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. 2017 Oct 24;15(10):329. doi: 10.3390/md15100329

Table A1.

Secondary metabolites from Penicillium strain of marine origin. Items are listed according to the metabolite numbers used in this review.

Metabolites Producing Stain Environment Source Type Cell Lines/Brine Shrimp IC50, LD50, or IR (%) Target Reference
Penochalasin A (1) Penicillium sp. Marine alga Indole alkaloid P388 0.4 μg/mL [8]
Penochalasin B (2) Penicillium sp. Marine alga Indole alkaloid P388 0.3 μg/mL [8]
Penochalasin C (3) Penicillium sp. Marine alga Indole alkaloid P388 0.5 μg/mL [8]
Penochalasin D (4) Penicillium sp. Marine alga Indole alkaloid P388 3.2 μg/mL [7]
Penochalasin E (5) Penicillium sp. Marine alga Indole alkaloid P388 2.1 μg/mL [7]
Penochalasin F (6) Penicillium sp. Marine alga Indole alkaloid P388 1.8 μg/mL [7]
Penochalasin G (7) Penicillium sp. Marine alga Indole alkaloid P388 1.9 μg/mL [7]
Penochalasin H (8) Penicillium sp. Marine alga Indole alkaloid P388 2.8 μg/mL [7]
Penochalasin I (9) P. chrysogenum V11 Mangrove Indole alkaloid MDA-MB-435, SGC-7901, A549 (7.55, 7.32, 16.13) μM [6]
Penochalasin J (10) P. chrysogenum V11 Mangrove Indole alkaloid MDA-MB-435, SGC-7901, A549 (36.68, 37.70, 35.93) μM [6]
Chaetoglobosin A (11) P. chrysogenum V11 Mangrove Indole alkaloid P388, MDA-MB-435, SGC-7901, A549 0.6 μg/mL (37.56, 7.84, 6.56) μM Cell-cycle arrest induction, membrane ruffling inhibition, and cell migration [6,8,9]
Chaetoglobosin C (12) P. chrysogenum V11 Mangrove Indole alkaloid MDA-MB-435, SGC-7901, A549 (19.97, 15.36, 17.82) μM [6]
Chaetoglobosin E (13) P. chrysogenum V11 Mangrove Indole alkaloid A549 36.63 μM [6]
Chaetoglobosin F (14) P. chrysogenum V11 Mangrove Indole alkaloid P388, MDA-MB-435, SGC-7901, A549 0.9 μg/mL, (37.77, 26.53, 27.72) μM [6,8]
Chaetoglobosin G (15) P. chrysogenum V11 Mangrove Indole alkaloid MDA-MB-435, SGC-7901, A549 (38.77, 25.86, 27.63) μM [6]
Chaetoglobosin O (16) Penicillium sp. Marine alga Indole alkaloid P388 2.4 μg/mL [7]
Cytoglobosin C (17) P. chrysogenum V11 Mangrove Indole alkaloid MDA-MB-435, SGC-7901, A549 (12.58, 8.15, 3.35) μM [6]
18 Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 3.4 μM [12]
19 Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 0.058 μM HMT G9a (IC50 = 55 μM) [12]
20 Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 0.11 μM [12]
21 Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 0.11 μM HMT G9a (IC50 = 58 μM) [12]
22 Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 0.056 μM HMT G9a (IC50 = 2.6 μM) [12]
Gliotoxin (23) Penicillium sp. JMF034 Deep sea sediment Diketopiperazine P388 0.024 μM HMT G9a (IC50 = 6.4 μM)
Dual inhibitor of farnesyltransferase and geranylgeranyltransferase I		 [12,13]
Gliotoxin G (24) Penicillium sp. JMF034
P. brocae MA-231		 Deep sea sediment Mangrove Diketopiperazine P388 A2780, A2780 CisR 0.02 μM (0.664, 0.661) μM HMT G9a (IC50 = 2.1 μM) [12]
[14]
Brozazine A (25) P. brocae MA-231 Mangrove Diketopiperazine Du145, Hela, HepG2, MCF-7, NCI-H460, SGC-7901, SW1990, SW480, U251 (4.2, 6.8, 6.4, 5.5, 4.9, 2.6, 6.0, 2.0, 5.2) μM [16]
