Chapter 12. The Genus Diaporthe: A Prolific Source of Novel Bioactive Metabolites

$39.50

María Victoria Castelli, Nathalie Ruiz Mostacero, Cecilia Luisa Fulgueira and Silvia Noelí López
Farmacognosia, Universidad Nacional de Rosario – CONICET, Rosario, Argentina

Part of the book: The Book of Fungal Pathogens

Abstract

Diaporthe genus is a cosmopolitan group of filamentous fungi with diverse ecological behaviors, including saprotrophs, endophytes and plant pathogens, some causing significant diseases on a wide range of economically important crops. In its asexual reproducing phase, this genus is characterized by ostiolate black conidiomata containing elongated cylindric phialides that produce alpha and beta hyaline nonseptate conidia. This fungal phase was originally named as Phomopsis, being this name no longer in use now. Diaporthe has been reported as one of the most frequently encountered genera of endophytic fungi in several plant hosts. Species of Diaporthe produce interesting bioactive secondary metabolites, especially if they have been isolated from healthy plant tissues. Examples of isolated compounds include xanthones, chromones, macrolides, cytochalasins, isobenzofuranones, oblongolides, diketopyperazines, and terpenoids, among others. Considering the diverse and complex nature of secondary metabolism, the novelty and promising bioactivity of some metabolites, and the information related to the enzyme production of species belonging to the Diaporthe genus, a comprehensive revision since 2000 to date of the available literature was carried out.

Keywords: Diaporthe, Phomopsis, bioactivity, secondary metabolites, enzymes


References


Adelin, E., Servy, C., Cortial, S., Lévaique, H., Martin, M. T., Retailleau, P., Le Goff, G., Bussaban, B.,
Lumyong, S. and Ouazzani, J. (2011). Isolation, structure elucidation and biological activity of metabolites
from Sch-642305-producing endophytic fungus Phomopsis sp. CMU-LMA.
Phytochemistry 72(18):2406–2412.
Agusta, A., Ohashi, K. and Shibuya, H. (2006). Bisanthraquinone metabolites produced by the endophytic
fungus Diaporthe sp. Chem. Pharm. Bull. 54(4): 579–582.
Ahmed, I., Hussain, H., Schulz, B., Draeger, S., Padula, D., Pescitelli, G., Van Ree, T. and Krohn, K. (2011).
Three new antimicrobial metabolites from the endophytic fungus Phomopsis sp. Eur. J. Org.
Chem. 9(15): 2867–2873.
Andolfi, A., Boari, A., Evidente, M., Cimmino, A., Vurro, M., Ash, G. and Evidente, A. (2015). Gulypyrones
A and B and phomentrioloxins B and C produced by Diaporthe gulyae, a potential mycoherbicide for
Saffron Thistle (Carthamus lanatus). J. Nat. Prod. 78(4): 623–629.
Brissow, E. R., da Silva, I. P., de Siqueira, K. A., Senabio, J. A., Pimenta, L. P., Januario, A. H., Magalhaes,
L. G., Furtado, R. A., Tavares, D. C., Sales Junior, P. A., Santos, J. L. and Soares, M. A. (2017).
18-Des hydroxy cytochalasin: An antiparasitic compound of Diaporthe phaseolorum-92C, an endophytic fungus
isolated from Combretum lanceolatum Pohl ex Eichler. Parasitol. Res. 116: 1823–1830.
Cai, R., Chen, S., Liu, Z., Tan, C., Huang, X. and She, Z. (2017). A new α-pyrone from the mangrove
endophytic fungus Phomopsis sp. HNY29-2B. Nat. Prod. Res. 31(2): 124–130.
Chang, H. S., Peng, C. J., Cheng, M. J., Wu, H. C., Chan, H. Y., Hsieh, S. Y., Yuan, G. F. and Chen, I. S.
(2018). Chemical constituents of the endophytic fungus Phomopsis asparagi isolated from the plant
Peperomia sui. Chem. Nat. Compd. 54: 504–508.
Chang, F. R., Wang, S. W., Li, C. Y., Lu, Y. Y., Vanson Liu, S. Y., Chen, C. Y., Wu, Y. C. and Cheng, Y. Bin.
(2019). Natural products from Diaporthe arecae with anti-angiogenic activity.
Isr. J. Chem. 59(5): 439–445.
Chapla, V. M., Zeraik, M. L., Ximenes, V. F., Zanardi, L. M., Lopes, M. N., Cavalheiro, A. J., Silva, D. H. S.,
Young, M. C. M., Fonseca, L. M., Bolzani, V. S. and Araujo, A. R. (2014). Bioactive secondary
metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis. Molecules 19: 6597-6608.
Chen, Yiguang, Pan, J., Xu, F., Liu, F., Yang, J. X., Huang, C., Xu, C., Lu, Y., Cai, X., She, Z. and Lin, Y.
(2010). A new indene derivative from the marine fungus Phomopsis sp. (No. GX7-4A).
Chem. Nat. Compd. 46(2): 230–232.
Chen, C. J., Liu, X. X., Zhang, W. J., Zang, L. Y., Wang, G., Ng, S. W., Tan, R. X. and Ge, H. M. (2015).
