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1 Vol.33No.05 Chemistry & Bioengineering doi: /j.issn dl ( ; ; ) : dl (+)-wickerola 2 harziandione 3~ : ; ; ;(+)-wickerola;harziandione :Q58 :A : (2016) DiterpenesandSteroidsfrom MarineAlga-Endophytic FungusTrichoderma Asperelum dl-34 LIANGXiao-rui 123 MIAOFeng-ping 1 SONGYin-ping 13 GUOZhan-yong 1 JINai-yun 1 (1.YantaiInstituteof CoastalZone ResearchChinese Academyof SciencesYantai264003China; 2.Naval AeronauticalEngineeringInstituteYantai264001China; 3.Universityof Chinese Academyof SciencesBeijing100049China) Abstract:Thebioactivemetabolitesfromamarinebrownalga-endophyticTrichodermaasperelum strain (dl-34) wereseparatedandpurifiedbychromatographytlcand HPLC.Sevenkindsofcompoundswereobtainedandtheirstruc- tureswereidentifiedbynmrmsandir.theabsoluteconformersofcompound1andcompound2wereconfirmedby quantumchemicalcalculations.resultsshowedthatcompound1was(+)-wickerolaanewditerpeneantipodeandcom- pound2washarziandioneaknownditerpeneandcompounds3~7wereergosterolderivatives.bioactivityexperimentalre- sultsshowedthatbothcompounds1and2exhibitedlethalactivityagainstartemiasalinaandcompound1alsoshowedan- tibacterialactivityagainstescherichiacoliandstaphylococusaureus. Keywords:Trichodermaasperelum;diterpene;steroid;(+)-wickerolA;harziandione (Trichodermaspp.) [2-5] [1] dl-34 [1] ~300 GF-254 : ( ) : : (1979-) : xrliang@yic.ac.cn; : nyji@yic.ac.cn
2 : / ;SephadexLH-20 ( - 1 1) ( - GE Healthcare SephadexLH-20 ( - 1 1) HPLC ChirascanCD SephadexLH-20 ( - 1 1) HPLC ;P-1020 FTIR4100 ( - 9 1) 5(4.0mg) 6(2.7mg) JASCO ;Avance Ⅲ HPLC( - 2 3) 7(5.3 (TMS ) Bruker ;AutospecPremier P776 Waters ;Agilent1260 (EclipseSB-C mm 250mm5μm) Agilent rvinsketch (2014) [7] Gaussian09 dl-34 Trichodermaasperel- [8] lum GenBank KR (TD-DFT) (PDA) ECD SpecDic (sigma=0.3) [9] (-)-wickerola [α] D 100 1L B3LYP/ G(2d2p) 300mL : 500 ml L -1 10g L -1 NaNO 32g L ml L d ~7 13 CNMR ( 1) 14.1g 2 1) 3(3.8mg) 14 ( - 9 1) 4(2.0mg) 16 mg) IR 1 HNMR 13 CNMR EIMS HREIMS B3LYP/6-31G(d) B3LYP/6-31G(d) : ;[α] 21 D1.2(c0.2CHCl 3 );IR (-)-wickerola 2 (-)-wickerola Ma- - (1 1 ) (KBr)νcm -1 : g 1099; 1 HNMR(500 MHzacetone-d 6 )δ:1.49(1h (TLC) (HPLC) mh-2)1.62(1hmh-3a)2.10(1hmh- 3b)1.48(1HmH-4a)2.01(1HmH-4b) g 15(1HmH-5)1.23(1HdddJ=14.0 Hz Hz 3.7 HzH -7a)1.67(1HmH -7b)1.44 TLC 22 (1HmH-8a)1.53(1HmH-8b)1.90(1H - (10 1) 8 dddj=13.4 Hz 10.0 Hz 6.3 HzH-10)1.58 SephadexLH (1HmH-11a)1.73(1HmH-11b)1.02(1H (10 mh-12a)1.37(1hddj=11.1 Hz 8.4 HzH- 1) 1(5.4mg) b)1.32(1HdJ=13.4 HzH-14)1.50(1H - (5 1) mh-15a)1.72(1hmh-15b)0.97(3hsh- 2(15.0mg) - (2 1) 16)1.07(3HsH-17)1.04(3HdJ=7.0 HzH 13 SephadexLH-20-18)1.07(3HsH-19)1.12(3HsH-
