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Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

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Abstract

Furanoditerpenoids are a special group of diterpenoids composing of one or more furan rings, which are rarely found in nature. This review aims to survey the various naturally occurring furanoditerpenoids and their pharmacological activities. A fairly large number of furanoditerpenoids have been reported from the families Euphorbiaceae, Fabaceae and Lamiaceae, and a few ones from the families Asteraceae, Codoniaceae, Dioscoreaceae, Fossombroniaceae, Jamesoniellaceae, Meliaceae, Menispermaceae, Olacaceae, Psathyrellaceae, Sapindaceae and Scapaniaceae. Their distribution correlates strongly with the taxonomic divisions. Most of these plants are widely used in traditional medicines, and furanoditerpenoids have therefore been disclosed with a wide range of bioactivities including anti-cancer, anti-inflammation and anti-microorganism. To structure this review, the furanoditerpenoids were classified into seven types, including clerodane-type (Type I), labdane-type (Type II), cassane-type (Type III), abietane-type (Type IV), spongian-type (Type V), prenylbisabolane-type (Type VI) and miscellaneous type (Type VII). On the basis of 170 references, this review covers the distribution, phytochemistry, synthesis and pharmacological activities of furanoditerpenoids, describing 444 compounds. The information provided in this review might shed light on further research and development of furanoditerpenoids as potential therapeutic agents.

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Abbreviations

CD:

Circular dichroism

D2R:

Dopamine-D2-receptor

DIBAL:

Diisobutylaluminium hydride

DMAP:

4-Dimethylaminopyridine

DMF:

Dimethylformamide

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

KOR:

κ-opioid receptor

LAH:

Lithium aluminium hydride

LPS:

Lipopolysaccharide

MIC:

Minimum inhibitory concentration

NMR:

Nuclear magnetic resonance

NO:

Nitric oxide

PCC:

Pyridinium chlorochromate

PPHG:

Postprandial hyperglycemia

TBAF:

Tetra-n-butylammonium fluoride

t-BuLi:

Tert-butyllithium

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

References

  • Afiyatullov SS, Kalinovsky AI, Antonov AS et al (2007) Isolation and structures of erylosides from the Carribean sponge Erylus goffrilleri. J Nat Prod 70:1871–1877

    Article  CAS  PubMed  Google Scholar 

  • Agbo E, Bashir S, Igoli N et al (2015) Caesaldekarin M, A new diterpene from Caesalpinia bonduc. J Nat Prod Res Updat 1:1–6

    Google Scholar 

  • Akaberi M, Mehri S, Iranshahi M (2015) Multiple pro-apoptotic targets of abietane diterpenoids from Salvia species. Fitoterapia 100:118–132

    Article  CAS  PubMed  Google Scholar 

  • Akimanya A, Midiwo JO, Matasyoh J et al (2015) Two polymethoxylated flavonoids with antioxidant activities and a rearranged clerodane diterpenoid from the leaf exudates of Microglossa pyrifolia. Phytochem Lett 11:183–187

    Article  CAS  Google Scholar 

  • Al-Yahya MA, El-Feraly FS, Dunbar DC et al (2002) Neo-clerodane diterpenoids from Teucrium oliverianum and structure revision of teucrolin E. Phytochemistry 59:409–414

    Article  CAS  PubMed  Google Scholar 

  • Awale S, Linn TZ, Tezuka Y et al (2006) Constituents of Caesalpinia crista from Indonesia. Chem Pharm Bull 54:213–218

    Article  CAS  PubMed  Google Scholar 

  • Bandurraga MM, Fenical W, Donovan SF et al (1982) Pseudopterolide, an irregular diterpenoid with unusual cytotoxic properties from the Caribbean Sea whip Pseudopterogorgia acerosa (Pallas) (Gorgonacea). J Am Chem Soc 104:6463–6465

    Article  CAS  Google Scholar 

  • Banskota AH, Attamimi F, Usia T et al (2003) Novel norcassane-type diterpene from the seed kernels of Caesalpinia crista. Tetrahedron Lett 44:6879–6882

    Article  CAS  Google Scholar 

  • Bautista E, Maldonado E, Ortega A (2012) Neo-clerodane diterpenes from Salvia herbacea. J Nat Prod 75:951–958

    Article  CAS  PubMed  Google Scholar 

  • Bautista E, Toscano A, Calzada F et al (2013a) Hydroxyclerodanes from Salvia shannoni. J Nat Prod 76:1970–1975

    Article  CAS  PubMed  Google Scholar 

  • Bautista E, Toscano RA, Ortega A (2013b) Microphyllandiolide, a new diterpene with an unprecedented skeleton from Salvia microphylla. Org Lett 15:3210–3213

    Article  CAS  PubMed  Google Scholar 

  • Bautista E, Toscano RA, Ortega A (2014) 5,10-seco-neo-Clerodanes and neo-clerodanes from Salvia microphylla. J Nat Prod 77:1088–1092

    Article  CAS  PubMed  Google Scholar 

  • Bedir E, Tasdemir D, Çalis I et al (1999) Neo-clerodane diterpenoids from Teucrium polium. Phytochemistry 51:921–925