Sesquiterpenoids isolated from an endophyte fungus Diaporthe sp. RSC Adv. 5(23): 17559–17565.
Chen, H., Huang, M., Li, X., Liu, L., Chen, B., Wang, J. and Lin, Y. (2018). Phochrodines A–D, first naturally
occurring new chromenopyridines from mangrove entophytic fungus Phomopsis sp. 33#.
Fitoterapia 124: 103–107.
Chen, S. C., Liu, Z. M., Tan, H. B., Chen, Y. C., Li, S. N., Li, H. H., Guo, H., Zhu, S., Liu, H. X. and Zhang,
W. M. (2019). Tersone A-G, new pyridone alkaloids from the deep-sea fungus Phomopsis tersa.
Mar. Drugs 17(7): 1–14.
Chen, Yan, Zhang, L., Zou, G., Li, C., Yang, W., Liu, H. and She, Z. (2020). Anti-inflammatory activities of
alkaloidsfrom the mangrove endophytic fungus Phomopsissp. SYSUQYP-23. Bioorg. Chem. 97: 103712.
Choi, J. N., Kim, J., Ponnusamy, K., Lim, C., Kim, J. G., Muthaiya, M. J. and Lee, C. H. (2013). Identification
of a new phomoxanthone antibiotic from Phomopsis longicolla and its antimicrobial correlation with other
metabolites during fermentation. J. Antibiot. 66(4): 231–233.
Cui, H., Yu, J., Chen, S., Ding, M., Huang, X., Yuan, J. and She, Z. (2017a). Alkaloids from the mangrove
endophytic fungus Diaporthe phaseolorum SKS019. Bioorg. Med. Chem. Lett. 27(4): 803–807.
Cui, H., Lin, Y., Luo, M., Lu, Y., Huang, X. and She, Z. (2017b). Diaporisoindoles A-C: three
isoprenylisoindole alkaloid derivatives from the mangrove endophytic fungus Diaporthe sp.
SYSU-HQ3. Org. Lett. 19(20): 5621–5624.
Cui, H., Liu, Y., Li, J., Huang, X., Yan, T., Cao, W., Liu, H., Long, Y. and She, Z. (2018). Diaporindenes A D:
Four unusual 2,3-dihydro-1 H-indene analogues with anti-inflammatory activities from the mangrove
endophytic fungus Diaporthe sp. SYSU-HQ3. J. Org. Chem. 83(19): 11804–11813.
Dai, C. C., Chen, Y., Tian, L. S., and Shi, Y. (2010). Correlation between invasion by endophytic fungus
Phomopsis sp. and enzyme production. Afr. J. Agric. Res. 5(11): 1324–1330.
Ding, B., Yuan, J., Huang, X., Wen, W., Zhu, X., Liu, Y., Li, H., Lu, Y., He, L., Tan, H. and She, Z. (2013).
New dimeric members of the phomoxanthone family: Phomolactonexanthones A, B and
deacetylphomoxanthone C isolated from the fungus Phomopsis sp. Mar. Drugs 11(12): 4961–4972.
Ding, B., Wang, Z., Xia, G., Huang, X., Xu, F., Chen, W. and She, Z. (2017). Three new chromone derivatives
produced by Phomopsis sp. HNY29-2B from Acanthus ilicifolius Linn. Chin. J. Chem. 35(12): 1889–1893.
Dissanayake, A. J., Chen, Y. Y. and Liu, J. K. (2020). Unravelling Diaporthe species associated with woody
hosts from karst formations (Guizhou) in China. J. Fungi 6(4): 1–29.
Du, G., Wang, Z. C., Hu, W. Y., Yan, K. L., Wang, X. L., Yang, H. M., Yang, H. Y., Gao, Y. H., Liu, Q. and
Hu, Q. F. (2017). Three new 3-methyl-2-arylbenzofurans from the fermentation products of an endophytic
fungus Phomopsis sp. and their anti-TMV activity. Phytochem. Lett. 21: 287–290.
Duan, Y., Jiang, Y., Guo, F., Chen, L., Xu, L., Zhang, W. and Liu, B. (2019). The antitumor activity of naturally
occurring chromones: A review. Fitoterapia 135: 114–129.
EFSA Panel on Contaminants in the Food Chain. (2012). Scientific Opinion on the risks for animal and public
health related to the presence of phomopsins in feed and food. EFSA J. 10(2): 1–52.
Evidente, M., Boari, S., Cimmino, A., Vurro, M., Ash, G., Superchi, S. and Evidente A. (2015). Structure and
absolute configuration of kongiidiazadione, a new phytotoxic 3-substituted-) diazenylcyclopentendione
produced by Diaporthe kongii. Chirality 27:557–562.
Fu, J., Zhou, Y., Li, H. F., Ye, Y. H. and Guo, J. H. (2011). Antifungal metabolites from Phomopsis sp. By254,
an endophytic fungus in Gossypium hirsutum. Afr. J. Microbiol. Res. 5: 1231–1236.
