Antimycobacterial extracts of a Penicillium sp. (isolate HL4-159-41B) and a Coniothyrium sp. (isolate HL6-097-027B) isolated from the rhizomes of the Canadian medicinal plant Aralia nudicaulis were found to contain palitantin (1) and botrallin (2), craterellin C (3), mycosporulone (4), spiromassaritone (5), and massarigenin D (6) respectively. Bioassays against Mycobacterium tuberculosis H37Ra revealed that 1-4 possess moderate antimycobacterial activity.
McCutcheonAR, StokesRW, ThorsonLM, EllisSM, HancockREW, TowersGHN. (1997) Anti-mycobacterial screening of British Columbian medicinal plants. Pharmaceutical Biology, 35, 77–83
2.
GrayCA, JohnsonJA, WebsterD. (2013) Canadian traditionally used medicinal plants: can they play a role in antituberculosis drug development?Future Medicinal Chemistry, 5, 853–855
3.
LiH, WebsterD, JohnsonJA, GrayCA. (2015) Anti-mycobacterial triterpenes from the Canadian medicinal plant Alnus incana. Journal of Ethnopharmacology, 165, 148–151
4.
O'NeillT, JohnsonJA, WebsterD, GrayCA. (2013) The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. Journal of Ethnopharmacology, 147, 232–237.
5.
EllsworthKT, ClarkTN, GrayCA, JohnsonJA. (2013) Isolation and bioassay screening of medicinal plant endophytes from eastern Canada. Canadian Journal of Microbiology, 59, 761–765.
6.
MierisovaS, ProksaB, LiptajT. (1996) H-l and C-13 NMR data for palitantine and its derivatives. Magnetic Resonance in Chemistry, 34, 414–415
7.
DemetriadouAK, LaueED, StauntonJ. (1988) Biosynthesis of palitantin, a polyketide metabolite of Penicillium brefeldianum - 13C NMR assignment and incorporation of 13C-, 2H-, and 1802- labeled acetates. Journal of the Chemical Society-Perkin Transactions1, 773–778.
8.
FuskaJ, KuhrI, NemecP, FuskovaA. (1970) Effect of palitantin, a metabolite of Penicillium frequentans on Leishmania brasilensis. Folia Microbiologica, 15, 111–116
9.
BirkinshawJH, RaistrickH. (1936) Studies in the biochemistry of micro-organisms. XLIX. Palitantin, C14H2204, a hitherto undescribed metabolic product of Penicillium palitans Westling. Biochemical Journal, 30, 801–808
10.
FrisvadJC, SamsonRA, RassingBR, van der HorstMI, van RijnFTJ and StarkJ. (1997) Penicillium discolor, a new species from cheese, nuts and vegetables. Antonie Van Leeuwenhoek International Journal of General and Molecular Microbiology, 72, 119–126
11.
HuangX-S, YangB, SunX-F, XiaG-P, LiuY-Y, MaL, SheZ-G. (2014) A New Polyketide from the Mangrove Endophytic Fungus Penicillium sp. skl4JW2P. Helvetica Chimica Acta, 97, 664–668.
12.
YamajiK, FukushiY, HashidokoY, YoshidaT, TaharaS. (1999) Characterization of antifungal metabolites produced by Penicillium species isolated from seeds of Picea glehnii. Journal of Chemical Ecology, 25, 1643–1653.
13.
Abdel-WahabMA, AsolkarRN, InderbitzinP, FenicalW. (2007) Secondary metabolite chemistry of the marine-derived fungus Massarina sp., strain CNT-016. Phytochemistry, 68, 1212–1218
14.
OhH, SwensonDC, GloerJB, ShearerCA. (2003) New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata. Journal of Natural Products, 66, 73–79
15.
KaouadjiM, DegusmaoNB, SteimanR, SeiglemurandiF. (1993) Mycosporulone, a metabolite from Coniothyrium sporulosum. Journal of Natural Products, 56, 2189–2192
16.
JungME, ChangJJ. (2012) Total Synthesis of the Proposed Structure of Mycosporulone: Structural Revision and an Unexpected Retro-Aldol/Aldol Reaction. Organic Letters, 14, 4898–4901
17.
KamedaK, AokiH, NamikiM, OvereemJC. (1974) Alternative structure for botrallin a metabolite of Botrytis allii. Tetrahedron Letters, 103–106
18.
ZhangL, ShenY, WangF, LengY, LiuJK. (2010) Rare merosesquiterpenoids from basidiomycete Craterellus odoratus and their inhibition of 11 beta-hydroxysteroid dehydrogenases. Phytochemistry, 71, 100–103.
19.
SunZL, ZhangM, ZhangJF, FengJ. (2011) Antifungal and cytotoxic activities of the secondary metabolites from endophytic fungus Massrison sp. Phytomedicine, 18, 859–862.
20.
GuiraudP, SteimanR, Seigle-MurandiF, de GusmaoNB. (1999) Antimicrobial and antitumor activities of mycosporulone. Journal of Natural Products, 62, 1222–1224.
21.
FlewellingAJ, JohnsonJA, GrayCA. (2013) Isolation and bioassay screening of fungal endophytes from North Atlantic marine macroalgae. Botanica Marina, 56, 287–297.
22.
O'NeillTE, LiHX, ColquhounCD, JohnsonJA, WebsterD, GrayCA. (2014) Optimisation of the Microplate Resazurin Assay for Screening and Bioassay-guided Fractionation of Phytochemical Extracts against Mycobacterium tuberculosis. Phytochemical Analysis, 25, 461–467
23.
CarpenterCD, O'NeillT, PicotN, JohnsonJA, RobichaudGA, WebsterD, GrayCA. (2012) Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis. Journal of Ethnopharmacology, 143, 695–700.