    Article  CAS  Google Scholar 

  • Bedir E, Manyam R, Khan IA (2003) Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L. Phytochemistry 63:977–983

    Article  CAS  PubMed  Google Scholar 

  • Bisio A, Fontana N, Romussi G et al (1999) Clerodane diterpenoids from Salvia blepharophylla. Phytochemistry 52:1535–1540

    Article  CAS  Google Scholar 

  • Bruno M, Fazio C, Piozzi F et al (1995) Neo-clerodane diterpenoids from Teucrium racemosum. Phytochemistry 40:505–507

    Article  CAS  Google Scholar 

  • Bruno M, Buscemi S, Rosselli S et al (2006) Photochemical reactivity of 6α-hydroxy-7-keto neoclerodane diterpenoids. J Photochem Photobiol A Chem 180:54–58

    Article  CAS  Google Scholar 

  • Carroll AR, Lamb J, Moni R et al (2008) Spongian diterpenes with thyrotropin releasing hormone receptor 2 binding affinity from Spongia sp. J Nat Prod 71:884–886

    Article  CAS  PubMed  Google Scholar 

  • Chaturvedula VP, Gao Z, Thomas SH et al (2004) New norditerpenoids and a diterpenoid from a sponge that inhibit the lyase activity of DNA polymerase β. Tetrahedron 60:9991–9995

    Article  CAS  Google Scholar 

  • Cheenpracha S, Srisuwan R, Karalai C et al (2005) New diterpenoids from stems and roots of Caesalpinia crista. Tetrahedron 61:8656–8662

    Article  CAS  Google Scholar 

  • Cheng YY, Li SF, Zhang Y et al (2012) Cleidbrevoids A-C, new clerodane diterpenoids from Cleidion brevipetiolatum. Fitoterapia 83:1100–1104

    Article  CAS  PubMed  Google Scholar 

  • Choudhary MI, Ismail M, Shaari K et al (2010) cis-Clerodane-yype furanoditerpenoids from Tinospora crispa. J Nat Prod 73:541–547

    Article  CAS  PubMed  Google Scholar 

  • Choudhary MI, Mohammad MY, Musharraf SG et al (2013) Biotransformation of clerodane diterpenoids by Rhizopus stolonifer and antibacterial activity of resulting metabolites. Phytochemistry 90:56–61

    Article  CAS  Google Scholar 

  • Citoglu G, Tanker M, Sever B et al (1998) Antibacterial activities of diterpenoids isolated from Ballota saxatilis subsp. saxatilis. Planta Med 64:484–485

    Article  CAS  PubMed  Google Scholar 

  • Das B, Ravinder Reddy M, Ramu R et al (2005) Clerodane diterpenoids from Pulicaria wightiana. Phytochemistry 66:633–638

    Article  CAS  PubMed  Google Scholar 

  • Das B, Srinivas Y, Sudhakar C et al (2010) New diterpenoids from Caesalpinia species and their cytotoxic activity. Bioorg Med Chem Lett 20:2847–2850

    Article  CAS  PubMed  Google Scholar 

  • Dickson RA, Houghton PJ, Hylands PJ (2007) Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana. Phytochemistry 68:1436–1441

    Article  CAS  PubMed  Google Scholar 

  • Dong L, Zhang XP, Liu MS et al (2013) Two new ent-3,4-seco-labdane diterpenoids from Callicarpa nudiflora. J Asian Nat Prod Res 15:30–34

    Article  CAS  PubMed  Google Scholar 

  • Dong R, Yuan J, Wu S et al (2015) Anti-inflammation furanoditerpenoids from Caesalpinia minax Hance. Phytochemistry 117:325–331

    Article  CAS  PubMed  Google Scholar 

  • Eguren L, Perales A, Fayos J et al (1982) New neoclerodane diterpenoid containing an oxetane ring isolated from Teucrium chamaedrys-X-ray structure determination. J Org Chem 47:4157–4160

    Article  CAS  Google Scholar 

  • Endale A, Bisrat D, Animut A et al (2013) In vivo antimalarial activity of a labdane diterpenoid from the leaves of Otostegia integrifolia Benth. Phytother Res 27:1805–1809

    Article  CAS  PubMed  Google Scholar 

  • Esquivel B, Cardenas J, Toscano A et al (1985) Structure of salvigenolide, a novel diterpenoid with a rearranged neo-clerodane skeleton from Salvia fulgens. Tetrahedron 41:3213–3217

    Article  CAS  Google Scholar 

  • Fan TP, Min ZD, Iinuma M et al (2000) Rearranged abietane diterpenoids from Clerodendrum mandarinorum. J Asian Nat Prod Res 2:237–243

    Article  CAS  PubMed  Google Scholar 

  • Farooq U, Khan A, Ahmad VU et al (2007) Two new rare-class tetracyclic diterpenoids from Otostegia limbata. Chem Pharm Bull 55:471–473

    Article  CAS  PubMed  Google Scholar 

  • Feld H, Hertewich UM, Zapp J et al (2005) Sacculatane diterpenoids from axenic cultures of the liverwort Fossombronia wondraczekii. Phytochemistry 66:1094–1099

    Article  CAS  PubMed  Google Scholar 

  • Fontana G, Savona G, Rodríguez B et al (2008) Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity. Tetrahedron 64:10041–10048