Gao, Y. H., Zheng, R., Li, J., Kong, W. S., Liu, X., Ye, L., Mi, Q. L., Kong, W. S., Zhou, M., Yang, G. Y., Hu,
Q. F., Du, G., Yang, H. Y. and Li, X. M. (2019). Three new diphenyl ether derivatives from the
fermentation products of an endophytic fungus
Phomopsis fukushii. J. Asian Nat. Prod. Res. 21(4): 316–322.
Hemtasin, C., Kanokmedhakul, S., Kanokmedhakul, K., Hahnvajanawong, C., Soytong, K., Prabpai, S. and
Kongsaeree, P. (2011). Cytotoxic pentacyclic and tetracyclic aromatic sesquiterpenes
from Phomopsis archeri. J. Nat. Prod. 74(4): 609–613.
Hilário, S., Santos, L., Phillips, A. J. L. and Alves, A. (2022). Caveats of the internal transcribed spacer region
as a barcode to resolve species boundaries in Diaporthe. Fungal Biol. 126(1): 54–74.
Hosseini, B., El-Hasan, A., Link, T. and Voegele, R. T. (2020). Analysis of the species spectrum of the
Diaporthe/Phomopsis complex in European soybean seeds. Mycol. Prog. 19(5): 455–469.
Hu, Z., Wu, Y., Xie, S., Sun, W., Guo, Y., Li, X. N., Liu, J., Li, H., Wang, J., Luo, Z., Xue, Y. and Zhang, Y.
(2017). Phomopsterones A and B, two functionalized ergostane-type steroids from the endophytic fungus
Phomopsis sp. TJ507A. Org. Lett. 19(1): 258–261.
Hu, H. B., Luo, Y. F., Wang, P., Wang, W. J. and Wu, J. (2018). Xanthone-derived polyketides from the Thai
mangrove endophytic fungus Phomopsis sp. xy21. Fitoterapia 131: 265–271.
Huang, Z., Cai, X., Shao, C., She, Z., Xia, X., Chen, Y., Yang, J., Zhou, S. and Lin, Y. (2008). Chemistry and
weak antimicrobial activities of phomopsins produced by mangrove endophytic fungus Phomopsis sp.
ZSU-H76. Phytochem. 69(7): 1604–1608.
Huang, Z., Yang, R., Guo, Z., She, Z. and Lin, Y. (2010). A new naphtho-γ-pyrone from mangrove endophytic
fungus ZSU-H26. Chem. Nat. Compd. 46(1): 15–18.
Huang, Z., Yang, J., Lei, F., She, Z. and Lin, Y. (2013). A new xanthone O-glycoside from the mangrove
endophytic fungus Phomopsis sp. Chem. Nat. Compd. 49(1): 27–30.
Huang, M., Li, J., Liu, L., Yin, S., Wang, J. and Lin, Y. (2016). Phomopsichin A-D; four new chromone
derivatives from mangrove endophytic fungus Phomopsis sp. 33#. Mar. Drugs 14(11): 1–11.
Huang, X., Zhou, D., Liang, Y., Liu, X., Cao, F., Qin, Y., Mo, T., Xu, Z., Li, J. and Yang, R. (2021).
Cytochalasins from endophytic Diaporthe sp. GDG-118. Nat. Prod. Res. 35(20): 3396–3403.
Hussain, H., Tchimene, M. K., Ahmed, I., Meier, K., Steinert, M., Draeger, S., Schulz, B. and Krohn, K. (2011).
Antimicrobial chemical constituents from the endophytic fungus Phomopsis sp. from Notobasis syriaca.
Nat. Prod. Commun. 6(12): 1905–1906.
Hussain, H., Ahmed, I., Schulz, B., Draeger, S. and Krohn, K. (2012). Pyrenocines J-M: Four new pyrenocines
from the endophytic fungus, Phomopsis sp. Fitoterapia 83(3): 523–526.
Isaka, M., Jaturapat, A., Rukseree, K., Danwisetkanjana, K., Tanticharoen, M. and Thebtaranonth, Y. (2001).
Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus
Phomopsis species. J. Nat. Prod. 64(8): 1015–1018.
Jouda, J. B., Tamokou, J. D. D., Mbazoa, C. D., Douala-Meli, C., Sarkar, P., Bag, P. K., Wandji, J. (2016).
Antibacterial and cytotoxic cytochalasins from the endophytic fungus Phomopsis sp. harbored in Garcinia
kola (Heckel) nut. BMC Complement. Altern. Med. 16: 462.
Khan, A. L., Shahzad, R., Al-Harrasi, A. and Lee, I.-J. (2017). Chapter 5: Endophytic microbes: a resource for
producing extracellular enzymes. In Maheshwari D. K. and Annapurna K. (eds.), Endophytes: Crop
Productivity and Protection, Sustainable Development and Biodiversity 16, 95-110.
Klaiklay, S., Rukachaisirikul, V., Phongpaichit, S., Pakawatchai, C., Saithong, S., Buatong, J., Preedanon, S.
and Sakayaroj, J. (2012). Anthraquinone derivatives from the mangrove-derived fungus Phomopsis sp.
PSU-MA214. Phytochem. Lett. 5(4): 738–742.
Kongprapan, T., Xu, X., Rukachaisirikul, V., Phongpaichit, S., Sakayaroj, J., Chen, J. and Shen, X. (2017).