3 34 : / Tab.1 1~7 13 CNMR (125 MHzδ) 13 CNMRDataforcompounds1~7 (125 MHzδ) 1 a 2 b 3 b 4 b 5 c 6 b 7 b C 49.6C 34.7CH2 32.6CH2 32.9CH2 32.8CH2 25.5CH CH 59.3CH 30.1CH2 30.6CH2 31.7CH2 30.9CH2 30.0CH CH C 66.5CH 66.4CH 66.4CH 67.8CH 67.2CH CH2 42.6CH2 37.0CH2 36.1CH2 40.7CH2 39.6CH2 36.9CH CH 29.9CH 82.2C 82.7C 74.9C 76.4C 79.6C C 51.6C 135.4CH 135.5CH 72.6CH 82.5CH 198.2C CH2 29.8CH CH 130.8CH 119.9CH 115.0CH 119.8CH CH2 29.5CH2 79.4C 78.4C 140.1C 143.7C 164.8C C 146.4C 51.1CH 142.6C 42.7CH 43.9CH 74.7C CH 149.4C 37.0C 38.0C 37.1C 37.3C 41.8C CH C 23.4CH CH 23.1CH2 22.9CH2 28.7CH CH2 60.0CH2 39.4CH2 41.2CH2 39.4CH2 39.4CH2 34.9CH C 39.9C 44.6C 43.6C 43.5C 43.9C 45.3C CH 53.0CH 51.7CH 48.2CH 54.6CH 54.9CH 51.8CH CH2 26.7CH2 20.6CH2 20.9CH2 21.8CH2 22.2CH2 22.4CH CH3 25.0CH3 28.6CH2 28.6CH2 28.2CH2 27.9CH2 27.9CH CH3 23.2CH3 56.2CH 55.9CH 55.8CH 56.0CH 56.0CH CH3 20.9CH3 12.9CH3 13.0CH3 12.5CH3 12.3CH3 12.3CH CH3 20.7CH3 18.2CH3 25.6CH3 18.2CH3 18.4CH3 20.4CH CH3 22.5CH3 39.7CH 39.9CH 40.4CH 40.4CH 40.3CH CH3 20.7CH3 21.4CH3 21.1CH3 21.1CH CH 135.1CH 135.9CH 135.4CH 135.1CH CH 132.4CH 131.8CH 132.1CH 132.5CH CH 42.8CH 42.5CH 42.8CH 42.8CH CH 33.1CH 32.9CH 33.1CH 33.1CH CH3 19.6CH3 19.9CH3 19.6CH3 19.6CH CH3 19.9CH3 20.2CH3 20.0CH3 20.0CH CH3 17.6CH3 17.8CH3 17.6CH3 17.6CH CH3 : a b CDCl3 c DMSO-d6 20); 13 CNMR 1;EIMSm/z(%):290(24) 275(57)272(100)257(41)247(38)232(60)217 (37)189(56)176(51)162(53)148(66)136(43) 126(56)110(55)98(53)85(51)73(46)59(50); HREIMSm/z: [M] + ( C 20 H 34 O ) 2.2 1~7 1 ([α] 21 D ) 1.2 C 20H 34O ) C 20H 34O 4 1 HNMR 4 δ:0.97(3h sh-16) 1.07(3HsH-17) 1.07(3HsH-19) 1.12(3HsH-20)1 δ:1.04(3h dj=7.0hzh-18) 13 CNMR( 1) DEPT [10] wicker- ola HMBC H-16 C-1 C- 3367cm -1 2 C-6 C-17 H-17 C-1 C-2 C-6 C (HREIMS)(m/z [M] H-18 C-4 C-5 C-6 H-19
4 : / NOE H-19 H-5 H H-5 C-19 H-14 H-16 H -20 H-14 C-1 C-20 C-12 C-13 C-14 C-15 H-20 C-8 C harzianone 292nm Coton -9 C-10 1 wick- C-3 erola H-10 H-14 B3LYP/6-31G(d) (J=13.4 Hz) 2 ECD 2 1 wickerola 1 [α] 21 [10] D wick- erola (-2.8) 1 (-)-wickerola (+)-wick- erola (-)-wickerola (+)-wicker- ola B3LYP/ G(2d2p) 2S5R 6R9S10S13S 14R [α] 21 D ([α] 21 D -3.7) (-)-wickerola (+)- wickerola 2R5S6S9R10R13R 14S (-)-wickerola 1 2 2S5R6R13S [13-14] 14S 13 CNMR 28 NMR 1 2 (-)-wickerola 3~7 NMR Fig.1 Energy-minimizedconformersofcompound2 [15-16] 3 and(-)-wickerola 4 5α8α- -69(11)22E- 2 1 HNMR 4 δ:0.98(3hsh-17)1.00(3hsh-16) π * ) 292nm(n π * ) 2 Coton 251nm(π π * ) Coton 337nm 251nm Coton 2 harzianone 2 2 ECD Fig.2 ExperimentalandcalculatedECDspectraofcompound ~7 1 HNMR δ0.5~ δ3.7~4.1 1 δ5.1~5.3 dd 13 CNMR ( 1) 6-3β- [15-17] 5 (22E24R) β- -3β 5α- [18] 6 [16] 1.52(3HsH-19) 2.13(3HsH-20);1 7 5α9α- - δ1.12(3hdj=7.2 HzH-17) 13 CNMR [18-19] 1~7 ( 1) DEPT ; δ197.8(c-11) α β [11-12] harziandione mm( 30μg) NMR 2 harzianone (ECD) 337nm(n LC μg ml μg ml -1