Brozazine B (26) P. brocae MA-231 Mangrove Diketopiperazine Du145, Hela, HepG2, MCF-7, NCI-H460, SGC-7901, SW1990, SW480, U251 (3.6, 5.3, 5.5, 6.1, 4.0, 2.4, 6.4, 1.2, 3.5) μM [16]
Brozazine E (29) P. brocae MA-231 Mangrove Diketopiperazine Du145, Hela, HepG2, MCF-7, NCI-H460, SGC-7901, SW1990, U251 (11.2, 4.3, 5.6, 9.0, 12.4, 3.3, 2.1, 6.1) μM [16]
Brozazine F (30) P. brocae MA-231 Mangrove Diketopiperazine Du145, Hela, HepG2, MCF-7, NCI-H460, SGC-7901, SW1990, U251 (1.7, 6.9, 2.9, 3.0, 0.89, 8.0, 5.9, 5.3) μM [16]
N-methylpretrichodermam ide B/adametizines A (32) P. adametzioides AS-53
Penicillium sp.		 Marine sponge/sediment/alga Diketopiperazine Artemia salina 4.8 μM [17,18,19]
L5178Y, 22Rv1, PC-3, LNCaP (2, 0.51, 5.11, 1.76) μM
Roquefortine C (33) Penicillium sp. Deep sea sediment Diketopiperazine Activate P-glycoprotein and inhibit P450-3A and other haemoproteins [20,22]
Roquefortine F (34) Penicillium sp. Deep sea sediment Diketopiperazine A549, HL-60, BEL-7402, MOLT-4 (14.0, 33.6, 13.0, 21.2) μM [22]
Roquefortine G (35) Penicillium sp. Deep sea sediment Diketopiperazine A549, HL-60 (42.5, 36.6) μM [22]
Meleagrin (38) Penicillium sp.
P. commune SD-118		 Deep sea sediment Indole alkaloid A549, HL-60 HepG2, NCI-H460, Hela, DU145, MDA-MB-231, (19.9, 7.4) μM (12.0, 22.0, 20.0, 11.0, 5.0) μg/mL Arrest the cell cycle through G2/M phase
Inhibitor of tubulin polymerization		 [21,22,23]
Meleagrin B (39) Penicillium sp. Deep sea sediment Indole alkaloid A549, HL-60, BEL-7402, MOLT-4 (2.7, 6.7, 1.8, 2.9) μM [21,22]
Meleagrin C (40) Penicillium sp. Deep sea sediment Indole alkaloid A549, BEL-7402, MOLT-4 (9.9, 10.0, 4.7) μM [22]
Meleagrin D (41) Penicillium sp. Deep sea sediment Indole alkaloid A549 32.2 μM [21]
Meleagrin E (42) Penicillium sp. Deep sea sediment Indole alkaloid A549 55.9 μM [21]
Penicimutanin (43) Mutant P. purpurogenum G59 Marine soil Diketopiperazine K562, Hela, MCF-7 IR% (100 μg/mL): 22.6%, 17.9%, 26.5% [24]
Penicimutanin A (44) Mutant P. purpurogenum G59 Marine soil Diketopiperazine K562, HL-60, Hela, BGC-823, MCF-7 (11.4, 5.4, 9.5, 8.0, 5.4) μM [24]
Penicimutanin B (45) Mutant P. purpurogenum G59 Marine soil Diketopiperazine K562, HL-60, Hela, BGC-823, MCF-7 (19.9, 12.1, 17.7, 16.6, 8.0) μM [24]
Fructigenine A (46) Mutant P. purpurogenum G59 Marine soil Diketopiperazine K562, Hela, MCF-7, BGC-823 IR% (100μg/mL): 20.8%, 55.3%, 65.6%, 34.8% [24,25]
11,11′-dideoxyverticillin A (49) Penicillium sp. Marine alga Diketopiperazine HCT-116 30 ng/mL Induce G2/M arrest through p38 MAPK pathway;
Epidermal growth factor receptor tyrosine kinase inhibitor		 [28,30,31]
11′-deoxyverticillin A (50) Penicillium sp. Marine alga Diketopiperazine HCT-116 30 ng/mL [28]
Penitrem A (51) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)
MDA-MB-231 (anti-invasion)		 (11.9, 9.8) μM
8.7 μM
IR% (15 μM)> 75%		 BK channel inhibitor [34]
Penitrem B (52) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (5.5, 13.7) μM
10.3 μM		 [34]
Penitrem D (53) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (8.3, 29.7) μM
9.2 μM		 [34]
Penitrem E (54) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (17.5, 25.4) μM