Cytosporone derivatives from the endophytic fungus Phomopsis sp. PSU-H188.
Phytochem. Lett. 22: 219–223.
Kornsakulkarn, J., Somyong, W., Supothina, S., Boonyuen, N. and Thongpanchang, C. (2015). Bioactive
oxygen-bridged cyclooctadienes from endophytic fungus Phomopsis sp. BCC 45011.
Tetrahedron 71(48): 9112–9116.
Krohn, K., Farooq, U., Hussain, H., Ahmed, I., Rheinheimer, J., Draeger, S., Schulz, B. and Van Ree, T. (2011).
Phomosines H-J, novel highly substituted biaryl ethers, isolated from the endophytic fungus Phomopsis
sp. from Ligustrum vulgare. Nat. Prod. Commun. 6(12): 1907–1912.
Li, S. (2010). Aggressiveness of Phomopsis longicolla and other Phomopsis spp. on soybean.
14. Plant. Dis. 94 (8): 1035-1040.
Li, G., Kusari, S., Kusari, P., Kayser, O. and Spiteller, M. (2015). Endophytic Diaporthe sp. LG23 produces a
potent antibacterial tetracyclic triterpenoid. J. Nat. Prod. 78(8): 2128–2132.
Li, X. B., Chen, G. Y., Liu, R. J., Zheng, C. J., Song, X. M. and Han, C. R. (2017). A new biphenyl derivative
from the mangrove endophytic fungus Phomopsis longicolla HL-2232.
Nat. Prod. Res. 31(19): 2264–2267.
Li, W. S., Hu, H. B., Huang, Z. H., Yan, R. J., Tian, L. W., & Wu, J. (2019). Phomopsols A and B from the
mangrove endophytic fungus Phomopsis sp. xy21: structures, neuroprotective effects, and biogenetic
relationships. Org. Lett. 21(19): 7919–7922.
Lin, X., Lu, C.-H. and Shen, Y.-M. (2008). One new ten-membered lactone from Phomopsis sp. B27, an
endophytic fungus of Annona squamosa. Chin. J. Nat. Med., 6(5): 391–394.
Lin, T., Lin, X., Lu, C., Hu, Z., Huango, W., Huang, Y. and Shen, Y. (2009). Secondary metabolites of
Phomopsis sp. XZ-26, an endophytic fungus from Camptotheca
acuminate. Eur. J. Org. Chem. 18: 2975–2982.
Liu, Yuanzhen, Hu, Z., Lin, X., Lu, C. and Shen, Y. (2013). A new polyketide from Diaporthe sp. SXZ-19, an
endophytic fungal strain of Camptotheca acuminate. Nat. Prod. Res. 27(22): 2100–2104.
Liu, Z., Zhao, J., Liang, X., Lv, X., Li, Y., Qu, J. and Liu, Y. (2018). Dothiorelone derivatives from an
endophyte Diaporthe pseudomangiferaea inhibit the activation of human lung fibroblasts MRC-5 cells.
Fitoterapia 127: 7–14.
Liu, Yena, Ruan, Q., Jiang, S., Qu, Y., Chen, J., Zhao, M., Yang, B., Liu, Y., Zhao, Z. and Cui, H. (2019a).
Cytochalasins and polyketides from the fungus Diaporthe sp. GZU-1021 and their anti-inflammatory
activity. Fitoterapia 137: 104187.
Liu, H., Chen, Y., Li, H., Li, S., Tan, H., Liu, Z., Li, D., Liu, H. and Zhang, W. (2019b). Four new metabolites
from the endophytic fungus Diaporthe lithocarpus A740. Fitoterapia 137: 104260.
Liu, Yonghong, Chen, S., Guo, H., Jiang, M., Wu, Q., Li, J., Shen, H. and Liu, L. (2022). Mono- and dimeric
xanthones with anti-glioma and anti-Inflammatory activities from the ascidian-derived fungus Diaporthe
sp. SYSU-MS4722. Mar. Drugs 20 (1): 51.
Luo, X., Lin, X., Tao, H., Wang, J., Li, J., Yang, B., Zhou, X. and Liu, Y. (2018). Isochromophilones A-F,
cytotoxic chloroazaphilones from the marine mangrove endophytic fungus Diaporthe sp. SCSIO 41011.
J. Nat. Prod. 81(4): 934–941.
Luo, Y. F., Zhang, M., Dai, J. G., Pedpradab, P., Wang, W. J. and Wu, J. (2016). Cytochalasins from mangrove
endophytic fungi Phomopsis spp. xy21 and xy22. Phytochem. Lett. 17: 162–166.
Ma, K. X., Shen, X. T., Huang, R., Wang, T., Xie, X. S., Liu, S. W., Wu, S. H. and He, J. (2014). Bioactive
metabolites produced by the endophytic fungus Phomopsis sp.
YM355364. Nat. Prod. Commun. 9(5): 669–670.
Ma, X., Wang, W., Li, E., Gao, F., Guo, L. and Pei, Y. (2016). A new sesquiterpene from the entomogenous
fungus Phomopsis amygdali. Nat. Prod. Res. 30(3): 276–280.