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Frija LM, Frade RF, Afonso CA (2011) Isolation, chemical, and biotransformation routes of labdane-type diterpenes. Chem Rev 111:4418–4452

    Article  CAS  PubMed  Google Scholar 

  • Fukuma Y, Sakai E, Nishishita K et al (2015) Cafestol has a weaker inhibitory effect on osteoclastogenesis than kahweol and promotes osteoblast differentiation. BioFactors 41:222–231

    Article  CAS  PubMed  Google Scholar 

  • Fumimoto R, Sakai E, Yamaguchi Y et al (2012) The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation. J Pharmacol Sci 118:479–486

    Article  CAS  PubMed  Google Scholar 

  • Galceran CB, Sertie JA, Lima CS et al (2011) Anti-inflammatory and analgesic effects of 6alpha,7beta-dihydroxy-vouacapan-17beta-oic acid isolated from Pterodon emarginatus Vog. fruits. Inflammopharmacol 19:139–143

    Article  CAS  Google Scholar 

  • Giang PM, Son PT, Matsunami K et al (2005) New labdane-type diterpenoids from Leonurus heterophyllus SW. Chem Pharm Bull 53:938–941

    Article  CAS  PubMed  Google Scholar 

  • Gómez-Hurtado MA, Álvarez-Esquivel FE, Rodríguez-García G et al (2013) Cassane diterpenes from Caesalpinia platyloba. Phytochemistry 96:397–403

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez MA (2015) Aromatic abietane diterpenoids: their biological activity and synthesis. Nat Prod Rep 32:684–704

    Article  CAS  PubMed  Google Scholar 

  • Gray CA, Rivett DE, Davies-Coleman MT (2003) The absolute stereochemistry of a diterpene from Ballota aucheri. Phytochemistry 63:409–413

    Article  CAS  PubMed  Google Scholar 

  • Gross H, Wright AD, Reinscheid U et al (2009) Three new spongian diterpenes from the Fijian marine sponge Spongia sp. Nat Prod Commun 4:315–322

    CAS  PubMed  Google Scholar 

  • Gu HS, Ma SG, Li YH et al (2014) Claoxylones A-I, prenylbisabolane diterpenoids with anti-Coxsackie B virus activity from the branches and leaves of Claoxylon polot. Tetrahedron 70:7476–7483

    Article  CAS  Google Scholar 

  • Guo DX, Zhu RX, Wang XN et al (2010) Scaparvin A, a novel caged cis-clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva. Org Lett 12:4404–4407

    Article  CAS  PubMed  Google Scholar 

  • Guo DX, Wang XN, Zhu RX et al (2012) cis-Clerodane diterpenoids from the Chinese liverwort Scapania parva Steph. Phytochem Lett 5:535–540

    Article  CAS  Google Scholar 

  • Hanson JR (2013) Diterpenoids of terrestrial origin. Nat Prod Rep 30:1346–1356

    Article  CAS  PubMed  Google Scholar 

  • Hanson JR (2015) Diterpenoids of terrestrial origin. Nat Prod Rep 32:1654–1663

    Article  CAS  PubMed  Google Scholar 

  • Hersel U, Steck M, Seifert K (2000) A new route to 2, 7-and 7-functionalized labdanes. Eur J Org Chem 2000:1609–1615

    Article  Google Scholar 

  • Hikawczuk VEJ, Rossomando PC, Giordano OS et al (2002) neo-Clerodane diterpenoids from Baccharis flabellata. Phytochemistry 61:389–394

    Article  Google Scholar 

  • Hiruma-Lima CA, Gracioso JS, Toma W et al (2001) Gastroprotective effect of aparisthman, a diterpene isolated from Aparisthmium cordatum, on experimental gastric ulcer models in rats and mice. Phytomedicine 8:94–100

    Article  CAS  PubMed  Google Scholar 

  • Hoberg E, Orjala J, Meier B et al (1999) Diterpenoids from the fruits of Vitex agnus-castus. Phytochemistry 52:1555–1558

    Article  CAS  Google Scholar 

  • Hu DP, Kawazoe K, Takaishi Y (1997) Diterpenoids from Salvia splendens. Phytochemistry 46:781–784

    Article  CAS  Google Scholar 

  • Huang C, Li W, Ma F et al (2012) Tinospinosides D, E, and tinospin E, further clerodane diterpenoids from Tinospora sagittata. Chem Pharm Bull 60:1324–1328

    Article  CAS  PubMed  Google Scholar 

  • Jenett-Siems K, Köhler I, Kraft C et al (2003) Cornutins C-L, neo-clerodane-type diterpenoids from Cornutia grandifolia var. intermedia. Phytochemistry 64:797–804

    Article  CAS  PubMed  Google Scholar 

  • Jiang HL, Wang XZ, Xiao J et al (2013) New abietane diterpenoids from the roots of Salvia przewalskii. Tetrahedron 69:6687–6692

    Article  CAS  Google Scholar 

  • Jogia MK, Andersen RJ, Parkanyi L et al (1989) Crotofolane diterpenoids from the African shrub Croton dichogamus Pax. J Org Chem 54:1654–1657