20.3 μM		 [34]
Penitrem F (55) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (15.0, 13.8) μM
35.0 μM		 [34]
6-bromopenitrem B (56) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)
MDA-MB-231 (anti-invasion)		 (19.3, 18.8) μM
30.3 μM
IR%(15 μM) > 40%		 [34]
6-bromopenitrem E (57) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (16.7, 8.5) μM
9.6 μM		 BK channel inhibitor [34]
Paspaline (58) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (12.8, 12.4) μM
7.6 μM		 [34]
Emnidole SB (59) P. commune isolate GS20 Sponge/Sediment Indole alkaloid MCF-7, MDA-MB-231 (antiproliferative)
MDA-MB-231 (antimigratory)		 (10.1, 21.3) μM
19.0 μM		 [34,37]
Communesin A (60) Penicillium sp. Marine alga/Sediment Indole alkaloid P388 3.5 μg/mL [38,40]
Communesin B (61) Penicillium sp. Marine alga/Sponge/Sediment Indole alkaloid P388, U-937, THP-1, NAMALWA, MOLT-3, SUP-B15 (0.45, 10.4, 11.4, 9.9, 8.1, 7.2) μg/mL [38,39,40]
Communesin C (62) Penicillium sp. Marine sponge Indole alkaloid U-937, THP-1, NAMALWA, MOLT-3, SUP-B15 (11.3, 13.1, 8.2, 8.6, 10.8) μg/mL [39]
Communesin D (63) Penicillium sp. Marine sponge Indole alkaloid U-937, THP-1, NAMALWA, MOLT-3, SUP-B15 (13.1, 16.2, 14.6, 9.9, 9.0) μg/mL [39]
Penioxamide (64) P. oxalicum EN-201 Mangrove Indole alkaloid A. salina 5.6 μM [42]
65 P. brefeldianum SD-273 Marine sediment Indole alkaloid A. salina 9.4 μM [43]
Penipaline B (66) P. paneum SD-44 Marine sediment Indole alkaloid A549, HCT-116 (20.44, 14.88) μM [44]
Penipaline C (67) P. paneum SD-44 Marine sediment Indole alkaloid A549, HCT-116 (21.54, 18.54) μM [44]
Terretrione A (68) P. vinaceum Marine sponge 1,4-diazepane alkaloid MDA-MB-231 17.7 μM [45]
Terretrione C (69) Penicillium sp.CYE-87 Marine tunicate 1,4-diazepane alkaloid MDA-MB-231 17.6 μM [46]
Terretrione D (70) Penicillium sp.CYE-87 Marine tunicate 1,4-diazepane alkaloid MDA-MB-231 16.5 μM [46]
Penicillenol A1 (71) Penicillium sp. GQ-7/P. citrinum Mangrove/Marine sediment Pyrrolidinone alkaloid A-375, HL-60, A549, BEL-7402, P388 3.2 μg/mL (0.76, 23.8, 13.03, 8.85) μM [47,49]
Penicillenol A2 (72) Penicillium sp. GQ-7/P. citrinum Mangrove/Marine sediment Pyrrolidinone alkaloid A-375
HL-60		 13.8 μg/mL
16.26 μM		 [47,49]
Penicillenol B1 (73) Penicillium sp. GQ-7/P. citrinum Mangrove/Marine sediment Pyrrolidinone alkaloid A-375
HL-60		 2.8 μg/mL
3.2 μM		 [47,49]
Penicillenol B2 (74) Penicillium sp. GQ-7/P. citrinum Mangrove/Marine sediment Pyrrolidinone alkaloid A-375
HL-60		 0.97 μg/mL
7.65 μM		 [47,49]
Penicillenol D1 (75) P. citrinum Marine sediment Pyrrolidinone alkaloid A549, HL-60 (17.2, 18.5) μg/mL [48]
Penicillenol D2 (76) P. citrinum Marine sediment Pyrrolidinone alkaloid A549, HL-60 (12.1, 14.5) μg/mL [48]
Penitrinine A (77) P. citrinum Marine sediment Pyrrolidinone alkaloid A-375, SPC-A1, HGC-27 (20.12, 28.67, 29.49) μM Upregulate Bax, downregulate Bcl-2, suppress MMP-9 and TIMP-1 [50]
78 P. janczewskii Sea water Quinolinone MDA-MB-231, DU-145, SKOV-3, HT-29, A549, CAKI-1, SK-MEL-2, K562 IR % (10 μg/mL) = 20~50% [52]
79 P. janczewskii Sea water Quinolinone MDA-MB-231, DU-145, SKOV-3, HT-29, A549, CAKI-1, SK-MEL-2, K562 IR % (10 μg/mL) = 30~90% [52]