Mandavid, H., Rodrigues, A. M. S., Espindola, L. S., Eparvier, V. and Stien, D. (2015). Secondary metabolites
isolated from the Amazonian endophytic fungus Diaporthe sp.
SNB-GSS10. J. Nat. Prod., 78(7): 1735–1739.
Masters, K. S. and Bräse, S. (2012). Xanthones from fungi, lichens, and bacteria: The natural products and
their synthesis. Chem. Rev. 112(7): 3717–3776.
Meister, J., Weber, D., Martino, V., Sterner, O. and Anke, T. (2007). Phomopsidone, a novel depsidone from
an endophyte of the medicinal plant Eupatorium arnottianum. C J. Biosci. 62(1–2): 11–15.
Meng, Y., Yang, Y., Qin, Y., Xia, C., Zhou, M., Gao, X., Du, G. and Hu, Q. (2015). Xanthone Derivatives
from the fermentation products of an endophytic fungus
Phomopsis sp. Nat. Prod. Commun. 10(2): 305–308.
Motoyama, T., Nogawa, T., Hayashi, T., Hirota, H. and Osada, H. (2019). Induction of nectriapyrone
biosynthesis in the rice blast fungus Pyricularia oryzae by disturbance of the two-component signal
transduction system. Chem Bio Chem, 20(5): 693–700.
Nakashima, K. ichi, Tomida, J., Kamiya, T., Hirai, T., Morita, Y., Hara, H., Kawamura, Y., Adachi, T. and
Inoue, M. (2018). Diaporthols A and B: bioactive diphenyl ether derivatives from an endophytic fungus
Diaporthe sp. Tetrahedron Lett. 59(13): 1212–1215.
Niaz, S. I., Khan, D., Naz, R., Safdar, K., Abidin, S. Z. U., Khan, I. U., Gul, R., Khan, W. U., Khan, M. A. U.
and Lan, L. (2021). Antimicrobial and antioxidant chlorinated azaphilones from mangrove Diaporthe
perseae sp. isolated from the stem of Chinese mangrove Pongamia
pinnata. J. Asian Nat. Prod. Res. 23(11): 1077–1084.
Noriler, S. A., Savi, D. C., Aluizio, R., Palácio-Cortes, A., Possiede, Y. M. and Glienke, C. (2018).
Bioprospecting and structure of fungal endophyte communities found in the Brazilian biomes, Pantanal,
and Cerrado. Front. Microbiol. 9(1526): 1-14.
Noriler, S. A., Savi, D. C., Ponomareva, L. V., Rodrigues, R., Rohr, J., Thorson, J. S., Glienke, C. and Shaaban,
K. A. (2019). Vochysiamides A and B: Two new bioactive carboxamides produced by the new species
Diaporthe vochysiae. Fitoterapia 138: 104273.
Ola, A. R. B., Debbab, A., Kurtán, T., Brötz-Oesterhelt, H., Aly, A. H. and Proksch, P. (2014).
Dihydroanthracenone metabolites from the endophytic fungus Diaporthe melonis isolated from Annona
squamosa. Tetrahedron Lett. 55(20): 3147–3150.
Pavesi, C., Flon, V., Mann, S., Leleu, S., Prado, S. and Franck, X. (2021). Biosynthesis of azaphilones: A
review. Nat. Prod. Rep. 38(6): 1058–1071.
Peng, X., Sun, F., Li, G., Wang, C., Zhang, Y., Wu, C., Zhang, C., Sun, Y., Wu, S., Zhang, Y., Zong, H., Guo,
R. and Lou, H. (2021). New Xanthones with anti agricultural fungal pathogen activities from the
endophytic fungus Diaporthe goulteri L17. J. Agric. Food Chem. 69(38): 11216–11224.
Porras-Alfaro, A. and Bayman, P. (2011). Hidden fungi, emergent properties: endophytes and microbiomes.
Ann. Rev. Phytopathol., 49: 291–315.
Promputtha, I., Hyde, K. D., McKenzie, E. H. C., Peberdy, J. F. and Lumyong, S. (2010). Can leaf degrading
enzymes provide evidence that endophytic fungi becoming saprobes? Fungal Divers. 41: 89–99.
Riga, R., Happyana, N., Quentmeier, A., Zammarelli, C., Kayser, O. and Hakim, E. H. (2021). Secondary
metabolites from Diaporthe lithocarpus isolated from Artocarpus
heterophyllus. Nat. Prod. Res. 35(14): 2324–2328.
Rönsberg, D., Debbab, A., Mándi, A., Vasylyeva, V., Böhler, P., Stork, B., Engelke, L., Hamacher, A.,
Sawadogo, R., Diederich, M., Wray, V., Lin, W., Kassack, M. U., Janiak, C., Scheu, S., Wesselborg, S.,
Kurtán, T., Aly, A. H. and Proksch, P. (2013). Pro-apoptotic and immunostimulatory tetrahydroxanthone
dimers from the endophytic fungus Phomopsis longicolla. J. Org. Chem. 78(24): 12409–12425.
Rukachaisirikul, V., Sommart, U., Phongpaichit, S., Sakayaroj, J. and Kirtikara, K. (2008). Metabolites from
the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry, 69(3): 783–787.