    Article  CAS  Google Scholar 

  • Kaplan ER, Naidu K, Rivett DE (1979) Diterpenoids of Leonofis species. Part III. 8b-hydroxymarrubiin from L. dysophylla Benth. J Chem Soc (C) 1656–1658

  • Karioti A, Heilmann J, Skaltsa H (2005) Labdane diterpenes from Marrubium velutinum and Marrubium cylleneum. Phytochemistry 66:1060–1066

    Article  CAS  PubMed  Google Scholar 

  • Katayama K, Shimazaki K, Tazaki H et al (2007) Parvitexins A-E, clerodane-type diterpenes isolated from the in vitro-cultured liverwort, Scapania parvitexta. Biosci Biotechnol Biochem 71:2751–2758

    Article  CAS  PubMed  Google Scholar 

  • Kawahara N, Tamura T, Inoue M et al (2004) Diterpenoid glucosides from Salvia greggii. Phytochemistry 65:2577–2581

    Article  CAS  PubMed  Google Scholar 

  • Kihampa C, Nkunya MH, Joseph CC et al (2009) Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from Tessmannia densiflora. Phytochemistry 70:1233–1238

    Article  CAS  PubMed  Google Scholar 

  • Kitagawa I, Simanjuntak P, Watano T et al (1994) Indonesian medicinal plants 11. Chemical structures of caesaldekarin A and caesaldekarin B, 2 new cassane-type furanoditerpenes from the roots of Caesalpinia major (Fabaceae). Chem Pharm Bull 42:1798–1802

    Article  CAS  Google Scholar 

  • Kittakoop P, Wanasith S, Watts P et al (2001) Potent antiviral potamogetonyde and potamogetonol, new furanoid labdane diterpenes from Potamogeton malaianus. J Nat Prod 64:385–388

    Article  CAS  PubMed  Google Scholar 

  • Kumar S, Narwal S, Kumar V et al (2011) Alpha-glucosidase inhibitors from plants: a natural approach to treat diabetes. Pharmacogn Rev 5:19–29

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lam SH, Ruan CT, Hsieh PH et al (2012) Hypoglycemic diterpenoids from Tinospora crispa. J Nat Prod 75:153–159

    Article  CAS  PubMed  Google Scholar 

  • Li W, Wei K, Fu HW et al (2007) Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of Tinospora sinensis. J Nat Prod 70:1971–1976

    Article  CAS  PubMed  Google Scholar 

  • Li W, Huang C, Li SP et al (2012) Clerodane diterpenoids from Tinospora sagittata (Oliv.) Gagnep. Planta Med 78:82–85

    Article  CAS  PubMed  Google Scholar 

  • Li RJ, Sun Y, Sun B et al (2014) Phytotoxic cis-clerodane diterpenoids from the Chinese liverwort Scapania stephanii. Phytochemistry 105:85–91

    Article  CAS  PubMed  Google Scholar 

  • Lin FW, Damu AG, Wu TS (2006) Abietane diterpene alkaloids from Salvia yunnanensis. J Nat Prod 69:93–96

    Article  CAS  PubMed  Google Scholar 

  • Liu SS, Zhu HL, Zhang SW et al (2008) Abietane diterpenoids from Clerodendrum bungei. J Nat Prod 71:755–759

    Article  PubMed  CAS  Google Scholar 

  • Liu CP, Xu JB, Zhao JX et al (2014a) Diterpenoids from Croton laui and their cytotoxic and antimicrobial activities. J Nat Prod 77:1013–1020

    Article  CAS  PubMed  Google Scholar 

  • Liu Q, Hu HJ, Li PF et al (2014b) Diterpenoids and phenylethanoid glycosides from the roots of Clerodendrum bungei and their inhibitory effects against angiotensin converting enzyme and α-glucosidase. Phytochemistry 103:196–202

    Article  CAS  PubMed  Google Scholar 

  • Look SA, Burch MT, Fenical W et al (1985) Kallolide A, a new antiinflammatory diterpenoid, and related lactones from the Caribbean octocoral Pseudopterogorgia kallos (Bielschowsky). J Org Chem 50:5741–5746

    Article  CAS  Google Scholar 

  • Lyder DL, Peter SR, Tinto WF et al (1998) Minor cassane diterpenoids of Caesalpinia bonduc. J Nat Prod 61:1462–1465

    Article  CAS  PubMed  Google Scholar 

  • Ma M, Jiang ZZ, Ruan JL et al (2012) The furano norclerodane diterpenoid disobulbin-D induces apoptosis in normal human liver L02 cells. Exp Toxicol Pathol 64:611–618

    Article  CAS  PubMed  Google Scholar 

  • Ma GX, Yuan JQ, Wu HF et al (2013) Caesalpins A-H, bioactive cassane-type diterpenes from the seeds of Caesalpinia minax. J Nat Prod 76:1025–1031

    Article  CAS  PubMed  Google Scholar 

  • Ma GX, Zhu YD, Sun ZH et al (2014) Three new cassane diterpenes from the seeds of Caesalpinia sappan. Phytochem Lett 8:141–144