80 P. janczewskii Sea water Quinolinone MDA-MB-231, DU-145, SKOV-3, HT-29 IR % (10 μg/mL) = 91.6%, 69.2%, 79.8%, 96.0% [52]
81 Penicillium sp. ghq208/Penicillium sp. Marine sediment/Mangrove Quinolinone 95-D, HepG2 (0.57, 6.5) μg/mL [53,54]
82 Penicillium sp. ghq208 Marine sediment Quinolinone HepG2 13.2 μM [53]
83 P. commune SD-118 Deep sea sediment Quinazolinone SW1990 20 μg/mL [23]
84 P. chrysogenum EN-118 Marine alga Quinazolinone DU145, A549, Hela 8 μg/mL [56]
85 P. oxalicum 0312F1 Marine (not clear) Quinazolinone SGC-7901, BEL-7404 IR % (200 μg/mL) = 30~40% [55]
Penipacid A (86) P. paneum SD-44 Deep sea sediment Amidine alkaloid RKO 8.4 μM [57]
Penipacid E (87) P. paneum SD-44 Deep sea sediment Amidine alkaloid RKO 9.7 μM [57]
88 P. paneum SD-44 Deep sea sediment Imine alkaloid Hela 6.6 μM [57]
Penipanoid A (89) P. paneum SD-44 Deep sea sediment Triazole alkaloid SMMC-7721 54.2 μM [58]
Bis-sclerotioramin (90) Penicillium 303# Mangrove Azaphilone alkaloid MDA-MB-231 7.13 μM [59]
Sorbicillactone (91) P. chrysogenum Marine sponge Miscellaneous Alkaloid L5178Y 2.2 μg/mL Selective anti-leukemic [60]
Brocaeloid B (92) P. brocae Mangrove Miscellaneous Alkaloid A. salina 36.7 μM [62]
Varitatin (93) Mutant P. varibile Mangrove Amide alkaloid HCT-116 2.8 μM IR%(1μM) = 50% and 40% (PDGFR-βand ErbB4) [63]
18-hydroxydecaturin B (94) P. oxalicum EN-201 Mangrove Pyridinyl-α-pyrone alkaloid A. salina 2.3 μM [42]
Xantocillin X (95) P. commune SD-118 Deep sea sediment Isocyanide alkaloid MCF-7, HepG2, NCI-H460, Hela, DU145, MDA-MB-231 (12, 7, 10, 10, 8, 8) μg/mL Inhibit MEK/EPK pathway and activate class III PI3K/Beclin 1 pathway [23,67]
96 Penicillium sp. PR19 N-1 Marine sludge Sesquiterpene HL-60, A549 (45.8, 82.8) μM [70]
97 Penicillium sp. PR19 N-1 Marine sludge Sesquiterpene HL-60, A549 (28.3, 5.2) μM [70]
98 Penicillium sp. PR19 N-1 Marine sludge Sesquiterpene HL-60, A549 (11.8, 12.2) μM [71]
99 Penicillium sp. BL 27-2 Sea mud Sesquiterpene P388, A549, HL-60, BEL-7402 (0.073, 0.096, 0.065, 4.59) μM [72]
Sporogen-AO 1 (100) Penicillium sp. BL 27-2 Sea mud Sesquiterpene P388, A549, HL-60, BEL-7402 (10.1, 8.81, 10.4, 5.7) μM [72]
101 Penicillium sp. BL 27-2 Sea mud Sesquiterpene P388, A549, HL-60, BEL-7402 (8.71, 3.51, 7.75, 11.8) μM [72]
Adametacorenol B (102) P. adametzioides AS-53 Marine sponge Diterpene NCI-H446 5.0 μM [17]
Conidiogenone B (103) Penicillium sp. Deep sea sediment Diterpene A549, HL-60 (40.3, 28.2) μM [22]
Conidiogenone C (104) Penicillium sp. Deep sea sediment Diterpene HL-60, BEL-7402 (0.038, 0.97) μM [22]
Conidiogenone D (105) Penicillium sp. Deep sea sediment Diterpene A549, HL-60, BEL-7402, MOLT-4 (9.3, 5.3, 11.7, 21.1) μM [22]
Conidiogenone E (106) Penicillium sp. Deep sea sediment Diterpene A549, HL-60, MOLT-4 (15.1, 8.5, 25.8) μM [22]
Conidiogenone F (107) Penicillium sp. Deep sea sediment Diterpene A549, HL-60, BEL-7402 (42.2,17.8, 17.1) μM [22]
Conidiogenone G (108) Penicillium sp. Deep sea sediment Diterpene A549, HL-60, BEL-7402, MOLT-4 (8.3, 1.1, 43.2, 4.7) μM [22]