Santos, J. M., Correia, V. G. and Phillips, A. J. L. (2010). Primers for mating-type diagnosis in Diaporthe and
Phomopsis: their use in teleomorph induction in vitro and biological species definition.
Fungal Biol. 114(2–3): 255–270.
Scherlach, K., Boettger, D., Remme, N. and Hertweck, C. (2010). The chemistry and biology of cytochalasans.
Nat. Prod. Rep. 27(6): 869–886.
Schloß, S., Hackl, T., Herz, C., Lamy, E., Koch, M., Rohn, S. and Maul, R. (2017). Detection of a toxic
methylated derivative of phomopsin A produced by the legume-infesting fungus Diaporthe toxica. J. Nat.
Prod. 80(6): 1930–1934.
Shiono, Y., Sasaki, T., Shibuya, F., Yasuda, Y., Koseki, T. and Supratman, U. (2013). Isolation of a
phomoxanthone A derivative, a new metabolite of tetrahydroxanthone, from a Phomopsis sp. isolated
from the mangrove, Rhizhopora mucronata. Nat. Prod. Commun. 8(12): 1735–1737.
Silva, G. H., Teles, H. L., Zanardi, L. M., Marx Young, M. C., Eberlin, M. N., Hadad, R., Pfenning, L. H.,
Costa-Neto, C. M., Castro-Gamboa, I., da Silva Bolzani, V. and Araújo, Â. R. (2006). Cadinane
sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis
(Leguminosae). Phytochemistry 67(17): 1964–1969.
Song, H. C., Qin, D., Han, M. J., Wang, L., Zhang, K. and Dong, J. Y. (2017). Bioactive 2-pyrone metabolites
from an endophytic Phomopsis asparagi SWUKJ5.2020 of Kadsura angustifolia.
Phytochem. Lett. 22: 235–240.
Sunitha, V. H., Devi, D. N. and Srinivas, C. (2013). Extracellular enzymatic activity of endophytic fungal
strains isolated from medicinal plants. World J. Agric. Sci. 9(1): 1–9.
Sutton, D. A., Timm, W. D., Morgan-Jones, G., & Rinaldi, M. G. (1999). Human phaeohyphomycotic
osteomyelitis caused by the coelomycete Phomopsis saccardo 1905: Criteria for identification, case
history, and therapy. J. Clin. Microbiol. 37(3): 807–811.
Talontsi, F. M., Islam, M. T., Facey, P., Douanla-Meli, C., Von Tiedemann, A. and Laatsch, H. (2012).
Depsidones and other constituents from Phomopsis sp. CAFT69 and its host plant Endodesmia
calophylloides with potent inhibitory effect on motility of zoospores of grapevine pathogen Plasmopara
viticola. Phytochem. Lett. 5(3): 657–664.
Tang, J. W., Wang, W. G., Li, A., Yan, B. C., Chen, R., Li, X. N., Du, X., Sun, H. D. and Pu, J. X. (2017).
Polyketides from the endophytic fungus Phomopsis sp. sh917 by using the one strain/many compounds
strategy. Tetrahedron 73(26): 3577–3584.
Taylor, J. One Fungus = One Name: DNA and fungal nomenclature
twenty years after PCR. IMA Fungus 2: 113-120.
Thao, L. D. and Matsumoto, M. (2020). Genetic diversity and pathogenic characteristics of Phomopsis
asparagi obtained from Asparagus officinalis and A. kiusianus
in Japan. J. Plant Dis. Prot. 127(6): 843–853.
Tian, W., Liao, Z., Zhou, M., Wang, G., Wu, Y., Gao, S., Qiu, D., Liu, X., Lin, T. and Chen, H. (2018).
Cytoskyrin C, an unusual asymmetric bisanthraquinone with cage-like skeleton from the endophytic
fungus Diaporthe sp. Fitoterapia 128: 253–257.
Tonukari, N. J. (2003). Enzymes and fungal virulence. J. Appl. Sci. and Environ. Manag. 7 (1): 5-8.
Udayanga, D., Liu, X., McKenzie, E. H. C., Chukeatirote, E., Bahkali, A. H. A. and Hyde, K. D. (2011). The
genus Phomopsis: Biology, applications, species concepts and names of common phytopathogens.
Fungal Divers. 50: 189–225.
Vedashree, S., Sateesh, M. K., Lakshmeesha, T. R. and Mohammed, S. S. (2013). Screening and assay of
extracellular enzymes in Phomopsis azadirachtae causing die-back
disease of neem. J. Agric. Technol. 9(4): 915–927.
Verekar, S. A., Mishra, P. D., Sreekumar, E. S., Deshmukh, S. K., Fiebig, H. H., Kelter, G. and Maier, A.
(2014). Anticancer activity of new depsipeptide compound isolated from an endophytic fungus. J.
Antibiot. 67(10): 697–701.
Wagenaar, M. M. and Clardy, J. (2001). Dicerandrols, new antibiotic and cytotoxic dimers produced by the
fungus Phomopsis longicolla isolated from an endangered mint. J. Nat. Prod. 64(8): 1006–1009.