    Article  CAS  Google Scholar 

  • Maldonado E, Ortega A (2000) Polystachynes A-E, five cis-neo-clerodane diterpenoids from Salvia polystachya. Phytochemistry 53:103–109

    Article  CAS  PubMed  Google Scholar 

  • María C, Rodríguez B, Bruno M et al (1997) Neo-clerodane diterpenoids from Teucrium sandrasicum. Phytochemistry 45:1653–1662

    Article  Google Scholar 

  • Maurya R, Manhas LR, Gupta P et al (2004) Amritosides A, B, C and D: clerodane furano diterpene glucosides from Tinospora cordifolia. Phytochemistry 65:2051–2055

    Article  CAS  PubMed  Google Scholar 

  • McKenzie JM, Green IR, Mugabo P (2006) Leonurun, a novel labdane diterpenoid from Leonotis leonurus. S Afr J Chem-S-Afr T. 59:114–116

    CAS  Google Scholar 

  • Mcpherson DD, Che CT, Cordell GA et al (1985) Diterpenoids from Caesalpinia pulcherrima. Phytochemistry 25:167–170

    Article  Google Scholar 

  • Mendelson JE, Coyle JR, Lopez JC et al (2011) Lack of effect of sublingual salvinorin A, a naturally occurring kappa opioid, in humans: a placebo-controlled trial. Psychopharmacol 214:933–939

    Article  CAS  Google Scholar 

  • Monti H, Tiliacos N, Faure R (1996) Two diterpenoids from copaiba oil. Phytochemistry 42:1653–1656

    Article  CAS  Google Scholar 

  • Mossa JS, Cassady JM, Antoun MD et al (1985) Saudin, a hypoglycemic diterpenoid with a novel 6,7-secolabdane carbon skeleton, from Cluytia richardiana. J Org Chem 50:916–918

    Article  CAS  Google Scholar 

  • Mossa JS, Muhammad I, AlYahya MA et al (1996) Five new modified 6,7-secolabdane diterpenoids from Cluytia richardiana. J Nat Prod 59:224–231

    Article  CAS  Google Scholar 

  • Muhammad I, Mossa JS, Mirza HH et al (1999) A new modified 6, 7-secolabdane diterpenoid from Clutia richardiana. Phytochemistry 50:1225–1227

    Article  CAS  Google Scholar 

  • Munro TA, Rizzacasa MA, Roth BL et al (2005) Studies toward the pharmacophore of Salvinorin A, a potent κ opioid receptor agonist. J Med Chem 48:345–348

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Nagy G, Günther G, Máthé I et al (1999) Diterpenoids from Salvia glutinosa, S. austriaca, S. tomentosa and S. verticillata roots. Phytochemistry 52:1105–1109

    Article  CAS  Google Scholar 

  • Narukawa Y, Niimura A, Noguchi H et al (2014) New diterpenoids with estrogen sulfotransferase inhibitory activity from Leonurus sibiricus L. J Nat Med 68:125–131

    Article  CAS  PubMed  Google Scholar 

  • Ngadjui BT, Abegaz BM, Keumedjio F et al (2002) Diterpenoids from the stem bark of Croton zambesicus. Phytochemistry 60:345–349

    Article  CAS  PubMed  Google Scholar 

  • Nieto M, Gallardo O, Rossomando PC et al (1996) 8-Hydroxysalviarin and 7,8-didehydrorhyacophiline, two new diterpenes from Salvia reflexa. J Nat Prod 59:880–882

    Article  CAS  Google Scholar 

  • Nozawa M, Suka Y, Hoshi T et al (2008) Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. Orga Lett 10:1365–1368

    Article  CAS  Google Scholar 

  • Ogawa K, Aoki I, Sashida Y (1992) Caesaljapin, a cassane diterpenoid from Caesalpinia decapetala var. japonica. Phytochemistry 31:2897–2898

    Article  CAS  Google Scholar 

  • Omosa LK, Amugune B, Ndunda B et al (2014) Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia. S Afr J Bot 91:58–62

    Article  CAS  Google Scholar 

  • Ortega A, Blount JF, Manchand PS (1982) Salvinorin, a New Trans-Neoclerodane Diterpene from Salvia Divinorum (Labiatae). J Chem Soc Perk T 1:2505–2508

    Article  Google Scholar 

  • Pan Z, Ning D, Wu X et al (2015) New clerodane diterpenoids from the twigs and leaves of Croton euryphyllus. Bioorg Med Chem Lett 25:1329–1332

    Article  CAS  PubMed  Google Scholar 

  • Papanov G, Malakov P, Tomova K (1998) 19-Hydroxygaleopsin, a labdane diterpenoid from Leonurus cardiaca. Phytochemistry 47:139–141

    Article  CAS  Google Scholar 

  • Paquette LA, Efremov I (2001) Teubrevin G and teubrevin H: the first total syntheses of rearranged neo-clerodanes including solutions to the problems of chirality merger and furan ring assembly. J Am Chem Soc 123:4492–4501

    Article  CAS  PubMed  Google Scholar 

  • Persianone AB, Savona G (1980) Diterpenoids from Galeopsis angustifolia. Phytochemistry 19:1805–1807

