties and mode of action. J Antibiot 57: 788–796 ( 2004)
- 9
Li X, Kim MK, Lee U, Kim S-K, Kang JS, Choi HD, Son BW . Myrothenones A and B, cyclopentenone derivatives with tyrosinase inhibitory activity from the marine-derived fungus Myrothecium sp. Chem Pharm Bull 53: 453–455 ( 2005)
- 10
Namikoshi M, Kobayashi H, Yoshimoto T, Meguro S, Akano K . Isolation and characterization of bioactive metabolites from marine-derived filamentous fungi collected from tropical and sub-tropical coral reefs. Chem Pharm Bull 48: 1452–1457 ( 2000)
- 11
Jarvis BB, Yatawara CS . Roritoxins, new macrocyclic trichothecenes from Myrothecium roridum. J Org Chem 51: 2906–2910 ( 1986)
- 12
Jarvis BB, Wang S . Stereochemistry of the roridins. Diastereomers of roridin E. J Nat Prod 62: 1284–1289 ( 1999)
Author information
Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xu, J., Takasaki, A., Kobayashi, H. et al. Four New Macrocyclic Trichothecenes from Two Strains of Marine-derived Fungi of the Genus Myrothecium. J Antibiot 59, 451–455 (2006). https://doi.org/10.1038/ja.2006.63
Received:
Accepted:
Issue Date:
Keywords
- Myrothecium roridum
- marine-derived fungus
- roridin Q
- roridin R
- macrocyclic trichothecene
- cytotoxicity
- L1210
Further reading
-
Antimicrobial compounds from marine fungi
Phytochemistry Reviews (2020)
-
Trichothecene macrolides from the endophytic fungus Paramyrothecium roridum and their cytotoxic activity
Fitoterapia (2020)
-
Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017
Molecules (2020)
-
Marine Natural Products from Indonesian Waters
Marine Drugs (2019)
-
Antifungal Macrocyclic Trichothecenes from the Insect-Associated Fungus Myrothecium roridum
Journal of Agricultural and Food Chemistry (2019)