Wang, P., Luo, Y. F., Zhang, M., Dai, J. G., Wang, W. J. and Wu, J. (2018). Three xanthone dimers from the
Thai mangrove endophytic fungus Phomopsis sp. xy21. J. Asian Nat. Prod. Res. 20(3): 217–226.
Wei, W., Gao, J., Shen, Y., Chu, Y. L., Xu, Q. and Tan, R. X. (2014). Immunosuppressive diterpenes from
Phomopsis sp. S12. Eur. J. Org. Chem. 2014(26): 5728–5734.
Wezeman, T., Bräse, S. and Masters, K. S. (2015). Xanthone dimers: A compound family which is both
common and privileged. Nat. Prod. Rep. 32(1): 6–28.
Wu, Q., Guo, Y., Guo, Z. K., Chu, Y. L., Wang, T. and Tan, R. X. (2013a). Two new cytosporones from the
culture of endophytic Phomopsis sp. Chem. Nat. Compd. 48(6): 938–941.
Wu, S. H., Huang, R., Miao, C. P. and Chen, Y. W. (2013b). Two new steroids from an endophytic fungus
Phomopsis sp. Chem. Biodivers. 10(7): 1276–1283.
Xie, X. G. and Dai, C. C. (2015). Degradation of a model pollutant ferulic acid by the endophytic fungus
Phomopsis liquidambari. Bioresour. Technol. 179: 35–42.
Xie, S., Wu, Y., Qiao, Y., Guo, Y., Wang, J., Hu, Z., Zhang, Q., Li, X., Huang, J., Zhou, Q., Luo, Z., Liu, J.,
Zhu, H., Xue, Y. and Zhang, Y. (2018). Protoilludane, illudalane, and botryane sesquiterpenoids from the
endophytic fungus Phomopsis sp. TJ507A. J. Nat. Prod. 81(6): 1311–1320.
Xu, J., Tan, H., Chen, Y., Li, S., Huang, Z., Guo, H., Li, H., Gao, X., Liu, H. and Zhang, W. (2018).
Lithocarpins A-D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived
fungus: Phomopsis lithocarpus FS508. Org. Chem. Front. 5(11): 1792–1797.
Xu, K., Zhang, X., Chen, J. W., Shen, Y., Jiang, N., Tan, R. X., Jiao, R. H. and Ge, H. M. (2019a).
Anti inflammatory diterpenoids from an endophytic fungus Phomopsis sp. S12.
Tetrahedron Lett. 60(38): 151045.
Xu, J., Tan, H., Chen, Y., Li, S., Guo, H., Huang, Z., Li, H., Gao, X., Liu, H. and Zhang, W. (2019b).
Lithocarpinols A and B, a pair of diastereomeric antineoplastic tenellone derivatives from the deep-sea
derived fungus Phomopsis lithocarpus FS508. Chin. Chem. Lett. 30(2): 439–442.
Xu, J., Liu, Z., Chen, Y., Tan, H., Li, H., Li, S., Guo, H., Huang, Z., Gao, X., Liu, H. and Zhang, W. (2019c).
Lithocarols A-F, six tenellone derivatives from the deep-sea derived fungus Phomopsis lithocarpus
FS508. Bioorg. Chem. 87: 728–735.
Xu, T. C., Lu, Y. H., Wang, J. F., Song, Z. Q., Hou, Y. G., Liu, S. S., Liu, C. S. and Wu, S. H. (2021). Bioactive
secondary metabolites of the genus Diaporthe and anamorph Phomopsis from terrestrial and marine
habitats and endophytes: 2010–2019. Microorganisms, 9(2): 1–49.
Yan, B. C., Wang, W. G., Hu, D. B., Sun, X., Kong, L. M., Li, X. N., Du, X., Luo, S. H., Liu, Y., Li, Y., Sun,
H. D. and Pin, J. X. (2016). Phomopchalasins A and B, two cytochalasans with polycyclic-fused skeletons
from the endophytic fungus Phomopsis sp. shj2. Org. Lett. 18(5): 1108–1111.
Yang, J., Xu, F., Huang, C., Li, J., She, Z., Pei, Z. and Lin, Y. (2010). Metabolites from the mangrove
endophytic fungus Phomopsis sp. (#zsu-H76). Eur. J. Org. Chem. 19 :3692–3695.
Yang, J. X., Chen, Y., Huang, C., She, Z. and Lin, Y. (2011). A new isochroman derivative from the marine
fungus Phomopsis sp. (No. ZH-111). Chem. Nat. Compd. 47(1): 15–17.
Yang, J. X., Qiu, S., She, Z. L. and Lin, Y. (2013a). A new xanthone derivative from Hypericum erectum.
Chem. Nat. Compd. 49(1): 31-33.
Yang, H. Y., Gao, Y. H., Niu, D. Y., Yang, L. Y., Gao, X. M., Du, G. and Hu, Q. F. (2013b). Xanthone
derivatives from the fermentation products of an endophytic fungus Phomopsis sp.
Fitoterapia 91: 189–193.
Yang, Z., Ding, J., Ding, K., Chen, D., Cen, S. and Ge, M. (2013c). Phomonaphthalenone A: A novel
dihydronaphthalenone with anti-HIV activity from Phomopsis sp.