    Article  Google Scholar 

  • Peter SR, Tinto WF, McLean S et al (1997) Bonducellpins A-D, new cassane furanoditerpenes of Caesalpinia bonduc. J Nat Prod 60:1219–1221

    Article  CAS  Google Scholar 

  • Pierre TH, Kamdem WJ, Ayafor F et al (1997) Peniankerine, an 18-norclerodane diterpenoid from the stem bark of Penianthus zenkeri. Phytochemistry 46:165–167

    Article  Google Scholar 

  • Prabhakar Reddy P, Tiwari AK, Ranga Rao R et al (2009) New Labdane diterpenes as intestinal alpha-glucosidase inhibitor from antihyperglycemic extract of Hedychium spicatum (Ham. Ex Smith) rhizomes. Bioorg Med Chem Lett 19:2562–2565

    Article  CAS  PubMed  Google Scholar 

  • Pranithanchai W, Karalai C, Ponglimanont C et al (2009) Cassane diterpenoids from the stem of Caesalpinia pulcherrima. Phytochemistry 70:300–304

    Article  CAS  PubMed  Google Scholar 

  • Pudhom K, Sommit D (2011) Clerodane diterpenoids and a trisubstituted furan from Croton oblongifolius. Phytochem Lett 4:147–150

    Article  CAS  Google Scholar 

  • Puebla P, López JL, Guerrero M et al (2003) Neo-clerodane diterpenoids from Croton schiedeanus. Phytochemistry 62:551–555

    Article  CAS  PubMed  Google Scholar 

  • Purushothaman KK, Kalyani K, Subramanian K et al (1981) Zeta-Caesalpin, a new caesalpin from Caesalpinia bonducella. Indian J Chem B 20:625–626

    Google Scholar 

  • Qin HL, Li ZH (2004) Clerodane-type diterpenoids from Nannoglottis ravida. Phytochemistry 65:2533–2537

    Article  CAS  PubMed  Google Scholar 

  • Qin J, Li HM, Gao LH et al (2014) New labdane diterpenoids from Leonurus japonicus and their anti-inflammatory activity. Phytochem Lett 10:313–317

    Article  CAS  Google Scholar 

  • Rakotobe L, Mambu L, Deville A et al (2010) Clerodane and 19-norclerodane diterpenoids from the tubers of Dioscorea antaly. Phytochemistry 71:1007–1013

    Article  CAS  PubMed  Google Scholar 

  • Reddy PP, Rao RR, Shashidhar J et al (2009) Phytochemical investigation of labdane diterpenes from the rhizomes of Hedychium spicatum and their cytotoxic activity. Bioorg Med Chem Lett 19:6078–6081

    Article  CAS  PubMed  Google Scholar 

  • Roach JS, McLean S, Reynolds WF et al (2003) Cassane diterpenoids of Caesalpinia pulcherrima. J Nat Prod 66:1378–1381

    Article  CAS  PubMed  Google Scholar 

  • Rodriguez B, Savona G, Piozzi F (1979) Two new unusual diterpenoids from Ballota hispanica. J Org Chem 44:2219–2221

    Article  CAS  Google Scholar 

  • Rodriguez B, Delatorre MC, Jimeno ML et al (1995) Rearranged Neoclerodane Diterpenoids from Teucrium brevifolium and Their Biogenetic Pathway. Tetrahedron 51:837–848

    Article  CAS  Google Scholar 

  • Rodríguez B, María C, Bruno M et al (1996) Neo-clerodane diterpenoids from three species of Teucrium. Phytochemistry 43:435–438

    Article  Google Scholar 

  • Rodriguezhahn L, Esquivel B, Sanchez AA et al (1988) Puberulin and isopuberulin, benzonorcaradiene and benzocycloheptatriene diterpenoids of clerodanic origin from Salvia puberula. J Org Chem 53:3933–3936

    Article  CAS  Google Scholar 

  • Rodriguezhahn L, Oreilly R, Esquivel B et al (1990) Tilifodiolide, tetraline-type diterpenoid of clerodanic origin from Salvia tiliaefolia. J Org Chem 55:3522–3525

    Article  CAS  Google Scholar 

  • Roengsumran S, Limsuwankesorn S, Ngamrojnavanich N et al (2000) Cassane diterpenoid from Caesalpinia major. Phytochemistry 53:841–844

    Article  CAS  PubMed  Google Scholar 

  • Romero-Gonzalez RR, Avila-Nunez JL, Aubert L et al (2006) Labdane diterpenes from Leonurus japonicus leaves. Phytochemistry 67:965–970

    Article  CAS  PubMed  Google Scholar 

  • Roth BL, Baner K, Westkaemper R et al (2002) Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proc Natl Acad Sci USA 99:11934–11939

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Rustaiyan A, Mossleminkupaii MH, Papastergiou F et al (1995) Persianone, a dimeric diterpene from Ballota aucheri. Phytochemistry 40:875–879

    Article  CAS  Google Scholar 

  • Sanchez AA, Esquivel B, Ramamoorthy T et al (1995) Clerodane diterpenoids from Salvia urolepis. Phytochemistry 38:171–174

    Article  CAS  Google Scholar 

  • Sato A, Kurabayashi M, Nagahori H et al (1970) Chettaphanin-I, a novel furanoditerpenoid. Tetrahedron Lett 11:1095–1098