Brevione I (109) Penicillium sp. Deep sea sediment Diterpene MCF-7 7.44 μM [73]
Brevione A (110) Penicillium sp. Deep sea sediment Diterpene MCF-7 28.4 μM [73]
Penicisteroid A (111) P. chrysogenum QEN-24S Marine alga Steroid Hela, SW1990, NCI-H460 (15, 31, 40) μg/mL [74]
112 Penicillium sp. Marine moss Steroid HepG2 10.4 μg/mL [75]
113 Penicillium sp. Marine moss Steroid HepG2 15.6 μg/mL [75]
114 Penicillium sp. Marine moss Steroid HepG2 20.7 μg/mL [75]
115 Penicillium sp. Marine moss Steroid HepG2 16.8 μg/mL [75]
116 Penicillium sp. Marine moss Steroid HepG2 21.3 μg/mL [75]
117 P. stoloniferum QY2-10 Sea squirt Steroid P388 4.07 μM [76]
118 Penicillium sp. Marine sponge Steroid K562 5.54 μM [77]
119 Penicillium sp. Marine sponge Steroid K562 4.38 μM [77]
Dankasterone A (120) Penicillium sp. Marine sponge Steroid HL-60, Hela, K562 (0.78, 4.11, 7.57) μM [77]
Dankasterone B (121) Penicillium sp. Marine sponge Steroid HL-60, Hela, K562 (3.25, 4.74, 7.89) μM [77]
7-deacetoxyyanuthone (122) Penicillium sp. Marine (not clear) Meroterpene A549, SKOV-3, SKMEL-2, XF498, HCT-15 (7.74, 6.35, 3.86, 10.04, 10.07) μg/mL [79]
Farnesylbenzenediol (123) Penicillium sp. Marine (not clear) Meroterpene A549, SKOV-3, SKMEL-2, XF498, HCT-15 (4.73, 5.31, 4.80, 5.94, 6.11) μg/mL [79]
Farnesylquinone (124) Penicillium sp. Marine (not clear) Meroterpene A549, SKOV-3, SKMEL-2, XF498, HCT-15 (25.44, 37.29, 18.41, 38.07, 42.56) μg/mL [79]
Penicillone A (125) Penicillium sp. F11 Marine (not clear) Meroterpene HT1080, Cne2 (45.8, 46.2) μM [80]
Phenylpyropene E (126) P. concentricum ZLQ-69 Sea water Sesquiterpene MGC-803 19.1 μM [81]
Phenylpyropene F (127) P. concentricum ZLQ-69 Sea water Sesquiterpene MGC-803 13.6 μM [81]
Penicillipyrone A (128) Penicillium sp. F446 Marine sediment Sesquiterpene K562, A549 (28, 15) μM [82]
Penicillipyrone B (129) Penicillium sp. F446 Marine sediment Sesquiterpene K562, A549 (50, 17) μM [82]
130 Penicillium 303# Mangrove Meroterpene MDA-MB-435, HepG2, HCT-116, A549 (34.25, 24.56, 33.72, 37.82) μg/mL [59]
131 Penicillium 303# Mangrove Meroterpene MDA-MB-435, HepG2, HCT-116, A549 (31.32, 23.87, 29.19, 34.06) μg/mL [59]
Ligerin (132) Penicillium sp. Sea water Merosesquiterpene POS1, SaOS2, MG63 (117/78, 137, 1459) nM [84,85]
Oxalicumone D (133) P. oxalicum SCSGAF 0023 Marine gorgonian Chromone BGC823, MOLT-4 (10.10, 5.74) μM [87]
Oxalicumone E (134) P. oxalicum SCSGAF 0023 Marine gorgonian Chromone H1975, U937, K5652, BGC823, MOLT-4, MCF-7, HL-60, Huh-7 (5.45, 4.16, 8.80, 1.96, 1.36, 4.32, 2.96, 6.33) μM [87]
Oxalicumone A (135) P. oxalicum SCSGAF 0023 Marine gorgonian Chromone H1975, U937, K5652, BGC823, MOLT-4, MCF-7, HL-60, Huh-7, A375, A549, Hela, HepG2, SW-620, L-02 (10.38, 2.35, 4.53, 4.89, 0.30, 11.30, 2.55, 9.49, 11.7, 41.9, 46.2, 77.8, 22.6, 99.0) μM [87,88]
Oxalicumone B (136) P. oxalicum SCSGAF 0023 Marine gorgonian Chromone U937, MOLT-4, HL-60, A375, Hela, SW-620 (5.00, 2.30, 6.41, 27.8, 60.9, 40.6) μM [87,88]
Chromosulfine (145) Mutant P. purpurogenum G59 Marine (not clear) Chromone K562, HL-60, BGC-823, Hela, MCF-7 (60.8, 16.7, 73.8, 75.4, 59.2) μM [91]