HCCB04730. Phytochem. Lett. 6(2): 257–260.
Yang, Y., Yang, H., Li, Y., Ye, Y., Hu, Q., Gao, X. and Du, G. (2014). A New xanthone from the fermentation
products of endophytic fungus of Phomopsis species. Asian J. Chem. 26(15), 4591–4593
Yang, H. Y., Duan, Y. Q., Yang, Y. K., Li, J., Liu, X., Ye, L., Mi, Q. L., Kong, W. S., Zhou, M., Yang, G. Y.,
Li, X. M. and Hu, Q. F. (2017). Three new napthalene derivatives from the endophytic fungus Phomopsis
fukushii. Phytochem. Lett. 22: 266–269.
Yang, Z., Wu, K., Xu, Y., Xia, X., Wang, X., Ge, M. and Shao, L. (2020a). Three novel chromanones with
biological activities from the endophytic fungus Phomopsis
CGMCC No. 5416. J. Antibiot. 73(3): 194–199.
Yang, Z. J., Zhang, Y. F., Wu, K., Xu, Y. X., Meng, X. G., Jiang, Z. T., Ge, M. and Shao, L. (2020b). New
azaphilones, phomopsones A-C with biological activities from an endophytic fungus Phomopsis sp.
CGMCC No.5416. Fitoterapia 145: 104573.
Yang, X., Wu, P., Xue, J., Li, H. and Wei, X. (2020c). Cytochalasans from endophytic fungus Diaporthe sp.
SC-J0138. Fitoterapia 145: 104611.
Yu, B. Z., Zhang, G. H., Du, Z. Z., Zheng, Y. T., Xu, J. C. Luo, X. D. (2008). Phomoeuphorbins A-D,
azaphilones from the fungus Phomopsis euphorbiae. Phytochemistry 69(13): 2523–2526.
Yuan, L., Huang, W., Du, G., Gao, X., Yang, H., Hu, Q. Ma, Y. (2015a). Isolation of xanthones from the
fermentation products of the endophytic fungus of Phomopsis amygdali.
Chem. Nat. Compd. 51(3): 460–463.
Yuan, L., Huang, W., Zhou, K., Wang, Y., Dong, W., Lou, J., Li, L., Du, G., Yang, H., Ma, Y. and Hu, Q.
(2015b). Xanthones from the fermentation products of an endophytic fungus
Phomopsis sp. Heterocycles 91(2): 381–387.
Zanardi, L. M., da S. Bolzani, V., Cavalheiro, A. J., Siqueira Silva, D. H. and Araujo, A. R. (2012).
Sesquiterpenos produzidos pelo fungo endofítico Phomopsis cassiae com atividade antifúngica e inibidora
de acetilcolinesterase [Sesquiterpenes produced by the endophytic fungus Phomopsis cassiae with
antifungal and acetylcholinesterase inhibitor activity]. Quim. Nova 35(11): 25–40.
Zang, L. Y., Wei, W., Guo, Y., Wang, T., Jiao, R. H., Ng, S. W., Tan, R. X. and Ge, H. M. (2012).
Sesquiterpenoids from the mangrove-derived endophytic fungus
Diaporthe sp. J. Nat. Prod. 75(10): 1744–1749.
Zhang, J., Bruton, B. D. and Biles, C. L. (1997). Polygalacturonase isozymes produced by Phomopsis
cucurbitae in relation to postharvest decay of cantaloupe fruit. Phytopathology 87(10): 1020–1025.
Zhang, W., Xu, L., Yang, L., Huang, Y., Li, S. and Shen, Y. (2014). Phomopsidone A, a novel depsidone
metabolite from the mangrove endophytic fungus Phomopsis sp. A123. Fitoterapia 96: 146–151.
Zhang, Q., Huang, Z., Zhao, Y., Zhao, Q., Chen, J., Ma, W. and Zhang, X. (2020). Six 19,20-
epoxycytochalasans from endophytic Diaporthe sp. RJ-47. Nat. Prod. Res.
Zhang, Q., Ma, W., Zhao, Q., Zhao, Y., Huang, Z., Xu, Y., Zhu, D., Li, J. and Zhang, X. (2021). α-pyrone
derivatives from endophytic fungus Diaporthe sp. RJ-41. Biochem. Syst. Ecol. 94: 104198.
Zhou, J., Li, X., Huang, P. W. and Dai, C. C. (2018). Endophytism or saprophytism: Decoding the lifestyle
transition of the generalist fungus Phomopsis liquidambari. Microbiol. Res. 206: 99–112.
Zhou, P., Yan, S., Lu, Y., Li, X. N., Zhang, M., Li, Q., Chen, X., Wang, J., Zhu, H., Chen, C. and Zhang, Y.
(2021). Five new secondary metabolites from the fungus Phomopsis asparagi. Fitoterapia 150: 104840.
Zhu, Y. L., Zhang, M. Q., Wang, L. S., Mei, Y. Z. and Dai, C. C. (2022). Overexpression of chitinase in the
endophyte Phomopsis liquidambaris enhances wheat resistance to Fusarium graminearum.
Fungal Genet. Biol. 158: 103650.

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