    Article  Google Scholar 

  • Sato A, Kurabayashi M, Ogiso A et al (1971) Chettaphanin-II, a novel furanoditerpenoid. Tetrahedron Lett 12:839–842

    Article  Google Scholar 

  • Savona G, Piozzi F, Hanson JR et al (1976) Structure of ballotinone, a diterpenoid from Ballota nigm. J Chem Soc Perkin Trans 1:1607–1609

    Article  Google Scholar 

  • Savona G, Piozzi F, Hanson JR et al (1977) The structure of ballotenol, a new diterpenoid from Ballota nigra. J Chem Soc Perkin Trans 1:497–499

    Article  Google Scholar 

  • Savona G, Passannanti S, Paternostro MP et al (1978) Two new diterpenoids from Teucrium fruticans. J Chem Soc Perkin Trans 1:356–359

    Article  Google Scholar 

  • Savona G, Paternostro MP, Piozzi F et al (1979) Splendidin, a new trans-clerodane from Salvia splendens. J Chem Soc Perkin Trans 1:533–534

    Article  Google Scholar 

  • Siebert DJ (1994) Salvia divinorum and salvinorin A: new pharmacologic findings. J Ethnopharmacol 43:53–56

    Article  CAS  PubMed  Google Scholar 

  • Simpson BS, Claudie DJ, Smith NM et al (2012) Rare, seven-membered cyclic ether labdane diterpenoid from Dodonaea polyandra. Phytochemistry 84:141–146

    Article  CAS  PubMed  Google Scholar 

  • Sivasubramanian A, Gadepalli Narasimha KK, Rathnasamy R et al (2013) A new antifeedant clerodane diterpenoid from Tinospora cordifolia. Nat Prod Res 27:1431–1436

    Article  CAS  PubMed  Google Scholar 

  • Spindola HM, de Carvalho JE, Ruiz ALTG et al (2009) Furanoditerpenes from Pterodon pubescens Benth with selective in vitro anticancer activity for prostate cell line. J Braz Chem Soc 20:569–571

    Article  CAS  Google Scholar 

  • Tane P, Akam MT, Tsopmo A et al (2004) Two labdane diterpenoids and a seco-tetranortriterpenoid from Turreanthus africanus. Phytochemistry 65:3083–3087

    Article  CAS  PubMed  Google Scholar 

  • Tang W, Kubo M, Harada K et al (2009) Novel NGF-potentiating diterpenoids from a Brazilian medicinal plant, Ptychopetalum olacoides. Bioorg Med Chem Lett 19:882–886

    Article  CAS  PubMed  Google Scholar 

  • Tazaki H, Nabeta K, Becker H (1998) Clerodane-type diterpenoids from axenic cultures of the liverwort Jamesoniella autumnalis. Phytochemistry 48:681–685

    Article  CAS  Google Scholar 

  • Teponno RB, Tapondjou AL, Gatsing D et al (2006) Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa. Phytochemistry 67:1957–1963

    Article  CAS  PubMed  Google Scholar 

  • Teponno RB, Tapondjou AL, Abou-Mansour E et al (2008) Bafoudiosbulbins F and G, further clerodane diterpenoids from Dioscorea bulbifera L. var sativa and revised structure of Bafoudiosbulbin B. Phytochemistry 69:2374–2379

    Article  CAS  Google Scholar 

  • Topcu G, Eris C, Ulubelen A et al (1995) New rearranged neoclerodane diterpenoids from Teucrium alyssifolium. Tetrahedron 51:11793–11800

    Article  CAS  Google Scholar 

  • Valdivia C, Kettering M, Anke H et al (2005) Diterpenoids from Coprinus heptemerus. Tetrahedron 61:9527–9532

    Article  CAS  Google Scholar 

  • Vasas A, Hohmann J (2014) Euphorbia diterpenes: isolation, structure, biological activity, and synthesis (2008–2012). Chem Rev 114:8579–8612

    Article  CAS  PubMed  Google Scholar 

  • Vigor C, Fabre N, Fourasté I et al (2001) Three clerodane diterpenoids from Croton eluteria Bennett. Phytochemistry 57:1209–1212

    Article  CAS  PubMed  Google Scholar 

  • Wang GC, Zhang H, Liu HB et al (2013a) Laevinoids A and B: two diterpenoids with an unprecedented backbone from Croton laevigatus. Org Lett 15:4880–4883

    Article  CAS  PubMed  Google Scholar 

  • Wang WX, Xiong J, Tang Y et al (2013b) Rearranged abietane diterpenoids from the roots of Clerodendrum trichotomum and their cytotoxicities against human tumor cells. Phytochemistry 89:89–95

    Article  CAS  PubMed  Google Scholar 

  • Waridel P, Wolfender JL, Lachavanne JB et al (2003) ent-Labdane diterpenes from the aquatic plant P otamogeton pectinatus. Phytochemistry 64:1309–1317

    Article  CAS  PubMed  Google Scholar 

  • Wazir V, Maurya R, Kapil RS (1995) Cordioside, a clerodane furano diterpene glucoside from Tinospora cordifolia. Phytochemistry 38:447–449