Secalonic acid F (146) Penicillium sp. Deep sea sediment Xanthone HL-60 Modulate Rho GDP dissociation inhibitor 2 Activate caspase 3 and caspase 9 [92,93]
Penimethavone A (147) P. chrysogenum Marine gorgonian Flavone Hela, rhabdomyosarcoma (8.41, 8.18) μM [94]
Bipenicillisorin (148) P. chrysogenum SCSIO 41001 Deep sea sediment Coumarin K562, A549, Huh-7 (6.78, 6.94, 2.59) μM [95]
Monocerin (149) Penicillium sp. Marine sponge Coumarin L5178Y 8.4 μM [96]
150 Penicillium sp. ZH16 Mangrove Coumarin KB, KBv200 (5, 10) μg/mL [97]
Citrinin (151) Penicillium sp FF001 Marine sponge Azaphilone polyketide Inhibit respiration complex III [99,101]
Penicitrinol L (152) P. citrinum Marine sediment Azaphilone polyketide SW-620 25.6 μM [48]
Penicitrinol M (153) P. citrinum Marine sediment Azaphilone polyketide SW-620 20.9 μM [48]
Berkelic acid (154) Penicillium sp. Acid mine lake Azaphilone polyketide OVCAR-3 (in NCI60) 91 nM Inhibit MMP-3 (GI50 = 1.87 μM) Inhibit caspase 1 (GI50 = 98 μM) [102]
Sargassopenilline C (155) P. thomii Marine alga Azaphilone polyketide Inhibit the oncogenic nuclear factor AP-1 (IC50 = 15 μM) [104]
Sculezonone A (156) Penicillium sp. Marine sponge Azaphilone polyketide Inhibit both DNA polymerases (α and β) [105]
Sculezonone B (157) Penicillium sp. Marine sponge Azaphilone polyketide Inhibit both DNA polymerases (α and β) [105]
Dicitrinone B (158) P. citrinum Marine sediment Azaphilone polyketide Induce apoptosis through ROS-related caspase pathway [106]
Perinadine A (159) P. citrinum Marine fish Azaphilone polyketide L1210 20 μg/mL [107]
Herqueiazole (160) Penicillium sp F011 Marine sediment Azaphilone polyketide A549 67.3 μM [108]
Comazaphilone D (161) P. commune QSD-17 Marine sediment Azaphilone polyketide SW1990 51 μM [109]
Comazaphilone E (162) P. commune QSD-17 Marine sediment Azaphilone polyketide SW1990 26 μM [109]
Comazaphilone F (163) P. commune QSD-17 Marine sediment Azaphilone polyketide SW1990 53 μM [109]
Pinophilin A (164) P. pinophilum Hedgcok Marine seaweed Azaphilone polyketide A549, BALL-1, HCT-116, Hela, NUGC-3 (52.5, 50.2, 51.3, 55.6, 54.7) μM Inhibit the mammalian DNA polymerases A, B, Y family [110]
Pinophilin B (165) P. pinophilum Hedgcok Marine seaweed Azaphilone polyketide A549, BALL-1, HCT-116, Hela, NUGC-3 (93.1, 90.4, 92.5, 99.0, 96.8) μM Inhibit the mammalian DNA polymerases A, B, Y family [110]
Sch 725680 (166) P. pinophilum Hedgcok Marine seaweed Azaphilone polyketide A549, BALL-1, HCT-116, Hela, NUGC-3 (65.7, 62.0, 64.6, 68.8, 66.4) μM Inhibit the mammalian DNA polymerases A, B, Y family [110]
Penostatin A (167) Penicillium sp. OUPS-79 Marine alga Polyketide P388 0.8 μg/mL PTP1B inhibitor (IC50 = 15.87 μM) [111,113]
Penostatin B (168) Penicillium sp. OUPS-79 Marine alga Polyketide P388 1.2 μg/mL PTP1B inhibitor (IC50 = 33.65 μM) [111,113]
Penostatin C (169) Penicillium sp. OUPS-79 Marine alga Polyketide P388, BSY-1, MCF-7, HCC2998, NCI-H522, DMS114, OVCAR-3, MKN1 (1.0, 2.0, 1.6, 2.0, 2.5, 1.9, 2.4, 1.7) μg/mL PTP1B inhibitor (IC50 = 0.37 μM) [111,113]
Penostatin D (170) Penicillium sp. OUPS-79 Marine alga Polyketide P388 11.0 μg/mL [111]