5 36 : / ~7 Fig.3 Structuresofcompounds1~7 3 dl : [1] REINOJLGUERRERO R FHERN NDEZ-GAL N Ret al.secondary metabolitesfrom speciesofthebiocontrolagent Trichoderma[J].PhytochemistryReviews20087(1): [2] CARO ESTARKSC MJENSEN PRetal.Trichodermamides AandBcytotoxicmodifieddipeptidesfromthemarine-derived fungustrichodermavirens[j].journalof NaturalProducts (3): [3] SUN YTIAN LHUANGJetal.TrichodermatidesA-Dnovel polyketidesfromthemarine-derivedfungustrichodermareesei [J].OrganicLeters200810(3): [4] SONGFDAIHTONG Yetal.TrichodermaketonesA-Dand 7-O-methylkoningininDfromthemarinefungusTrichoderma koningi[j].journalofnaturalproducts201073(5): (-)- wickerola dl-34 wickerane harziane [5] CHEN LZHONGPPANJRetal.AsperelinesGand Htwo newpeptaibolsfromthemarine-derivedfungustrichodermaas- perelum[j].heterocycles201387(3): MIAOFPLIANG X RYIN XLetal.Absoluteconfigurations ofuniqueharzianediterpenesfrom Trichodermaspecies[J].Or- ganicleters201214(15): dictionandcalculation[z/ol].2014.chemaxonmarvin6.2.2 [ ].htp:// [8] FRISCH MJTRUCKSG WSCHLEGEL H Betal.Gaussian 09RevisionC [Z/OL].[ ].htp://www. gaussian.com. [9] BRUHN TSCHAUML FFEL AHEMBERGER Yetal.SpecDis: quantifyingthecomparisonofcalculatedandexperimentalelectronic circulardichroismspectra[j].chirality201325(4): [7] Marvinsketchwithcalculatorpluginsforstructurepropertypre- [10] YAMAMOTO TIZUMINUIHetal.WickerolsAandB:novelanti -influenzavirusditerpenesproducedbytrichodermaatroviridefki- 3849[J].Tetrahedron201268(45): [11] GHISALBERTIELHOCKLESSDCRROWLANDCetal.Harzi- andioneanewclassofditerpenefrom Trichodermaharzianum [J]. JournalofNaturalProducts199255(11): [12] ADELIN ESERVY CMARTIN M Tetal.Bicyclicandtetra- cyclicditerpenesfromatrichodermasymbiontoftaxusbaccata [J].Phytochemistry201497: [13] MANNINA LSEGRE A LRITIENIAetal.A newfungal growthinhibitorfrom Trhichodermaviride[J].Tetrahedron (9): [14] KOBAYASHINMURANAKA AMACKJ.CircularDichroismand MagneticCircularDichroism SpectroscopyforOrganicChemists[M]. London:RoyalSocietyofChemistry2012: [15] GRECA M DMANGONILMALINARO Aetal.5β 8β- Epidioxyergosta-622-dien-3β-olfromTyphalatifolia[J]. GazzetaChimicaItaliana (6): [16] KWON H CZEES DCHO S Yetal.Cytotoxicergosterols frompaecilomycessp.j300[j].archivesofpharmacalresearch (6): [17] CATENIGDOLJAKBZACCHIGNA Metal.Newbiological- lyactiveepidioxysterolsfromstereum hirsutum[j].bioorganic& MedicinalChemistryLeters200717(22): [18] KAWAGISHIHKATSUMIRSAZAWA Tetal.Cytotoxic steroidsfromthe mushroom Agaricusblazei[J].Phytochemis- try198827(9): [19] XIONG H YFEID QZHOUJSetal.Steroidsandothercon- stituentsfromthemushroom Armilarialueovirens[J].Chemis- tryofnaturalcompounds200945(5):
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