    Article  CAS  Google Scholar 

  • Wilson SR, Neubert LA, Huffman JC (1976) The chemistry of the Euphorbiaceae. A new diterpene from Croton californicus. J Am Chem Soc 98:3669–3674

    Article  CAS  PubMed  Google Scholar 

  • Wu H, Fronczek FR, Ferreira D et al (2011) Labdane diterpenoids from Leonurus sibiricus. J Nat Prod 74:831–836

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wu H, Li J, Fronczek FR et al (2013) Labdane diterpenoids from Leonotis leonurus. Phytochemistry 91:229–235

    Article  CAS  PubMed  Google Scholar 

  • Wu JM, Chen G, Xu XT et al (2014a) Seven new cassane furanoditerpenes from the seeds of Caesalpinia minax. Fitoterapia 92:168–176

    Article  CAS  PubMed  Google Scholar 

  • Wu L, Luo J, Zhang YM et al (2014b) Cassane-type diterpenoids from the seed kernels of Caesalpinia bonduc. Fitoterapia 93:201–208

    Article  CAS  PubMed  Google Scholar 

  • Xu G, Peng LY, Niu XM et al (2004) Novel diterpenoids from Salvia dugesii. Helve Chim Acta 87:949–955

    Article  CAS  Google Scholar 

  • Xu YJ, Zhang J, Tang CP et al (2013) A new diterpenoid from the seeds of Caesalpinia sappan Linn. Rec Nat Prod 7:124–128

    CAS  Google Scholar 

  • Yang ZY, Yin YH, Hu LH (2009) Five New Cassane-Type Diterpenes from Caesalpinia crista. Helv Chim Acta 92:121–126

    Article  CAS  Google Scholar 

  • Yodsaoue O, Cheenpracha S, Karalai C et al (2008) Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn. Phytochemistry 69:1242–1249

    Article  CAS  PubMed  Google Scholar 

  • Yodsaoue O, Karalai C, Ponglimanont C et al (2010) Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk. Phytochemistry 71:1756–1764

    Article  CAS  PubMed  Google Scholar 

  • Yodsaoue O, Karalai C, Ponglimanont C et al (2011) Pulcherrins D-R, potential anti-inflammatory diterpenoids from the roots of Caesalpinia pulcherrima. Tetrahedron 67:6838–6846

    Article  CAS  Google Scholar 

  • Zanin JLB, De Carvalho BA, Salles Martineli P et al (2012) The genus Caesalpinia L. (Caesalpiniaceae): phytochemical and pharmacological characteristics. Molecules 17:7887–7902

    Article  CAS  PubMed  Google Scholar 

  • Zhang JY, Wu FH, Qu W et al (2012) Two new cassane diterpenoids from the seeds of Caesalpinia sappan Linn. Chin J Nat Med 10:218–221

    Article  CAS  Google Scholar 

  • Zhang J, Abdel-Mageed WM, Liu M et al (2013a) Caesanines A-D, new cassane diterpenes with unprecedented N bridge from Caesalpinia sappan. Org Lett 15:4726–4729

    Article  CAS  PubMed  Google Scholar 

  • Zhang L, Dong L, Huang J et al (2013b) 3, 4-seco-Labdane diterpenoids from the leaves of Callicarpa nudiflora and their inhibitory effects on nitric oxide production. Fitoterapia 89:218–223

    Article  CAS  PubMed  Google Scholar 

  • Zhang ZX, Li HH, Qi FM et al (2014) A new halimane diterpenoid from Croton crassifolius. B Korean Chem Soc 35:1556–1558

    Article  CAS  Google Scholar 

  • Zhao Q, Qing C, Hao XJ et al (2008) Cytotoxicity of labdane-type diterpenoids from Hedychium forrestii. Chem Pharm Bull 56:210–212

    Article  CAS  PubMed  Google Scholar 

  • Zhao P, Chen HQ, Wang H et al (2013) Four new cassane diterpenes from the seeds of Caesalpinia minax. Phytochem Lett 6:606–609

    Article  CAS  Google Scholar 

  • Zheng Y, Zhang SW, Cong HJ et al (2013) Caesalminaxins A-L, cassane diterpenoids from the seeds of Caesalpinia minax. J Nat Prod 76:2210–2218

    Article  CAS  PubMed  Google Scholar 

  • Zheng Y, Zhang SW, Xuan LJ (2015) Trinorcassane and cassane diterpenoids from the seeds of Caesalpinia minax. Fitoterapia 102:177–181

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

Financial support by Science and Technology Development Fund, Macao S.A.R (FDCT 120/2013/A3) and the Research Fund of University of Macau (MYRG2014-00020-ICMS-QRCM and MYRG2015-00153-ICMS-QRCM) are gratefully.

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  1. State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau, China

    Han Bao, Qingwen Zhang & Ligen Lin

  2. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu-Chong-Zhi Road, Zhangjiang High-tech Park, Shanghai, 201203, China

    Yang Ye

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  1. Han Bao
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Correspondence to Ligen Lin.

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Bao, H., Zhang, Q., Ye, Y. et al. Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities. Phytochem Rev 16, 235–270 (2017). https://doi.org/10.1007/s11101-016-9472-2

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