Penostatin E (171) Penicillium sp. OUPS-79 Marine alga Polyketide P388 0.9 μg/mL [111]
Penostatin F (172) Penicillium sp. OUPS-79 Marine alga Polyketide P388 1.4 μg/mL [112]
Penostatin G (173) Penicillium sp. OUPS-79 Marine alga Polyketide P388 0.5 μg/mL [112]
Penostatin H (174) Penicillium sp. OUPS-79 Marine alga Polyketide P388 0.8 μg/mL [112]
Penostatin I (175) Penicillium sp. OUPS-79 Marine alga Polyketide P388 1.2 μg/mL [112]
176 P. oxalicum HSY05 Marine sediment Phenolic polyketide DNA topoisomerase I inhibitor [117]
177 Co-cultured Penicillium sp. WC-29-5 Mangrove Phenolic polyketide H1975 3.97 μM [118]
178 Co-cultured Penicillium sp. WC-29-5 Mangrove Phenolic polyketide H1975, HL-60 (5.73, 3.73) μM [118]
(+)-5-chlorogriseofulvin (179) P. canescens MMS460 Sea water Phenolic polyketide KB IR% (0.6 μM) = 49% [119]
Griseophenone I (180) P. canescens MMS460 Sea water Phenolic polyketide KB IR% (0.6 μM) = 58% [119]
Griseophenone G (181) P. canescens MMS460 Sea water Phenolic polyketide KB IR% (0.6 μM) = 47% [119]
Iso-monodictyphenone (182) Penicillium sp. MA-37 Mangrove Phenolic polyketide A. salina 25.3 μM [120]
Penikellide A (183) Penicillium sp. MA-37 Mangrove Phenolic polyketide A. salina 14.2 μM [120]
Penikellide B (184) Penicillium sp. MA-37 Mangrove Phenolic polyketide A. salina 39.2 μM [120]
Penicillide (185) Penicillium sp. ZLN29 Marine sediment Phenolic polyketide HepG2 (6.7/9.7, 7.8) μM ACAT and nonpeptide calpain inhibitor [121,122,124,125]
Prepenicillide (186) Penicillium sp. ZLN29 Marine sediment Phenolic polyketide HepG2, RD 9.9 μM [124]
Hydroxypenicillide (187) P. pinophilum Marine gorgonian Phenolic polyketide Hela 6.1 μM [125]
Nidurufin (188) P. flavidorsum SHK1-27 Marine sediment Anthraquinone K562 12.6 μM Induce cell cycle arrest at G2/M transition [126]
Averantin (189) P. flavidorsum SHK1-27 Marine sediment Anthraquinone K562 12.6 μM [126]
190 P. terrestre Marine sediment Polyketide A549, P388 (5.3, 15.7) μM [128]
191 P. terrestre Marine sediment Polyketide A549, P388 (7.6, 10.5) μM [128]
Dihydrobisvertinolone (192) P. terrestre Marine sediment Polyketide A549, P388 (0.52, 1.7) μM [128]
193 P. terrestre Marine sediment Polyketide A549 1.4 μM [128]
194 P. terrestre Marine sediment Polyketide A549, P388 (2.1, 2.8) μM [129]
195 P. terrestre Marine sediment Polyketide A549, P388 (4.3, 8.8) μM [129]
Trichodimerol (196) P. terrestre Marine sediment Polyketide A549, P388 (4.7, 0.33) μM [129]
Chloctanspirone A (197) P. terrestre Marine sediment Polyketide HL-60, A549 (9.2, 39.7) μM [131]
Chloctanspirone B (198) P. terrestre Marine sediment Polyketide HL-60 37.8 μM [131]
(10E,15S)-10,11-Dehydrocurvularin (199) Penicillium sp. DRF2 Marine sponge Macrolide 36 tumor cell lines 0.28~6 μM [133,134]
Curvularin (200) Penicillium sp. DRF2 Marine sponge Macrolide HSP90 inhibitor [132]
Tanzawaic acid P (201) Penicillium sp. CF07370 Marine sediment Polyketide Jurkat, K562, Raji (28.6, 30.2, 20.3) μM Active the mitochondrial apoptotic pathway [137]
Tanzawaic acid D (202) P. steckii Marine (not clear) Polyketide Bind to the FOXO1 which regulates EFGR signaling and stabilizes the FOXO1-DNA conformation [138]
Penicimutamide A (203) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 10~40% [140]
Penicimutamide B (204) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 25~40% [140]
Penicimutamide C (205) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 10~40% [140]
Penicimutamide D (206) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 20~40% [140]
Penicimutamide E (207) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 10~45% [140]
Penicimutamide F (208) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 10~50% [140]
Penicimutamide G (209) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 10~20% [140]
Fellutamide A (210) P. fellutanum Marine fish Lipopepetide P388, L1210 (0.2, 0.8) μg/mL [139]
Fellutamide B (211) P. fellutanum Marine fish Lipopepetide P388, L1210 (0.1, 0.7) μg/mL [139]
Fellutamide C (212) Mutant P. purpurogenum G59 Marine soil Lipopepetide K562, HL-60, Hela, BGC-823, MCF-7 IR% (100 μg/mL) = 30~50% [140]
Peniphenylane A (213) P. fellutanum HDN14-323 Deep sea sediment Polyphenol Hela 14.5 μM [141]
Peniphenylane B (214) P. fellutanum HDN14-323 Deep sea sediment Polyphenol Hela, HCT-116 (11.4, 15.8) μM [141]
Peniphenylane D (215) P. fellutanum HDN14-323 Deep sea sediment Polyphenol Hela, HL-60, HCT-116 (9.3, 18.2, 31.7) μM [141]
Peniphenylane F (216) P. fellutanum HDN14-323 Deep sea sediment Polyphenol Hela 29.3 μM [141]
Peniphenylane G (217) P. fellutanum HDN14-323 Deep sea sediment Polyphenol Hela, HL-60, HCT-116 (16.6, 23.2, 24.7) μM [141]
Terrestol B (218) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (6.1, 5.8, 18.3, 62.3) μM [142]
Terrestol C (219) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (5.5, 5.6, 18.2, 57.3) μM [142]
Terrestol D (220) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (5.3, 5.5, 14.3, 38.5) μM [142]
Terrestol E (221) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (54.7, 6.4, 9.6, 59.0) μM [142]
Terrestol F (222) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (55.0, 58.1, 13.8, 63.2) μM [142]
Terrestol G (223) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (5.1, 6.5, 5.7, 6.0) μM [142]
Terrestol H (224) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (6.3, 5.8, 33.8, 61.9) μM [142]
Terrestol A (225) P. terrestre Marine sediment Polyphenol HL-60, MOLT-4, A549, BEL-7402 (33.3, 5.5, 23.5, 57.0) μM [142]
Expansol A (226) P. expansum 091006 Mangrove Polyphenol HL-60 15.7 μM [143]
Expansol B (227) P. expansum 091006 Mangrove Polyphenol HL-60, A549 (5.4, 1.9) μM [143,144]
Expansol C (228) P. expansum 091006 Mangrove Polyphenol HL-60 18.2 μM [143]
Expansol E (229) P. expansum 091006 Mangrove Polyphenol HL-60 20.8 μM [143]
Patulin (230) Penicillium sp. Marine alga Other P388, BSY-1, MCF-7, HCC2998, NCI-H522, DMS114, OVCAR-3, MKN1 (0.06, 0.34, 0.65, 1.54, 0.30, 0.57, 0.37, 0.39) μg/mL Potassium-uptake inhibitor
Ion flux across cell membranes inducer		 [111]
(+)-Epiepoxydon (231) Penicillium sp. Marine alga Other P388 0.2 μg/mL [111]
232 Penicillium sp. Mangrove Other KB, KBv200 (6, 10) μg/mL [145]
Penicillic acid (233) Penicillium sp. Sea water Other POS1, AT6-1, L299 (7.8, 29.4, 12.9) μM [84]